August 24, 2023

Unit 8: Organic Chemistry - HL

[IB Topics 10 & 20]

The chemistry of carbon compounds

There are more carbon-based compounds then all others combined!

This is due to carbon's unique ability to form chains and rings with
itself as a result of its four valence electrons and tendency to form
4 covalent bonds.

There is tremendous variety possible in organic compounds, yet in

terms of drawing structures there is a very simple rule that C, H, O
and N follow in organic chemistry:

The number of valence electrons = The number of Covalent Bonds

Carbon - C - Forms 4 bonds. Usually connects with other carbon

atoms (and occasionally O and/or N atoms) to form the "backbone" of
organic molecules.

Hydrogen - H - Forms 1 bond. No exceptions. Always on the

outside of molecules. Never in between two atoms. So common to
organic molecules it is actually left out and assumed when using
skeletal structural formulas.

Oxygen - O - Forms 2 bonds. This can either be a double bond to

one atom, or one bond to two different atoms. Usually sticks off the
main chain, but can act as part of the backbone in certain molecules.

Nitrogen - N - Forms 3 bonds. This can be done with any

combination of single, double and triple bonds. Until we get to
biochemistry, nitrogen will usually be off of the main chain.

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Types of Formulas

Empirical Formula - shows the lowest whole number (mole) ratio

of elements in a compound.

Molecular Formula - shows the actual number of each atoms of

each element in a molecule of a compound. This is one or more
whole number times the empirical formula.

Important for Organic Chemistry

Full Structural Formula - Shows every atom and every bond.

VSEPR geometries and non-bonding electron pairs are generally
not shown, though showing them will not result in lost marks.

pentane

Condensed Structural Formula - Shows every atom, but all (or

most) bonds are not shown and similar groups can be grouped
together. Gives the minimum amount of information that can still
unambiguously represent a specific compound.

*There may be multiple equally acceptable ways to represent a

condensed structural formula.

CH3CH2CH2CH2CH3 CH3CH2COCH3

CH3(CH2)3CH3

Skeletal Structural Formulas - Omits carbon and Hydrogen

atoms. C-C bonds are shown, and other atoms (O, N, S) are shown.
Carbon atoms are assumed at the end of each line segment if no
other letter is written in.

-The number of hydrogens can be determined by ensuring every

carbon atom ends up with 4 covalent bonds.

-**Note - you must be able to interpret these structures, but you

are not allowed to draw them on the IB Exam.

Skeletal formulas are probably most relevant for phenyl groups

(benzene rings), as they are generally presented in skeletal form.

What are the molecular formulas of the above molecules?

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Alkanes
There are MANY classes (families) of organic compounds. Each has
a certain general formula and a specific functional group that
distinguishes it from others. Each also gets its own naming suffix
or prefix to help distinguish it.

Functional Group - an atom, group of atoms, or specific bond that

characterizes a family of organic compounds & has specific
chemical and physical properties.

Alkanes
The simplest class of organic compounds are the ALKANES.

General Formula: CnH2n+2

Functional Group: None

IUPAC Naming Suffix: -ane

IUPAC Naming Prefix (for branches): alkyl-

Some general properties to know:

Completely nonpolar

Generally have a low reactivity due to relatively strong C-C and C-H
bonds

Readily undergo combustion reactions, producing the relatively

more stable (with stronger bonds) CO2 & H2O. Being completely
"un-oxidized" means when they combust (and get oxidized) the
amount of enthalpy change is more significant than fuels that begin
somewhat oxidized (like alcohols). They therefore have very large
enthalpy of combustion values.This, along with their otherwise
relative stability, makes them excellent fuels, as they are easy to
store and transport.

The only other typical reaction is "Free Radical Substitution" which

we will learn about shortly.

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Alkane Homologous Series & IUPAC Naming

Homologous Series is another term that means almost the same thing
as "class" or "family." It means:

-a series of compounds where each successive member differs

by one CH2 group.

- The "first" member usually has 1-carbon atom, but for certain
families the smallest possible example has 2 or 3 carbon atoms.

-The compounds have similar chemical properties and show trends

in their physical properties due to increasing nonpolar carbon
chain, surface area & London Forces

In IB Chemistry you are responsible for knowing how to draw

and name molecules with up to a 6-carbon atom chain.

The first 6 members of the alkane homologous series are listed

below.

Name Molecular Structural Condensed Structural Physical

Formula Formula Formula(s) Properties

IUPAC Naming

Root/ Parent Name = the number of carbon atoms in the longest

continuous chain.

Meth Eth Prop But Pent Hex

.
Suffix = The class of compound

-ane = alkane (no functional group)

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Isomerism
As organic molecules get bigger, there becomes an ever greater
variety of possibilities for how the same atoms can be arranged
structurally.

Structural Isomers (or just "Isomers") are molecules that have

the same molecular formula, but different structural formulas.

As a result, the need for condensed structural formulas instead

and a detailed naming system becomes readily apparent!

Isomers of Butane
Molecular Formula

Empirical Formula

Possible

Structural

Formulas

Condensed

Structural

Formulas

IUPAC Name

o o
Boiling point -0.5 C -11.7 C

Additional IUPAC Naming Rule:

-Carbon chains that branch off to the side of the main carbon
chain are recognized in names as prefixes ending "-yl"

-CH3 methyl

-CH2CH3 or -C2H5 ethyl

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Isomerism - Practice

Isomers of Pentane

Molecular Formula

Empirical Formula

Possible

Structural

Formulas

Condensed

Structural

Formulas

IUPAC Name

Isomers of Hexane
Molecular
. Formula

Empirical Formula

Possible

Structural

Formulas

Condensed

Structural

Formulas

IUPAC Name

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IUPAC Naming
The following table introduces a few other classes of organic
compounds and their associated IUPAC naming prefixes or suffixes.
Use this information to draw the structural formulas of the
molecules listed below the table.

Alkanes Halogenoalkanes Alcohols Carboxylic Acids

CnH2n+2 CnH2n+2O CnH2nO2

-X (X = halogen) -OH -COOH

-ane fluoro- -anol -anoic acid

chloro-

alkyl- bromo-

iodo-

Practice Drawing Structural Formulas

1. methyl propane

2. dimethyl propane

3. methyl butane

4. 2,3-dimethyl butane

5. 2,2-dimethyl butane

6. 1,2,3-trichloropropane

7. propan-2-ol

8. methyl propan-2-ol

9. pentanoic acid

10. 3-bromo hexanoic acid

IUPAC Naming - Summary of Rules & Things to Watch Out for

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IUPAC Naming
Name the following compounds using the IUPAC System.

1. 2.
H

3. 4.

5. 6.

7. 8.

H
H CH
H H H
9. 10. H C C C CH
H H H
HCH

HC H
H

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IUPAC Naming
Name the following compounds using the IUPAC System.

11. 12.

13. 14.

15. 16.

17. 18. CH3CH2CH(CH3)CH2COOH

19.HOOCCH2CH2COOH 20. CF3CH2F

21. Comment on the IUPAC naming for the 2 molecules shown below.

22. Draw all the isomers for trichloropropane. Name each based on
the IUPAC system.

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Free Radical Substitution

Free-Radical Substitution can achieve the following conversion:

Alkanes --> Halogenoalkanes

Alkanes will undergo this reaction in the presence of a free radical.

Free radical - a species with an unpaired electron.

NOT AN ION

Halogen Free Radical: Chlorine or Bromine

. .
Cl Br

Halogen free radicals are produced in the presence of ultraviolet

(UV) light (a well-lit classroom will provide enough to start this
process)

Overall Reaction for Free Radical Substitution

Alkanes + Halogen --> Halogenoalkane + Hydrogen Halide

(Purity is usually low,

multiple products produced)

Example: Overall Chemical Equation for the reaction between

ethane and chlorine:

C2H6 + Cl2 --> C2H5Cl + HCl

Summary

Reaction type: Substitution

Mechanism: Free Radical

Condition Needed: Ultraviolet Light

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Free Radical Substitution: Mechanism

Condition Needed: ultraviolet Light

-splits the Cl-Cl or Br-Br bond evenly via Homolytic Fission

Free-Radical Substitution Mechanism:

Initiation:
.
Cl2 --> 2Cl

Propagation:
. .
Cl + C2H6 --> HCl + C2H5
. .
C2H5 + Cl2 --> C2H5Cl + Cl

Other propagation steps you are not responsible for showing, but should
understand are possible through this mechanism:

. .
Cl + C2H5Cl --> HCl + C2H4Cl

. .
C2H4Cl + Cl2 --> C2H4Cl2 + Cl

Termination: (all the following are possible)

. .
C2H5 + Cl --> C2H5Cl
. .
C2H5 + C2H5 --> C4H10
. .
Cl + Cl --> Cl2

Reasons for low purity in halogenoalkane product:

-multiple propagation steps are possible (more than one halogen can
be substituted for hydrogen)

-multiple termination steps possible (multiple products possible)

Other Key things to remember:

.
-A hydrogen radical is never produced (H )

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Free Radical Substitution: Practice

1.) a)Write the overall equation for the reaction of bromine and
methane. [1]

b) State the conditions necessary for the reaction to occur. [1]

c) State what is meant by the terms free radical and homolytic

fission. [2]

d) State the name of the reaction and mechanism occurring. [2]

Reaction:

Mechanism:

e) Write out the mechanism for the reaction including initiation,

propagation and termination steps. [4]

Initiation:

Propagation:

Propagation:

Termination:

f) Draw the structural formulas of two other possible products

when methane undergoes free radical substitution with bromine. [1]

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Nucleophillic Substitution
Nucleophillic Substitution Reactions can achieve the following
conversion:

Halogenoalkanes --> Alcohols

Halogenoalkanes have many uses in our world as refrigerants and

aerosols, as well as many negative environmental impacts such as
ozone destruction and contributing to global warming.

They are also useful intermediate compounds in the synthesis

pathways from organic starting materials to desired products
(useful chemical feedstock). For the IB exam you only need to know
their role as a starting material for producing alcohols.

The reaction that converts halogenoalkanes into alcohols is a

substitution reaction. An -OH group, which is a "nucleophile,"
substitutes for a Halogen atom.

Overall Chemical Equation for Nucleophillic Substitution:

- -
R-X + OH --> R-OH + X

Summary

Reaction type: Substitution

Mechanism Type: Nucleophillic

**Just so you've seen it: The hydroxide ions can be provided by any
strong base (sodium hydroxide, potassium hydroxide, etc.), which is
why this reaction is sometimes referred to as "alkaline
hydrolysis"**

The term "nucleophillic" implies that the species that is substituting

onto the molecule is a nucleophile.

nucleophile - a species that has at least one non-bonding electron

pair and may carry a negative charge.

Nucleohphiles "like a nucleus" because they are electron rich. This

means they are attracted to atoms with positive charges, including
partial positive charges.

Since halogen atoms are more electronegative than carbon, the C-X
bond in halogenoalkanes is polar, giving the carbon atom a partial
-
positive charge. For this reason, the OH nucleophile is attracted to
it, causing the nucleophillic substitution reaction to occur.

The hydroxide nucleophile donates an electron pair, forming a

coordinate covalent bond with the carbon atom, and forcing the
bond with the halogen atom to break at the same time. The halogen
leaves with the full bonding electron pair, making it a halide ion.

The classification of the halogenoalkane reactant and alcohol

product are the same.

Primary halogenoalkanes --> Primary alcohols

Secondary halogenoalkanes --> Secondary alcohols

Tertiary halogenoalkanes --> Tertiary alcohols

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Classification of Halogenoalkanes, Alcohols & Amines
.
For certain classes of compounds, the structural isomers are
grouped into different classifications known as primary, secondary
and tertiary isomers.

This can be useful, as these different classifications tend to have

slightly different physical and chemical properties, due to the
differences in the position of their functional group.

For the IB exam, you must be able to classify isomers of alcohols,

halogenoalkanes and amines.

Primary C-Atom Secondary C-atom Tertiary C-atom

The halogen is The halogen is The halogen is

attached to a carbon attached to a carbon attached to a carbon
that is only attached that is attached to 2 that is attached to
to 1 other carbon other carbons/ has 2 3 other carbons/ has
bonds to carbon.
(R-CH2X or CH3X) 3 bonds to carbon.
(R-CHX-R') (R-CX-R')

R"
Halogenoalkanes

IUPAC Names?

Alcohols

Primary, secondary or tertiary? IUPAC names?

CH3CH2CH2OH CH3CHOHCH3

COH(CH3)3 CH3C(CH3)OHCH2CH3

Amines
.

What classification are the amines in adenine?

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Nucleophillic Substitution Mechanisms

Nucleophillic Substitution reactions can proceed via two different
mechanisms.

SN1: Substitution that is Nucleophillic and Unimolecular

This means that the rate determining step of the mechanism (the
slowest step) only includes 1 reactant, and therefore, the rate of
this reaction depends on only the concentration of that reactant.

SN2: Substitution that is Nucleophillic and Bimolecular

This means that the rate determining step of the mechanism (the
slowest step) includes 2 reactants, and therefore, the rate of this
reaction depends on the concentration of both reactants.

SN2 Mechanism
The reaction between 1-bromobutane & Hydroxide

SN1 Mechanism
The reaction between 2-bromo-2-methyl butane & Hydroxide

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Differentiating SN1 vs. SN2

SN1 SN2
Mechanism Details:

2 steps (1st step is RDS) 1 Step

Carbocation intermediate High Ea transition state

Lower Ea than SN2

transition state

(Faster Reaction Rate)

Potential Energy
Potential Energy

Extent of Reaction Extent of Reaction

Classification

Mechanism for Tertiary RX Mechanism for Primary RX

(Secondary RX can undergo

either type of mechanism)

-Steric hindrance prevents SN2 -Minimal Steric hindrance

-Positive Inductive Effect of -Minimal positive inductive

alkyl groups stabalizes carbocation effect. Carbocation too

unstable.

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Rate Factors - Nucleophillic Substitution

SN1 SN2
Rate: k[halogenoalkane] Rate: k[halogenoalkane][nucleophile]

1st Order Reaction 2nd Order Reaction

-
rate only depends on [RX] Rate Depends on [OH ] & [RX]

Non-Collision Theory Factors that Affect the rate of

Nucleophillic Substitution Reactions:

1) Identify/ Nature of Halogen

R-F R-Cl R-Br R-I

2) Identity/ Nature of Nucleophile

-
OH vs. H2O

3) Classification of Halogenoalkane (mechanism)

Primary Secondary Tertiary

4) Nature of the solvent (specific to each mechanism)

Polar, protic solvent Polar, aprotic solvents

-OH & -NH -No H-NOF

(hydrogen bonding) (dipole-dipole forces)

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Alcohols & Ethers

Ethers are a class of compounds that are functional group isomers
with alcohols. They can have the same chemical formula as a
corresponding alcohol, but a different functional group and
structure.

C2H6O

Example: CH3CH2OH CH3OCH3

Structural

Formula

IUPAC Name ethanol methoxymethane

*Longest chain

*shorter chain

Functional Group hydroxyl ether

Name

IMF Differences

Physical Properties

Comparison

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Aldehydes, Ketones, Carboxylic Acids & Esters

Class Aldehydes Ketones Carboxylic Acids Esters

General CnH2nO CnH2nO CnH2nO2 CnH2nO2

Formula

Functional

Group

F.G. aldehyde Carbonyl Carboxyl Ester

Name (carbonyl)

Examples C3H6O C3H6O C3H6O2 C3H6O2

Condensed

Structural CH3CH2CHO CH3COCH3 CH3CH2COOH CH3COOCH3

Formula HCOOCH2CH3

Structural

Formula

IUPAC Propanal propanone propanoic acid methyl ethanoate

Name ethyl methanoate

Suffix -al/ -anal -one/ -anone -oic acid/ -anoic acid alkyl -oate/

alkyl -anoate

Special

Naming *No # w/ FG *No # until 5C *No # w/ FG *No # w/ FG

Consideration or alkyl group

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Oxidation of Alcohols
Oxidation Reactions can achieve the following conversion:

Primary Alcohols --> Aldehydes --> Carboxylic Acids

Secondary Alcohols --> Ketones

Tertiary Alcohols --> (No Reaction)

Oxidation Reaction

Alcohols can be partially oxidized with certain oxidizing agents to

produce compounds with C=O bonds (carbonyl & carboxyl groups).

Unlike in total oxidation (combustion) the carbon chain remains in

tact.

Oxidizing Agents [O]:

2- +
(Acidified) dichromate (VI) Cr2O7 / H
- +
(Acidified) manganate (VII) MnO4 / H

Bonds between C & O replace bonds between C-H on the hydroxyl

carbon atom. This means that depending on the classification of
the alcohol, different products will be formed and oxidation can
take place a different number of times.

Primary Alcohols can be oxidized once or twice by these oxidizing

agents, depending on conditions, as there are 2 C-H bonds that can
be replaced with C-O bonds. A single oxidation produces an
aldehyde, while a second oxidation can produce a carboxylic acids.

Secondary Alcohols can be oxidized once by these oxidizing agents,

as there is only 1 C-H bonds that can be replaced. The product is a
ketone.

Tertiary Alcohols cannot be oxidized by these oxidizing agents, as

they have no C-H bonds to be replaced.

No Rxn

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Oxidation of Alcohols: Reaction Conditions

Of all the organic reaction, the conditions for the oxidation of
alcohols requires the most detail and explanation. This is especially
the case for primary alcohols, as the conditions used can determine
which product, an aldehyde or carboxylic acid, are formed.

Primary alcohols: To obtain only the aldehyde, use distillation

-The aldehyde cannot form hydrogen bonds (unlike the alcohol), so it

has a much lower boiling point.

-Distillation causes it to boil off as soon as it is formed, and it can

be collected in a separate container.

Primary alcohols: To obtain only the carboxylic acid, heat the

reactants under reflux.

-This will keep all of the reactants and the aldehyde in the reaction
vessel long enough for them to be oxidized completely into
carboxylic acid.

-Use an excess of your oxidizing agent and acid, to ensure the

alcohol is the limiting reagent and completely converts to carboxylic
acid.

Heating under Reflux with excess oxidizing agent is also used to

efficiently convert:

-secondary alcohols to ketones

-aldehydes to carboxylic acids

Color Changes

As the alcohol gets oxidized, the oxidizing agent is getting

. reduced.

The reduction of dichromate is shown table 24 of the data booklet.

As chromium changes from a +6 to +3 oxidation state, its color

changes from orange to green.

-This means that as primary and secondary alcohols get oxidized,

the reaction mixture will change color from orange to green.

-Since tertiary alcohols are not oxidized, however, no color change

occurs for tertiary alcohols.

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Reduction of Carbonyl Compounds

The reduction reactions are simply the reverse reactions from the
oxidation of alcohol reactions.

Carboxylic Acids --> primary Alcohols

Aldehydes --> primary alcohols

Ketones --> secondary alcohols

Reducing Agents & Conditions

.
Lithium Aluminum Hydride LiAlH4 Dry Ether/anhydrous

**More reactive, less safe

**The only reactant capable of reducing a carboxylic acid to a

primary alcohol (it does not create any aldehyde)

Sodium Borohydride NaBH4 Aqueous/ Alcoholic

**Safer, but not reactive enough to reduce carboxylic acids.

-
Both reducing agents produce the hydride ion, H , which acts as a
nucelophile and removes oxygen from the carbonyl compounds.\

-This may be shown as [+H] above the reaction arrow.

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Esterification/ Condensation Reaction

Esterification Reactions can achieve the following conversion:

Alcohols + Carboxylic Acids --> Esters

Condensation Reaction = bonding two molecules together and the in

the process removing/ producing a water molecule.

*Esterification is when a condensation reaction produces an

ester and water.

*Esters tend to have very nice smells, and are often used as
artificial flavors and smells.

Overall Chemical Equation of Esterification/Condensation Reaction:

Carboxylic Acid + Alcohol --> Ester + Water

Conc.
H2SO4
+

+ H2 O

Summary

Reaction Type: Esterification/ Condensation

(Mechanism: nucleophliic substituion)

Reaction Condition: Concentrated sulfuric acid (H2SO4) catalyst

Obtaining a Pure Product (Not on the IB Exam for Esters)

-Esters can be separated from the reaction mixture by distillation,

as they cannot hydrogen bond, they have lower boiling points than
the reactants that form them.

-Esters often separate naturally into an insoluble layer, as they

cannot hydrogen bond with water as well as the carboxylic acids and
alcohols they form from.

Remember:

Your crazy Aunt Ester (COOC) got "-yl" from the alcohol and the
(Carboxylic) acid that she "-oate."

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IUPAC Naming & Other Practice
Apply the correct IUPAC name to the following.

1.) 2.)

3.) 4.) CH3CH(CH3)CH2CHOHCH3

5.) CH3CH2CH2OCH2CH3 6.) (CH3)3CCHO

7.) HCOOCH2CH2CH3 8.) CH3COOCH(CH3)2

9.)

10.)

11.)

12.)

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Organic Reactions Practice Questions
1.) Butanol has 4 structural isomers that are alcohols.

a) Draw all 4 isomers and name them.

b) Identify the isomer that will not cause a color change when
mixed with acidified potassium dichromate.

c) Identify the isomer that will produce butanone when mixed with
acidified potassium dichromate.

d) Identify the isomer that can be used to produce butanal and

butanoic acid, stating the reaction conditions necessary to produce
each product.

2.) State the regents and conditions necessary to convert propanoic

acid into propan-1-ol.

3.) Write the balanced half-equations & overall equation for the
-
reaction between Methanol & Manganate (VII), MnO4 , in acidic
solution to produce methanoic acid and Manganese (II) ions.

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Synthetic Route Practice Questions
Describing a Synthetic Route is the process of writing out the
chemical equations to show the step-by-step process of synthesizing
a particular organic compound. Usually the starting compound and the
final desired product are specified, as well as the number of steps
(different reactions) in the synthetic route.

The DP Syllabus states that synthetic routes with up to 4 stages

could be assessed.

Usually, it is best to work backwards (retro synthesis) from the final

organic product, eventually getting back to the specified starting
compound(s).

Each step of the synthetic converts one functional group into

another. The product of the first step gets used as a reactant in the
next step, and so on, until the final product is produced.

Example: Describe the 3-stage synthetic route to convert

propane into propanoic acid, stating all the necessary reagents
and conditions.

Begin with the final product and work backwards. So begin by

figuring out stage 3 of the synthetic route.

We know propanoic acid can be produced via oxidation of primary

alcohols with heating under reflux and a strong, acidified oxidizing
agent.

Stage 3: Propan-1-ol --> Propanoic acid

Reagents & Conditions: acidified dichromate (VI), reflux

Now, figure out a reaction that can produce propan-1-ol for stage 2.

Stage 2: 1-bromopropane --> Propan-1-ol

Reagents & Conditions: sodium hydroxide (nucleophllic substitution)

Lastly, figure out stage 1 to produce the 1-bromopropane.

Stage 1: propane --> 1-bromopropane

Reagents & Conditions: Bromine & UV Light

In the correct order, the 3-Stage Synthetic Route is:

Stage 1: propane --> 1-bromopropane

Reagents & Conditions: Bromine & UV Light

Stage 2: 1-bromopropane --> Propan-1-ol

Reagents & Conditions: sodium hydroxide

Stage 3: Propan-1-ol --> Propanoic acid

Reagents & Conditions: acidified dichromate (VI), reflux

Practice Questions

1.) Propanone can be produce in 2 stages from a chloroalkane.

a) State the name of this chloroalkane.

b) Write out the chemical equations to show the 2 step synthetic

route to produce propanone from this chloroalkane, including any
necessary conditions and reactants needed.

2.) Ethyl ethanoate can be produced in a 2 stage process beginning

with bromoethane.

Write out 2 overall chemical equations showing the synthesis of ethyl

ethanoate from bromoethane, including any necessary conditions and
reactants needed.

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Reaction Jackson:
Your Guide for Synthetic Routes

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Alkanes, Alkenes & Alkynes

Class Alkane Alkene Alkyne

Functional

Group Name alkyl alkenyl alkynl

General CnH2n+2 CnH2n CnH2n-2

Formula

Examples C2H6 C2H4 C2H2

Structural

Formula

IUPAC Name ethane ethene ethyne

Special *As both of these FGs are always between 2

Naming carbon atoms, when you need to number them

Considerations use the lower of the 2 numbers.

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Alkenes (& Alkynes): Other Properties

Reactivity

Alkenes & Alkynes are more reactive than corresponding alkanes,

because the second (and third) bonds are more reactive than the
original carbon-to-carbon single bonds.

They combust readily (like alkanes), but their reactions have many
other uses as well.

Isomers

While the isomers of alkenes can be drawn by moving around the

C-to-C double bonds and rearranging the carbon chain, there are
some other, less obvious isomers.

Alkene Cycloalkane

Physical Properties

Alkenes and alkynes, like alkanes, can be referred to as hydrocarbons

because they contain only carbon and hydrogen.

Are they polar or nonpolar?

What are the bond angles and hydrobidization types around the
carbon atoms in these 3 hydrocarbon classes?

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IUPAC Naming Practice

Apply the correct IUPAC name to the following.

1.) 2.)

3.) 4.) CH3C(CH3)CHCH2CH3

5.) CH3CH2CHCH2 6.) (CH3)2C=C(CH3)2

7.) Draw all of the structural isomers of C5H10 and name each with
the correct IUPAC name.

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Amines, Amides & Nitriles

Class Amine Amide Nitrile

Functional

Group Name Amine carboxamide Nitrile

General CnH2n+3N CnH2n+1NO CnH2n-1N

Formula

Examples C2H5NH2 CH3 CONH2 CH3 CN

Structural

Formula

IUPAC Name ethanamine ethenamide ethanenitrile

Special *As both of these FGs are always on the #1

Naming carbon atom, no number is required.

Considerations

*The IB Syllabus states you do not need to name these classes of

compounds.

Physical Properties

What are IMFs are in of these 3 classes of compounds?

How will their physical properties compare?

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Identifying Functional Groups

In addition to naming organic compounds, you should also be able to
identify and name functional groups within larger molecules.
Sometimes the class and functional group name is the same, other
times it is not.

Identify the functional groups in the following compounds.

Identify the circled functional groups in the anticancer drug, taxol.

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Summary of IUPAC Naming (tables taken from Kognity)

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Addition Reactions
Addition Reactions can achieve the following conversion:

Alkenes --> Halogenoalkanes

--> Dihalogenoalkanes

--> Alkanes

--> Alcohols

--> Addition Polymers (plastics)

General Addition Reaction

Specific Types of Addition Reactions

Br Br Addition
Bromination
Polymerization

Hydrogenation Hydration
Halogenation

H H H X H OH

Chemical Equations, Conditions & Uses of Addition Reactions

Bromination

Hydrogenation

Halogenation

Hydration

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Addition Polymerization
Monomer Repeating Unit Section of Polymer

Bromination: Alkanes vs. Alkenes

Alkanes and alkenes can both react with halogens, but the
conditions needed are different. Most commonly, their reaction
with bromine is used to compare and contrast the classes.

Bromine has a reddish-brown color. Bromo-alkanes are colorless.

Alkenes rapidly decolorize any bromine (or bromine water) that is

added to them, as the bromination (addition) reaction happens very
quickly without any other reaction condition necessary. This means
it can take place even in the dark.

Alkanes will only decolorize bromine/bromine water in the presence

of UV light/ in a well-lit classroom. This reaction will not occur in
the dark.

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Practice Addition Reactions Questions
1. What is the product of the reaction between propene and
steam?

2. Write the chemical equation for the reaction between ethene

and hydrogen. State the conditions needed.

3. Determine the structural formulas of the two possible products

of the reaction between hydrogen chloride and but-1-ene.

4. State the name of the following reaction and explain one use of
this reaction.

C5H10 + Br2 --> C5H10Br2

5. What reactants and conditions are needed to produce

propan-2-ol in a 1 step reaction?

6. 3-chloropropene acts a monomor for a polymer. Draw the

repeating unit of that polymer.

7. The following is a section of a polymer. Determine the

structural formula and name of the monomer.

8. Bromoethane can be produced by both a 1-step and a 2-step

process beginning with ethane.

a) State the type of reaction that can produce bromoethane in one

step, and write then chemical equation.

b) Write the balanced equations for both steps of the 2-step

process to create bromoethane. Name each reaction and state and
conditions needed.

9. Outline a method to distinguish between propane and propene.

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Electrophillic Addition Mechanism

Alkenes contain C=C double bonds. The pi bond above and below
the bond axis creates two areas of electron density. This makes
the pi-bond more reactive than sigma bonds.

Because of its electron-rich nature, the pi bond is prone to

reacting with electrophiles. An electrophile is an electron deficient
species that tends to accept electron pairs in reactions (Lewis
Acid).

2 Reactions to know electrophillic addition mechanism for:

-Bromination & Halogenation

-Electrophiles: Br2 & HBr

Bromination Mechanism

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Electrophillic Addition Mechanism

Halogenation Mechanism

Halogenation with Asymmetric Alkenes: Major vs. Minor Product

Positive Inductive Effect & Carbocation Stability

Determining the Major Product

Markovnikov's Rule:

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Practice Alkene/Addition Questions

1) Illustrate the mechanism for the reaction between bromine and

but-1-ene.

2) a) Determine the structural formulas of the 2 possible products

when hydrogen chloride reacts with 1-propene.

b) Name both products.

c) State and explain which product is the major product and explain
your reasoning.

d) Write out the mechanism for the reaction between hydrogen

chloride and 1-propene, showing the formation of the major product.

3) Write out the mechanism for the reaction between 1-butene and
BrCl, showing the formation of the major product only.

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Benzene - Physical Evidence of Structure

What are the physical properties that support that

benzene's structure contains delocalized electrons, not
alternating single and double?

Bond Lengths

Isomers

Bond Enthalpies

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Benzene - Reactions & Chemical Evidence of Structure

Molecules with C=C bonds readily undergo addition

reactions.

Benzene, however, more readily undergoes substitution

reactions than addition reactions.

Example - The reaction of Benzene and Chlorine:

Expected Addition Reaction: C6H6 + Cl2 --> C6H6Cl2

Observed Substitution Reaction:

C6H6 + Cl2 --> C6H5Cl + HCl

Electrophillic Substitution Reactions of Benzene

+
The Reaction of Benzene & the Nitronium Ion, NO2 (The
Nitration of Benzene)

Overall Chemical Equation:

C6H6 + HNO3 --> C6H5NO2 + H2O

o
Conditions: Concentrated H2SO4, heated to at least 50 C.

The Reaction of Benzene & Halogens

Overall Chemical Equation & Conditions (example halogen is chlorine):

C6H6 + Cl2 --> C6H5Cl + HCl

Conditions: Mixed with AlCl3 in dry ether

Benzene & Bromination

Without these conditions, benzene does not react with halogens

(including bromine). So a bromination test (and bromination IB
questions), may focus on the differences between alkane, alkene and
benzene reactions for bromine.

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Benzene - Chemical Evidence of Structure

Enthalpies of Hydrogenation

-Theoretical values the hydrogenation of cyclohexene,

cyclohexa-diene and cyclohexa-triene are shown with
dotted lines. These assume addition reactions are
occuring.

-Actual experimental values for cyclohexene, cyclohexa-

diene and benzene are shown in bold lines.

+3H2

+2H2

cyclohexene
+3H2
+H2

cyclohexane

This is further evidence that benzene's structure does

not contain 3 C=C bonds. If it did, the enthalpy change
would be larger (closer to the theoretical value of -360 kJ
-1
mol ).

This can be explained by the delocalized electrons in

benzene. These stabalize benzene, making it have a lower
potential energy (enthalpy) than it would have as
cyclohexa-triene.

-This results in a smaller change enthalpy as it converts to

cyclohexane through full hydrogenation.

.
.

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The Electrophilic Substitution Mechanism

Nitration of Benzene to form nitrobenzene

Conditions: Concentrated HNO3 & H2SO4

+
Electrophile: NO2

+
Formation of Nitronium Ion (NO2 ):

Overall Chemical Equation:

Mechanism (not needed for IB Exam)

Overall Reaction for the nitration of benzene with nitronium:

Reaction Mechanism for the nitration of benzene with nitronium:

Summary Equation & Conditions for the nitration of benzene

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The Electrophilic Substitution Reactions of Benzene

The delocalized pi-electrons in benzene can seek out electron
deficient species (electrophiles) and form new covalent bonds with
those species.

The delocalized pi-electrons are re-established after temporarily

being broken in the carbocation intermediate, releasing a hydrogen
ion in the process.

In the end, the electrophile substitutes for a hydrogen atom on the

benzene ring.

Major reason for Benzene not undergoing addition reactions - the

stabalizing ring of delocalized electrons would be broken if addition
took place, which would be energetically unfavorable.

Potential Energy diagram for Electrophillic Substitution:

Potential Energy

Rxn Coordinate

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Other Benzene Reactions [No Mechanism Required]

Nitrobenzene Reduction to Phenylamine (Aniline)

Reaction 1) Reaction of nitrobenzene with a mixture of

concentrated hydrochloric acid and tin (Sn). This produces
+
phenylammonium ions, C6H5NH3 .

Conditions Needed:

Heating Under Reflux

Concentrated HCl

Tin (Sn)

Overall Change for Nitrobenzene:

Overall Chemical Reaction:

Reaction 2) The phenylammonium ions are reacted with hydroxide

ions (a base/proton acceptor) to remove the extra proton and
produce phenylamine (aniline), C6H5NH2.

Overall Change for benzene-compound:

Overall Chemical Reaction:

Summary 2-Stage Synthetic Route of aniline from nitrobenzene:

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Stereoisomerism: cis-trans & E/Z Isomerism

Stereoisomerism occurs when 2 molecules have the same chemical
formula AND all of the atoms are connected to the same atoms in
each structure.

The difference between the 2 isomers is the orientation of certain

atoms, or groups, in space.

There are 2 major branches of stereoisomerism: Conformational

Isomerism and Configurational Isomerism (IB focuses on this one).
The most important terms to know have been highlighted in red.

Isomerism

Structural Isomerism Stereoisomerism

(includes functional group

isomerism)

Configurational
Conformational
Isomerism
Isomerism

cis-trans and E/Z Optical

Isomerism Isomerism

Conformational isomers are not very important for the IB exam,

but it is relevant to more advanced organic chemistry and it is
helpful to cover them briefly in order to better understand the
difference with cis-trans and E/Z isomers.

Conformational isomers occur when there is rotation around a

single, sigma bond.

Different orientations (staggered and eclipsed) are possible and

have different stabilities. These are the different conformational
isomers.

Sigma bond between carbon

o
atoms allows for 360 of
rotation.

Newman Projections -
Representation of 2 carbon
atoms, looking directly
down the bond axis.

(not needed for IB Exam)

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Cis-Trans & E/Z Isomerism

Isomers where all atoms are connected to the same atoms, but in
which certain atoms/ groups are oriented differently due to a bond
with restricted rotation. The two terms (cis-trans & E/Z) are siply
different naming systems for this same type of isomerism.

Alkenes
Bond restriction occurs with C=C double bonds, as the nature of the
pi-bond relies on parallel p-orbitals. Rotating would break the pi-
bond.

Cis-Trans Naming

Cycloalkanes
Bond restriction also occurs with cycloalkanes, as at least 1 sigma-
bond would need to be broken for another bond to rotate.

Cis-Trans Naming

Not every alkene or cycloalkane has cis-trans or E/Z isomerism.

Sometimes there is only 1 possible structure, so these naming
additions are not needed. This is relevant for many of the examples
listed above (ethene, cyclopropane, etc.) as well as examples like
that shown below.

But-1-ene

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Cis-Trans Practice
For the following molecules:
i) Determine if the molecule does, or does not, have cis-trans forms
ii) If it does: Draw & Name both the cis and trans isomers.

1.) 1,2-dichloropropene

2.) Pent-2-ene

3.)1,2- dichlorocyclopropane

4.) Propene

5.) 1,1-difluorocyclopentane

6.) 1,3-dichlorocyclobutane

7.) 1,2-dichlorobenzene

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E/Z Isomers
The E/Z system is also used for isomers that are possible due to
bonds that cannot rotate. It is mainly used when the cis-trans
would not give as clear or obvious names.

Example: 2-bromo-1-chloro-1-fluoroethene

HIGHER PRIORITY
In the E/Z system, it is necessary to identify which atoms/ groups
have (Cahn-Ingold-Prelog) PRIORITY on each side of the restricted
bond.

-Higher priority goes to the atom with the higher atomic number

st
-If the 1 atom is the same, then continue on to the next atom in
the chain, and check again for atomic number. Higher priority goes
to the atom with the higher atomic number at the first point of
difference.

Once priority is established, you can determine whether the isomer

is E or Z.

E – The highest priority atoms/groups are on opposite sides of the

bond (sort of like trans) (Think: they are "Enemies")

Z – The highest priority atoms/groups are on the same side of the

bond (sort of like cis) (Think: on "Zee Zame Zide")

E/Z Names

2-bromo-1-chloro-1-fluoroethene 2-bromo-1-chloro-1-fluoroethene

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Practice E/Z Naming

For the following molecules:

i) Determine if the molecule does, or does not, have E/Z forms
ii) If it does: Draw & Name both the E/Z isomers.

1.) 1-bromo-1-chloropropene

2.) 2-bromo-1,1-dichloroethene

3.) 3-methylpent-2-ene

4.) 4-methylhept-3-ene

5.)1-bromo-1-chloro-2-fluoro-2-iodocyclobutane

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cis-trans & E/Z Isomers: Differences in Physical Properties

The direction that structures within molecules are oriented can have
a direct impact on the strength of their intermolecular forces, which
in turn affect their physical properties.

Effect on Polarity & Dipole-Dipole Forces

Effect on Straightness/ Surface Area & London Forces

cis-but-2-ene-1,4-dioic acid

Effect on the ability to Hydrogen Bond between molecules

cis-but-2-ene-1,4-dioic acid trans-but-2-ene-1,4-dioic acid

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cis-trans & E/Z Isomers: Differences in Chemical Properties

cis-but-2-ene-1,4-dioic acid - Upon heating, undergoes condensation
reaction with itself, forming an anhyride.

+ H 2O

trans-but-2-ene-1,4-dioic acid - Upon heating, undergoes melting. No

chemical reaction.

(s) (l)

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Stereoisomerism: Chirality & Optical Isomerism
Optical isomerism occurs when a molecule contains one or more
carbon atoms that are bonded to 4 unique atoms/ groups.

A carbon atom with 4 unique attachments is known as a chiral

carbon atom. The molecule is also said to display chirality or be
chiral (the term comes from the Greek term related handed-ness)

Chirality allows for 2 different spatial orientations of the 4

attachments around each chiral carbon atom, both of which are
asymmetric.

When there is just one chiral carbon in the molecule, then there
are only possible two optical isomers, which end up being non-
superimposable mirror images of each other. These types of
optical isomers are more specifically referred to as enantiomers.

Stereochemical Dash-Wedge Structural Formulas:

Optical Isomers: Differences in Properties

Differences in Physical & Chemical Properties:

-As optical isomers have essentially the exact same 3-D structural
(often just mirror images of one another), their physical and
chemical properties are identical under normal circumstances.

*Their only physical property difference is that they rotate plane

polarized light in opposite directions. This is where the term
"optical" isomers come from.

Chiral-Specific Properties:

-Different optical isomers will react differently with other species

that ALSO contain chiral carbon atoms.

-This is of special importance and relevance in biochemical

processes, where enzymes and receptors will only work effectively
. well with) one optical isomer. In fact, biochemistry is so highly
(fit
stereospecific that often only one enantiomer is produced and used
in nature!

Amino Acids Carbohydrates

L-Alanine D-Alanine

-What we think of as "carbs"

-Major component of
are composed almost entirely cellulose & Dietary Fiber,
of long chains of alpha which our bodies lack the
glucose enzymes to digest

-Our main unit of energy

-Only energy source for the

brain

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Identifying Chirality & Drawing Enantiomers
For the following molecules:
-Draw all structural isomers.
-Identify any molecules that display optical isomerism/ chirality.
-Mark the chiral carbon with a “*”.
-Draw the enantiomers for the chiral molecules using the
stereochemical structural formula (dash-wedge).

Class Example: Butanol

1. Chloropentane

2. Trifluoro propane

3. Pentanol

Chiral Carbons in larger structures

Identify any chiral carbon atoms with a “*” in the following
structural formulas. There may be more than one!

D - Glucose Serine Vitamin C

(ascorbic Acid)

Ibuprofen Thalidomide

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Optical Isomers: Distinguishing Enantiomers

Polarimeter - A Device that can distinguish between

optical isomers (enantiomers). It measures the angle
that plane polarized light gets deflected.

Plane polarized light - Light that is oscillating in only

1-direction. Achieved using a polarizing filter.

Enantiomers - Pure samples of 1 enantiomer will rotate plane

polarized light by the same angle, but in opposite directions.

Light rotated by +𝜽

Light
Light rotated by -𝜽
Source

Small rotation
to the left

A Racemic Mixture is a 50:50 mixture of two enantiomers.

If both enantiomers are present in equal concentration, then their

rotary effects will cancel each other out, and the mixture will not
be optically active.

How can 2 enantiomers be distinguished? (Mark Scheme Wording)

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Optical Isomers & Nucleophillic Substitution Mechanisms
Stereoisomerism

SN1 SN2

Non-stereospecific Stereospecific

carbocation is planar and The "backside attack" inverts

can be attacked by stereoisomerism for chiral

nucleophile from either side. halogenoalkanes.

One enantiomer of a chiral One enantiomer of a chiral

halogenoalkane will produce halogenoalkane will produce

a racemic mixture of alcohols one enantiomer of an alcohol

that is not optically active. that is optically active.

This is especially relevant for secondary halogenoalkanes as they

are often chiral and can undergo either mechanism

Practice:

2-chlorobutane is an optically active compound that can undergo

nucleophillic substitution by both SN1 or SN2 mechanisms to form
butan-2-ol. Butan-2-ol can exist as two enantiomers that rotate
o
plane polarized light by +/- 40 .

Upon completing the above reaction, the products can be tested

using a polarimeter. Explain the meaning of the following results
with regard to the mechanisms above.

a) No optical activity is detected.

o
b) An angle of -40 is detected.

o
c) An angle of -20 is detected.

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More than one chiral carbon atom: Diastereomers
If there is more than one chiral carbon in the same molecule, then
there are more than 2 optical isomers possible (theoretically there
n
are 2 isomers possible, where n= # of chiral carbons. Not all of
them may actually exist).

In this scenario it is possible to have optical isomers that are not

enantiomers (mirror images) of each other.

Molecules that are optical isomers of each other, but NOT mirror
images of each other, are known as diastereomers.

*This topic is not of major importance on the IB Exam. You will not
be asked to draw diastereomers, but it doesn't hurt to have seen
this vocab term.*

Both chiral carbons inverted

1 inverted 1 inverted

chiral carbon chiral carbon

Both chiral carbons inverted

Practice Examples:

- Draw all optical isomers & determine which are enantiomers and
diastereomers.

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Unit 7 Topic List

Classes of Organic Compounds, Isomerism & IUPAC Naming

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SL Reactions and Mechanisms

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HL Reactions and Mechanisms

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Stereoisomerism

61