O

IB CHEM SL TOPIC 10

rganic Chemistry
 Features of Members of a Homologous Series

1. With the same functional group

Example
All alkenes have carbon carbon double bond

2. With the same general formula

Example
The general formula for alkane is CnH2n+2

3. Each successive member differs from a CH2 unit

Example
The formula of propane is CH3CH2CH3 and that of butane is
CH3CH2CH2CH3
 Features of Members of a Homologous Series (Cont’d)

4. With similar chemical properties

Example
All alkene can undergo addition reactions.

5. With a gradual change in physical properties

Example
Boiling point increases down a series
Explanation
Molecular size increases down a series
 van der waals’ force increases
 boiling point increases
 Examples of Homologous Series
Note:
1. X represents numbers
2. IUPAC naming for the homologous series shaded in purple is not required.
Homologous Functional General Naming
series group formula
Alkane No CnH2n+2 -ane
Alkene CnH2n -X-ene
C C

Haloalkane Cl / Br --- X -chloro- /

X- bromo -
Alcohol O H CnH2n+1OH -an-X-ol
Carboxylic O CnH2n-1COOH -anoic acid
acid
C O H
Aldehyde O CnH2n-1COH -anal
C H
Ketone O CnH2n-1COH -an-X-one
C
Ester O --- ---
C O
Amine NH2 --- ---
Benzene --- ---
 Formulas for Organic Compounds

Formulas Descriptions Examples (butane)

Empirical Show the simplest ratio of C2H5
formula the atoms present
Molecular Show only the atoms present C4H10
formula but not the bonds
Structural Show every atoms and bonds H H H H
formula
H C C C C H

H H H H
Condensed Same as structural formula CH3(CH2)2CH3
Structural but with bonds omitted
formula
IUPAC Naming
 Alkyls Name
CH3– Methyl-
CH3CH2– Ethyl-
CH3CH2CH2– Propyl-
CH3CH2CH2CH2– Butyl-
Isomerism
Isomers are compounds with the same molecular formula but with
different arrangements of atoms.
Isomers of Alkane with 4 Carbons
Isomer H H H H H CH 3 H

H C C C C H H C C C H

H H H H H H H
Name Butane methylpropane
Isomers of Alkane with 5 Carbons
H H H H H H CH 3 H H CH 3 H
Isomer H

H C C C C C H H C C C C H H C C C H

H H H H H H H H H H CH 3 H

Name Pentane (2-)methylbutane Dimethylpropane

Isomerism (Cont’d)
Isomers of Alkane with 6 Carbons
H H H H H H H CH3 H H H CH3 H
Isomer H H H

H C C C C C C H H C C C C C H H C C C C C H

H H H H H H H H H H H H H H H H

Name hexane 2-methylpentane 3-methylpentane

 Isomer H H CH 3 H H H CH 3 H

H C C C C H H C C C C H
H H CH 3 H H CH 3 H H
Name 2,2-dimethylbutane 2,3-dimethylbutane

Isomerism (Cont’d)
(Straight Chain) Isomers of Alkene with 4 Carbons
Isomer H H H H H H H H

H C C C C H H C C C C H

H H H H
Name but-1-ene but-2-ene

(Straight Chain) Isomers of Alkene with 5 Carbons

 Isomer H H H H H H H H H H

H C C C C C H H C C C C C H

H H H H H H
Name pent-1-ene pent-2-ene

Isomerism (Cont’d)

(Straight Chain) Isomers of Alkene with 6 Carbons

H H H H H H
Isomer H H H H H H

H C C C C C C H H C C C C C C H

H H H H H H H H

Name hex-1-ene hex-2-ene

 H H H
Isomer H H H

H C C C C C C H

H H H H
Name hex-3-ene

Primary, Secondary and Tertiary Alcohol

Primary Secondary Tertiary

Description OH attached to the OH attached to the OH attached to the
C atom with only C atom with only C atom with three
one alkyl group two alkyl groups alkyl groups
Example H H H H OH H H OH H

H C C C OH H C C C H H C C C H

H H H H H H H CH 3 H

Primary, Secondary and Tertiary Haloalkane

Primary Secondary Tertiary

Description X attached to the C X attached to the C X attached to the C
atom with only one atom with only two atom with three
alkyl group alkyl groups alkyl groups
Example H H H H Cl H H Cl H

H C C C Cl H C C C H H C C C H

H H H H H H H CH 3 H

Physical Properties of Organic Compounds

Melting / Explanation
Homologous
Solubility boiling Volatility (attractive forces
series present)
point
Alkane Low Low High Van der waals’
 Alkene force only
Haloalkane Low Dipole dipole
Aldehyde Medium Medium attraction
Medium
Ketone
Alcohol High High H bonds
Carboxylic Low
Very High High Many H bonds
acid

Organic Reactions: Any Organic Compounds

Combustion
Comparison between complete and incomplete combustion
Complete Incomplete combustion
combustion
Conditions With sufficient O2 O2 insufficient / for large
hydrocarbons
Products CO2 + H2O CO / C + H2O

Note: CO is toxic as it combines with heamoglobin in RBC  O2 carrying

capacity of RBC decreases.

Organic Reactions: Alkane (-ane)

Free Radial Substitution *

Alkane + Halogen (Cl2 / Br2)  Haloalkane + Hydrogen halide

Example:
CH4 + Cl2  CH3Cl + HCl
or CH3Cl + Cl2  CH2Cl2 + HCl
or CH3Cl2 + Cl2  CH2Cl3 + HCl
or CHCl3 + Cl2  CCl4 + HCl (in excess Cl2)

(1) UV light needed to form radicals

(2) One halogen can only substitute ONE hydrogen atom
(3) A mixture of haloalkanes is produced
Organic Reactions: Alkane (-ane)
Free Radial Substitution*
Mechanism
Chain Initiation (UV light required) Homolytic fission

Homolytic fission: molecules are split into two identical radicals

Chain Propagation

Chain Termination
OR

Organic Reactions: Alkene (-X-ene)

Addition Reaction
1.
Alkene + Halogen (F2 / Cl2 / Br2 / I2)  Dihaloalkane
Example:
(1) Observation: Halogen is decolourised
(2) A test for unsaturation (double or triple bonds)
(3)  light to prevent substitution

Organic Reactions: Alkene (-X-ene)

Addition Reaction
2.
Alkene + Hydrogen  Alkane
Example:
(1) Ni (Catalyst) / 150C
(2) Application: (Hydrogenation) convert double bonds in liquid oil into
single bonds to form solid fat called margarine

Organic Reactions: Alkene (-X-ene)

Addition Reaction
3.

Alkene + Hydrogen halide (HF / HCl / HBr / HI)  Haloalkane

Example:

Haloalkane can be used as starting material for making alcohol.

Organic Reactions: Alkene (-X-ene)

Addition Reaction
4.

Alkene + Steam (Water)  Alcohol

Example:

(1) H3PO4 (catalyst) / 600K / 6MPa

(2) Industrial production of ethanol

Organic Reactions: Alcohol (-an-X-ol)

A. Primary Alcohol
Oxidation Reaction
Primary alcohol + Oxidizing agent  Aldehyde  Carboxylic acid

Example:

(1) In the presence of conc. H2SO4

(2) K2Cr2O7 is used as an oxidizing agent, other O.A. (e.g.KMnO4) can
be used
(3) Heating with distillation to prevent further oxidation to
carboxylic acid  aldehyde (lower b.p.) obtained as distillate
(4) Heating under reflux (with excess oxidizing agent) retains the
aldehyde for further oxidation  carboxylic acid is major product

(5) K2Cr2O7 solution turns from orange to green

Organic Reactions: Alcohol (-an-X-ol)

B. Secondary Alcohol
Oxidation Reaction
 Secondary alcohol + Oxidizing agent  Ketone

Example:

(1) In the presence of conc. H2SO4

(2) K2Cr2O7 is used as an oxidizing agent., other O.A.(e.g.KMnO4) can be

used
(3) No further oxidation to carboxylic acid (Unlike primary alcohol)
(4) K2Cr2O7 solution turns from orange to green
(5) 3 alcohol cannot be oxidised

Haloalkane (-chloro / bromo-…-ane)

Substitution Reaction*

Haloalkane + Sodium hydroxide  Alcohol + Sodium halide

Example:
H H H H

H C C Cl + OH H C C OH + Cl

H H H H
(1) In aqueous solution / reflux
(2) Rate of hydrolysis: RI > RBr > RCl > RF
(Bond enthalpy: CF > CCl > CBr > CI)

Haloalkane (-chloro / bromo-…-ane)

Substitution Reaction*

Mechanism SN1
 (SN1: The rate determining step only involves one molecule.)

1. C – X bond break to form carbonium ion Heterolytic fission

[ A partial +ve charge is developed around C and a partial –ve charge is
developed around X as X is more electronegative than C (refer to the
partial charges)]
[ X gets the bonding e- (refer to the curly arrows)]

2. Carbonium ion combines with OH-

 Heterolytic fission: fission in which a cation and anion form

Nu can be OH-, CN- or NH3

Haloalkane (-chloro / bromo-…-ane)

Substitution Reaction*

Mechanism SN2
(SN2: The rate determining step involves two molecules.)

1. OH- attack the carbon centre on the other side of X

[ A partial +ve charge is developed around C and a partial –ve charge is
developed around X as X is more electronegative than C (refer to the
partial charges)]
[ The positive carbon centre attracts OH- which tends to donate e-]
2. C – X bond breaks and C – OH bond forms at the same time
Nu can be OH-, CN- or NH3

Haloalkane (-chloro / bromo-…-ane)

Substitution Reaction*

Mechanism SN1 VS SN2

Prediction on the mechanism of substitution reaction

1 haloalkane 2 haloalkane 3 haloalkane

Mechanism Mainly SN2 Both SN1 and SN2 Mainly SN1
 Summary
Reaction Mechanisms (SL)