COURSE LEARNING OUTCOMES

CLO OUTCOMES
1 Explain basic concepts and principles of physical and organic chemistry
in novel and real life situations.
C2, PLO1, MQF LOD 1
Teaching & Learning Strategy : LECTURE

2 Demonstrate the correct techniques in handling laboratory apparatus

and chemicals when carrying out experiments.
P3, PLO2, MQF LOD 2
Teaching & Learning Strategy : PRACTICAL, DEMONSTRATION

3 Solve chemistry related problems by applying basic concepts and

principle in physical chemistry.
C4, PLO4, CTPS3, MQF LOD 6
Teaching & Learning Strategy : TUTORIAL

1
 CHEMISTRY
SK025

MODE : LECTURE (CLO 1)

Student Learning Time (SLT) for lecture :

Non Face-to-face Face-to-face

(Preparation) (During Class)
2.5 hour 2.5 hour

2
Assessment of learning outcomes :

CLO T&L Strategy Assessment

1 Lecture Final
Tutorial Examination
(paper 1)
2 Practical Practical Test
Demonstration
3 Tutorial Assignment
Lab Report and
Final Examination
(paper 2)

3
 TEACHING LEARNING OUTCOMES
(WEEK 9, 3rd HOUR)

At the end of the lesson, student should be able to :

5.2: ALKENES
g) Explain the addition reaction of alkenes with (C2):
(i) Hydrogen in the presence of catalyst
(ii) Halogen (CI2 or Br2) in inert solvent (CH2CI2)
(iii) Halogen (CI2 or Br2) in water
(iv) Hydrogen halides (HCI or HBr)
(v) Acidified water
 

5
 PREPARATION OF ALKENES

 2 methods by elimination reactions:

i) Dehydration of Alcohol

 elimination of H2O from alcohol

ii) Dehydrohalogenation of haloalkanes

 elimination of HX from haloalkanes

 1) DEHYDRATION OF ALCOHOLS

 Reactant: alcohol
 Conditions:
• Concentrated H2SO4 or
other strong acids
• Heat or reflux
acid , heat
C C C C + H2O
H OH
H and OH eliminated!
 EXAMPLE:
(a)
CH3
Concd. H2SO4 CH3
CH3 C CH2 + H2O
 CH3 C═CH2
OH H 2–methylpropene
2–methyl–2–propanol

(b) OH
Concd. H2SO4
+ H2O

H
(c) OH

CHCH2 CH═CH2
Concd. H2SO4
H  + H2 O

Cl Cl
 2) DEHYDROHALOGENATION
OF HALOALKANES
 Reactant: alkyl halide (RX)

 Conditions:

• Base such as KOH , alcohol

or alkoxide ion ( –OR)
• Heat or reflux

Or reflux
EXAMPLE:

CH3 CH3
KOH, ethanol
CH3–C–CH3 CH3–C═CH2
heat 2–methylpropene
Cl
2–chloro–2–methylpropane
• Certain alcohols/haloalkanes undergo elimination to
produce more than one alkenes

,
heat

•Saytzeff’s rule is used to determine the

major product.
 SAYTZEFF’S RULE
 In an elimination reaction, the major
product is the most stable alkene,
commonly the most highly substituted
alkene
 EXAMPLE:
CH3

CH3—C—CH2CH3

OH
2–methyl–2–butanol

Concd. H2SO4
∆
minor major
H CH3 CH3 H
C C + C C
H CH2CH3 CH3 CH3
2–methyl–1–butene 2–methyl–2–butene
disubstituted alkene trisubstituted alkene
 EXAMPLE 1

Predict the products of the following reactions.

When more than one product is expected,
Predict which one will be the major product.
Conc. H2SO4
a) heat
OH
2–methyl–2–butanol
CH3
Conc. H2SO4
CH3—CH—C—CH3
b) heat
CH3 OH
2,3–dimethyl–2–butanol
 ANSWER:

(a)

Conc. H2SO4
heat major
OH
2–methyl–2–butanol 2–methyl–2–butene

+
minor

2–methyl–1–butene
) CH3 CH3
Conc. H2SO4
CH3—CH—C—CH3 CH3—C═C—CH3
heat
CH3 OH CH3 major
2,3–dimethyl–2–butanol 2,3–dimethyl–2–butene
+
CH3

CH3—C—C═CH2
CH3 minor
2,3–dimethyl–1–butene
 EXERCISE 2

Draw all products formed from alkyl halide in

elimination reaction and predict the major product
using the Saytzeff's rule.
CH3
(a) CH3CH2CH2CCH2CH2CH3

Br
4–bromo–4–methylheptane
KOH,ethanol
∆
?
(b) CH3
Cl

CH3
1–chloro–1,2–dimethylcyclohexane

KOH,ethanol
∆

?
ANSWER:

CH3
(a)
CH3CH2CH2CCH2CH2CH3

Br
4–bromo–4–methylheptane
KOH,ethanol
CH3 ∆ CH2
CH3CH2CH═CCH2CH2CH3 + CH3CH2CH2CCH2CH2CH3
major minor
(b) CH3
Cl

CH3
1–chloro–1,2–dimethylcyclohexane

KOH,ethanol
∆

CH3 CH3 CH2

+ +
CH3 CH3 CH3

major minor minor

 MECHANISM OF DEHYDRATION

 STEP 1:
• Protonation of –OH group

protonated alcohol
+

 + H OSO3H C C O H
C C O H

H H H

The curved arrow begins with a covalent

bond or unshared electron pair (a site of + HSO4‒
higher electron density) and point toward a
site of electron deficiency
 STEP 2:

• Loss of water and formation

of carbocation

+
 C C+ O H
C C O H +
H H H
H

carbocation
 STEP 3:

• Removal of proton (H+) from the

neighbouring carbon.

C C+ C C + H2SO4

H alkene
‒
OSO3H
 EXAMPLE:

CH3
CH3
 Conc. H2SO4
CH3 C O H
 heat CH2 C CH3
CH3 2–methylpropene

STEP 1
CH3 CH3
 +

CH3 C O H + H OSO3H CH3 C O H

CH3 CH3 H
2–methyl–2–propanol
+ HSO4‒
STEP 2

CH3 remove
H CH3
+

H2O
CH3 C O H H C C+
CH3 H H CH3

STEP 3

H CH3
CH3
H C C+ remove H (1 )
+ o

CH2 C CH3
H CH3
2–methylpropene
‒
OSO3H + H2SO4
 EXAMPLE:
major
CH3 CH2 CH CH3 Conc. H2SO4 CH3 CH CH CH3
heat 2–butene
 OH

+
2–butanol CH3 CH2 CH CH2
1–butene
minor

STEP 1
H OSO3H
CH3 CH2 CH CH3 CH3 CH2 CH CH3
 OH  OH2
 +
+ HSO4‒
STEP 2 remove
H2O
CH3 CH2 CH CH3 CH3 CH2 CH CH3
 OH2
+
+ 2o carbocation
STEP 3

remove H+ (2o) major

CH3 CH CH CH3
CH3 CH CH CH3
+
H 2–butene

‒
OSO3H + H2SO4
STEP 3

CH3 CH2 CH CH2

+ remove H+ (1o)
H CH3 CH2 CH CH2
1–butene
‒
OSO3H minor

+ H2SO4
 CARBOCATION
REARRANGEMENT
 Rearrangement of a less stable to a
more stable carbocation by a shift of
a hydrogen atom or an alkyl group

 1,2–hydride shift (1,2−H− shift)

 1,2–methanide shift (1,2−CH3− shift)

1,2–shift
C C C C
+ +
R R
(R = CH3 or H) (R = CH3 or H)
EXAMPLE:

H H
+ 1,2–hydride shift +
CH3 C CH CH3 CH3 C CH CH3
CH3 CH3

2o carbocation 3o carbocation

CH3 CH3
+ 1,2–methanide shift + CH3
CH3 C CH CH3 CH3 C CH

CH3 CH3

2 carbocation
o 3o carbocation
EXAMPLE 1:
major
 Conc. H2SO4
CH3–CH2–CH–CH2–OH CH3–CH═C–CH3
 heat
CH3 CH3
2–methyl–1–butanol 2–methyl–2–butene

+
CH3–CH2–C═CH2
CH3
2–methyl–1–butene
minor
STEP 1

+
CH3–CH2–CH–CH2–OH2
 H OSO3H 
CH3–CH2–CH–CH2–OH
 CH3
CH3
+ HSO4‒

STEP 2 H
+ remove H2O +
CH3–CH2–CH–CH2–OH2 CH3–CH2–C–CH2

1o carbocation CH3
CH3

+ 1,2–hydride
CH3–CH2–C–CH3 shift
3o carbocation CH3
STEP 3

CH3 CH3–CH═C–CH3
remove H+ (2o)
+ H2SO4
CH3–CH–C–CH3 CH3
+ 2–methyl–2–butene
H
‒
OSO3H
major
3o carbocation
CH3 remove H+ (1o) CH3–CH2–C═CH2
CH3–CH2–C– CH2 + H2SO4
CH3
+
H 2–methyl–1–butene
‒
OSO3H
minor
3o carbocation
 ….STEP 3

H
‒
+ OSO3H
CH3–CH2–C═CH2
CH3–CH2–C– CH2
CH3
CH3 remove H (3 )
+ o
2–methyl–1–butene
1o carbocation
minor

+ H2SO4
 CH3
EXAMPLE 2:
CH3–C—CH–CH3
CH3OH

3,3–dimethyl–2–butanol

heat Conc. H2SO4

CH3 CH3 CH3

CH2═C–CH–CH3 CH3–C═C–CH3 CH3–C–CH═CH2

CH3 CH3 CH3

minor major minor

STEP 1
CH3
CH3
H OSO3H CH3–C—CH–CH3
CH3–C—CH–CH3
CH3OH2
CH3OH +

+ HSO4‒
STEP 2
CH3 CH3
remove H2O
+
CH3–C—CH–CH3 CH3–C–CH–CH3
CH3OH2 CH3
2o carbocation CH
+ 3

CH3–C–CH–CH3
+ 1,2–methanide
CH3 shift
3o carbocation
STEP 3 CH3

CH3 CH3 CH3–C═C–CH3

remove H (3 )
+ o

CH3–C – C–CH3 CH3 major

+ + H2SO4
H ‒OSO H
3

3o carbocation

CH3 CH3
remove H+ (1o)
H2C–C–CH–CH3 CH2═C–CH–CH3
+
H CH3 ‒
OSO3H minor CH3
+ H2SO4
3 carbocation
o
…STEP 3

CH3 CH3
remove H+ (1o)
CH3–C–CH–CH2 CH3–C–CH═CH2
+
CH3 H ‒OSO H CH3 minor
3

2o carbocation
+ H2SO4
 EXAMPLE 3

Show how the hydration of alcohol X forms

alkene Y using a 1,2–hydride shift.

OH

CH–CH3 Conc. H2SO4 CH2–CH3

+ H2O
heat

X Y
 ANSWER:

STEP 1 H H
●
● O
●
●
●+
O—H
●

CH–CH3 H OSO3H CH–CH3

+ HSO4‒
H
STEP 2 ●
+
O—H
2o carbocation +
●
CH–CH3
remove H2O
CH–CH3 H

+ CH2–CH3 1,2–hydride
shift
3o carbocation
 …STEP 3

Y
+ CH2–CH3 remove H+ (2o) CH2–CH3

H ‒
OSO3H 1–ethylcyclohexene

3o carbocation major

+ H2SO4

Note: Y is the major product, there are two minor products

 EXAMPLE 4

Dehydration of 2–methylcyclopentanol gives

a mixture of three alkenes.
Propose mechanisms to account for these
three products.
CH3 CH3 CH3
H2SO4
heat +
OH
major minor
CH2

minor
 ANSWER:

STEP 1 CH3 CH3

H OSO3H H
●●
O–H +
O–H
●●
●●
+ HSO4‒
STEP 2
CH3 CH3
remove H2O
H H 2o
carbocation
+
O–H +
●●
+ CH3
1,2–hydride
shift
3o carbocation H
 ANSWER:

…STEP 3

+ CH3
remove H+ (2o) CH3 major

H ‒OSO H + H2SO4
3

3o carbocation

+ CH2
CH2
remove H+ (1o)
H ‒
OSO3H minor

+ H2SO4
 ANSWER:

…STEP 3
CH3
CH3
H remove H+ (3o) + H2SO4
+
major
2o carbocation
CH3 CH3
remove H+ (2o)
+ + H2SO4

H minor
 REACTION IN ALKENES

C=C is a site of high electron density (nucleophilic

site), becomes the site of electrophilic attack.

Reactions of alkenes are mainly electrophilic

addition reaction.

C C + A—B
C C

A B
 I) HYDROGENATION

 Addition of H2(g) in the presence of catalyst

(Pt /Pd /Ni)

Examples:
 EXAMPLE 5
What alkane is formed when each alkene is
treated with H2 and a Pd catalyst?

(a) CH3 (b)

CH2CH(CH3)2
C C
CH3 H

(c) (d)
CH3
CH═CH2
 ANSWER:

(a)
CH3 CH2CH(CH3)2 CH3 CH2CH(CH3)2
H2 , Pd
C C CH3—C — C—H
CH3 H H H
2,5–dimethyl–2–hexene 2,5–dimethylhexane

(b)

H2 , Pd

4–methyl–3–heptene 4–methylheptane
ANSWER:

(c)
CH3 CH3
H2 , Pd

1–methylcyclohexene methylcyclohexane

(d)
H2 , Pd
CH═CH2 CH2CH3

cyclopentylethene ethylcyclopentane
 II) HALOGENATION OF ALKENES
IN INERT SOLVENT (CH2Cl2)

CH2Cl2
C C + X—X C C

X X
 Reactant: alkene and halogen (Cl2, Br2)
 Product: vicinal dihalide

vicinal (vic) = next to

another
 EXAMPLE:

CH2Cl2 Br
+ Br2

Br
1,2–dibromocyclohexane

CCl4 CH3CH—CHCH3
CH3CH═CHCH3 + Cl2
Cl Cl
2,3–dichlorobutane

54
 EXAMPLE 6

Predict the product of the following reaction:

(a) cyclooctene + Br2 in CH2Cl2

(b) 3–decene + Br2 in CCl4

(c)
+ Cl2 in CHCl3

(d)
+ 2Cl2 in CH2Cl2
 ANSWER:

(a)

cyclooctene

Br2 in CH2Cl2

Br

Br

1,2–dibromocyclooctane
 ANSWER:

(c)
Cl
Cl2
in CHCl3 Cl

(d) Cl
2Cl2 Cl Cl
in CHCl3 Cl
 III) HALOGENATION OF
ALKENES IN WATER
C C
C C + X2 + H2O
X OH
 X adds to C that has greater halohydrin
number of H
EXAMPLE:

CH3 CH3
H2O
CH3–CH–CH═CH2 + Cl2 CH3–CH–CH–CH2
3–methyl–1–butene
OH Cl
1–chloro–3–methyl–2–butanol
 EXAMPLE 7

Draw the major product of each reaction.

(a) Br2
CH2 ?
CH2Cl2

(b) Br2
CH2 ?
H2O
 ANSWER:

(a)
Br2 Br
CH2
CH2Cl2 CH2Br

(b)

Br2 OH
CH2
CH2Br
H2O
 MARKOVNIKOV’S RULE

 In addition of HX to an alkene, H atom

adds to the C atom of the double bond
that already has the greater number of
H atoms
C with the
greater number
of H
CH3 CH CH2 CH3 CH CH2
H
X

X H
 IV) HYDROHALOGENATION

EXAMPLE:

ethene
bromoethane
EXAMPLE:

H H H H
C C + HBr H C C H
H H
H Br
ethylene
bromoethane

+ HCl

cyclohexene H Cl
chlorocyclohexane
 EXAMPLE 8

Draw the products formed when each

alkene is treated with HCl.
(a)
CH3

(b) CH3
C CH2
CH3

(c) CH3CH2CH2CH2C═CH2
CH
 ANSWER:

(a) CH3
CH3 HCl
Cl

1–methylcyclopentene 1–chloro–1–methylcyclopentane

(b) CH3 CH3

HCl
C CH2 CH3—C—CH3
CH3 Cl
2–methylpropene 2–chloro–2–methylpropane
ANSWER:

(c) CH3CH2CH2CH2C═CH2
CH3
2–methyl–1–hexene

HCl

Cl

CH3CH2CH2CH2CCH3
CH3
2–chloro–2–methylhexane
 V) HYDRATION

 Electrophilic addition of water

+ –
H3O+
C C + H—OH C C

H OH
alcohol

 Conditions: with Catalyst, dilute H2SO4 (aq)

 Follow Markovnikov Rule
 EXERCISE 5
Give the major product obtained from the
acid–catalyzed hydration of each of the
following alkenes

(a) (b)
1‒hexene
CH2

(c) (d) CH3

CH2═CCH2CHCH3

CH3
 ANSWER:

(a)
OH
H2O
CH2
H2SO4 CH3

(b)

H2O
CH3CH2CH2CH2CH═CH2 CH3CH2CH2CH2CHCH3
H2SO4
OH
ANSWER:

(c)
OH

H2O
H2SO4

(d)

CH3 CH3
H2O
CH2═CCH2CHCH3 CH2CCH2CHCH3
H2SO4
CH3 OH CH3
 MECHANISM OF HYDROHALOGENATION

STEP 1Formation of carbocation and halide ion

H
–
 C C C C+ +

x
X H +

 +
–
electrophile nucleophile carbocation
STEP 2

Halide ion donate electron pair to carbocation


H H X 
–

C C+ + x C C

electrophile nucleophile
EXAMPLE:

–
+  +
CH3—C═CH2 + H—Br CH3—C—CH3

CH3 CH3
2–methylpropene 3o carbocation
–
Br 


Br

CH3—C—CH3
CH3
2–bromo–2–methylpropane
 EXAMPLE 9

Outline mechanism for the electrophilic

addition of HCl to 2–methyl–2–butene.
 ANSWER:

–
+ 
CH3—C═CH—CH3 + H—Cl

CH3
2–methyl–2–butene

 
Cl
 – 
+  Cl 
CH3—C—CH2—CH3  CH3—C—CH2—CH3
CH3 CH3
3o carbocation 2–chloro–2–methylbutane
 MECHANISM OF HYDRATION

STEP 1:Formation of carbocation

CH2 CH3

C + H C+
H3C CH3 H3C CH3

3o carbocation

O H
+
H
 STEP 2:

 Formation of protonated alcohol

CH3 CH3
●●
+
C+ + O H
CH3 C O H
H3C CH3 CH3 H
H
protonated alcohol
 STEP 3:

 Elimination of H+

O H
CH3 H CH3
+ ●● ●● +
CH3 C O H CH3 C O–H + H3O
●●

CH3 H CH3
2–methyl–2–propanol
 EXAMPLE 10

Write the mechanism of the acid–catalyzed

hydration of 1–butene.
 ANSWER:

2o carbocation
+
CH3—CH2—CH═CH2 + H CH3—CH2—CH—CH3
1–butene

O H
H
CH3—CH2—CH—CH3 CH3—CH2—CH—CH3

O+ H
●
O ●●
●

●
●

2–butanol H O
H H
H
+ protonated alcohol
+ H3O
 ANTI–MARKOVNIKOV
ADDITION
Occurs only when HBr is used in the presence of
peroxide (R–O–O–R)- Examples: H2O2, CH3OCH3

H atom attached to C atom with fewer H atoms

C with fewer H atoms

H2O2
CH3 CH CH2 CH3 CH CH2
H Br
H Br
EXAMPLE:

ANTI-MARKOVNIKOV
H2O2
CH3CH═CH2 + HBr CH3CH2CH2Br
1–bromopropane

MARKOVNIKOV

CH3CH═CH2 + HBr CH3CHBrCH3

2–bromopropane
 EXAMPLE 11
Predict the major products of the following
reactions.
(a)
HBr
CH3CH2CH═CH2
ROOR

(b)
HBr
CH2CH═CH2
ROOR

83
ANSWER:

(a)
HBr
CH3CH2CH═CH2 CH3CH2CH2CH2Br
ROOR

(b)

HBr
CH2CH═CH2 CH2CH2CH2Br
ROOR
 UNSATURATED TEST

 To test the presence of C=C

 To distinguish alkene and alkane

BROMINE TEST BAEYER TEST

 I) BAEYER TEST

 At room temperature

C C + KMnO Dilute, OH ‒
C C
4 + MnO2
cold OH OH Brown
diol precepitate

 Observation:
Purple color of KMnO4 decolourised

Brown Precipitate formed

EXAMPLE:
CH3CH—CH2
CH3CH═CH2 KMnO4 Dilute, OH‒ OH OH
+
cold
propene 1,2–propanediol

+ MnO2

OH
+ KMnO4 Dilute, OH‒
cold
OH
cyclohexene
1,2–cyclohexanediol
+ MnO2
 II) BROMINE TEST (Br2 in CH2Cl2)

CH2Cl2
C C + Br2 C C

Br Br

 Observation:
Reddish-brown color of Br2 decolourised
EXAMPLE:
Br
Br2
CH2Cl2 Br
cyclohexene 1,2–dibromocyclohexane

Observation:
The reddish-brown color of
bromine decolourised
 III) BROMINE TEST IN WATER

H2O
C C + Br2 C C

Br OH

 Observation:
Reddish–brown color of Br2 decolourised
EXAMPLE:
Br
Br2
H2O OH
cyclohexene 2–bromocyclohexanol

Observation:
The reddish-brown color of
bromine decolourised
 OXIDATIVE CLEVAGE OF C=C

i) Ozonolysis

ii) Reaction of Alkene with hot,

acidified KMnO4
 I) OZONOLYSIS

 Reactant: alkene

 Product: aldehyde and / or ketone

 Conditions: O3 followed by Zn , H2O

OR O3 Followed by (CH3)2S

R R R’
R’ [i] O3
C C C O + O C
R H R H
[ii] Zn, H2O
ketone aldehyde
EXAMPLE: CH3
CH3C═O
CH3 acetone
[i] O3
CH3C═CHCH3 +
[ii] Zn, H2O O
CH3CH
acetaldehyde

CH3 O

CH3 CH3CH–CH
[i] O3
CH3CH–CH═CH2 isobutyraldehyde
[ii] Zn, H2O
O
+ formalde
HCH
hyde
 EXAMPLE 12
Draw the products formed when each alkene
is treated with O3 followed by Zn, H2O.
(a) (CH3)2C═CHCH2CH2CH2CH3

(b) 3–heptene

(c) CH3
 ANSWER:

(a)
(CH3)2C═CHCH2CH2CH2CH3

[i] O3
[ii] Zn, H2O

O O

CH3CCH3 + CH3CH2CH2CH2CH

propanone pentanal
ANSWER:

(b)
CH3CH2CH═CHCH2CH2CH3

[i] O3
[ii] Zn, H2O

O O
CH3CH2CH + CH3CH2CH2CH
propanal butanal
ANSWER:

(c)
CH3

[i] O3
[ii] Zn, H2O

O O
CH3CCH2CH2CH2CH2CH
 EXAMPLE 13

Draw the products formed when each diene

is treated with O3 followed by Zn, H2O.

(a)

(b)
ANSWER:

(a)

[i] O3
[ii] Zn, H2O

O O
+ H O

O
H H

100
ANSWER:

(b)

[i] O3
[ii] Zn, H2O

O O O
H +
H H H
O
101
 Ozonolysis can be used to determine the
structure of an unknown alkene

EXAMPLE: working
backwards

H3C CH2CH2CH3 CH3

C O + O C CH3C═CHCH2CH2CH3
H3C H
acetone butanal 2–methyl–2–hexene

ozonolysis products alkene that

underwent ozonolysis
102
 ii) REACTION WITH HOT,
ACIDIFIED KMnO4
 Reagent:

 KMnO4, H+,Heat i)KMnO4, OH‒, Heat

OR
ii) H3O+
Product: ketone and / or carboxylic
acid
or CO2 and H2O
R R’ R R’
KMnO4 , H
+

C C C O + O C
R H ∆ R OH
ketone
carboxylic acid
EXAMPLE:

O
KMnO4 , H+
CH3CH═CHCH3 CH3COH
∆

CH3 CH3
KMnO4 , H+ CH3CH2C═O
CH3CH2C═CH2
∆
+ CO2
Terminal C=C
+ H2O
EXAMPLE:

KMnO4 , H+

∆ +

OH

═ C
O
 EXAMPLE 14

Draw the products formed for the following

reactions

(a) [i] KMnO4, OH– , heat

[ii] H3O+

CH3 KMnO4 , H+

(b) ∆
 ANSWER:

(a) O O
[i] KMnO4, OH– , heat
HOCCH2CH2CH2CH2COH
[ii] H3O+
hexanedioic acid

(b)
O O
CH3 KMnO4 , H+
CH3CCH2CH2CH2CH2COH
∆
 Valuable tool for structure determination
of unknown compounds (alkenes)

EXAMPLE:

Oxidation products:

O O

CH3CH2C–OH + HO–CCH2CH2CH2CH3
propanoic acid pentanoic acid

join these two C to deduce the starting material

CH3CH2CH═CHCH2CH2CH2CH3
3–octene
 EXAMPLE 15

Show the structures of alkenes that give the

following products on oxidative cleavage with
hot concentrated KMnO4 solution:

(a) CH3CH2CO2H + CO2

(b) (CH3)2C═O + CH3CH2CH2CO2H

(c) ═O + (CH3)2C═O
 ANSWER:

(a) O
CH3CH2C–OH + CO2

CH3CH2CH═CH2

1–butene
 ANSWER:

(b)
CH3C═O + O═CCH2CH2CH3
CH3 OH

CH3C═CHCH2CH2CH3
CH3
2–methyl–2–hexene
ANSWER:

(c)

═O + O═CCH3
CH3

═CCH3
CH3