Organic Chemistry

Code of Lecture : D10B. 03E0318

The Unit of Semester credits (SKS) : 2 (2-0)
Semester : Fm/1
Day/Time : Thursday, 13.00 – 14.40 am

Laboratorium Kimia Organik – Jurusan Kimia

Fakultas Matematikan dan Ilmu Pengetahuan Alam
Universitas Padjadjaran
2009
 Organic Chemistry
1. Introduction to Organic Chemistry
(Orbitals and their role in Covalent Bonding, Isomerism
and stereochemistry)
2. Nomenclature of Organic Compounds
3. Properties of aliphatic and Aromatic Compounds
(alkanes, alkenes, alkynes and benzene)
4. Functional Group of Organic Compounds
(alcohol, eter, aldehyde, keton and carbocylic acid and
derivatives)
5. Basic of Spectrofotometry for Identification of Organic
Compounds
(UV-Vis, IR, 1D- and 2D-NMR, MS)

12/08/2021 2
 What is Organic Chemistry?
It is defined as the study of hydrocarbons (compounds of
hydrogen and carbon) and their derivatives

Carbocylic acid &

Alkane Alkenes Alkyne Alcohol Aldehyde Ketone
derivatives

25 million Organic Compounds

1.75 million Inorganic Compounds

Animal and plant matter, Foods, Pharmaceuticals, Cosmetics,

Fertilizers, Plastics, Petrochemicals, Clothing
 Introduction to Organic Chemistry
1. How are organic molecules classified?
Be able to classify organic molecules into functional group families.

2. What are the structures of organic molecules?

Be able to recognize the main carbon chain in a molecules and identify constitutional
isomers.

3. How are organic molecules drawn?

Be able to convert between structural and condensed or line structures.

4. How are alkanes and cycloalkanes named?

Be able to name alkane or cycloalkane from its structure or write the structure, given
the name.

5. What are the general properties of alkanes?

Be able to describe such properties as polarity, water solubility, flammability, toxicity,
and chemical reactivity.

6. What are the major chemical reaction of alkanes?

Be able to describe the products formed in combustion and halogenation of alkanes.
Organic Chemistry, Pharmacy-2009. 01 of 50
 The Nature of Organic Molecules

1. Carbon is always tetravalent; it always forms four bonds.

Organic Chemistry, Pharmacy-2009. 01 of 50

 The Nature of Organic Molecules

2. Organic molecules contain covalent bonds.

Organic Chemistry, Pharmacy-2009. 01 of 50

 The Nature of Organic Molecules

3. Organic molecules contain polar covalent bonds when carbon bonds to

an element on far right or far left of the periodic table.

Organic Chemistry, Pharmacy-2009. 01 of 50

 The Nature of Organic Molecules

4. Carbon can form multiple covalent bond by sharing more than two
electrons with a neighboring atom.

Organic Chemistry, Pharmacy-2009. 01 of 50

 The Nature of Organic Molecules
5. Covalently bonded molecules have specific three-dimensional shapes.

Organic Chemistry, Pharmacy-2009. 01 of 50

 The Nature of Organic Molecules
6. Hydrogen, nitrogen, and oxygen are elements most often present in
organic molecules in addition to carbon.

Organic Chemistry, Pharmacy-2009. 01 of 50

Families of Organic Molecules: Functional Groups
 At last count, there were more than 25 million organic compounds
described in the scientific literatures.

 Each compound has unique physical properties (such as melting point

and boiling point) and each has unique chemical properties.

 The organic compounds can be classified into families according to their

structural feature and that the chemical behavior of members of a family
is often predictable.

 Instead of 25 million compounds → there are just a few general families

of organic compounds → Functional Group
↓
A part of a larger molecules and is composed of an atom or group of
atoms that has characteristic chemical behavior

 The chemistry of an organic molecules, regardless of size and complexity,

is determined by the functional groups it contains.
Families of Organic Molecules: Functional Groups

Ethylene

Cholesterol
Fig. 2 The reaction of (a) ethylene and (b) cholesterol with hydrogen.
The carbon-carbon double bond functional groups adds two hydrogen atoms in both cases,
regardless of the complexity of the rest of the molecules.
Families of Organic Molecules: Functional Groups
Families of Organic Molecules: Functional Groups
The Structure of Organic Molecules
 Hydrocarbons : Organic compounds containing only carbon and
hydrogen
 Alkanes, Alkenes, Alkynes, and arenes are hydrocarbons when no other
functional groups are present in their molecules
 Alkanes are the one family of organic compounds that contain no
fungctional groups, for alkanes are constructed entirely of carbon and
hydrogen atoms joined by single bonds → the absence of functional
groups makes alkanes relatively unreactive.
The Structure of Organic Molecules
 Every member of the other families is essentially an alkane in which one
or more hydrogen atoms have been replaced by functional groups.

 The families of organic compounds:

Group 1: The hydrocarbons of the first for families.
Group 2: Those whose functional groups contain only single bonds (alkyl
halides, alcohols, ethers, and amines).
Gropu 3: Those whose functional groups contain a carbon-oxygen double
bond (aldehyde, ketones, carboxyclic acids and anhydride, esters,
and amines).
 The Structure of Organic Molecules
Alkanes and Their Isomers
Alkanes: Molecules that contain only carbon and hydrogen, and that have
only single bond → only one possibility structure → → No Isomers
 The Structure of Organic Molecules
Alkanes and Their Isomers
 If larger numbers of carbons and hydrogens combine (≥ 4 carbons),
more than one kind of molecules can be formed, straight- and branced-
chains→ Compounds with the same molecules formula but with
different connections between atoms →→Isomers
 The Structure of Organic Molecules
Alkanes and Their Isomers
 If larger numbers of carbons and hydrogens combine (≥ 4 carbons),
more than one kind of molecules can be formed, straight- and branced-
chains→ Compounds with the same molecules formula but with
different connections between atoms →→Isomers
 The Structure of Organic Molecules
Alkanes and Their Isomers
 If larger numbers of carbons and hydrogens combine (≥ 4 carbons),
more than one kind of molecules can be formed, straight- and branced-
chains→ Compounds with the same molecules formula but with
different connections between atoms →→Isomers

 Its important to realize that different constitutional isomers are

completely different chemical compounds.
 They have:
• different structures
• different physical properties ( such as melting point and boiling point)
• Potentially different physiological properties
 The Structure of Organic Molecules
Alkanes and Their Isomers
 Its important to realize that different constitutional isomers are
completely different chemical compounds.
 They have:
• different structures
• different physical properties ( such as melting point and boiling point)
• Potentially different physiological properties
Drawing Organic Structures
Drawing Structural Formulas

↓
Structural Formula
(A formula that shows how
atoms are connected to
each other)

↓
↓
Time consuming and awkward
 Drawing Organic Structures

Structural Formula Condensed Structure

Condensed Structure:
A structure in which central atoms and the atoms connected to
them are written as a groups.

Convenience → Simpler but show the essential information about

which functional groups are present and how
atoms are connected
 The Shapes of Organic Molecules
Condensed Structures don‘t imply any particular three-dimensional
shape of molecules, they only show that compounds (e. g.,
butane) have a continuous chain of four carbon atoms and
indicate the cdonnections between atoms without
specifying geometry

In fact, butane has no one single shape because rotation is possible

around carbon-carbon single bonds → Conformations
↓
The exact three dimentional
shape of a molecule at any
given instant
 The Shapes of Organic Molecules

Some possible conformations of butane. There are many other conformations as well.

An actual sample of butane contains a great many molecules that

are constantly changing shape, however, most of the
molecules have the less crowded extended confomation .
 Naming Alkanes
In earlier times when relatively few pure organic chemical were
known, new compounds were named at whim of their
discovered.

Urea → a crystalline substance first isolated from urine

Morphine → a plant extract that's a sedative and is named after

Morpheus (the Greek god of dreams).

Nomenclature
(A systematic method of naming compounds)

IUPAC
(International Union of Pure and Applied Chemistry)
 Naming Alkanes
IUPAC System for Organic Compounds

Prefic : Where the location of functional groups and other

substituents on the chain.
Root : The overall size of the molecule by telling how many
carbon atoms are present in the longest continuous
chain.
Suffic : Identifies what family the molecules belongs to
 Naming Alkanes
The straight-chain alkanes are named simply by counting the
number of carbon atom in the chain and adding the family suffix
–ane to the root name to give the name of the parent compound.
 Naming Alkanes

Alkyl group : The part of an alkane that remains when one –H atom is
removed
Methyl group : -CH3, the alkyl group derived from methane
Ethyl group : -CH2CH3, the alkyl group derived from ethane
n-Propyl group : -CH2CH2CH3, the alkyl group derived by removing a –H from
an end carbon of propane
Isopropyl group : -CH(CH3)2, the alkyl group derived by removing a –H from
the central carbon of propane
 Naming Alkanes

n-Propyl group : -CH2CH2CH3, the alkyl group derived by removing a –H from

an end carbon of propane
Isopropyl group : -CH(CH3)2, the alkyl group derived by removing a –H from
the central carbon of propane
 Naming Alkanes
Some Common Alkyl Groups

Alkyl group : The part of an alkane that remains when one –H atom is
removed
Methyl group : -CH3, the alkyl group derived from methane
Ethyl group : -CH2CH3, the alkyl group derived from ethane
n-Propyl group : -CH2CH2CH3, the alkyl group derived by removing a –H from
an end carbon of propane
Isopropyl group : -CH(CH3)2, the alkyl group derived by removing a –H from
the central carbon of propane
 How to Write the Naming of Branched-chain?

Step 1. Name the main chain

Find the longest continuous chain of carbons present in the molecule and name the chain
using the root for the number of carbons it contain.

Name as a substituted pentane, not

as a substituted butane, because the
longest chain has five carbons.

Step 2. Number the carbon atoms in the main chain

Beginning at the end nearer the first branch point, number each carbon atom in the
main chain.
The first (and only) branch occurs at
C2 if we start numbering from the
left, but would occur at C4 if we
started from the right by mistake
 How to Write the Naming of Branched-chain?

Step 3. Identify and number the branching substituents.

Assign a number to each branching substituent on the main chain accoring to its point of
attachment.

The main chain is a pentane. There

is one –CH3 substituent group
connected to C2 of the chain.

The main chain is a hexane. There

are two substituents, a –CH3 and a
–CH2CH3, both connected to C3 of
the chain.
How to Write the Naming of Branched-chain?
Step 4. Write the name as a single word.
 Use hyphens to separate the numbers
from the different prefixes and use
commas to separate numbers if
necessary.

 If two or more different substituents

groups are present, cite them in
alphabetical order.

 If two or more identical substituents

are present, use one of the prefixes di-,
tri-, tetra- and so forth, but don‘t use
these prefixes for alphabetizing
purposes.
How to Write the Naming of Branched-chain?
2-Methylpentane
(a five-carbon main chain with a 2-
methyl substituent)

3-Ethyl-3-methylhexane
(a six-carbon main chain with a 3-
ethyl and 3-methyl substituents
cited alphabetically)

3,3-Dimethylhexane
(a six-carbon main chain with two
3-methyl substituents)
 How to Write the Naming of Branched-chain?

Based on the number of other carbon atom attached to a given

carbon atom, there are four possibility substituent pattern for
carbon, called primary, secondary, tertiary, and quartenary.

Primary carbon Secondary carbon Tertiary carbon Quternary carbon

(1) (2) (3) (4)

Primary carbon (1) : A carbon atom that is bonded to one other carbon atom
Secondary carbon (2) : A carbon atom that is bonded to two other carbon atom
Tertiary carbon (3) : A carbon atom that is bonded to three other carbon atom
Quaternary carbon (4) : A carbon atom that is bonded to four other carbon atom
 Properties of Alkanes
Alkanes contain only nonpolar carbon-carbon and carbon-hydrogen bonds, so
the only intermolecular forces influencing their properties are the weak London
forces

Fig. 4 Boiling and melting points for C1-C15 staight-chain

alkanes.
 Properties of Alkanes

 Odorless or mild odor, colorless, tasteless.

 Non-polar; insoluble in water and soluble in non polar
organic solvent.
 Less dense than water.
 Flammable.
 Regular increase in melting and boiling points with
molecular weight.
 Not very reactive
 Chemical Reactions of Alkanes
Combustion
 Alkanes show little chemical affinity for other molecules
and are inert to acids, bases, and most other common
laboratory reagents.
 The major reactions are those with oxygen Combustion
and the halogens (Halogenation or Substitution reactions).

 Combustion is The chemical reaction of alkanes with oxygen

occurs during the combustion of fuels in engines or furnaces.

CO2 or/ and CO + H2O Heat and Light

Chemical Reactions of Alkanes
Halogenation
 Cycloalkanes

• Cycloalkane is an alkane that contains a ring of carbon atoms

• Compounds of all ring sizes from 3 through 30 carbon atoms and beyond
have been prepared in the laboratory.

• Cyclic and acyclic alkanes are similar in many of their properties, for the
cycloalkanes are also non polar molecules.
• Because of their cyclic structure, cycloalkane molecules are more rigid
and less flexible than their open-chain counterpart. Rotation is not
possible around the carbon-carbon bonds in cycloalkanes without
breaking open the ring.
 Cycloalkanes

The chair conformation of cyclohexane.

All bond angles are close to the 109.5 tetrahedral values.

• The six-membered cyclohexane ring exist in a puckered, nonplanar shape

known as the chair conformation, in which the carbon atoms have nearly
tetrahedral bond angles.
• The cyclohexane ring is therefore very stable, and many naturally
occuring and biochemically active molecules contain cyclohexane rings.
 Drawing and Naming Cycloalkanes
Line structure → A shorthand way of representing ring structures as
polygons without showing individual carbon atoms.

• Cycloalkanes are named by a straightforward extension of rules for open-

chain alkanes.
• The carbon ring is equivalent to the main chain.
 Drawing and Naming Cycloalkanes
Step 1. Use the cycloalkane name as the parent.
Compounds should be named as alkyl-substituted cycloalkanes rather than as cycloalkyl-substituted alkanes. If there
is only one substituent on the ring, it’s not even necessary to asiggn a number since all ring positions are equivalent.

Parent compound: Cyclohexane

Name: Methylcyclohexane
(not cyclohexylmethane)

Step 2. Number the substituents.

Start numbering at the group that has alphabetical priority and proceed around the ring
in the direction that gives the second substituents the lowest possible number.

Name: 1-Ethyl-3-methylcyclohexane
(not 1-Ethyl-5-methylcyclohexane
1-Methyl-3-ethylcyclohexane
1-Methyl-5-ethylcyclohexane)