One or more options correct
Correct statement(s) about nucleophilic substitution is(are)
- A. -2-bromobutane reacts with in acetone to give -2-iodobutane
- B. -3-bromo-3-methylhexane on hydrolysis in aqueous acetone gives an optically active alcohol with complete inversion
- C. tert-Butyl bromide with sodium ethoxide in ethanol gives mainly tert-butyl ethyl ether
- D. 1-Bromo-2,2-dimethylpropane undergoes faster than bromoethane
Show answer and solution
Answer: A
Option A is correct: in acetone is a strong nucleophile in a polar aprotic solvent, so the secondary bromide reacts by with inversion; because I keeps the same CIP priority order as Br (I > ethyl > methyl > H), inversion converts into . Option B is wrong: a tertiary halide in a polar protic solvent ionises () to a planar carbocation, giving a racemic alcohol, not complete inversion. Option C is wrong: a tertiary bromide treated with a strong base such as ethoxide undergoes E2 elimination (back-side attack at the tertiary carbon is blocked), giving 2-methylpropene as the main product. Option D is wrong: the neopentyl substrate has a quaternary carbon next to the reaction centre, so back-side attack is severely hindered and it reacts far more slowly than bromoethane.
Saved on this device. Sign in or create a free account to keep it on every device.