DAT Organic MasterContent

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DAT Organic Chemistry Rapid Learning Series – Course GuideBook
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COURSE TABLE OF CONTENTS – TOPICAL SUMMARY
Core Unit #1 – Foundation of DAT Organic Chemistry
Tutorial 01: Introduction to DAT Organic Chemistry

Dental Admissions Test
Computer based test format of the DAT
The DAT Natural Sciences focus areas
DAT Organic Chemistry comprehension areas
Test-preparation strategies
Test-taking strategies
How to attack and solve Organic Chemistry problems
Tutorial 02: Chemistry Review: Structure and Bonding

Atomic and Molecular Structure
Molecular Shape
Types of Carbon Molecules
Intramolecular Bond Interactions
Molecular Orbitals
Resonance
Intermolecular Forces
Core Unit #2 – Nomenclature
Tutorial 03: IUPAC Rules – Organic Nomenclature I

IUPAC Nomenclature
Parent chain
Alkyl prefixes
Substituents
Numerical prefixes
Halogen prefixes
Rules used in naming compounds
Common Nomenclature
Classification of carbons
Tutorial 04: IUPAC Rules – Organic Nomenclature II

IUPAC Nomenclature
Rules for naming alcohols, ethers, aldehydes, ketones, carboxylic acids, and
amines
Rules for naming carboxylic acid derivatives
Common Nomenclature
Rules for naming alcohols, ethers, ketones, and amines
Tutorial 05: Drawing Organic Structures

Importance of Drawing Structures
Types of Structures
Isomers
Abbreviations

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Tutorial 06: Functional Groups of Organic Compounds

The chemistry of carbon
Functional Groups
Acids and Bases
Electron Pushing
Core Unit #3 – Stereochemistry and Conformation
Tutorial 07: Stereochemistry

Isomers
Constitutional isomers
Stereoisomers
Conformational isomers
Basic Concepts of Stereochemistry
Stereochemistry overview
Chirality
Stereoisomers
Enantiomers
Diastereomers
Assigning R and S Configurations to Chiral Centers
Distinguishing enantiomers pairs by assigning their R and S configurations
Assigning the absolute configuration to chiral compounds
Meso compounds
Stereoisomers of Alkenes
Relative configuration
Absolute configuration
Tutorial 08: Conformational Analysis

Basic Concepts
Conformations of Ethane
Conformations of Butane
Bond Angles of Cycloalkanes
Conformations of Cyclohexane
Core Unit #4 – Hydrocarbons and Reactions
Tutorial 09: Saturated Hydrocarbons

Definitions
Hydrocarbons
Alkanes
Cycloalkanes
Alkyl halides
Properties and Uses of Alkanes and Cycloalkanes
Properties
Structure and conformations
Uses
Properties and Uses of Alkyl Halides
Properties
Uses

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Alkane and Cycloalkane Nomenclature

IUPAC nomenclature
Common nomenclature
Nomenclature of Alkyl Halides
IUPAC nomenclature
Common nomenclature
Reactions of Alkanes
Combustion
Cracking
Halogenation
Tutorial 10: Unsaturated Hydrocarbons

Background Information for Alkenes, Alkynes, and Dienes
Nomenclature of Alkenes, Alkynes, and Dienes
Synthesis of Alkenes
Synthesis of Alkynes
Reactions of Alkenes
Reactions of Alkynes
Polymerization of Alkenes
Oxidation of Alkenes and Alkynes
Core Unit #5 – Aromatics
Tutorial 11: Aromatic Compounds and Aromaticity

Background Information for Aromatic Compounds
Nomenclature of Aromatic Compounds
Reactions of Aromatic Compounds
Core Unit #6 – Functional Groups and Reactions
Tutorial 12: Alcohols and Ethers

Background Information for Alcohols and Ethers
Definitions
Properties
Uses
Classification of alcohols
Nomenclature for Alcohols and Ethers
IUPAC nomenclature
Common nomenclature
Physical Properties of Alcohols
Hydrogen bonding
Boiling points of alcohols
Water solubility of alcohols
Acidity of alcohols
Synthesis of Alcohols
From alkenes
From alkyl halides
From organometallic reagents reacting with aldehydes and ketones
From reduction of aldehydes and ketones

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Reactions of Alcohols
Formation of alkoxide ions
Formation of alkyl halides
Dehydration
Oxidation
Esterification
Pinacol rearrangement
Preparation of leaving groups
Synthesis and Reactions of Ethers
Williamson ether synthesis
Cleavage of ethers
Tutorial 13: Aldehydes and Ketones

Background Information for Aldehydes and Ketones
Structure
Shape
Properties
α-Hydrogens
Keto-enol tautomerism
Nomenclature for Aldehydes and Ketones
IUPAC nomenclature
Common nomenclature
Synthesis of Aldehydes and Ketones
Oxidation of alcohols
Friedel-Crafts acylation of benzene
Ozonolysis of alkenes
From acid halides
Reactions of Aldehydes and Ketones
Reactions with organometallic reagents
Reduction to alcohols
Reduction to alkanes
Formation of imine derivatives
Oxidation
Acetal formation
Reactions at the α-carbon
Acetoacetic ester synthesis
Aldol condensation
Haloform reaction
Tutorial 14: Carboxylic Acids

Background Information for Carboxylic Acids
Structure
Shape
Physical properties
Acidity
Acidity of carboxylic acids
Resonance stability of the carboxylate anion
Inductive effects on acidity
Nomenclature of Carboxylic Acids
IUPAC nomenclature
Common nomenclature
Synthesis of Carboxylic Acids

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Oxidation of primary alcohols

Oxidation of aldehydes
Carboxylation of Grignard reagents
Hydrolysis of nitriles
Reactions of Carboxylic Acids
Reduction to primary alcohols
Conversion to acid halides
Esterification
Conversion to anhydrides
Decarboxylation
Tutorial 15: Acid Derivatives

Background Information for Acid Derivatives
Shape
Properties
Relative reactivity of acid derivatives
Nomenclature of Acid Derivatives
Rules for acid halides
Rules for esters
Rules for anhydrides
Rules for amides
Reactions of Acid Halides
Hydrolysis
Conversion to esters
Conversion to amides
Reduction to aldehydes
Conversion to ketones
Reactions of Esters
Hydrolysis
Saponification
Transesterification
Reactions of Anhydrides
Hydrolysis
Reactions of Amides
Hydrolysis
Hofmann Rearrangement
Reduction to amines
Dehydration
Tutorial 16: Keto Acids and Esters

Background Information for Keto Acids and Esters
Definitions
Nomenclature
Acidity of the α-hydrogen
Reactions of Keto Acids and Esters
Decarboxylation

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Acetoacetic acid synthesis
Tutorial 17: Amines

Background Information for Amines
Classification of amines
Shape
Properties
Uses
Nomenclature of Amines
IUPAC nomenclature
Common nomenclature
Amine salts
Synthesis of Amines
Reduction of nitro compounds
Reduction of nitriles
Reduction of amides
Alkylation of amines
Reductive amination of aldehydes and ketones
Reactions of Amines
Reaction with alkyl halides
Reaction with aldehydes and ketones
Acylation
Reaction with sulfonyl chlorides
Hofmann elimination
Reaction with nitrous acid
Core Unit #7 – Organic Analysis and Separation
Tutorial 18: Infrared and UN Spectroscopy

Basic Information for Infrared
Background
Intensity of infrared absorptions
Bonds with similar infrared absorptions
Molecular vibrations
Index of hydrogen deficiency
Functional groups
Infrared Interpretation Trends
Zones
By functional groups
Infrared Absorption Frequency Tables
Abbreviations
Frequencies
Infrared Spectra Problem Solving
Steps
Examples
Basics of UV/Vis Spectroscopy
Theory of UV/Vis spectroscopy
Absorption of UV/Vis light
Conjugation
Tutorial 19: NMR and Mass Spectrometry

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Basic Information for NMR

Background
Theory
Definitions
Proton NMR Spectroscopy
Background information
Splitting of signals
Proton resonance frequencies tables
Problem solving
Examples
Carbon-13 NMR Spectroscopy
Carbon magnetic frequencies tables
Problem solving
Examples
Background Information for Mass Spectrometry
History
The mass spectrometer
The molecular ion
The base peak
Isotopes and mass spectrometry
The Mass Spectrum
Fragmentations of alkanes
Fragmentations of alcohols
Fragmentations of amines
Fragmentations of ethers
Fragmentations of aldehydes and ketones
The McClafferty rearrangement
Analyzing Mass Spectra
Guidelines for analysis
Sample spectra
Tutorial 20: Separations and Purifications

Extractions
Theory of extraction
Liquid-liquid extraction
Acid-base extraction
Distillation
Boiling points
Theory of distillation
Simple distillation
Chromatography
Theory of chromatography
Column chromatography
Gas-liquid chromatography
Paper chromatography
Thin-layer chromatography
Recrystallization
Theory of recrystallization
Solvent selection

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Core Unit #8 – Individual Reactions, Multistep Reactions and

Mechanisms
Tutorial 21: Organic Reactions

Terminology of Organic Reactions
Mechanism, stoichiometry, thermodynamics, kinetics
Transition state, activation energy, Hammond postulate
Kinetic versus thermodynamic control, reactive intermediate, catalyst, solvent effect
Reactions of Alkyl Halides
Substitution with nucleophiles to form other compounds
Elimination with KOH to form alkenes
Reaction with lithium to form alkyl lithiums
Reaction with magnesium to form Grignard reagents
Addition of HX to form alkyl halides
Addition of H2O to form alcohols
Addition of X2 to form dihaloalkanes
Addition of hydrogen to form alkanes
Oxidation with KMnO4 to form diols
Oxidation with O3 to form aldehydes and ketones
Addition of 2 HX to give dihaloalkanes
Addition of 2 X2 to give tetrahaloalkanes
Addition with 2 H2 to give alkanes
Oxidation with KMnO4 to give diketones
Oxidation with O3 to give carboxylic acids
Reaction with X2 and catalyst to give ArX
Reaction with HNO3 and H2SO4 to give ArNO2
Reaction with SO3 and H2SO4 to give ArSO3H
Reaction with RX and AlCl3 to give ArR
Reaction with R(C=O)X and AlCl3 to give ketones
Reactions of Amines
Reaction with RX, followed by lost of HX, to yield larger amines
Reaction with HX, to yield ammonium salts
Reaction with acid halides to yield amides
Reaction with sulfonyl chlorides to yield sulfonamides
Reaction with metals to yield alkoxide ions
Reaction with HX, PX3, or POCl3 to yield RX
Reaction with heat and acid to yield alkenes
Dihalides are treated with 2 KOH to yield alkynes
Oxidation
Reaction with RCOOH and acid to yield esters
Reaction with organometallic reagents to form alcohols
Reaction with primary amines to yield imines
Reductive amination to yield amines
Oxidation of aldehydes to carboxylic acids

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Reaction with thionyl chloride to yield acid chlorides
Reaction with alcohols and acid to give esters
Reaction with acid halides to give anhydrides
Hydrolysis to form carboxylic acids
Reaction with alcohols to form esters
Reaction with amines to form amides
Reaction with R2CuLi to form ketones
Reactions of Esters
Reaction with water and acid to yield carboxylic acids and alcohols
Reaction with amines to yield amides and alcohols
Hydrolysis of anhydrides to yield carboxylic acids
Reaction with alcohols to yield esters and carboxylic acids
Reaction with amines to yield amides and carboxylic acids
Reactions of Amides
Reaction with aqueous acid to yield carboxylic acids and ammonium ions
Reaction with water and hydroxide ion to yield carboxylate anions and amines
Reduction to amines
Dehydration to nitriles
Tutorial 22: Synthesis, Multistep and Retrosynthesis

Principles of Synthesis
Definition of synthesis
Total synthesis
Methodology
Retrosynthesis
Retrosynthetic analysis
Disconnections
Evaluation
Tutorial 23: Organic Reaction Mechanisms

Terminology in Mechanisms
Double headed arrows, heterolytic bond cleavage, heterogenic bond formation
Single headed arrows, homolytic bond cleavage, homogenic bond formation
Polar reactions
Substitution Reactions
Sn1 reactions
Sn2 reactions
Elimination Reactions
E1 reactions
E2 reactions
Mechanism of Addition Reactions
Mechanism for the addition of HX to alkenes
Mechanism for addition of halogens to alkenes
Nucleophilic Addition to Carbonyl Compounds
Reaction of a Grignard reagent with aldehydes

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Reaction of aldehydes with primary amines

Electrophilic Aromatic Substitution
Mechanism of electrophilic aromatic substitution
Example
Acid-Base Reactions
Deprotonation
Protonation
Carbocation Mechanisms
1,2-Hydride shift
1,2-Alkyl shift
Anion Mechanisms
Mechanism for the alkylation of carbonyl compounds with LDA
Mechanism for the addition of the hydride ion
Radical Reactions
Halogenation of alkenes
Mechanism Basics
Understanding mechanisms
Arrow Drawing Skills
Basic arrow drawing skills for heterolytic bonds
Examples of nucleophiles
Basic arrow drawing skills for homolytic bonds
Movement of Electrons with Arrows
An unshared electron pair becomes a shared electron pair
A shared electron pair becomes an unshared electron pair
A shared electron pair becomes another shared electron pair
Intermediates
Formation of intermediates
Characteristics of good intermediates
Characteristics of unlikely intermediates
Core Unit #9 – Acids and Bases
Tutorial 24: Acid-Base Chemistry

Definitions of acids and bases
Arrhenius acids and bases
Brønsted-Lowry Theory
Lewis acids and bases
Conjugate acids and bases
Equilibria in acid-base reactions
Molecular structure considerations
Resonance in acid-base chemistry
Inductive effects

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COURSE FEATURES
This tutorial series is a carefully selected collection of core concept topics that cover the
essential concepts. It consists of three parts:
1. Concept Tutorials – 24 essential topics
2. Problem-Solving Drills – 24 practice sets
3. Super Condense Cheat Sheets – 24 super review sheets
Core Tutorials
+ Self-contained tutorials…not an outline of information which would need to be
supplemented by an instructor.
+ Concept map showing inter-connections of new concepts in this tutorial and those
previously introduced.
+ Definition slides introduce terms as they are needed.
+ Visual representation of concepts.
+Conceptual explanation of important properties and problem solving techniques
+ Animated examples of processes and cycles in human physiology.
+ A concise summary is given at the conclusion of the tutorial.
Problem Solving Drills

Each tutorial has an accompanying Problem Set with 10 problems covering the material
presented in the tutorial. The problem set affords the opportunity to practice what has
been learned.
Condensed Cheat Sheet

Each tutorial has a one-page cheat sheet that summarizes the key concepts and
vocabularies and structures presented in the tutorial. Use the cheat sheet as a study guide
after completing the tutorial to re-enforce concepts and again before an exam.

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Chapter by Chapter Detailed Content Descriptions
01: Introduction to DAT Organic Chemistry
Chapter Summary
In this first tutorial, we will give you the introduction to the test you are about to take. In
particularly, you will learn more about this DAT Organic Chemistry course and get ready for
the extensive coverage on required knowledge in the chemistry section of biological survey
subtest. The DAT and CBT are defined and the scope of the organic chemistry section is
introduced. The test-prep and test-taking strategies are also discussed. Finally, the tips in
how to solve chemistry problems are described.
Tutorial Features
• Concept map showing inter-connections of concepts.

• Definition slides introduce terms as they are needed.
• Examples given throughout to illustrate how the concepts apply.
• A concise summary is given at the conclusion of the tutorial.
Key Concepts
Dental Admissions Test

Computer based test format of the DAT
The DAT Natural Sciences focus areas
DAT Organic Chemistry comprehension areas
Test-preparation strategies
Test-taking strategies
How to attack and solve Organic Chemistry problems
Chapter Review
DAT - The DAT is the Dental College Admissions Test by American Dental Association
(ADA). Its computer based test is a standardized exam that most US and Canadian dental
schools require in order to consider a student for admission.
DAT Organic Chemistry - The science section of the DAT consists of 100 items that
includes questions about: General Chemistry, Organic Chemistry and Biology. Organic
Chemistry usually consists of about 30 items broken down as shown with the numbers
representing the number of items usually tested within each focus area.
Test -Prep Strategies: (1) Smart Time Management (2) Key Concept Mastery (3)
Practice-Practice-Practice (4) Systematic Review
Test-Taking Strategies: (1) Know the Test (2) Plan Your Attack (3) Build Focus (4)
Zoom In On The Answer (5) Guess The Right Way
Organic Chemistry Problem Solving: (1) Think of the answer before scanning the
answer choices (2) Beware of the familiar (3) Aware of the Absolute (4) Deal with the

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Similar and Opposites (5) Know about the elimination and answer selection (6) Make
educated guesses.

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02: Chemistry Review – Structure and Bonding
Chapter Summary
Organic chemistry is the study of carbon compounds. In order to learn more about carbon
compounds, and the reactions they undergo, one must understand some basic, underlying
principles of chemistry first. It is essential to have a firm grasp of concepts like atomic
structure, molecular orbitals, intra- and intermolecular interactions, and resonance. With
these basic concepts as the foundation, learning about organic compounds and how they
react will be much easier.
Tutorial Features

• Color coded atoms in examples to enable the reader to better follow the action.
• Visual representation of concepts.
Key Concepts
Atomic and Molecular Structure

Atomic structure
Electronic configuration
Valence electrons
Isotopes, ions and radicals
Lewis structures
Formal charges
Molecular Shape
VSEPR (valence shell electron pair repulsion) theory
Predicting molecular shape
Structural formulas of heteroatoms
Types of Carbon Molecules
Stable, neutral molecules
Carbanions
Carbocations
Radicals
Electronegativity
Bond polarity
Bonding
Bond breaking
Molecular Orbitals
Sigma and pi bonds
Hybridization
Resonance
Theory of resonance
Delocalized electrons

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London Dispersion forces
Dipole-dipole forces
Hydrogen bonding
Chapter Review
Atomic Number
The number of protons in an atom.
Electronic Configuration
The arrangement of an atom or ion’s electrons into atomic orbitals. There are four types of
atomic orbitals: s orbitals (maximum of 2 electrons), p orbitals (maximum of 6 electrons),
d orbitals (maximum of 10 electrons), and f orbitals (maximum of 14 electrons).
Valence Electrons
The electrons that comprise the outer shell of an atom and are typically the electrons
involved in bonding.
Isotope
An atom having the same number of protons in its nucleus as other varieties of the
element but has a different number of neutrons.
Ion
An atom or group of atoms that has either lost or gain an electron(s) resulting in a charged
species.
Radical
An atomic or molecular species with an unpaired electron.
Formal Charge
The charge that an atom would have if the bonding electrons in every bond to it were
equally shared. Formal charges are useful for accounting for the electrons in a molecule,
but they do not have any intrinsic physical meaning. The equation used to determine the
formal charge of an atom(s) is below:
Formal charge = [number of valence electrons] – [nonbonding electrons] – ½[bonding

electrons]
Lewis Structures
Diagrams that show the bonding between atoms of a covalently bonded molecule and any
lone pairs of electrons that may exist in the molecule. Lewis structures are drawn using
only the valence electrons.
VSEPR Theory
Valence shell electron pair repulsion theory (VSEPR) is a model in chemistry that attempts
to predict the shape of a molecule based on the valence electrons of a molecule. The
theory states that the areas of electron density in a molecule will repel each other, and in
doing so, adopt regular, predictable shapes.
Carbanion

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A molecule that contains a carbon which has gained a pair of electrons and is negatively
charged.
Carbocation
A molecule that contains a carbon which has lost a pair of electrons and is positively
charged.
Carbon Radical
A carbon that is neutral and possesses a single, unpaired electron.
Stable, Neutral Carbon Compound

A compound that has not lost or gained any electrons.
Electronegativity
The ability of an atom to attract electrons.
Dipole
The separation of charge between two covalently bonded atoms.

Bonding interactions within a molecule.
Ionic Bonding
Type of intramolecular bonding interaction that involves the actual transfer of electrons
from one atom to another.
Covalent Bonding
Type of intramolecular bonding interaction that involves the sharing of electrons between
atoms. The difference in electronegativity, as well as other factors, between atoms in a
bond can affect the extent to which the electrons are shared.
Polar Covalent Bonding

Type of covalent bonding where the atoms participating in a bond differ in electronegativity
so the electrons in the bond are shared unequally.
Nonpolar Covalent Bonding

Type of covalent bonding where the atoms in a bond have the same electronegativity and
share the electrons in the bond equally.
Homolytic Bond Cleavage

Process in which each atom involved in a bond obtains one electron forming radicals.
Heterolytic Bond Cleavage

Process in which one atom involved in bond obtains both electrons while the other atom
gets no electrons. Ions are formed as a result.
Molecular Orbitals
Orbitals obtained by combining atomic orbitals in a molecule together.
Sigma Bonds
Bonds formed by the overlapping of orbitals in such a way that the electron density of the
bond is located between the nuclei of the two atoms involved in the bond. Single bonds

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obtained by one of three ways: two s orbitals overlapping, one s overlapping with an end of
one p orbital, or two p orbitals overlapping end-on-end.
Pi Bonds
Bonds formed by the overlapping of orbitals in such a way that the electron density of the
bond is located both above and below the plane of the nuclei involved in the bond. Pi
bonds can be obtained by the side-to-side overlap of two p orbitals.
Hybrid Orbitals
The combination of two or more atomic orbitals to form a new orbital.
Resonance
A tool used in organic chemistry to describe molecules that can be drawn in more than one
way.
Resonance Structure
Structures that can be drawn for a given molecule that differ only by the distribution of
electrons. Each structure contributes to the overall picture of a molecule.
Resonance Hybrid
A composite of the various contributing resonance structures that gives a better description
of a molecule than a single resonance structure could by itself.
Delocalized Electrons
Electrons that are not associated with just one atom or bond. Delocalized electrons are
thought to lead to increased molecular stability.
Attractive forces between molecules.
London Dispersion Forces

Forces that occur between nonpolar molecules.
Dipole-Dipole Forces
Forces that occur between polar molecules.
Hydrogen Bonding
A type of dipole-dipole force that occurs between molecules with –OH, -NH, or HF.

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03: IUPAC Rules: Organic Nomenclature I
Chapter Summary
Organic nomenclature, the rules for naming organic compounds, has two functions. First,
the rules established in systems of nomenclature act to ensure that a person who hears or
reads the name is under no ambiguity as to the compound to which it refers. One name
can refer only to one chemical compound. Second, each name preferably conveys some
information about the structure of a compound. In organic chemistry, the student is
expected to be familiar with two systems of nomenclature: IUPAC nomenclature and
common nomenclature. IUPAC nomenclature is a system of naming chemical compounds
developed by the International Union of Pure and Applied Chemistry. It is a more
formalized system than common nomenclature. IUPAC nomenclature uses a system of
prefixes and suffixes to indicate the type of compound (what functional group is present in
the molecule) present, the number of carbons in the longest, continuous chain in the
molecule, and the type, number, and location of substituents on the parent chain.
Common nomenclature uses prefixes to indicate the presence of certain common structural
motifs in molecules. In order to fully understand the naming prefixes of common
nomenclature, a discussion of the classification of carbons is also included.
Tutorial Features

• Visual representation of basic concepts of nomenclature.
Key Concepts
IUPAC (International Union of Pure and Applied Chemistry) Nomenclature

Parent chain
Alkyl prefixes
Substituents
Numerical prefixes
Halogen prefixes
Common Nomenclature
Classification of carbons
Chapter Review
IUPAC Nomenclature
A system of naming chemical compounds developed by the International Union of Pure and
Applied Chemistry. This system of nomenclature standardized the naming of compounds
so that scientists around the world could communicate about molecules without confusion.

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Parent Chain
The parent chain is the longest, continuous chain of carbons in a molecule.
Alkyl Prefixes
Prefixes that indicate the number of carbon atoms in the main chain. The table below lists
the different alkyl prefixes:
Number of Carbons Alkyl Prefix

1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
7 Hept-
8 Oct-
9 Non-
10 Dec-
Substituents
Any atom or group of atoms not part of the parent chain in a molecule.
Numerical Prefixes
Prefixes used to indicate when more than one of a particular substituent exists in a
molecule. The table below lists the numerical prefixes used for naming identical groups:
Number of Identical Group Present Numerical Prefix

1 Mono-
2 Di-
3 Tri-
4 Tetra-
5 Penta-
6 Hexa-
7 Hepta-
8 Octa-
9 Nona-
10 Deca-
Halogen Prefixes
Prefixes used to indicate when a halogen (fluorine, chlorine, bromine, or iodide) is present
as a substituent in a compound. The table below lists the halogen prefixes for each atom:
Halogen Atom Halogen Prefix

Fluorine (F) Fluoro-
Chlorine (Cl) Chloro-
Bromine (Br) Bromo-
Iodine (I) Iodo-
IUPAC Rules for Naming Compounds

There are two parts to every organic compound name in the IUPAC system: (1) the parent
and (2) the substituents. The parent conveys the number of carbon atoms present in the

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longest chain through the use of an alkyl prefix and the functional group of the compound
through the use of an appropriate suffix. The substituents are listed alphabetically before
the parent in the name. Numerals are used to indicate their location on the main chain and
numerical prefixes are used to indicate when more than one of a particular substituent
exists. The following are rules used to name alkanes, alkenes, alkynes and alkyl halides:
1. Determine the longest, continuous chain of carbon atoms in the molecule. If the
molecule contains an alkene or alkyne functional group, then the multiple bond(s)
must be a part of the parent chain. Select the correct alkyl prefix that
corresponds to the number of carbon atoms in the parent chain.
2. Determine the correct functional group suffix to use. Use the suffixes –ane for
alkanes, -ene for alkenes, and –yne for alkynes. With alkyl halides, the molecules
are named as alkanes with the halogens serving as substituents on the parent
alkyl chain.
3. For alkanes, number the parent chain from the end that gives the lower number to
the substituent encountered first.
4. For alkenes and alkynes, number the chain so that the multiple bonds have the
lowest possible number. Place this location number in front of the parent name.
5. Naming substituents: For halogen substituents, use the halogen prefixes. For
alkyl substituents, use the appropriate alkyl prefixes + -yl. Use numerical prefixes
if more than one of a particular substituent exists in the molecule. Give the
location of all substituents by placing the number of the carbon it is attached to in
front of the substituent name.
6. Alphabetize the substituent groups, ignoring all numerical prefixes, in front of the
parent name.
7. For alkenes, determine the relative configuration of the alkene if possible (cis
versus trans). Place cis or trans in front of the substituent groups.
Common Nomenclature
Common nomenclature uses prefixes to indicate the presence of certain common structural
motifs in molecules. The table below lists the different structural motifs in common
nomenclature:
Name of Structural Motif Structure of Motif

Straight Chain/Normal (n-)
CH3 n
Iso-
Secondary (sec-)
Tertiary (tert-)
Neo-

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The following are rules for naming alkyl halides using common nomenclature:
1. Name the compound as an alkyl halide. Use all of the carbons in the “alkyl”
name.
2. Use the prefix “n” if the structure is a straight chain with the halogen on one end.
3. Use the prefix “iso” if the structure contains two methyl groups attached to a
methine (CH) carbon.
4. Use the prefix “sec” if halogen is attached to the secondary carbon of a four
carbon chain.
5. Use the prefix “tert” if the halogen is attached to the tertiary carbon of a group of
four or five carbons.
6. Use the prefix “neo” if the halogen is attached to a carbon attached to four other
carbons.

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04: IUPAC Rules: Organic Nomenclature II
Chapter Summary
The theme of organic nomenclature is continued in this tutorial with the rules for naming
alcohols, ethers, aldehydes, ketones, carboxylic acids, amines and carboxylic acid
derivatives being the focus of study. The IUPAC rules for naming alcohols, ethers,
aldehydes, ketones, carboxylic acids, amines and carboxylic acid derivatives build on those
rules learned in the previous tutorial for alkanes, alkenes, alkynes, and alkyl halides. Also,
the common nomenclature rules for naming alcohols, ethers, ketones, and amines will be
examined.
Tutorial Features
• Examples and practice problems in the tutorial: Naming alcohols, ethers,

aldehydes, ketones, amines and carboxylic acid derivatives.
• Visual representation of basic concepts of nomenclature.
Key Concepts
IUPAC Nomenclature
Rules for naming alcohols, ethers, aldehydes, ketones, carboxylic acids, and amines
Rules for naming carboxylic acid derivatives
Common Nomenclature
Rules for naming alcohols, ethers, ketones, and amines
Chapter Review
Functional Group Suffixes

The functional group suffix makes up part of the parent’s name and communicates the
functional group of the molecule immediately upon hearing/reading the compound’s name.
The table below lists the suffixes for the most commonly encountered functional groups in
organic chemistry:
Functional Group Suffix

Alkane -ane
Alkene -ene
Alkyne -yne
Alkyl Halide* -ane
Ether* -ane
Alcohol -anol
Aldehyde -anal
Ketone -anone
Carboxylic Acid -anoic acid
Amine -anamine

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Ester -anoate
Anhydride Alkanoic alkanoic anhydride
Acid Halide -anoyl halide
Amide -anamide
Naming Alcohols, Ethers, Aldehydes, Ketones, Carboxylic Acids, and Amines

The rules for naming alcohols, ethers, aldehydes, ketones, carboxylic acids, amines, and
carboxylic acid derivatives in this tutorial build on those from the previous tutorial entitled
“Organic Nomenclature I: How to Name Alkanes, Alkenes, Alkynes, and Alkyl Halides.” The
following are rules for naming alcohols, ethers, aldehydes, ketones, carboxylic acids, and
amines:
1. Determine the appropriate alkyl prefix and functional group suffix for the parent
chain in the molecule.
2. Number the chain so that the C-O or C-N bond has the lowest possible number.
Indicate the position of the functional group using a number in front of the parent
chain name.
3. For ethers, the compound is named as an alkane with the –OR group named as a
substituent of the parent chain.
4. For amines, give the location of the attachment of the nitrogen to the parent
amine and identify any groups attached to the nitrogen as substituents.
5. Give the location of each substituent with a number. Use numerical prefixes if
more than one identical group is present.
6. Alphabetize the substituents, ignoring all numerical prefixes, in front of the parent
chain’s name.
Naming Carboxylic Acid Derivatives

In addition to the rules seen thus far for naming organic compounds, the following are
IUPAC rules to be used in the naming of acid derivatives:
1. An ester is named by numbering the longest carbon chain beginning at the

carbonyl carbon. List the alkyl group attached to the oxygen before any
substituents.
2. An anhydride is named as an alkanoic alkanoic anhydride.
3. An acid halide is named as an alkanoyl halide.
4. An amide is named as an alkanamide. Any group attached to the nitrogen is
numbered as “N”.
Common Nomenclature
In addition to the common nomenclature rules seen thus far, the following are common
nomenclature rules for naming alcohols, ethers, ketones, and amines:
1. Use common prefixes as needed.

2. An alcohol is named as an alkyl alcohol.
3. An ether is named as an alkyl alkyl ether. Alphabetize the two alkyl groups,
ignoring any common prefixes like tert- or iso-.
4. A ketone is named as an alkyl alkyl ketone. . Alphabetize the two alkyl groups,
ignoring any common prefixes like tert- or iso-.
5. For amines, the longest carbon chain attached to the nitrogen is the parent chain.
List any additional substituents on the nitrogen in alphabetical order.

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05: Drawing Organic Structures
Chapter Summary
Structures, not formulas, must be used in drawing organic structures. Double and triple
bonds need to be shown in the structures. Structural formulas can be described as Lewis
structures, condensed structures, skeletal structures, and sawhorse structures. Isomers
can be classified as constitutional, configurational, or conformational. The common organic
abbreviations are given in terms of names and structures.
Tutorial Features

Key Concepts
Importance of Drawing Structures

Structures, not Formulas
Show Multiple Bonds
Types of Structures
Lewis Structures
Condensed Structures
Skeletal Structures
Sawhorse Structures
Isomers
Constitutional Isomers
Configurational Isomers
Conformational Isomers
Abbreviations
Names
Structures
Chapter Review
Importance of drawing structures

A structure must be given, otherwise the product of the reaction cannot be determined.
The location of single, double, and triple bonds must be specified.
Types of Structures
In Lewis structures, all individual bonds are shown. Formal charge is a way of keeping
track of the electrons. Formal charge is equal to [number of valence electrons] B
[nonbonding electrons] B 0.5 [bonding electrons]. In condensed structural formulas, atoms

26
are bonded to a central atom are listed after the atom. In a skeletal structure, carbon
atoms are assumed to be where two lines meet or at the end of the line. Hydrogens are
not shown. In a sawhorse structure, the drawing is looking down the carbon-carbon bond.
Isomers
Constitutional isomers have the same formula, but different points of attachment.
Configurational isomers have the same formula and the same point of attachment, but
different orientation in space. Conformational isomers have the same formula and the
same point of attachment, but the rotation about single bonds is different. In the eclipsed
conformation of ethane, the front hydrogens block the back hydrogens. In the staggered
conformation, the hydrogens are as far away from each other as possible. The staggered
conformation is the most stable. For the conformations of butane, the front two carbons
remain in place and the back two carbons rotate around the carbon 2 and carbon 3 bond.
In the totally eclipsed conformation, one methyl blocks the other methyl. In the gauche
conformation, the methyls are 60o apart. In the eclipsed conformation, the methyls are
120o apart. In the anti conformation, the methyls are 180o apart. The stability of butane
is anti > gauche > eclipsed > totally eclipsed.
Abbreviations
Me is an abbreviation for methyl, a CH3-. Et is an abbreviation for ethyl, a CH3CH2-. Pr is
an abbreviation for propyl, a CH3CH2CH2-. Butyl is an abbreviation for butyl, a
CH3CH2CH2CH2-. Ph is an abbreviation for phenyl, a benzene ring. Ar is an abbreviation for
aromatic or aryl, a benzene ring. Ac is an abbreviation for acetyl, a methyl next to a C=O.
Bz is an abbreviation for benzoyl, a benzene next to a C=O. Bn is an abbreviation for
benzyl, a benzene attached to a CH2. Pyr is an abbreviation for pyridine, a six-membered
ring with alternating double and single bonds and containing nitrogen.

27
06: Functional Groups and Organic Compounds
Chapter Summary
Organic compounds can be categorized based on the functional groups they contain.
Functional groups are specific, reactive groups of atoms that are responsible for the
characteristics of the molecule that contains them. Molecules containing the same
functional groups will undergo similar reactions. Also included in this tutorial is a section
on acids and bases. Three different concepts of acidity and basicity are covered in this
section: Arrhenius acid-base theory, Bronsted-Lowry acid-base theory, and Lewis acid-base
theory. The different theories developed as our understanding of acids and bases grew.
Finally, the tutorial looks at the basic rules for electron pushing in mechanisms.
Tutorial Features
• Concept map showing inter-connections of new concepts in this tutorial and those
• Visual representation of concepts.
Key Concepts
Organic Chemistry
The chemistry of carbon
Language of organic chemistry
Functional Groups
Alkane, alkene, alkyne, aromatic
Alkyl halide, alcohol, ether, thiol, sulfide
Aldehyde, ketone, acid halide
Carboxylic acid, ester, anhydride
Amine, amide, nitrile
Acids and Bases
Arrhenius
Bronsted-Lowry
Lewis
Electron Pushing
Electrons and mechanisms
Resonance and delocalization
Chapter Review
Organic Chemistry
The study of the chemistry of carbon compounds.
Functional Groups

28
Specific groups of atoms that impart characteristic reactivity to the molecules that contain
them. The table below describes the structures of the most commonly encountered
functional groups:
Functional Group Structure
Alkane
C C
Alkene
C C
Alkyne
C C
Aromatic
Alkyl Halide
R X
Alcohol R OH
Ether R O R
Thiol R SH
Sulfide R S R
Aldehyde
O
H
Ketone
O
Acid Halide
O
X
Carboxylic Acid
O
OH
Ester
O

29
Anhydride
O O
O
Amine
N
Amide
O
N
Nitrile
C N
Arrhenius Acid
A substance that dissociates to give the hydronium ion (H3O+).
Arrhenius Base
A substance that dissociates to give the hydroxide ion (-OH).
Bronsted-Lowry Acid
A substance that can donate a proton (H+).
Bronsted-Lowry Base
A substance that can accept a proton (H+).
Conjugate Acid
A substance that results from the Bronsted-Lowry base gaining a proton (H+).
Conjugate Base
A substance that results from the Bronsted-Lowry acid losing a proton (H+).
Amphoteric Compound
A compound that can react as an acid or a base.
Lewis Acid
A substance that can accept electron pairs to form new bonds.
Lewis Base
A substance that can donate electron pairs to form new bonds.
Mechanism
A step by step explanation of what happens in a chemical reaction.
Nucleophile
The compound that donates the electrons in a mechanism (electron rich compound).
Electrophile
The compound that accepts the electrons in a mechanism (electron poor compound).

30
Delocalization
Electrons that are distributed among more than two atoms that are bonded together.
Electron Pushing
The process of moving electrons in a mechanism to illustrate what is occurring during a
chemical reaction. Basic rules for drawing the movement of electrons in mechanisms have
been established:
1. Identify the nucleophile. The nucleophile is typically the electron rich species and as
such donates the electrons in a mechanism.
2. Identify the electrophile. The electrophile is typically the electron poor species and
as such accepts the electrons in a mechanism.
3. The flow of electrons in a mechanism is always from the most electronegative atom
to the least electronegative atom (or negative to positive).

31
07: Stereochemistry
Chapter Summary
Often times in chemistry, one runs across molecules that have the same molecular formula
but possess a different structure. These molecules are called isomers. Isomers can be
divided into three types: constitutional isomers, stereoisomers, and conformational
isomers. The student must learn to distinguish between these three types of isomers. In
this tutorial, the student will also be introduced to the concept of chirality and will learn
how to find stereogenic centers in a molecule. This leads to a discussion of the different
types of stereoisomers: enantiomers, diastereomers, and cis/trans (E/Z) isomers of
alkenes. The student will learn how to distinguish enantiomers and diastereomers by
assigning either an R or S configuration using the rules set forth in the R/S system.
Finally, the tutorial will cover how to determine the relative and absolute configurations of
alkenes including the rules for the E/Z system.
Tutorial Features
• Concept map showing inter-connections of new concepts in this tutorial and those
• Visual representation of basic concepts of stereochemistry.
Key Concepts
Isomers
Constitutional isomers
Stereoisomers
Conformational isomers
Basic Concepts of Stereochemistry
Stereochemistry overview
Chirality
Stereoisomers
Enantiomers
Diastereomers
Assigning R and S Configurations to Chiral Centers
Distinguishing enantiomers pairs by assigning their R and S configurations
Assigning the absolute configuration to chiral compounds
Meso compounds
Stereoisomers of Alkenes
Relative configuration
Absolute configuration
Chapter Review

32
Molecules with the same molecular formula, but different points of attachment.
Molecules with the same molecular formula and points of attachment but differ by the
rotation of a single bond.
Chirality
Chiral objects are not superimposable upon their mirror images while achiral objects can be
superimposed upon their mirror images. Hands, ears, feet, and keys are examples of
chiral objects. These objects do not contain planes of symmetry as symmetry is often an
indicator of an object being achiral.
Chiral Carbon (Stereogenic Center, Stereocenter)

Carbon that has four different groups attached to it.
Stereoisomers
Molecules with the same molecular formula and points of attachment but different spatial
orientation. There are three types of stereoisomers: enantiomers, diastereomers, and
cis/trans (E/Z) isomers of alkenes. One can calculate the maximum number of
stereoisomers that can exist for a chiral molecule by the solving the formula 2n where n is
the number of chiral centers present in the molecule.
Enantiomers
A molecule and its nonsuperimposable mirror image.
Assigning R/S Configurations to Chiral Centers

Chiral centers are assigned either R or S configurations based on the spatial arrangement
of the groups on the stereogenic carbon. The method for assigning configurations involves
determining the priority of the groups bound to the carbon.
1. Assign priority to the different groups on carbon with (1) being the highest priority
group and (4) being the lowest priority group. The groups with the higher atomic
mass/number will be given the higher priority. If the atomic mass/number of two
groups is equal, then give the higher priority to the group that contains more
branching.
2. Orient the molecule so that the lowest priority group is facing away from you.
3. Trace from priority group (1) through (2) to (3). If it is clockwise, assign the R
configuration to the center. If it is counterclockwise, assign the S configuration to the
center.
Diastereomers
Non-mirror image stereoisomers that contain more than one stereogenic center.
Meso Compounds
Molecules that contain more than one chiral center but that are achiral due to the presence
of a plane of symmetry.
Relative Configuration of Alkenes

The relative configuration of an alkene is determined from the orientation of the parent
chain through the double bond. An alkene is trans if the parent chain is on opposite sides
of the double bond. An alkene is cis if the parent chain is on the same side of the double

33
bond. The cis/trans system is typically used just for disubstituted alkenes as it becomes
more difficult to assign a relative configuration to tri- and tetra-substituted alkenes.
Absolute Configuration of Alkenes

The absolute configuration of any alkene can be determined using the E/Z system. The
E/Z system uses the priority rules used for assigning R/S to chiral centers. To assign the
absolute configuration:
1. Divide the alkene at the double bond mentally or draw a line through the double
bond to visually isolate the two ends of the double bond.
2. Assign priorities to each group attached to the double bond.
3. Compare the priorities. If the higher priority groups are coming off the same side
of the double bond, then the configuration is Z. If the higher priority groups are
coming off opposite sides of the double bond, then the configuration is E.

34
08: Conformational Analysis
Chapter Summary
Constitutional isomers, stereoisomers, and conformational isomers are defined. The

conformations of ethane are staggered and eclipsed. The conformations of butane are anti,
eclipsed methyl-hydrogen, gauche, and eclipsed. The bond angles of the cycloalkanes are
given. Cyclohexane has the conformations of chair, boat, and twist-boat. The carbons in
cyclohexane can be equatorial or axial.
Tutorial Features

Key Concepts
Basic Concepts
Stereoisomers
Staggered
Eclipsed
Anti
Eclipsed Methyl-Hydrogen
Gauche
Eclipsed
Bond Angles of Cycloalkanes
Chair
Boat
Twisted Boat
Chapter Review
Basic Concepts
Conformational analysis deals with the shapes that molecules can adopt by rotations about
single bonds. These structures are called conformational isomers or conformers. The
following isomers cannot interconvert between each other without breaking bonds.
Constitutional isomers have the same formula, but different connectivity. Stereoisomers
have the same formula, the same connectivity, but different arrangement in space.
Conformational isomers are interconvertable isomers of the same molecule that result from

35
rotations of single bonds. They interconvert constantly and are not separable.
Conformations of alkanes can best be viewed using either Newman projections or sawhorse
representations. A Newman Projection is an end-on view of 2 carbons attached by a sigma
bond. The front carbon is shown as the intersection of 3 bonds and the rear carbon is
shown as a circle. The substituents are attached accordingly.
Ethane can adopt either staggered or eclipsed conformations. Staggered is the lowest
energy conformer, with the hydrogens as far away from each other. Eclipsed is the highest
energy conformer and the least stable. It is 3 kcal higher in energy than the staggered
form due to repulsion between electrons in C-H bonds.
As butane rotates about its sigma bond, four distinct conformational possibilities exist.
Staggered, or anti, where the methyl groups are farthest apart; eclipsed methyl-H
interactions; gauche, where the methyl groups are adjacent; and eclipsed, or syn, where
the methyl groups are eclipsed.
Cycloalkanes
The interior angles of cycloalkanes deviate from the tetrahedral so strain develops.
Cyclopropane has a bond angle of 60o; Cyclobutane has a bond angle of 90o; Cyclopentane
has a bond angle of 108o; Cyclohexane has a bond angle of 109.5o.
Cyclohexane=s Newman Projection illustrates the staggered, low energy conformation that
the chair form results. In addition to the chair, cyclohexane can also adopt the boat form
by flipping one hydrogen up. This form is higher in energy due to steric and eclipsing
strain. By twisting the boat, cyclohexane adopts yet another form, the twist-boat, a result
of relieving some of the boat=s strain. Cyclohexane=s carbons have two substitution
positions, axial and equatorial. The axial is vertical and equatorial is parallel to the
adjacent C-C bond in the chair.

36
09: Saturated Hydrocarbons
Chapter Summary
Now that the student has learned the basics of organic chemistry in the first six tutorials,
the student will begin learning about the more specific aspects of each functional group—
their properties, uses and reactions. In this, the seventh tutorial, the physical properties,
uses, structures, nomenclature, and reactions of alkanes, cycloalkanes, and alkyl halides
are examined.
Tutorial Features
• Concept map showing interconnections of new concepts in this tutorial and those
• Visual representation of basic concepts.
• Step by step mechanisms of key reactions which show the movement of the
electrons in the reaction.
Key Concepts
Definitions
Hydrocarbons
Alkanes
Cycloalkanes
Alkyl halides
Properties and Uses of Alkanes and Cycloalkanes
Properties
Structure and conformations
Uses
Properties and Uses of Alkyl Halides
Properties
Uses
IUPAC nomenclature
Common nomenclature
Nomenclature of Alkyl Halides
IUPAC nomenclature
Common nomenclature
Reactions of Alkanes
Combustion
Cracking
Halogenation

37
Chapter Review
Hydrocarbons
Organic compounds that contain only carbons and hydrogens.
Alkanes
Non-cyclic hydrocarbons; simplest functional group.
Cycloalkanes
Cyclic hydrocarbons.
Alkyl Halides
Alkanes or cycloalkanes that contain a halogen atom(s).
Hydrophobic
Literally ‘water hating”. Often used to described molecules or parts of molecules that will
not dissolve in water.
Eclipsed Conformation
Describes a molecular conformation where the atoms attached to one carbon line up with
the atoms attached to an adjacent carbon (i.e. the dihedral angle is 0 degrees.).
Staggered Conformation
Describes a molecular conformation where the atoms attached to one carbon are as far
away from the atoms attached to an adjacent carbon atom. Staggered conformations are
more stable than eclipsed conformations.
Gauche Conformation
Describes a molecular conformation where two observed atoms on adjacent carbons are 60
degrees apart.
Anti Conformation
Describes a molecular conformation where two observed atoms on adjacent carbons are
180 degrees apart.
Chair Conformation
Describes a molecular conformation of cyclohexane where the hydrogens on the ring are
the furthest apart. This is the most stable conformer of cyclohexane.
Boat Conformation
Describes a molecular conformation of cyclohexane where the hydrogens are very close to
each other. This is the least stable conformer of cyclohexane.

The student is reintroduced to alkane nomenclature, both IUPAC and common, in this
tutorial. In addition, new rules for cycloalkanes are covered. The following are the IUPAC
rules for naming cycloalkanes:
1. Number the cycloalkane so that the lowest possible combination of numbers are
used for the substituents.

38
2. If the compound contains an aliphatic ring and a chain, the parent compound is
the one with the most carbons.
The common rules for naming cycloalkanes:
1. Use the common prefixes as needed.

2. List substituents alphabetically in front of the cycloalkane name.
Key Reactions of Alkanes:
1) Combustion of Alkanes
Converts alkanes to carbon dioxide and water. To determine what the balanced reaction
equation would be for any alkane, one can use the following formula where n is the number
of carbons in the alkane:
CnH(2n+2) + 3n+1 O2 nCO2 + (n+1)H2O

2
2) Cracking of Alkanes
Cracking of hydrocarbons at high temperatures (usually a catalyst is also required) yields a
mixture of smaller alkanes and alkenes.
3) Halogenation of Alkanes
Alkanes can be halogenated in the presences of heat or light and X2, where X is a halogen.
Halogenation of alkanes occurs through a radical mechanism that can be divided into three
different types of steps: initiation, propagation, and termination.
Initiation Step
The first step of a radical halogenation reaction of an alkane. In this step, the initial
halogen radicals are formed by the interaction of a diatomic halogen with light or heat.
Propagation Step
The second part of a radical halogenation reaction of an alkane where radicals are both
consumed and formed. In these steps, the initial halogen radical attacks an alkane and
abstracts a hydrogen from it to form an alkyl radical and a molecule of HX. Next, the alkyl
radical attacks a molecule of X2 to form a haloalkane and a halogen radical. One should
always (1) have a radical on either side of the arrow in propagation steps and (2) reform
the initial halogen radical at the end of the second propagation step.
Termination Step
The last step of a radical halogenation reaction where radicals are consumed. Two radicals
will react to form a neutral, stable organic compound.

39
10: Unsaturated Hydrocarbons
Chapter Summary
Background information for alkenes, alkynes, and dienes are described in terms of
definitions, properties, uses, structures, and classification. The rules for the IUPAC
nomenclature of alkenes, alkynes, and dienes are discussed. Alkenes are additionally
named using cis and trans or E and Z. Alkenes are synthesized by the dehalogenation of
alkyl halides and the dehydration of alcohols. Alkynes are synthesized by the
dehydrohalogenation of vicinal and geminal dihalides. Alkyl halides are formed by the
reaction of alkenes with hydrogen halides. Alkenes are halogenated to give dihaloalkanes.
Alkenes are hydrated to give alcohols. Reduction of alkenes give alkanes. Alkynes react
with hydrogen halides to give dihaloalkanes or with halogens to give tetrahaloalkanes.
Hydrogenation of alkynes give alkanes. Alkenes are polymerized. Alkenes are oxidized to
diols with potassium permanganate or to aldehydes and / or ketones with ozone. Alkynes
are oxidized to diketones with potassium permanganate or to carboxylic acids with ozone.
Tutorial Features

Key Concepts
Background Information for Alkenes, Alkynes, and Dienes

Definitions
Properties
Uses
Structure
Classification
IUPAC
Cis and Trans
E and Z
Dehalogenation of Alkyl Halides
Dehydration of Alcohols
Products of Elimination Reactions
Dehydrohalogenation of Vicinal Dihalides
Dehydrohalogenation of Geminal Dihalides
Definitions
Addition of Hydrogen Halides

40
Halogenation
Hydration
Hydrogenation
Addition of Hydrogen Halides
Halogenation
Hydrogenation
Polymerization of Alkenes
Definitions
Examples
Oxidation of Alkenes and Alkynes
Potassium Permanganate Oxidation
Ozonolysis
Chapter Review
Background for Alkenes, Alkynes, and Dienes

Alkenes contain carbon-carbon double bonds. Alkynes contain carbon-carbon triple bonds.
Dienes contain more than one carbon-carbon double bond. Alkenes, alkynes, and dienes
are less dense than water, are nonpolar, and have boiling points and melting points similar
to alkanes. The carbon in an alkene is sp2, has a bond angle of 120o, and a trigonal planar
shape. A carbon-carbon double bond contains one sigma bond and one pi bond. No
rotation is possible around a carbon-carbon double bond. The carbon in an alkyne is sp,
has a bond angle of 180o, and a linear shape. A carbon-carbon triple bond contains one
sigma bond and two pi bonds. In dienes, allenes contains two double bonds that share a
carbon. Conjugated dienes have double bonds that alternate with single bonds. Isolated
dienes have double bonds that are separated by two or more single bonds. In an
unsubstituted alkene, no alkyl groups are attached to a carbon-carbon double bond. In a
monosubstituted alkene, one R group is attached to the carbon-carbon double bond. In a
disubstituted alkene, two alkyl groups are attached to the carbon-carbon double bond. In a
trisubstituted alkene, three alkyl groups are attached to the carbon-carbon double bond.
In a tetrasubstituted alkene, four alkyl groups are attached to the carbon-carbon double
bond. A terminal alkyne contains at least one hydrogen attached to the carbon-carbon
triple bond. An alkyne that is not terminal contains two alkyl groups attached to the
carbon-carbon triple bond.

Circle the longest continuous carbon chain as the parent compound. Use Aene@ for alkene,
and Ayne@ for alkyne. Number from whichever end that gives the lowest possible number
for the multiple bonds. Name and number substituents. If both a double bond and a triple
bond are present, number from whichever end that gives the lowest possible number for
the multiple bonds. If the double bond and a triple bond are equal distance, then the
double bond has priority over the triple bond. Name compounds with a double bond and a
triple bond as enyne, giving positions of the multiple bonds. OH has priority over double
and triple bonds. Cis has the same group on the same side. Trans has the same group on
opposite sides. In the Cahn-Ingold-Prelog rules, Z has the highest ranking group on the
same side and E has the highest ranking group on opposite sides. Rank the first atoms
directly attached to the carbon-carbon double bond. The atom with the highest atomic
number has the highest ranking. If the priority cannot be determined by Rule 1, then
compare the next group of atoms. Double bonds are duplicated and triple bonds are
triplicated, with imaginary atoms.

41
Alkyl halides are dehydrohalogenated with base to form alkenes. Alcohols are dehydrated
with heat and acid to form alkenes. The product with the most number of carbons attached
to the carbon-carbon double bond is formed in the higher yield.
Vicinal dihalides are dehydrohalogenated twice with base to form alkynes. Geminal
dihalides are dehydrohalogenated twice with base to form alkynes.
In Markovnikov addition, H of HZ adds to carbon with most hydrogens directly attached;
the more stable carbocation intermediate is formed. In anti addition, the groups add on
opposite sides of the double bond. In syn addition, the groups add on the same side of the
double bond. A regioselective reaction is a reaction in which one of two possible isomers
predominates. A regiospecific reaction is a reaction in which one of two possible isomers is
formed exclusively. An hydrogen halide adds across a double bond to form an alkyl halide,
via Markovnikov addition. Halogen adds across a double bond to form a dihalolalkane, with
anti addition. Water adds across a double bond to produce an alcohol, via Markovnikov
addition. Hydrogen adds across a double bond, via syn addition, to form an alkane.
Hydrogen halide adds across a triple bond, via Markovnikov addition and with anti or syn
addition, to form dihaloalkanes. Halogen adds across a triple bond to form a
tetrahaloalkane. Hydrogen adds across a triple bond to make an alkane.
Polymers of Alkenes
Ethylene is polymerized to polyethylene, which is used for bags, films, and bottles.
Propylene is polymerized to polypropylene, which is used for plastics. Styrene is
polymerized to polystyrene, which is used for plastics, plastic cups, and foam insulation.
Methyl α-methacrylate is polymerized to polymethyl α-methacrylate, which is used for
plexiglass and Lucite paints. Acrylonitrile is polymerized to polyacrylonitrile, which is used
as Orlon or Acrylan fibers. Tetrafluoroethylene is polymerized to polytetrafluoroethylene,
which is used as Teflon. Vinyl chloride is polymerized to polyvinyl chloride, which is used in
plastics, films, and plumbing. Vinylidene chloride is polymerized to polyvinylidene chloride,
which is used in Saran.
Oxidation Reactions of Alkenes and Alkynes

Potassium permanganate oxidizes alkenes to diols, with syn addition. Ozone oxidizes
alkenes to aldehydes and / or ketones. Potassium permanganate oxidizes alkenes to
diketones. Ozone oxidizes alkynes to carboxylic acids.

42
11: Aromatic Compounds and Aromaticity
Chapter Summary
Kekule proposed the structure of benzene in 1865. The carbons in benzene are sp2
hybridized, have a bond angle of 120o, and have a trigonal planar shape. The equation for
Huckel=s rule is given. The criteria for aromatic, antiaromatic, and not aromatic are
described. The special names for the monosubstituted benzenes are listed. The rules for
the nomenclature of aromatic compounds are described. Ortho, meta, and para definitions
are given. The structures of anthracene, naphthalene, and phenanthrene are drawn out.
The mechanism for electrophilic aromatic substitution is discussed, along with specific
examples of other examples. Halogenation of benzene produces halobenzene. Nitration of
benzene gives nitrobenzene. Sulfonation of benzene yields benzenesulfonic acid. The
Friedel-Craft alkylation of benzene gives alkylbenzene. The Friedel-Craft acylation of
benzene produces a ketone.
Tutorial Features

Key Concepts
Background Information for Aromatic Compounds

History Lesson
Structure of Benzene
Drawing Benzene
Determining Aromaticity
Special Names
IUPAC Nomenclature
Disubstituted Benzene Derivatives
Aromatic Fused Rings
Halogenation
Nitration
Sulfonation
Friedel-Craft Alkylation
Friedel-Craft Acylation

43
Chapter Review
Background for Aromatic Compounds

Kekule proposed the structure of benzene in 1865. The carbons in benzene are sp2
hybridized, have a bond angle of 120o, and have a trigonal planar shape. Benzene can be
drawn with all carbons and hydrogens, with just lines, or using a circle in the ring.
Aromaticity, Huckel=s rule

Pi electrons are counted as follows: each double bond counts as two pi electrons, each +
charge counts as zero pi electrons, each B charge counts as two pi electrons, each radical
counts as one pi electron. Set the total number of pi electrons as equal to 4n + 2; solve
for n. If the compound is aromatic, then it is cyclic with a continuous ring of overlapping p
orbitals and n equals a whole number. If the compound is antiaromatic, then it is cyclic
with a continuous ring of overlapping p orbitals, but n does not equal a whole number. If
the compound is not aromatic, then it is noncyclic or is cyclic without a continuous ring of
overlapping p orbitals.

C6H5CH3 is named toluene. C6H5OH is named phenol. C6H5NH2 is named aniline.
C6H5OCH3 is named anisole. C6H5CH=CH2 is named styrene. A benzene with an aldehyde
group is named benzaldehyde. A benzene with a methyl ketone group is called
acetophenone. A benzene with a carboxylic acid group is named benzoic acid. The
benzene is the parent compound. Number the ring so that the groups have the lowest
possible numbers. If a special name is used for a benzene derivative, then that group is in
position one; then number the other groups. Ortho means that the two groups are on
adjacent carbons or on the 1,2 positions. Meta means that the two groups are separated
by one carbon or on the 1,3-positions. Para means that the two groups are on opposite
ends or on the 1,4-positions. The fused ring structures of anthracene, naphthalene, and
phenanthrene are drawn out.

Benzene is halogenated with bromine and iron (III) bromide; chlorine and aluminum
chloride; or iodine and nitric acid to give a halobenzene. Nitration of benzene with nitric
acid, in the presence of sulfuric acid, produces nitrobenzene. Benzene is sulfonated with
sulfur trioxide, in the presence of sulfuric acid, to yield benzenesulfonic acid. In Friedel-
Craft alkylation, benzene reacts with aluminum chloride and alkyl halide to form an
alkylbenzene. In Friedel-Craft acylation, benzene reacts with aluminum chloride and an
acid halide to form a ketone.

44
12: Alcohols and Ethers
Chapter Summary
Alcohols and ethers are both oxygen containing functional groups. In this tutorial, the
student will learn about the structures and properties of each functional group. The IUPAC
nomenclature of alcohols and ethers will also be re-introduced. The different reactions
used to synthesis alcohols and ethers will be covered as will the reactions each functional
group undergoes.
Tutorial Features
Key Concepts
Background Information for Alcohols and Ethers

Definitions
Properties
Uses
Classification of alcohols
IUPAC nomenclature
Common nomenclature
Physical Properties of Alcohols
Hydrogen bonding
Boiling points of alcohols
Water solubility of alcohols
Acidity of alcohols
Synthesis of Alcohols
From alkenes
From alkyl halides
From organometallic reagents reacting with aldehydes and ketones
From reduction of aldehydes and ketones
Formation of alkoxide ions
Formation of alkyl halides
Dehydration
Oxidation
Esterification
Pinacol rearrangement
Preparation of leaving groups

45
Synthesis and Reactions of Ethers

Williamson ether synthesis
Cleavage of ethers
Chapter Review
00 Alcohol
Alcohol with no alkyl groups attached to the carbon bearing the hydroxyl group.
Primary Alcohol
Alcohol with one alkyl group attached to the carbon bearing the hydroxyl group.
Secondary Alcohol
Alcohol with two alkyl groups attached to the carbon bearing the hydroxyl group.
Tertiary Alcohol
Alcohol with three alkyl groups attached to the carbon bearing the hydroxyl group.
Phenol
Alcohol where the hydroxyl group is attached to a benzene ring.

The student is re-introduced to the IUPAC and common nomenclature rules used to name
alcohols and ethers. Remember that ethers are named as an alkane with the –OR group
given as a substituent.
Reactions Used to Synthesis Alcohols:
1) Hydration of Alkenes
Alkenes react with water in the presence of acid to form alcohols.
2) Formation from Alkyl Halides

Alkyl halides react with a source of hydroxide to produce alcohols.
3) Reaction of Organometallic Reagents with Aldehydes and Ketones

Aldehydes and ketones react with organolithium reagents or Grignard reagents followed by
treatment with an aqueous acid to produce alcohols.
4) Reduction of Aldehydes and Ketones

Aldehydes and ketones may be reduced to alcohols using several different reducing agents:
hydrogen gas and Raney nickel, lithium aluminum hydride, or sodium borohydride.
Reactions of Alcohols:
1) Formation of Alkoxide Ions

Alcohols are deprotonated with sodium or potassium metal to form an alkoxide ion.
Hydrogen gas is a by product.
2) Formation of Alkyl Halides

46
(1) Alcohols react with hydrogen halides to displace the hydroxyl group and form alkyl
halides. (2) Alcohols can react with phosphorus trihalides to produce alkyl halides. (3)
Alcohols can react with thionyl chloride to produce alkyl chlorides.
3) Dehydration
Alcohols, when treated with acid and heat, will undergo elimination of the hydroxyl group
to form alkenes.
4) Oxidation of Alcohols
(1) Primary alcohols are oxidized with PCC (pyridinium chlorochromate) to form aldehydes.
(2) Primary alcohols are oxidized to carboxylic acids using several different oxidants:
potassium permanganate, sodium hypochlorite, nitric acid, chromium trioxide, etc. (3)
Secondary alcohols are oxidized to ketones using several different oxidants: potassium
permanganate, sodium hypochlorite, nitric acid, chromium trioxide, PCC, etc.
Remember, tertiary alcohols can not be oxidized.
5) Esterification
Alcohols react with carboxylic acids in the presence of acid to form esters.
6) Pinacol Rearrangement
A reaction in which a diol is dehydrated to form a rearranged ketone product.
7) Preparation of Leaving Groups

Alcohols can be converted into better leaving groups by reacting them with sulfonyl
chlorides to form alkyl sulfonates.
Synthesis and Reactions of Ethers:
1) Williamson Ether Synthesis

Alkoxide ions will react with alkyl halides to form ethers.
2) Cleavage of Ethers
Ethers can be cleaved using hydrogen halides to form alkyl halides and alcohols. The alkyl
group that comprises the alkyl halide is usually the least hindered alkyl group from the
ether.

47
13: Aldehydes and Ketones
Chapter Summary
Aldehydes and ketones are carbonyl containing functional groups with very interesting and
useful chemistries. In this tutorial, the student will learn about the structure of these
compounds, their keto-enol tautomerism, and the reactions they undergo. Additionally,
the nomenclature rules for these groups will be reviewed. New functional groups will also
be introduced and are summarized in a table at the end of this summary.
Tutorial Features
Key Concepts
Background Information for Aldehydes and Ketones

Structure
Shape
Properties
α-Hydrogens
Nomenclature for Aldehydes and Ketones
IUPAC nomenclature
Common nomenclature
Synthesis of Aldehydes and Ketones
Oxidation of alcohols
Friedel-Crafts acylation of benzene
Ozonolysis of alkenes
From acid halides
Reactions with organometallic reagents
Formation of imine derivatives
Oxidation
Acetal formation
Reactions at the α-carbon
Acetoacetic ester synthesis
Aldol condensation
Haloform reaction

48
Chapter Review
α-Carbon
A carbon atom next to a carbonyl.
α-Hydrogen
A hydrogen on an α-carbon. These hydrogens are somewhat acidic due to the negative
charge on the resulting enolate being delocalized by resonance.
Keto-Enol Tautomerism
Process by which an aldehyde or ketone and its enol equilibrate.
Nomenclature of Aldehydes and Ketones

The student is re-introduced to the IUPAC and common nomenclature rules applied to
aldehydes and ketones that were originally covered in tutorial 6.
Synthesis of Aldehydes and Ketones:
1) Oxidation of Alcohols
(1) Primary alcohols are oxidized with PCC (pyridinium chlorochromate) to form aldehydes.
(2) Secondary alcohols can be oxidized with several different oxidants: potassium
permanganate, sodium hypochlorite, nitric acid, PCC, chromium trioxide, etc.
2) Friedel-Crafts Acylation of Benzene

Benzene will react with acid halides in the presence of aluminum trichloride to produce
ketones.
3) Ozonolysis of Alkenes
Alkenes are oxidized to aldehydes/ketones with ozone (O3). Whether one obtains
aldehydes, ketones, or a mix of both depends on the substitution pattern of the alkene.
4) Conversion from Acid Chlorides

(1) Acid halides can be reduced with tri-tert-butyl lithium aluminum hydride to form
aldehydes. (2) Acid chlorides react with dialkyl copper lithium reagents to form ketones.
Reactions of Aldehydes and Ketones:
1) Reaction with Organometallics

Aldehydes and ketones react with organolithium or Grignard reagents, followed by
acidification, to produce alcohols.
2) Reduction to Alcohols
Several different reducing agents can reduce aldehydes and ketones to alcohols: hydrogen
and Raney nickel, lithium aluminum hydride, or sodium borohydride.
3) Reduction to Alkanes
(1) Aldehydes and ketones are reduced to alkanes with zinc-mercury amalgam
(Zn(Hg))and hydrochloric acid. This is called the Clemmenson reduction. (2) Aldehydes
and ketones are reduced to alkanes with hydrazine (NH2NH2) and potassium hydroxide.
This is called the Wolff-Kishner reduction.

49
4) Formation of Imine Derivatives

(1) Aldehydes and ketones react with ammonia, primary amines, and their derivatives in
the presence of an acid catalyst to form imine derivatives.
5) Formation of Enamines
Secondary amines will react with aldehydes or ketones to form enamines. The β-carbon of
an enamine is nucleophile and can react readily with primary and secondary alkyl halides
and acid halides.
6) Oxidation to Carboxylic Acids

Aldehydes can be oxidized to carboxylic acids using several different oxidants: potassium
permanganate, nitric acid, chromium trioxide, sodium hypochlorite, etc.
7) Acetal Formation
Aldehydes and ketones react with alcohols to form hemiacetals and acetals.
Reactions at the α-Carbon of Ketones and Aldehydes:
1) Reactions of Enamines
Enamines, formed by the reaction of aldehydes or ketones with secondary amines, can act
as nucleophiles and attack different electrophiles like alkyl halides and acid halides.
2) Oxidative Cleavage of Cyclic Ketones

Cyclic ketones can undergo oxidative cleavage at the α-carbon via reaction with their enol
forms.
3) Acetoacetic Ester Synthesis

β-Keto esters contain acidic α-hydrogens that can be deprotonated to form an enolate
anion. The enolate, which is nucleophilic, can then be used to attack electrophiles. This
type of reaction would form a new bond between the α-carbon and the electrophile. In
addition, the ester may be hydrolyzed to the β-keto acid and then decarboxylated to form a
ketone product.
4) Aldol Condensation
Condensation of two aldehydes or ketones that can be either base- or acid-catalyzed. The
initial product of the aldol condensation is a β−hydroxyketone. The β−hydroxyketone will
dehydrate in the presence of heat and an acid catalyst to form a α, β-unsaturated ketone.
5) Haloform Reaction
A base catalyzed (usually a hydroxide base) halogenation of methyl ketones that proceeds
via an enolate anion. If an excess of base is present, the trihalomethyl ketone, the initial
product, will then undergo nucleophilic attack from the hydroxide ion to yield a haloform
(CHX3) and a carboxylic acid.
New Functional Groups Introduced in this Tutorial:
Functional Group Structure of Group

50
Imine
R
N
Oxime
OH
N
Hydrazone
NH2
N
Phenylhydrazone
NHC6H5
N
Enamine
N
Hemiacetal
OH OR
R(H)
Acetal
OR OR
R(H)
β-Ketoesters
O O

51
14: Carboxylic Acids
Chapter Summary
Carboxylic acids act not only as a functional group but also as the source for several other
functional groups known collectively as acid derivatives. In this tutorial, the student will
learn about the structure, acidity and other properties of carboxylic acids. The IUPAC
nomenclature rules for naming acids are re-introduced. Finally, the different reactions
used to synthesize acids and the reactions acids undergo will be examined.
Tutorial Features
Key Concepts
Background Information for Carboxylic Acids

Structure
Shape
Physical properties
Acidity
Acidity of carboxylic acids
Resonance stability of the carboxylate anion
Inductive effects on acidity
Nomenclature of Carboxylic Acids
IUPAC nomenclature
Common nomenclature
Synthesis of Carboxylic Acids
Oxidation of primary alcohols
Oxidation of aldehydes
Carboxylation of Grignard reagents
Hydrolysis of nitriles
Reduction to primary alcohols
Conversion to acid halides
Esterification
Conversion to anhydrides
Decarboxylation
Chapter Review

52
Carboxylate Anion
The anion formed with the acidic proton of a carboxylic acid is deprotonated. This anion is
resonance stabilized.
IUPAC Nomenclature Rules for Carboxylic Acids

The rules for naming carboxylic acids, previously introduced in tutorial 6, are examined
again.
Reactions Used to Synthesize Carboxylic Acids:
1) Oxidation of Primary Alcohols

Primary alcohols may be oxidized to the carboxylic acid using a number of different
oxidants: nitric acid, sodium hypochlorite, potassium permanganate, chromium trioxide,
etc.
2) Oxidation of Aldehydes
Aldehydes may be oxidized to the carboxylic acids using a number of different oxidants:
nitric acid, sodium hypochlorite, chromium trichloride, etc.
3) Carboxylation of Grignard Reagents

Reaction of Grignard reagents with carbon dioxide followed by treatment with aqueous acid
forms carboxylic acids.
4) Hydrolysis of Nitriles
Nitriles may be hydrolyzed with aqueous acid to form carboxylic acids.
Reactions of Carboxylic Acids:
Acids may be reduced to primary alcohols using lithium aluminum hydride followed by
treatment with aqueous acid.
2) Conversion to Acid Halides

Carboxylic acids react with thionyl chloride to form acid chlorides.
3) Esterification
Reaction of carboxylic acids with alcohols in the presence of acid forms esters.
4) Conversion to Anhydrides
Reaction of carboxylic acids with acid chlorides to form anhydrides.
5) Decarboxylation
When heated, carboxylic acids can undergo loss of carbon dioxide.

53
15: Acid Derivatives
Chapter Summary
Acid derivatives are different functional groups that can all be synthesized directly from
carboxylic acids. The different acid derivatives (acid halides, anhydrides, esters, amides)
are introduced in this tutorial. The student will learn about their structure, relative
reactivity, nomenclature, and reactions.
Tutorial Features
Key Concepts
Background Information for Acid Derivatives

Structure
Shape
Properties
Relative reactivity of acid derivatives
Nomenclature of Acid Derivatives
Rules for acid halides
Rules for esters
Rules for anhydrides
Rules for amides
Hydrolysis
Conversion to ketones
Reactions of Esters
Hydrolysis
Saponification
Transesterification
Hydrolysis

54
Reactions of Amides
Hydrolysis
Hofmann Rearrangement
Reduction to amines
Dehydration
Chapter Review
Acid Derivatives
Functional groups that can be made directly from carboxylic acids.
IUPAC Nomenclature Rules for Naming Acid Derivatives

The student is re-introduced to the IUPAC nomenclature rules for naming acid derivatives
that were originally covered in tutorial 6.
1) Hydrolysis
Acid halides are hydrolyzed to carboxylic acids using water.
2) Conversion to Esters
Acid halides will react with alcohols to form esters.
3) Conversion to Amides
Amines will react with acid halides to form amides.
Acid halides can be reduced to form alcohols using lithium aluminum hydride.
5) Reduction to Aldehydes
Using tri-tert-butyl lithium aluminum hydride, acid halides can be reduced to form
aldehydes.
6) Conversion to Ketones
Acid halides can be converted to ketones by using dialkyl copper lithium reagents.
Reactions of Esters:
1) Hydrolysis
Esters are hydrolyzed to carboxylic acids and alcohols using aqueous acid.
2) Saponification
Base catalyzed hydrolysis of esters using a strong base to form the salt of a carboxylic acid
and an alcohol.
3) Transesterification
Reaction of an ester with an alcohol in the presence of an acid catalyst to form a new ester.
Esters react with lithium aluminum hydride to produce alcohols.

55
Esters react with amines to yield amides and alcohols.
Reactions of Anhydrides:
1) Hydrolysis
Anhydrides can be hydrolyzed with water to form carboxylic acids.
2) Conversion to Esters
Anhydrides react with alcohols to produce esters and carboxylic acids.
Anhydrides can be converted to amides and carboxylic acids using amines.
Reactions of Amides:
1) Hydrolysis
(1) Amides are hydrolyzed with aqueous acid to form carboxylic acids and ammonium ions.
(2) Amides can be hydrolyzed with base to form anions of carboxylic acids and amines.
2) Hofmann Rearrangement
Reaction in which amides are converted to a primary amine with one less carbon than the
starting amide. The reaction is catalyzed by a strong base and diatomic bromine.
3) Reduction
Amides are reduced in the presence of lithium aluminum hydride to form amines.
4) Dehydration
Primary amides can be dehydrated with POCl3 or P2O5 to form nitriles.

56
16: Keto Acids and Esters
Chapter Summary
Keto acids and esters offer a large range of synthetic possibilities to a chemist. In this
tutorial, the student will learn about their structure, their nomenclature, and the reactions
they undergo. The student will also examine their keto-enol tautomerism and will learn
how their tautomerism differs from that of a compound containing a single carbonyl
functionality.
Tutorial Features
Key Concepts
Background Information for Keto Acids and Esters

Definitions
Nomenclature
Acidity of the α-hydrogen
Reactions of Keto Acids and Esters
Decarboxylation
Acetoacetic acid synthesis
Chapter Review
β-Keto Acid
Carboxylic acids with a carbonyl group two carbons away at the β position (carbon-3).
β-Keto Ester
Esters with a carbonyl group two carbons away at the β position (carbon-3).
Nomenclature of Keto Acids and Esters

The IUPAC nomenclature rules for naming keto acids and esters are covered in this
tutorial:
1. Keto acids are named as carboxylic acids. The ketone group is listed as a
substituent using the prefix “oxo-”.
2. Keto esters are named as esters. The ketone group is listed as a substituent
using the prefix “oxo-“.

57
α-Hydrogen
A hydrogen on the carbon between the carbonyls of a keto acid or ester. This type of
hydrogen is acidic due to the resonance stabilization of the enolate resulting from
deprotonation.
Keto-Enol Tautomerism
If at least one α-hydrogen is present on the α-carbon of a keto acid or ester, then the
compounds will exist in equilibrium with their enol forms.
Decarboxylation of β-Keto Acids

A type of reaction that β-keto acids undergo, but not β-keto esters, where the carboxylic
acid group of the molecule, when heated, is lost as a molecule of carbon dioxide. A ketone
is the final product of this reaction.
Acetoacetic Synthesis
Previously covered in tutorial 10, “Aldehydes and Ketones,” this reaction involved
deprotonating the α-carbon of a β-keto ester to form an enolate. The enolate anion acts as
a nucleophile and attacks an electrophile forming a new carbon-carbon bond to the α-
carbon. One may isolate the alkylated β-keto ester or the ester product can then be
hydrolyzed to form a carboxylic acid and then decarboxylated to form a ketone.

58
17: Amines
Chapter Summary
Amines are one of the few functional groups that can act both as a nucleophile and base.
In this tutorial, the student will learn about the structure of amines, their physical
properties, and their basicity. In addition, the IUPAC and common nomenclature rules for
naming amines are revisited. Finally, the reactions that form amines or use amines as a
reagent are covered.
Tutorial Features
Key Concepts
Background Information for Amines

Classification of amines
Shape
Properties
Uses
Nomenclature of Amines
IUPAC nomenclature
Common nomenclature
Amine salts
Synthesis of Amines
Reduction of nitro compounds
Reduction of nitriles
Reduction of amides
Alkylation of amines
Reductive amination of aldehydes and ketones
Reactions of Amines
Reaction with alkyl halides
Reaction with aldehydes and ketones
Acylation
Reaction with sulfonyl chlorides
Hofmann elimination
Reaction with nitrous acid
Content Review

59
Primary Amine
An amine with one alkyl group attached to the nitrogen.
Secondary Amine
An amine with two alkyl groups attached to the nitrogen.
Tertiary Amine
An amine with three alkyl groups attached to the nitrogen.
Quaternary Amine
An amine with four alkyl groups attached to the nitrogen.
IUPAC and Common Nomenclature for Amines

The IUPAC and common nomenclature rules for amines are re-introduced in this tutorial.
In addition, a new common nomenclature rule for amine salts are given: Amine salts are
named as ammonium salts.
Ways to Synthesize Amines:
1) Reduction of Nitro Compounds

Nitro compounds (those containing –NO2) can be reduced using H2/catalyst or H+/metals to
primary amines.
2) Reduction of Nitriles
Nitriles are reduced to primary amines with hydrogen and nickel.
3) Reduction of Amides
Amides are reduced to amines using lithium aluminum hydride followed by hydrolysis. The
classification of the amine product (primary, secondary, or tertiary) depends on how many
carbons were attached to the nitrogen in the amide.
4) Reaction of Alkyl Halides with Amines

Alkyl halides react with ammonia or amines to yield amines.
5) Reductive Amination of Oximes

Aldehydes and ketones react with hydroxylamine and acid to form oximes. Oximes can
then be reduced to the amine using several different conditions: hydrogen and nickel;
lithium aluminum hydride then H3O+, or zinc and hydrochloric acid.
6) Reductive Amination of Imines

Aldehydes and ketones react with primary amines and acid to form imines. Imines can
then be reduced to the secondary amine using various conditions: hydrogen and nickel; or
lithium aluminum hydride then H3O+.
7) Reductive Amination of Enamines

Aldehydes and ketones react with secondary amines and acid to form imines. Imines can
then be reduced to the tertiary amine using sodium triacetoxyborohydride.
Key Reactions of Amines:
1) Formation of Ammonium Salts

60
Amines react with hydrogen halides to form ammonium salts.
2) Formation of Imines
Aldehydes and ketones react with ammonia derivatives and in the presence of acid to form
imine derivatives.
3) Formation of Amides
Acid chlorides react with amines to form amides.
4) Sulfonamide Formation
Sulfonyl chlorides react with amines to yield sulfonamides.
5) Hofmann Elimination
Quaternary ammonium halides undergo β-elimination when treated with strong bases to
form a tertiary amine and the less substituted alkene.
6) Formation of Arenediazonium Salts

Primary aromatic amines react with nitrous acid (Na2NO2) to form arenediazonium salts.
These salts are extremely electrophilic so they react readily with various nucleophiles to
form a wide range of products.
Sandmeyer Reaction
Reaction of an arenediazonium salt with a copper salt.

61
18: Infrared and UV Spectroscopy
Chapter Summary
Often in the laboratory, a chemist synthesizes a compound and needs to confirm its
structure or is confronted with an unknown compound and needs to determine its
structure. Techniques are available to chemists that allow them to determine the structure
of a compound. This tutorial covers two such techniques called infrared spectroscopy and
UV/Vis spectroscopy.
Tutorial Features
Key Concepts
Basic Information for Infrared

Background
Intensity of infrared absorptions
Bonds with similar infrared absorptions
Molecular vibrations
Functional groups
Zones
By functional groups
Infrared Absorption Frequency Tables
Abbreviations
Frequencies
Infrared Spectra Problem Solving
Steps
Examples
Basics of UV/Vis Spectroscopy
Theory of UV/Vis spectroscopy
Absorption of UV/Vis light
Conjugation
Chapter Review
Infrared Spectroscopy
Method of structure determination based upon the amount of infrared light absorbed by a
compound.
Index of Hydrogen Deficiency

62
A calculation that gives the total number of pi bonds and rings present in a molecule from
the molecular formula.

Similar functional groups have similar atoms and will absorb photons of similar energies.
In an infrared spectrum, similar functional groups will predictably show absorbances in the
same region of the spectrum. Because of this fact, it is possible to scan an IR spectrum
and determine the functional groups present in a sample and from that determine the
structure of the molecule.
Fingerprint Region
Region of an IR spectrum (1450-400 cm-1) that contains many absorptions specific to a
given molecule.
Electronic Spectrum
The spectrum produced when an organic molecule absorbs light in the visible or ultraviolet
region that results in an electronic excitation.
Electronic Transition
The movement of a single electron from an occupied orbital to an unoccupied orbital.
HOMO
Highest Occupied Molecular Orbital
LUMO
Lowest Unoccupied Molecular Orbital
Beer-Lambert Law
Law that states the absorption of UV radiation is dependent on the sample, the
concentration of the sample, and the size of the sample. The mathematical representation
of the law is below:
A = εcl
A = absorbance
ε = molar absorptivity
c = concentration of sample
l = path length
Molar Absorptivity
Measure of how strongly the sample absorbs light at that wavelength.
Conjugation
Alternating single and multiple bonds (either double of triple bonds). Conjugation
decreases the energy gap between the HOMO and LUMO energy levels in a molecule.

63
19: NMR and Mass Spectrometry
Chapter Summary
In the previous tutorial, the student learned about two techniques used by chemists to
determine a molecule’s structure. Two more techniques are introduced in this tutorial.
The first technique, NMR spectroscopy, is a method of structure determination based on
the relative position of hydrogens and carbons in spectra. The second technique, mass
spectrometry, can help elucidate the molecular formula and structure of a compound by
analyzing how the compound fragments after it is hit by electron beam.
Tutorial Features
Key Concepts
Basic Information for NMR

Background
Theory
Definitions
Splitting of signals
Proton resonance frequencies tables
Problem solving
Examples
Carbon magnetic frequencies tables
Problem solving
Examples
Background Information for Mass Spectrometry
History
The mass spectrometer
The molecular ion
The base peak
Isotopes and mass spectrometry
The Mass Spectrum
Fragmentations of alkanes
Fragmentations of alcohols
Fragmentations of amines

64
Fragmentations of ethers
Fragmentations of aldehydes and ketones
The McClafferty rearrangement
Analyzing Mass Spectra
Guidelines for analysis
Sample spectra
Chapter Review
Nuclear Magnetic Resonance (NMR) Spectroscopy

Method of structure determination based on the relative positions of hydrogens and
carbons in the spectra.
Chemical Shift
The difference in parts per million (ppm) between the frequency of TMS and the frequency
of the observed atom.
Tetramethylsilane (TMS)
An internal standard for NMR spectroscopy that has a chemical shift of δ0.00.
Integration
The area under a peak that is proportional to the number of hydrogens that gave rise to
the signal.
Spin-Spin Splitting
A splitting of signals into multiplets when the magnetic field of the proton is affected by
protons on adjacent carbons.
Coupling Constant
Distance between the peaks of a multiplet.

Type of NMR spectroscopy based on the hydrogen nucleus. In 1H NMR, the number of
signals equals the number of different types of protons present in the molecule. The
chemical shift is indicative of the electronic environment of the observed proton and the
splitting of the signal indicates the number of protons on adjacent carbons.

Type of NMR spectroscopy based on the carbon-13 nucleus. In 13C NMR, the number of
signals equals the number of different types of carbons present. The chemical shift
indicates the type of functional group the observed carbon is a part of and the splitting of
the signal is determined by the number of hydrogens attached to the observed carbon.
Mass Spectrometry
An analytical tool used to determine the molecular formula and molecular structure for
unknown organic compounds.
Molecular Ion
The species formed when the sample molecule loses one electron to become a radical
cation. Also known as the parent peak.

65
Base Peak
The peak in a mass spectrum that is set to 100% relative abundance.
McClafferty Rearrangement
A rearrangement undergone by carbonyl compounds in mass spectrometry. In this
rearrangement, the γ hydrogen is abstracted by the carbonyl resulting in the formation of
an alkene and an enol.

66
20: Separations and Purifications
Chapter Summary
As important as synthesizing compounds is in organic chemistry, the separation and

purification of these compounds is just as important. There are several techniques that a
chemist may use to purify compounds made in the laboratory. This tutorial covers
techniques like distillation, extraction, chromatography, and recrystallization.
Tutorial Features
Key Concepts
Extractions
Theory of extraction
Liquid-liquid extraction
Acid-base extraction
Distillation
Boiling points
Theory of distillation
Simple distillation
Chromatography
Theory of chromatography
Column chromatography
Gas-liquid chromatography
Paper chromatography
Thin-layer chromatography
Recrystallization
Theory of recrystallization
Solvent selection
Chapter Review
Extraction
The process of selectively removing one or more components of a solid, liquid, or gaseous
mixture into a separate phase.
Liquid-Liquid Extraction
An extraction where the components of a mixture are partitioned between two immiscible
liquids.
Acid-Base Extractions

67
A type of extraction that is useful for separation of acidic or basic compounds from a
mixture.
Distillation
A chemical technique used to separate a component of a mixture from less volatile
components on the basis of boiling points.
Boiling Point
The temperature at which the vapor pressure of a liquid is equal to the atmospheric
pressure.
Chromatography
The separation of components of a mixture based on their unequal distribution between
two immiscible phases.
Column Chromatography
A form of solid-liquid adsorption chromatography.
Eluant
The solvent system used for chromatography.
Gas-Liquid (GC) Chromatography

A common analytical technique used for separating mixtures whose components may differ
in boiling point by as little as 0.5 0C.
Retention Time
The elapsed time from injection of a mixture to detection of the desired component.
Paper Chromatography
A form of solid-liquid chromatography where the stationary phase is a piece of paper.
Retention Factor (Rf Factor)

A physical constant for a compound that can be used for qualitative analysis by comparing
the experimental value to standard values. It is calculated by dividing the distance the
sample traveled up the chromatography paper by the distance the solvent traveled.
Thin-Layer Chromatography (TLC)

A form of solid-liquid chromatography where the stationary phase is either alumina or silica
gel that has been deposited on a glass plate.
Recrystallization
Dissolution of a solid in an appropriate solvent at elevated temperatures and the
subsequent reformation of the crystals upon cooling such that any impurities present are
left in the solution.
Dielectric Constant
A measure of a solvent’s polarity.

68
21: Organic Reactions
Chapter Summary
Students will be introduced to more organic terminology in this tutorial with the aim that
understanding the terms will translate to a better understanding of organic reactions.
Reactions from previous tutorials are also reviewed here.
Tutorial Features
Key Concepts
Terminology of Organic Reactions

Mechanism, stoichiometry, thermodynamics, kinetics
Transition state, activation energy, Hammond postulate
Kinetic versus thermodynamic control, reactive intermediate, catalyst, solvent effect
Reactions of Alkyl Halides
Substitution with nucleophiles to form other compounds
Elimination with KOH to form alkenes
Reaction with lithium to form alkyl lithiums
Reaction with magnesium to form Grignard reagents
Addition of HX to form alkyl halides
Addition of H2O to form alcohols
Addition of X2 to form dihaloalkanes
Addition of hydrogen to form alkanes
Oxidation with KMnO4 to form diols
Oxidation with O3 to form aldehydes and ketones
Addition of 2 HX to give dihaloalkanes
Addition of 2 X2 to give tetrahaloalkanes
Addition with 2 H2 to give alkanes
Oxidation with KMnO4 to give diketones
Oxidation with O3 to give carboxylic acids
Reaction with X2 and catalyst to give ArX
Reaction with HNO3 and H2SO4 to give ArNO2
Reaction with SO3 and H2SO4 to give ArSO3H
Reaction with RX and AlCl3 to give ArR
Reaction with R(C=O)X and AlCl3 to give ketones
Reactions of Amines
Reaction with RX, followed by lost of HX, to yield larger amines

69
Reaction with HX, to yield ammonium salts

Reaction with acid halides to yield amides
Reaction with sulfonyl chlorides to yield sulfonamides
Reaction with metals to yield alkoxide ions
Reaction with HX, PX3, or POCl3 to yield RX
Reaction with heat and acid to yield alkenes
Dihalides are treated with 2 KOH to yield alkynes
Oxidation
Reaction with RCOOH and acid to yield esters
Reaction with organometallic reagents to form alcohols
Reaction with primary amines to yield imines
Reductive amination to yield amines
Oxidation of aldehydes to carboxylic acids
Reaction with thionyl chloride to yield acid chlorides
Reaction with alcohols and acid to give esters
Reaction with acid halides to give anhydrides
Hydrolysis to form carboxylic acids
Reaction with alcohols to form esters
Reaction with amines to form amides
Reaction with R2CuLi to form ketones
Reactions of Esters
Reaction with water and acid to yield carboxylic acids and alcohols
Reaction with amines to yield amides and alcohols
Hydrolysis of anhydrides to yield carboxylic acids
Reaction with alcohols to yield esters and carboxylic acids
Reaction with amines to yield amides and carboxylic acids
Reactions of Amides
Reaction with aqueous acid to yield carboxylic acids and ammonium ions
Reaction with water and hydroxide ion to yield carboxylate anions and amines
Reduction to amines
Dehydration to nitriles
Chapter Review
Mechanism
Complete step-by-step description of the bond breaking and the bond forming steps of a
reaction.
Stoichiometry
The relationship between reactants and products in a chemical reaction.

70
Thermodynamics
The study of the energy changes that accompany the physical and chemical changes.
Kinetics
The study of the rates of chemical reactions.
Transition State
The energy state between reactants and products.
Activation Energy
The energy needed to initiate a chemical reaction.
Hammond Postulate
States the structure of a transition state is most similar to the structure of the stable
species closest to it in energy.
Kinetic versus Thermodynamic Control

In a reaction, the kinetic product predominates at low temperatures while the
thermodynamic product predominates at high temperatures.
Reactive Intermediate
A short lived species that is an intermediate in a chemical reaction.
Catalyst
A compound that increases the rate of reaction without being consumed.
Solvent Effect
The effect that a solvent has on the rate of reaction.
Reactions Listed in Tutorial

The reactions in this tutorial are from previous tutorials and are listed for review purposes.

71
22: Synthesis, Multistep and Retrosynthesis
Chapter Summary:
Multistep synthesis is an important goal of organic chemistry as most molecules can not be
made in just one reaction. Different types of multistep syntheses are covered in this
tutorial as well as a problem solving process called retrosynthesis analysis that can be used
to determine the best synthetic route to a target molecule.
Tutorial Features

Key Concepts
Principles of Synthesis
Definition of synthesis
Total synthesis
Methodology
Retrosynthesis
Retrosynthetic analysis
Disconnections
Evaluation
Chapter Review:
Synthesis
Purposeful execution of chemical reactions to get to a desired product.
Synthetic Intermediate
A compound that is a product of one reaction and a starting material for the next reaction.
Total Synthesis
Complete chemical synthesis of complex organic molecules from simple, commercially
available precursors.
Linear Synthesis
A type of total synthesis where each reaction produces a synthetic intermediate that is
used as a starting material for the next reaction.
Convergent Synthesis
A type of total synthesis where a set of synthetic intermediates are formed. These
intermediates are then joined together to form the final product.
Methodology

72
The development of reactions and methods that give high yields and are reliable for a
broad range of substrates.
Retrosynthetic Analysis
A problem-solving technique for transforming the structures of a synthetic target molecule
to a sequence of progressively simpler molecules along a pathway that eventually leads to
simple, commercially available compounds.
Retrosynthesis
A series of reactions that work backwards from a target molecule to the starting material.
Synthon
A structural unit within a molecule which is related to possible synthetic operations.
Disconnections
Strategic bonds in the target molecule that are potential synthetic linkages.

73
23: Organic Reaction Mechanisms
Chapter Summary
Understanding reaction mechanisms in organic chemistry enables students to better predict

the products obtained in a reaction. In this tutorial, more reaction terminology,
mechanism and arrow drawing basics, and criteria for good reaction intermediates are
covered. Several reactions from prior tutorials are reviewed in detail with particular
attention paid to their mechanisms. The mechanistic details of these reactions illustrate
the basic types of reactions common to organic chemistry.
Tutorial Features
Key Concepts
Terminology in Mechanisms
Double headed arrows, heterolytic bond cleavage, heterogenic bond formation
Single headed arrows, homolytic bond cleavage, homogenic bond formation
Polar reactions
Substitution Reactions
Sn1 reactions
Sn2 reactions
Elimination Reactions
E1 reactions
E2 reactions
Mechanism of Addition Reactions
Mechanism for the addition of HX to alkenes
Mechanism for addition of halogens to alkenes
Nucleophilic Addition to Carbonyl Compounds
Reaction of a Grignard reagent with aldehydes
Reaction of aldehydes with primary amines
Mechanism of electrophilic aromatic substitution
Example
Acid-Base Reactions
Deprotonation
Protonation
Carbocation Mechanisms
1,2-Hydride shift
1,2-Alkyl shift

74
Anion Mechanisms
Mechanism for the alkylation of carbonyl compounds with LDA
Mechanism for the addition of the hydride ion
Radical Reactions
Halogenation of alkenes
Mechanism Basics
Understanding mechanisms
Arrow Drawing Skills
Basic arrow drawing skills for heterolytic bonds
Examples of nucleophiles
Basic arrow drawing skills for homolytic bonds
Movement of Electrons with Arrows
An unshared electron pair becomes a shared electron pair
A shared electron pair becomes an unshared electron pair
A shared electron pair becomes another shared electron pair
Intermediates
Formation of intermediates
Characteristics of good intermediates
Characteristics of unlikely intermediates
Chapter Review
Double Headed Arrow

Arrow used to show the movement of a pair of electrons.
Heterolytic Cleavage
A type of bond breaking where one atom involved in the bond receives both electrons while
the other atom receives no electrons.
Heterogenic Bond Formation

Bond formation in which one reactant donates both electrons to form the bond.
Single Headed Arrow

Arrow used to show the movement of one electron.
Homolytic Bond Cleavage

A type of bond breaking in which each atom involved in the bond receives one electron.
Homogenic Bond Formation

Bond formation in which each reactant donates an electron to form the bond.
Polar Reaction
A reaction in which a nucleophilic species attacks an electrophilic species.
SN1 Reaction
Substitution reaction in which a nucleophile attacks an electrophile displacing a leaving
group. The reaction proceeds with first order of kinetics and through a carbocation
intermediate.
SN2 Reaction

75
Substitution reaction in which a nucleophile attacks an electrophile displacing a leaving

group. The reaction proceeds with second order kinetics and is a concerted reaction.
Protic Solvents
Solvents that can participate in hydrogen bonding.
Aprotic Solvents
Solvents that can not participate in hydrogen bonding.
Concerted Reactions
Reactions in which all the bond breaking and formation occur in a single step. In contrast
to a stepwise reaction involving intermediates.
E1 Reaction
Elimination reaction in which a base deprotonates an alkyl halide displacing a leaving group
to form an alkene. The reaction proceeds with first order kinetics and through a
carbocation intermediate.
E2 Reaction
Elimination reaction in which a base deprotonates an alkyl halide displacing a leaving group
to form an alkene. The reaction proceeds with second order kinetics and is a concerted
reaction.
Deprotonation
Reaction in which a base abstracts an acidic hydrogen in a molecule.
Protonation
Reaction in which a molecule gains a proton from an acid.
1,2 Hydride Shift

A carbocation rearrangement in which a hydrogen takes the electrons from the carbon-
hydrogen bond it is involved in and moves to an adjacent carbon.
1,2 Alkyl Shift

A carbocation rearrangement in which an alkyl group takes the electrons from the carbon-
carbon bond it is involved in and moves to an adjacent carbon.

76
24: Acid-Base Chemistry
Chapter Summary
In this tutorial you will learn about the definitions of acids and bases including Arrhenius
acids and bases, Brønsted-Lowry Theory, Lewis acids and bases. You will also learn about
Conjugate acids and bases As well as Equilibria in acid-base reactions. Finally, we will look
at molecular structure considerations including Resonance and Inductive effects.
Tutorial Features

Key Concepts
Definitions of acids and bases

Arrhenius acids and bases
Brønsted-Lowry Theory
Lewis acids and bases
Conjugate acids and bases
Equilibria in acid-base reactions
Molecular structure considerations
Resonance in acid-base chemistry
Inductive effects
Chapter Review
Arrhenius
Acids increase H+; Bases increase OH- .
Brønsted-Lowry
Acids donate protons; Bases accept protons.
Lewis
Acids accept a pair of electrons from Bases forming a new covalent bond.
Conjugate Acid-Base Pair

1. Acid that donates a proton becomes a Conjugate Base
2. Base that accepts a proton becomes a Conjugate Acid
Acid Strength
Strong acids dissociate complety in aqueous solution:
HA(aq) Æ H+(aq) + A-(aq)
Weak acid dissociation is an equilibrium process. Stability of A- is key to acid strength:

77
HA(aq) Æ H+(aq) + A-(aq)

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1

DAT Organic Chemistry Rapid Learning Series – Course GuideBook

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COURSE TABLE OF CONTENTS – TOPICAL SUMMARY

Core Unit #1 – Foundation of DAT Organic Chemistry

Tutorial 01: Introduction to DAT Organic Chemistry

Tutorial 02: Chemistry Review: Structure and Bonding

Core Unit #2 – Nomenclature

Tutorial 03: IUPAC Rules – Organic Nomenclature I

Tutorial 04: IUPAC Rules – Organic Nomenclature II

Tutorial 05: Drawing Organic Structures

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Tutorial 06: Functional Groups of Organic Compounds

Core Unit #3 – Stereochemistry and Conformation

Tutorial 07: Stereochemistry

Tutorial 08: Conformational Analysis

Core Unit #4 – Hydrocarbons and Reactions

Tutorial 09: Saturated Hydrocarbons

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Alkane and Cycloalkane Nomenclature

Tutorial 10: Unsaturated Hydrocarbons

Core Unit #5 – Aromatics

Tutorial 11: Aromatic Compounds and Aromaticity

Core Unit #6 – Functional Groups and Reactions

Tutorial 12: Alcohols and Ethers

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Tutorial 13: Aldehydes and Ketones

Tutorial 14: Carboxylic Acids

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Oxidation of primary alcohols

Tutorial 15: Acid Derivatives

Tutorial 16: Keto Acids and Esters

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Acetoacetic acid synthesis

Tutorial 17: Amines

Core Unit #7 – Organic Analysis and Separation

Tutorial 18: Infrared and UN Spectroscopy

Tutorial 19: NMR and Mass Spectrometry

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Basic Information for NMR

Tutorial 20: Separations and Purifications

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Core Unit #8 – Individual Reactions, Multistep Reactions and

Tutorial 21: Organic Reactions

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Reactions of Carboxylic Acids

Tutorial 22: Synthesis, Multistep and Retrosynthesis

Tutorial 23: Organic Reaction Mechanisms

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Reaction of aldehydes with primary amines

Core Unit #9 – Acids and Bases

Tutorial 24: Acid-Base Chemistry

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Problem Solving Drills

Condensed Cheat Sheet

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Chapter by Chapter Detailed Content Descriptions

01: Introduction to DAT Organic Chemistry