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Halide Substitutions and Eliminations

Examine the ten structural formulas shown at the bottom of this page, and select those that satisfy each of the following conditions. Enter one or more letters (A through J) in each answer box, reflecting your choice for each.

1. Which compounds give an SN2 substitution reaction on treatment with alcoholic NaSH? ...
2. Which compounds give an E2 elimination reaction on treatment with alcoholic KOH? .......
3. Which compounds do not react under either of the previous reaction conditions? ................

A
Bromobenzene: benzene ring bonded to a bromine atom
B
tert-Butyl chloride, (CH3)3C-Cl, a tertiary alkyl chloride
C
(Bromomethyl)cyclohexane: cyclohexane ring with a CH2Br group, a primary bromide
D
CH3-I
E
Benzyl bromide: benzene ring with a CH2Br group
F
Chlorocyclohexane: cyclohexane ring bonded to a chlorine atom, a secondary chloride
G
Neopentyl chloride, (CH3)3C-CH2Cl, a hindered primary chloride
H
Methallyl chloride, 3-chloro-2-methyl-1-propene, an allylic chloride
I
Bromide on a cyclopentane ring bearing four methyl groups, a hindered neopentyl-type secondary bromide
J
Chloride on a bridged bicyclic norbornane (bicyclo[2.2.1]) framework, a bridgehead-constrained chloride

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