7.

ORGANIC CHEMISTRY
ORGANIC MOLECULES:
An organic molecule is any molecule that contains carbon atoms with the exceptions of carbon dioxide,
diamond, graphite, carbonates, carbides and cyanides.
All living matter contains organic compounds.
FUNCTIONAL GROUPS AND HOMOLOGOUS SERIES:
activity in the molecule.
Afunctional group is an atom or a group of atoms that form the centre of chemical
same functional group and have the
A homologous series is a series of similar compounds which have the
a single CHz unit.
same general formula, in which each member differs from the previous onc by

CARBON:
Carbon atoms have a valency of four. This means it makes four bonds.
When carbon atoms bond they can form single, double and triple bonds as shown below.
Single bond Double bond Triple bond

Alkane Alkene Alkyne (not examined in IEB)

(saturated) (unsaturated) (unsaturated)

A hydrocarbon is a compound which contains only carbon and hydrogen atoms.

thc homologous
If all the bonds between carbon atoms are single the compound is saturated and belongs to
series AIkanes.
Alkanes have the general formula: CHH2n+2
belongs to the
If there are any double bonds between two carbon atoms. the compound is unsaturated and
homologous series AIkenes (see below).
Alkenes have the general formula: C,H2n
The general formula for an alkene only applies if there is one double bond in the compound.
Only one double bond is considered when using the general fornmula for alkenes.
If there are any triple bonds between two carbon atoms, the compound is unsaturated and belongs to the
homologous series Alkynes (not examined in IEB).

The homologousseries andFunctional groups examined in IEB are summarised in the table below:
Homologous Series
Functional Group
Structure Name/ Description
Alkanes Saturated Hydrocarbon

Alkenes Double carbon-carbon bond

Haloalkanes -F -Br Halogen atom bonded to a

(Alkylhalides) -CI -I carbon atom

Alcohols -0-H Hydroxyl group

Carboxylic acids -C-0-H Carboxyl group

Esters
-0-C Ester group
 NAMING ORGANIC COMPOUNDS:
Every organic compound consists of 3 parts:
1. Substituent Prefix
2. Root
3. Suffix substituent prefix Root Suffix

Steps to naming organic compounds:

1. Locate the longest carbon chain
(The longestcarbon chain must contain any functional groups and double bonds)
2 Number he longest carbon chain with carbon number l being closest to the functional group
When numbering carbons the order of prcfcrence is functional group, double bonds then
substituent.
Always number carbons so that they have the lowest possible number following the correct
order of preference.
When numbering according to substitucnts, halogens do not get preference over alkyl groups.
Numbering must give the lowest value tothe substituents.
If two halogens have the same number when numbered from different ends of the chain the
carbons must be numbered according to alphabetical order of the halogens.
3. Name the longest chain according tothe number of carbons in it. This is the root name.
4 Name the suffix according to the functional group. Halogens are named as a substituent prefix.
5. Name alkyl and halogen substituents according to the above rules. These are the prefix in the name.
6. If there is more than one identical substituent use the prefix di- (for two) or tri- (for three).
1. Write the substituents in alphabetical order in the name of the compound ignoring the prefix di or
tri.
Number of carbon Atoms Name of Alkane
Root Name
in the main chain (without substituents or functional groups)
1 Meth Methane

2 Eth Ethane

3 Prop Propane
But Butane

Pent Pentane

6 Hex Hexane

7 Hept Heptane
Oct Octane

Numbers are separated by commas

Numbersand letters are separated by dashes
Dashes are never used to separate letters and there are never spaces between letters except for
esters.

Number of Substituent
Name Formula
Substituent substituents Prefix

Methyl CH, 2 di
(lcarbon atom in the side chain)
Alkyl
(side chain) Ethyl
chain) CH,CH) tri
(2 carbon atoms in the side
Fluorine: fluoro F
Chlorine: chloro C 4 tetra
Halogen Bromine: bromo Br
lodine: iodo
main chain.
A maximum of three substituent chains are allowed on the
406
CCon
 NAMING EXAMPLES:
Condensed Structural
Name Structural formula
Formula

H H H
CH,CH;CH;
propane H- -C-C-H
H

H
H-C-H
H H H
I-YIH CH;CH(CH)CH;CH,CH;CH
2-methylhexane
C- - -C-H
H H H H H H

H H
CH,CHCH,CH,
but-1-ene H-=C -I
-C C-H
H H

H H H H
CH,CHCH,CHCHCH,
hexa-1,4-diene H-C=- -c =C-C-H
H

H CI H
T--I
I--=
H- - - -H CH;CHCCH,
2-chloropropane
H H H

H-C-C- -C-H CH,CCCHCCCH;

1,2-dichloropropane
H H

H H

4-bromo-3-iodobut-1-ene -U-I -C-C-H CH,CHCHICH,Br

H H Br

H
H-Ç-H
H-C-H
3-methylhexane H H I H CH,CH,CH(CH;)CH,CH;CH;
H-C- C C C-H
H H H H

H
HÇ-H
H-C-H
4-methylhex-1-ene H H H CH;CHCH,CH(CH,)CH;CH;
H -C-H

H H H

Prefixes are written in alphabetical order irrespective of the carbon they are attached to.
Always use the longest chain for the root name.
longest chains do not have to be in a straight line. Double bonds must be in the longest chain
Double bonds take preference over substituent prefixes while numbering carbons.
Thecarbons must be numbered so that the double bond has the lowest possible numbering.
for dienes,
For cuphonic purposes, the vowel "a" must be added to the name before the suffix
c.g. buta- 1,3-diene is correct,and but-1,3-diene is incorrect.

407 -
CCopyrnght Kevin Smith
NAMING ALCOHOLS AND CARBOXYLIC ACIDs
Naming Alcohols
Suffix -ol is added to the cnd of the root name Naming Carboxylic Acids
Suffix -oic acid is added to the end of the root
name
2. For cuphonic purposes, the vowel "e" is
removed from the name before the suffix. 2. Carboxylic acids are never numbered as they
e.g. butan-1-ol not butane-1-ol. howcver, this can only be on the cnd of a chain.
is not done for diols, e.g. butane- 1.2-diol is
correct, aund not butan-1,2-diol
ALCOHOL EXAMPLES:
Name Structural formula Condenscd Structural Formula

Methanol
or
Methan-l-ol
H-C-0-H CH,OH
H

Ethanol H H
or
Ethan-1-ol
H----0-H CH,CH;OH
H H

H HI-0-I
H

Butan-1-ol H- --C-0-H CH,CH,CH,CH;OH

H H H H

H
I-0-u
H H
Pentane-1,3-diol I-)I-)I H
CH,CHOHCH;CH;0H
H-¢--c-c-0-H
H H H

H H
Propane-1,1-diol CH,CH,CH(OH):
H H
-0-H
H

CARBOXYLIC ACID EXAMPLES:

Name Structural formula Condensed Structural Formula

Methanoicacid H-C-0-H
HCOOH

Ethanoicacid H-C-C-0-H CH,COOH

H
I-Y-I
I-9-ITI
Butanoic acid
1
H-Ç-ç--c-0-H CH,CH;CH;COOH
H H

H H H H

Hexanoic acid H-C -Ç-Ç-Ç-C-c-0-H CH,CH;CH;CH;CH,COOH

-I -I
H H H H
FORMATION OF ESTERS
An ester is formed by a condensation reaction between an alcoholand carboxylic acid.
For the reaction to oceur, the carboxylic acidand alcohol must be heated with concentrated sulfuric
acid (H;SO:).
The sulfuric acid acts as a catalyst and dehydrating agent in the reaction.
Ester Link
H H H H H H

H-C--C-0-H +
H-0-C-C--c-H ’ H-C-C-0-C-C-C-H H
H H H
When an ester fons, the hydroxyl group (OH) from the carboxylic acid and the hydrogen from the hydroxyl
of the alcohol are removed from the molecules and bond to forn water.
NAMING ESTERS
Esters are named according to the alcohol and carboxylic acid they are formed from.
Thefirst part of the name comes from the aleohol and end with letters -yl.
The second part of the name comes from the carboxylic acids and ends with the letters -oate.
When naming esters, break the ester at the oxygen atom between two carbons. This is shown as the ester
link on the above diagram. The portion that has the double bond oxygen comes from the carboxylic acid and
ends in -oate while the other part comes from the alcohol and ends in -yl.
For the diagram above the ester formed would be called ethyl propanoate.
The tablc below shows the names and structural formulas of various esters as well as the alcohol and carboxylic
acid which the ester was formed from.

Name of Ester Structural formula Alcohol Carboxylicacid

H H

methyl ethanoate H-C-0-C--C-H methanol cthanoic acid

ethyl methanoate H-C-C-0-(-H cthanol methanoic acid

H H

HH H HH HH
ethyl hexanoate H-C-C-0-C-C-C-(-C--H ethanol hexanoic acid
H H HH H H H
HH H H 9 H H
butyl propanoate H-C-C-C-C-0-C-C-C-H butan-1-ol propanoic acid
H # HH HH
H HH HH
propylpropanoate H-C-C-C-0-C-C-C-H propan-|-ol propanoc acid
H H H H H

H H H H

methyl butanoate H-C-0-C-C-C-(-H methanol butanoic acid

H H H H

H
H
propyl methanoate H-C-(--C-0-C-H propan-|-ol methanoc acid
H
 ISOMERS
Structural isomers are compounds which have the same molecular formuia but different
formula. You are equired to identify structural isomers of compounds structural
with up to 8 carbon atoms.
There are 3typesof structural isomers that w1ll be cxam1ncd:
1 Chain Isomers
2. Positional Isomers
3. Functional Isomers.
CHAIN ISOMERS
Chain isomers have different structures due to branching. In other words, they are isomers duc lo
chains on the molecule. The thrcc chain isomers of pentanc are shown below. side

H H H H H

H-C-C -C-CH |-C-C-(-H

H I|-(-(-(-c-H
H H H
Pentanc
2-methylbutanc
2.2-d1methy Ipropanc
POSITIONAL ISOMERS
Positional isomers have different positions of the same functional group on thc parent chain.
Exanples of two positional isomers are shown.
H CI H H H H H H

H-C-c-H H-C=C-C-C-H H-C-C-0-C-H

H H H H
H
but-I-ene cthyl methanoate
2-chloropropane

CI H H H
H-C-0-C-(-H
H- -- -H H-¢-(=¢-¢-H
H H H H
H H H
but-2-ene methyl cthanoate
1-chloropropane

FUNCTIONAL ISOMERS
but contain diflerent functional groups.
Functional isomers have the same molecular formula isomers required in matric.
Carboxylic acids andesters are the only functional shown below
(CiH0:) and ethyl methanoate (CH.O,) are
The functional isomers propanoic acid
H H
H
H-0-C-i--H H-C-C-0-C-H

H
H H
ethylmethanoate
propanoc acid
 REACTIONS
COMBUSTION (OXIDATION) REACTIONS
exothermic.
Combustion reactions with alkanes, alkenes and alcohols are when they
cncrgy into hcat and cnergyapplications
transfer alarge amount ofchemical potential
rossil Tucls(such asoil) in an abundance of
This is the reason fossil fucls are used
re burnt in the prescnce of oxygen,
such as the powering of motor vchicles and aeroplanes. combustion of alkanes, alkenes
rcquired to write balanced chemical cauations of thecomplete always carbon dioxide
ToU are products of these combustion reactions arc
nd aicohols with excess oxygen. The
and water.
Steps to balancing combustion reactions:
I. Balance carbons and hydrogens first. necessary.
last. Use a fraction with division by 2 if
2 Balance theoxygen on the left-hand side all numbers by Z.
3 IT the balancing number for oxygen isa fraction, multiply
Examples of balancing combustion reactions are shown below:
complete combustion of hexane.
Example 1: Write down a balanced equation for the
CoHj4 + O, ’ CO, + H;0
Step 1: balance carbons and hydrogens first:
on the right-hand side)
CoHa + O; ’6CO, + 7H,0 (you are now left with 19 oxygens
Step 2: balance Oxygens on the left-hand side last:

CGHj4 +0,
19, ’ 6CO, +7 H,0 (you cannot have a mole ratio as a fraction)
2
Step 3: if the balancing number for oxygen is a fraction multiply by 2:
2C,H)4 + 190, -- 12C0, + 14H,0

Example 2: Write down a balanced equation for the complete combustion of hexene.
CoHi2 + O, ’CO, + H,0
Step 1: balance carbons and hydrogens first:
CoH)) +O, ’6CO, + 6H;0 (you are now left with 18 oxygens on the right-hand side )
Step 2: balance oxygens on the left-hand side last:
CoH) + 90, -’ 6C0, + 6H,0

Example 3: Writedown abalanced equation for the complete combustion of propanol.

C;H,OH +O, ’ CO, + H,0
Step 1: balance carbons and hydrogens first:
CHOH +O, ’ 3CO, +4H;0 (you are now left with l0 oxygens on the right-hand side)
Step 2: balanceOxygens on the left-hand side last:
9
C;H,OH +0,
2
’ 3CO, +4H,0
Step 3: if the balancing number for oxygen is a fraction multiply by 2:
2C,H,OH +90, ’ 6CO, +8H,0
 SUBSTITUTION REACTIONS
Asubstitution reaction occurs when an
substitution reactionsexchange
There are two typcs of of atoms in the
you are required to rcactants takes place.
, Halogenation (frec radical halogenation ) know.
2. Hydrolysis

1. Halogenation:
lalogenation occurs when an alkane reacts with a
substitution halogen to fom ahaloalkane.
This is a reaction which requires heat or
UV
When halogenation 0ccurs, a hydrogen from the alkane is light.
Anexample of a halogenation reaction is shown substituted with one of the atoms in the halogen.
below.
HHHH
H-C-C-C-C-H + Cl-CI UV light
H-C-C-C-C-H + H-CI
H H H H
H H H CI
Butane
| -Chlorobutane
Halogenation is a 'slow' reaction which requires the presence of heat or UV light.

2. Hydrolysis:
Hydrolysis occurs when a haloalkane is heated under reflux with a dilute base to form an alcohol.
An Example of a hydrolysis reaction is shown below.
I-0 I
H H Br H H

H-C-C-C-H + Na-Br
H-¢-¢-¢-H + NaOH

H H H H H H

1-Bromopropane I-propanol
The alcohol that forms during hydrolysis has a low boiling point and willturn into a gas when
exposed to high heat. Heating under reflux means that a condenser is attached to the reaction
vessel so that any alcohol vapours formed during the reaction, condense and fall back into the
reaction vessel.

ADDITION REACTIONS
molecule. All
Addition reactions occur when a double bond is broken, and atoms are added onto a
addition reactions occur with alkenes.
know.
There are four types of addition reactions you are required to
1. Hydrogenation
2. Halogenation
3. Hydrohalogenation
4. Hydration

When two addition products are possible, either will be accepted

I. Hydrogenation:
alkene.
iydrogenation occurs when hydrogen (H) is added to any
The alkene must be dissolved in an organic solvent with a platinum (P), Nickel (Ni) or palladium (Pd)
catalyst.
Anexample of a hydrogenation reaction is shown below.

H-ç=C-C-C-H + H-H H-C-C-C-C-H

|
H H H H H

but-1-cne butane
2. IMalogenation:
Halogenation occurs vwhen a halogen (F. Cl, Br; or l2) is added to any alkene.
An example of ahalogenation reaction is shown below.
H-C-C-C-C-H
H-C=C-C-C-H + Br-Br

H H Br Br H H
1,2-dibromobutane
but-|-ene
an alkene, it will rapidly
Addition reactions take place quickly. If bromine water added to
decolourise as the double bonds of the alkenc are broken.
and is used to distinguish between an
This is usually called the bromine test for saturation
alkene and an alkane.

3. Hydrohalogenation:
alkene.
Hydrohalogenation occurs when a hydrogen halide (HF, HCL, HBr or HI) is added to any this
Water may not be present in reaction.
Anexample of a hydrohalogenation reaction is shown below.
H H H H
H-C-C-C-C-H
H-C=C-C-C-H + H-1

H H H H H

but-1-ene 2-iodobutane

4. Hydration:
Hydrationoccurs when water (H;0) is added to any alkene in the presence of stcam and a suitable catalyst
such as phosphoric acid (H,PO).
Ancxample of ahydration reaction is shown below.

H-C=C-C-C-H + H-C-C-C-C-H
H H
H H H O H H
but-1-ene H
butan-2-ol
ELIMINATION REACTIONS:
Elimination reactions take place when atoms or molecular fragments are removed from adjacent atoms in
a molccule which forms an alkene. These reactions are the opposite of addition.
There are three types of climination reactions you are requircd to know.
1. Dehydrohalogenation
2. Dehydration
3. Cracking of hydrocarbons

When two elimination products are possible, either will be accepted.

1. Dehvdrohalogenation:
Dehydrohalogenation occurs when ahydrogen halide (HF, HCL, HBr or H) is removed from a
haloalkane.
Dehydrohalogenation takes place in asolution of hot concentrated sodium hydroxide (NaOH) or
potassium hydroxide (KOH) dissolved in ethanol. No water can be present in the reaction.
The balanced equation for dehydrohalogenation can be written in two ways:
a) Where the base (NaOH or KOH)docs not take part in the reaction,.
b) Where the base (NaOH or KOH) takes part in the reaction and a salt and water are formed
Examples of cach of these reactions are shown over the page.

If asked to write a balanced equation for dehydrohalogenation, either reaction (ith

or without the base taking part)would be acceptable.
 a) Dehydrohalogenation where the base does not take Dart in the reaction.
H-C-C-C-C-H| H-C-C-C=C-H + ||-CI
H HH c H I|
|-chlorobutane but-1-ene
h) Dehydrohalogenation where the base (akes part in the reaction.
H-CC-C-C-H + NaOH H-C-C-C=(-H + NaCt + I,0
H H H CO
HH
1-chlorobutane Salt water
but-1-cne
2. Dehvydration:
Dehydration occurs when water is removed from an alcohol.
Dehydration requires the heating of an alcohol with an excess of concentrated sulfuric acid (H2SO) or
phosphoric acid (HPO) which acts as a catalyst.
¢n example of a dehydration reaction is shown bclow.
H H
H-C-C-0-H H-C=C-H +
H H
ethan-1-ol cthene water

3. Cracking of bydrocarbons:
Short chain hydrocarbons are useful as fuel as they undergocombustion more readily. Crude oil (which
petrol is made from) is made up long chain hydrocarbons.
The process of cracking breaks up long hydrocarbon chains into smaller, useful hydrocarbons.
The products of ceracking are a smaller hydrocarbon and one or more smallalkenes.
There are two types of cracking:
1. Thermal cracking
2. Catalytic Cracking
Thermal cracking takes place under high pressures and temperatures without a catalyst.
Catalytic cracking takes place at lower temperatures and pressures in the presence of a catalyst.
An example of cracking is shown below.

H-C-C-C-C-C-C-H H-C-C-C-H + H-C=C-C-H

H H H H H H H
H H
propane prop-|-ene
hexane
CONDENSATION REACTIONS (ESTERIFICATION)
for clarity with additional infomation
Esterification has already been covered on page 409 and is repcated here
on esters.
reaction between an alcohol and carboxylic acid.
An ester is formed by a condensation heated with concentrated sulfuricacid
For the reaction to occur the carboxylicacid and alcohol must be
dehydrating agent in the reaction.
(H:SO.). The sulfuric acid acts as a catalyst and
hydroxyl
When an ester foms. the hydroxyl group (OH)from the carboxylic acid and the hydrogen from the
moleculcs and bond to form water.
the
of the alcohol are removed from
reaction is shown below.
Anexample of acondensation
Tster Lnk
H H
H H
H H
H-0-(---H’H-C-(-0-(-(-H
H-C-C-0-H +

H H H H H
H
H
propanoic acid ethylpropanoate water
cthan-1-ol
 INTERMOLECULAR FORCES IN ORGANICCHEMISTRY
Latermolecular forces are weak forces of attraction bctween molecules or between atoms of
Intermolecular forces exist between molecules in the solid, liquid or gas phase. noble gases.
Thestrength of the forces increases as molecules change phases from
As the strength of the intermolecular forces increase so do the gas to liquid to solid phase.
molecule. This is because more energy is rcquired to overcome the melting and boiling points of he
The strength of the intermolecular forces increases as molecules forces.
As molecules increase in size, the number of electrons increase in size.
incrcase.
This results in a greater electron density and greater interactive surface.
This causes themolccules to form larger temporary dipoles which last
longer.
This causes stronger forces of attraction betwcen the molecules.
Thetable below summarizes the intermolccular forces which cxist between organic
molecules.
Type of intermolecular
force Force Properties Forces Exist Between
Occurs between highly polar molecules
wherc hydrogen is bonded to nitrogen, 1. Alcohols
OXygen or fluorine.
(onc bonding site)
Hydrogen Bonding
Strongest intermolecular force between 2. Carboxylic Acids
organic molecules. (two bonding sites)
High boiling point
Stronger than London forccs but weaker
than hydrogen bonds.
Esters
Dipole-Dipole Higher boiling point than London forccs
Van but lower than hydrogen bonding. 2. Alkyl Halides
der Acts between polar molcculcs.
Waals Act between non-polar molecules
Forces
London Forms temporary (momentary) dipolcs Alkanes
between molecules.
Forces 2 Alkenes
Weak intennolecular forces with low
boiling points.

The intermolecular forces between carboxylic acids are stronger than those betwcen
alcohols since carboxylic acids have two sites for hydrogen bonding to occur.
This means that carboxylic acids have a higher melting and boiling point than alcohols
(of the same chain length) as more energy is required to overcome the intermolecular
forces.
Branches (sidechains) decrease the interactive surface area for intermolecular forces to
take place and lowers the strength of these forces.

When explaining the difference in boiling points between molecules, vou bave to so.
moreenergy is required to OVERCOME the forces between molecules

DO NOT say break bonds between molecules as no bonds arebeing broken. It is merev
aforce of attraction between molecules that is being overcome.,
 des ) des) t dry)

Long alkane broken into smaller alkanes and alkenes

There are 2 types of cracking:
Copynght C 1.Thermal cracking: High pressure and temperaturc
2. Catalytic Cracking: Requires a lower temperature and pressure than themal cracking SUMMARY
General Type of Reaction: Elimination
Kevin
Specific Type\Name of Reaction: Cracking
X, isF,, Ci,, Br, or i,
HX is HE, HCI, HBr or HI
Smth
Gencral Type of Reaction: Substitution with X,
OF
Alkane
Specific Type\Name of Reaction: Halogenation
Reaction Condition: Ultraviolet light or Hcat
ORGANIC
General Type ofReaction: Addition of H,
Specific Type\Name of Reaction: Hydrogenation
Catalyst: Pt, Pd or Ni
General Type of Reaction: Addition of H-X
Specific Type Name of Reaction. Hydrohalogenation
Reaction Condition: No water present
REACTIONS
Reaction Condition: Alkene dissolved
in organic solvent
General Type of Reaction: Addition of X,
415. Specific TypelName of Reaction: Halogenation
co, + H,o Alkene Haloalkane
General Type of Reaction: Elimination of H-X
General Type of Reaction: Combustion
Specific Type Name of Reaction: Dehydrohalogenation
Specific Type\Name of Reaction: Oxidation Reaction Condition: Hot concentrated solution
Reaction Condition: Heat and Oxygen of NaOH or KOH dissolved in
ethanol. (Water cannot be present)
General Type of Reaction: Elimination of H,O General type of reaction: Addition of H,0
Specific Type\Name of Reaction: Dehydration Specific Type Nameof Reaction: Hydration
Reaction Condition: Heat with excess Reaction Condition: Steam
H,SO, or H,PO,
Catalyst: H,PO,(there are many suitable cataly sts)

General Type of Reaction: Substitution with a dilute base

CarboxylicAcid Alcohol
Specific type Name of Reaction: Hydroly sis
Reaction Condition: Heat under reflus (base must be dilute)

General Type of Reaction: Condensation Specific TypeName of Reaction: Esterification

Reaction Condition: Heat Catalyst: Concentrated H,SO, (Sulphuric acid)
Ester + H,O