KCET2026ChemistryHaloalkanes and Haloarenes
In S _ N 1 reaction, the alkyl halide that on hydrolysis produces racemic mixture is
Options
- ATertiary butyl bromide
- B2-bromobutane
- CIsopropyl bromide
- DMethyl bromide
Correct answer
B. 2-bromobutane
Step-by-step solution
In an S _ N 1 reaction, the formation of a racemic mixture occurs only if the product formed has a chiral center. Tertiary butyl bromide on hydrolysis gives tertiary butyl alcohol, which is achiral. 2-bromobutane on hydrolysis forms a planar secondary carbocation intermediate. The nucleophile (water) can attack from either face of the planar carbocation with equal probability, leading to the formation of d and l enantiomers of 2-butanol. Since 2-butanol has a chiral carbon, a racemic mixture is produced. Isopropyl