2016/2017 (TOPIC ALKENE)

8. D is the isomer of an alkane with molecular formula C6H14 which possesses a

quaternary carbon. The reaction scheme that involves D is shown below.

conc. H2SO4 H2 Br2

C6H14O C6H12 C6H14 C
B  C Pd D uv (major)

(i) Dehydration of secondary alcohol B produces compound C. Suggest the structure

of B and write the mechanism of this transformation. [6 marks]
(ii) Suggest the structural formulae for C and D. [2 marks]
(iii) E is the major product of the reaction of D with Br2 in the presence of UV. Draw
and classify the structure of E. [2 marks]
(iv) Suggest a chemical test to distinguish between C and D. Write the chemical
equations and state your observations. [5 marks]
2012/2013 (TOPIC HYDROXY)

Give reason for each of the following statements:

(i) 1-butanol is less acidic than phenol

(ii) CH3CH(OH)COOH has higher boiling point than CH3COCOOH
(iii) 2-methyl-2-propanol cannot undergo oxidation
(iv) 2-Hexanol gives yellow precipitate with iodine in NaOH solution
(v) Both phenol and 1-propanol react with sodium but only phenol dissolves in aqueous NaOH.
[5 marks]
2008/2009 (Conversion Reaction/ Synthesis)

8. Propose a synthetic route for the preparation of cyclopentanecarboxylic acid from cyclopentane
via Grignard reagent. Cyclopentanecarboxylic acid reacts with ammonia to form Y, and upon
heating, Y yields Z. Draw the structures of Y and Z.
[8 marks]
2016/2017 (Conversion reaction and synthesis)

13. Consider the following reaction scheme.

CH3CH2COOH
L

OH
Q
(i) O3 R
CH3CH2CH=CHCH2CH3 M CH3CH.2 CH
(ii) Zn, H2O
K .
H2N-NH2 CN

P
N

(a) Draw the structures of M and N and give the reagents Q and R. [4 marks]
(b) Suggest the products formed when L reacts with:
(i) SOCl2
(ii) LiAlH4 followed by hydrolysis
(iii) sodium metal
(iv) NH3/ [4 marks]
(c) Arrange K, L and M in order of increasing boiling point. Explain. [4 marks]
(d) State the observation and write the chemical equation when M reacts with Tollens’ reagent.
Suggest one (1) chemical test that can be conducted to confirm the presence of functional
group in M. [3 marks]
2011/2012 (Deducing structure)

16. 2-methylpentane reacts with Br2 in the presence of light to yield L, a monobromination
product. Dehydrohalogenation of compound L forms M and N as the respective major
and minor products. Oxidative cleavage on M gives ketone P and carboxylic acid Q;
whereas similar reaction on N forms ketone R and CO2 Treatment of M with acidified
water yields S.
Write the chemical equations for complete combustion of 2-methylpentane;
dehydrohalogenation of L; and oxidative cleavage of M. Suggest the structures of L, M,
N, P, Q, R and S. Write the mechanism for the formation of S.
Show how Q can be synthesized from ethane.
[20 marks]
2008/2009 (Deducing Structure)

12. Reduction of compound AA, C7H12O gives BB. Dehydration of BB yields CC, and
ozonolysis of CC forms OHCCH2CH2CH(CH3)CH2CHO. Compound DD obtained when
AA reacts with HCN. Acid Hydrolysis of DD gives EE.
Determine the structures of AA, BB, CC, DD and EE. Write all the reaction equations
involved.
[10 marks]