NARAYANA SRI CHAITANYA IIT

ACADEMY
KAVURI HILLS, MADHAPUR, HYDERABAD.
Section: Junior Alkanes Date: 02-01-2014
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SUBJECTIVE TYPE
1. If the reactivity of 1°:2°:3° hydrogen towards chlorination is 1:3.8:5 calculate the % composition of
products formed by the chlorination of butane.
2. If the relative reactivity of 1°:2°:3° hydrogen towards bromination is 1:82:1600, calculate the
percentage of different products formed by the bromination of 2-methylbutane.
3. When sulfuryl chloride(SO2Cl2) is used to chlorinate an alkane, an organic peroxide is used as an
initiator. SO2 is also a product. Write a mechanism for the chlorination, including the role of peroxide.
4. Free radical chlorination of CD4 occurs 12 times slower than CH4. Why?
5. Singlet methylene (:CH2), generated by the decomposition of diazomethane, CH2N2, inserts between
the C – H bond in an alkane. It reacts with pentane to give different products. Identify all the products
and their relative percentage yields if probability only controls the product distribution.
6. What is the activation energy of the process  Cl2? Draw the energy profile diagram for this
reaction.
7. If oxygen is present during a free radical reaction, there is an induction period, after which the reaction
rate increases. Why?
8. Prepare the following compounds using indicated starting materials and Cl2/Br2, D2O, D2 and 14CH3I.
A compound once made can be used in a later synthesis.
(a) CH3CHDCH2D from propane (b) Me2CH14CH3 from propane
9. The following alkanes on monochlorination give only one product. Give the structures of each alkane
and its chloride:
(a) C5H12 (b) C8H18
ONE OR MORE OPTIONS CORRECT
10. Major product of monochlorination of isobutene is
(A) n-butylchloride (B) isobutylchloride (C) t-butylchloride (D) sec-butylchloride
mcq
11 . Which of the following alkanes give only one product on monobromination?

(A) (B) (C) (D)

12. Predict the product of the following reaction:

(A) (B) (C) (D)

13. Which of the following hydrocarbon has the highest calorific value?
(A) n-pentane (B) 2-methylbutane (C) 2,2-dimethylpropane (D) All have the same
14. Predict the product of the following reaction:
 (A) (B) (C) (D)

15. Monobromination of methylcyclohexane mainly gives

(A) (B) (C) (D)

INTEGER TYPE
16. The total number of products formed by chlorination of ethane is
17. The number of fractions on distillation of the dibromo product mixture obtained by photobromination
of butane is
18. The number of products formed by the monochlorination of 3,3-diethylpentane is
19. The number of products formed by the monobromination of n-hexane is
ANSWERS
1. 1-chlorobutane: 28 %; 2-chlorobutane: 72%

2.
3. ROOR→2RO·
RO·+R'H→ R'· + ROH
R'· + SOCl2→ R' Cl'·
·SO2Cl→SO2 + Cl·
Cl·+R'H→ ·R'+ HCl
4. C-D bond is slightly stronger than C-H and hence the enthalpy change for the abstraction of C-D bond
is greater than that for C-H bond.

5.
6. Ea = 0
7. Oxygen being a diradical reacts with alkyl radicals to form organic peroxide which stops the reaction
for a moment. However peroxide can then dissociate to give radicals by absorbing suitable energy and
hence the rate increases after a while.
8. Prepare the following compounds using indicated starting materials and Cl2/Br2, D2O, D2 and 14CH3I.
A compound once made can be used in a later synthesis.
(a) Propane + Br2 →2-bromopropane Propene CH3CHDCH2D

(b) Propane + Br2 →2-bromopropane Me2CH14CH3

9. (a) (b)
10 B 11 AB 12 B 13 A 14 C 15 B 16 7 17 7
18 3 19 4