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I.
A. B.

Alkanes
Cracking
very long alkane
heat , catayst

long alkane + short alkene y

Combustion
y

C.

CxHy + (x + 4 ) O2(g) xCO2(g) + 2 H2O(l) Chlorination Chain initiation (chain initiating step)
h Cl Cl Cl + Cl Cl radical is generated.

Chain propagation (chain propagating step)

H Cl H C H H H Cl Cl C H H Cl + Cl Cl H + H C H H H C H H Cl radical is regenerated. Cl radical is consumed.

Chain termination (chain terminating step)

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

Energy

radical is destroyed.

A mixture of products would be obtained.

Summary of Organic Reactions (II. Alkenes and alkynes)

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II.
A. 1.

Alkenes and alkynes

Addition reactions Reaction with bromine in CCl4
Br2 + in
CCl4

C R

C R

in dark

Br Br R C
R
C R

1,2-dibromoalkane

Note : Test for C=C or CC bond

2.

Reaction with bromine water

Br2(aq) +

C C R R

in dark

Br OH R C
C R

R R halohydrin

Note : Test for C=C or CC bond

3.

Reaction with hydrogen bromide

H Br H C H H C C C H H H H propene
H
+

H
C
H

C
H

major product

Br

2-bromopropane Br H H H C
H

C
H

C
H

minor product

1-bromopropane

Note : Follows Markownikov's orientation

4.

Reaction with conc. sulphuric(VI) acid

OH conc. H2SO4(l) +
R C
R

C
R

O H R C

O C R

R R alkyl hydrogensulphate(VI)

Note : A reversible reaction

OH O H
R C

S O
C

O + H2O(l)
R

H R C
R

OH C
R

R + H2SO4(aq)

R R alkyl hydrogensulphate(VI)

alcohol

Note : Laboratory preparation of alcohol

5.

Reaction with water

CH2 CH2 + H2O ethane
H3PO4

300 C

CH3 CH2 OH ethanol

Note : Industrial preparation of alcohol

6.

Catalytic hydrogenation of oil

Note : hardening of oil

Summary of Organic Reactions (II. Alkenes and alkynes) B. Ozonolysis of alkene

CH3 CH3CHCH CH2 3-methylbut-1-ene (1) O3, CH2Cl2, -78 C (2) Zn / H2O CH3 O CH3CH C H 2-methylpropanal O + H C H methanal

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Note : Can be used to determine the structure of the alkene with characterization of the derivatives of carbonyl compounds formed.

C.

Oxidation cleavage of double bond

CH3CH2 CH3CH2
C C

CH3 CH3

(1) KMnO4, OH , hot

+
CH3CH2

O
C
CH2CH3

O
+
H3C

CH3

(2) H pentan-3-one
-

3-ethyl-2-methylpent-2-ene CH3 CH CHCH CH

3

propanone

(1) KMnO4, OH , hot

2

CH3

O
C

CH CH
3

OH + CO2

+ H2 O

3-methylbut-1-ene

(2) H

2-methylpropanoic acid

Note : The outcomes are different from the ones from ozonolysis.

a)

Reaction with cold acidic or alkaline permanganate solution

H H H
H C

H
C H

cold KMnO4(aq)
H3O or OH
+ -

H C C H
O O

ethane

H H ethane-1,2-diol

D.

Oxymercuration of alkyne
HgSO
R C C H terminal alkyne H
4(aq)

R C C H O H Markovinkov orientation

H SO
2

keto-enol tautomerization

H R C C H O H methyl ketone

4(aq)

Summary of Organic Reactions (II. Alkenes and alkynes) E. Polymerization of alkenes

Chain initiating step
O O R C O O C R Diacylperoxide heat O 2R C O 2 R + 2 CO2 alkyl radical

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Chain propagating step

H R H C C H H H R C H H C H

H H R C C H H

H C C H

H H

H H H H R C C C C H H H H

etc.

long chain polymer

Chain terminating step

H R (CH2 CH2) n
C

H
C

H
C

H
C

combination (CH2 CH2) n R R (CH2 CH2) n

H H
C C

H
C

H
C

(CH2 CH2) n R

H H R H (CH2 CH2) n
C

H H
C

H H
C

H H R

H H H (CH2 CH2) n C oxidation product

C

H H H
C

H
C

disproportionation (CH2 CH2) n R

H
C

(CH2 CH2) n R

reduction product