DAV PUBLIC SCHOOL

SUB: CHEMISTRY
HALOALKANES AND HALOARENES
TIME: 1 HR F.M = 25
The following questions are multiple choice questions. Choose the
most appropriate answer. [1x6=6]
1. 3-Chloro-5-methylhex-2-ene is a which type of halide?
(a) Allyl halide (c) Vinyl halide
(b) Secondary halide (d) Primary halide
2. p-djchlorobenzene has higher melting point than its o- and m- isomers
because
(a) p-dichlorobenzene is more polar than o- and m- isomer.
(b) p-isomer has a symmetrical crystalline structure.
(c) boiling point of p-isomer is more than o- and m-isomer.
(d) All of these are correct reasons.
3. Identify A,B,C and D: D
AgCN

B Alc.KOH C2H5Br Aq. KOH A

KCN

a) A-C2H5OH, B-C2H5OK, C-C2H5CN, D-C2H5NC

b) A-C2H5OH, B-C2H4, C-C2H5CN, D-C2H5NC
c) A-C2H5OH, B-C2H4, C-C2H5NC, D-C2H5CN
d) A-C2H4, B-C2H5OH, C-C2H5COOH, D-C2H5NC

4. Which of the following sequence of reactions can be used for conversion

of C6H5CH3 to C6H5CH=CH2?

(a) SOCl2; H2O (b) SO2Cl2; alc.KOH

(c) Cl2/hυ; H2O (d) SOCl2; alc.KOH

5. Which of the following organohalogen compounds when heated with

alcoholic KOH does not undergo dehydrohalogenation reaction?

(a) secondary butyl chloride (b) Neopentyl chloride

 (c) Isobutyl chloride (d) tertiary butyl chloride
6. The increasing order of nucleophilicity would be?
(a) Cl– < Br– < I– (b)I– < Cl– < Br–
(c) Br– < Cl– < F- (d)I– < Br– < Cl–
The following questions, Q.No 7-11 are short answer Type I and carry 2
marks each. [2x5=10]
7. Give reasons :
(i) n-Butyl bromide has higher boiling point than iso-butyl bromide.
(ii) Racemic mixture is optically inactive.
8. How will you carry out the following conversions :
(i) Chlorobenzene to biphenyl
(ii) Propene to 1-nitropropane
9. (i) Which alkyl halide from the following pair is chiral and undergoes faster
SN2 reaction?

(ii) Complete the reaction:

10. Account for the following :

(i) The C – Cl bond length in chlorobenzene is shorter than that in CH3 – Cl.
(ii) Chloroform is stored in closed dark brown bottles.

11. (a) Write the structural formula of A, B, C and D in the following sequence
of reaction:

Q.No 12-14 are Short Answer Type II and carry 3 marks each. [3x3=9]
12. Arrange the compounds in increasing order of the property indicated:
(a)1-Bromo butane, 1- Bromo-2,2-dimethyl propane, 1- Bromo-2-methylbutane,
1-Bromo-3-methylbutane (SN2 reactivity)
(b) C6H5CH2Br, C6H5C (CH3) (C6H5) Br, C6H5CH (C6H5) Br, C6H5CH (CH3) Br
(SN1 reactivity)
(c) 1-Bromo butane, 1- Bromo-2,2-dimethyl propane, 1- Bromo-2-
methylbutane, 1-Bromo-3-methylbutane (Boiling point)
13. Write the major product(s) in the following:
14. How are the following conversions carried out?
(i) Benzyl chloride to benzyl alcohol,
(ii) Methyl magnesium bromide to 2-methyl- propan-2-ol.
Q. No. 15 carrys 5 mark. [5x1=5]
15. (a) An organic compound ‘A’ having molecular formula C3H6 on treatment
with aqueous H2SO4 gives ‘B’ which on treatment with Lucas reagent gives
‘C’. The compound ‘C’ on treatment with alcoholic KOH gives back ‘A’.
Identify A, B and C.
(b) What is Freon-12? Write one of its use.