Daily Practice Problem Sheet-1

(Alkanes)
1. What is the IUPAC name for CH3CH2C(CH3)2CH2CH(CH3)2?
(a) 3,3,5-trimethylhexane
(b) 2,2,5-trimethylhexane
(c) 2,4,4-trimethylhexane
(d) 1,1,3,3-tetramethylpentane
2. The radical halogenation of 2-methylpropane gives two products: (CH 3)2CHCH2X (minor) and (CH3)3CX
(major). Chlorination gives a larger amount of the minor product than does bromination, Why?
(a) Bromine is more reactive than chlorine and is able to attack the less reactive 3 C-H.
(b) Bromine atoms are less reactive (more selective) than chlorine, and preferentially attack the weaker 3
C-H bond.
(c) The methyl groups are more hindered to attack by the larger bromine atom.
(d) Bromination is reversible and the more stable 3-alkyl bromide is formed exclusively.
3. How many dichlorinated isomers can be formed by the halogenation of CH 3CH2CH2CH3 with Cl2 in the
presence of light?
(a) 2
(b) 3
(c) 5
(d) 6
4. A sec-butyl group is?
(a) (CH3)4C
(b) (CH3)3C(c) (CH3)2CHCH2(d) CH3CH2CH(CH3)5. A chiral C6H12 hydrocarbon undergoes catalytic hydrogenation to yield an achiral C6H14 product. What
is the starting compound?
(a) cis-2-hexene
(b) 3-methyl-2-pentene
(c) 4-methyl-2-pentene
(d) 3-methyl-1-pentene
6. The highest boiling point is expected for
(a) Isooctane
(b) n-octane
(c) 2,2,3,3-tetramethylbutane (d) n-butane
7. In which of the following reactions a new C C bond is formed
(a) Sabatier-Sandrens reaction
(b) Wurtz reaction
(c) Clemmensen reduction
(d) Wolf-kishner reduction
8. Propose synthesis of n-hexane from each of the following
(a) CH3CH2CH2CH2CH2CH2Br
(b) CH3CH=CHCH2CH2CH3
(c) CH3CH2CH2Br
(d) CH3CH2CH2CH2CH2CHO
9. Propose a synthesis of CH3D from CH4
10. Arrange the following in order of decreasing melting point
(a) Octane, Hexane and decane,
(b) n-octane, 3,3-dimethylhexane and 2,2,3,3 tetramethylbutane
11. Write equations for the preparation of n-butane from
(a) n-butyl bromide
(b) sec-butyl bromide (c) ethyl chloride
(d) 1-butene
(e) 2-butene
12. draw structures of all products expected from monochlorination at room temp of
(a) n-hexane
(b) iso-hexane
(c) 2,2,4-trimethylpentane
(d) 2,2-dimethylbutane