REVISION SET 5

SUGGESTED ANSWER SCHEME

QUESTION 1

SUGGESTED ANSWER MARKS

(a) (i)
1

(ii)
1

(iii)

(iv)
1

(b) O
HO NH C CH3
1 3
3
2

Functional Group

1 Hydroxyl
3
2 Aromatic ring

3 Amide

1|SES_KMM
(c) Number of primary hydrogen
12 1
Number of secondary hydrogen
8 1

(d) (i) Same compound 1

(ii) Functional group isomer 1

(iii) Same compound 1

(iv) Chain isomer 1

(e) Carbocation A is more stable than carbocation B. 1

Carbocation A bonded to three alkyl groups while carbocation B only bonded to 2 1
alkyl groups.

Total:18 marks

2|SES_KMM
QUESTION 2

SUGGESTED ANSWER MARKS

(a) (i) 4-tert-butyl-3,5-dimethylheptane 1

(ii) 2,2-dimethylhexane 1

(b) ● The molecular weight of C < D because C is an alkane with 4 carbon atoms 1
while D is an alkane with 5 carbon atoms.
● The strength of van der Waals forces between molecules of C < D. 1
● The energy needed to overcome the van der Waals forces between
molecules of C < D. 1
● Thus, the boiling point of C < D. 1

(c)

Total:8 marks

3|SES_KMM
QUESTION 3

SUGGESTED ANSWER MARKS

(a) (i) cis-5-chloro-3,4-dimethyl-3-octene 1

(ii) 2,3-diethylcyclopentene 1

(iii) 4,5-dibromo-2-chloro-2-heptene 1

(iv) 2,3,5-trimethyl-2-hexene 1

(b) (i) Saytzeff’s rule state that, in an elimination reaction, the major product is an alkene
with greater number of alkyl group directly bonded to the carbon - carbon double 1
bond (C=C).

(ii)

Major product. 1
This structure has three alkyl group directly bonded to the C=C. 1

Minor product
1
This structure has three alkyl group directly bonded to the C=C
1

(iii) Phosphoric acid, H3PO4 1

(c)

Total:14 marks

4|SES_KMM
QUESTION 4

SUGGESTED ANSWER MARKS

(a) (i) 3-methyl-3-heptanol 1

Tertiary alcohol 1

(ii) 2-aminocyclohexanol 1
Secondary alcohol 1

(b) ● Ethane-1,2-diol has 2 hydroxyl groups in its structure 1

● The presence of these two hydroxyl groups allow ethane-1,2-diol to form
more Hydrogen bonds with water molecules. 1

(c) Name of the test: Lucas’s test 1

3-methyl-3-pentanol
1

1
The solution turns cloudy immediately and two layers formed.
2-pentanol

The solution turn cloudy within 5 to 10 minutes and two layers formed.
1-pentanol

The solution does not turn cloudy after 10 minutes and no formation of two layers.

Total:11 marks

5|SES_KMM
QUESTION 5

SUGGESTED ANSWER MARKS

(a) (i)
1

(ii)

(iii)

(iv)
1

(b) (i) Reduction by using LiAlH4 followed by the addition of water @ Reduction by using 1
NaBH4 in methanol

(ii) Hot acidified potassium manganate(VII) solution @ Hot acidified sodium 1

dichromate(VI) solution @ Hot acidified potassium dichromate(VI) solution

(c) (i) 3

(ii) 1

(iii) 1

6|SES_KMM
(d) Reagent F
Hot acidified potassium manganate(VII) solution @ Hot acidified sodium
dichromate(VI) solution @ Hot acidified potassium dichromate(VI) solution 1

Reagent G
NaCN in HCl or KCN in HCl
1
Reagent H
Excess iodine in aqueous sodium hydroxide solution
1

Total:14 marks

7|SES_KMM
QUESTION 6

SUGGESTED ANSWER MARK

(a) (i) 2,2-dimethylpropanoic acid 1

(ii) 3-bromo-4-phenylbutanoic acid 1

(b) (i) 1

(ii) 1

(c) ● Boiling point of ethanedioic acid > pentanoic acid. 1

● Both molecules have -COOH and are able to form stable hydrogen bonded
dimer between their molecules. 1
● Ethanedioic acid has more -COOH groups than pentanoic acid. 1
● Ethanedioic acid can form more hydrogen bonded dimer between
molecules than pentanoic acid. 1
● Strength of stable hydrogen bonded dimer between molecules of
ethanedioic acid > pentanoic acid. 1
● Energy needed to overcome the forces between molecules of ethanedioic
acid > pentanoic acid. 1

(d)
3

Total: 13 marks
Max: 12 marks

8|SES_KMM