Consider all the structural isomers with molecular formula C5H11Br are separately treated with KOH(aq)
Q. Consider all the structural isomers with molecular formula C5H11Br are separately treated with KOH(aq) to give respective substitution products, without any rearrangement. The number of products which can exhibit optical isomerism from these is ____.
Correct Answer: 3

Explanation

First, list all possible structural isomers of C5H11Br.

There are 8 structural isomers of C5H11Br.

On treatment with KOH(aq), all these undergo nucleophilic substitution to form corresponding alcohols (C5H11OH).

Now, check each product for the presence of a chiral carbon (carbon attached to four different groups).

After substitution:

1-bromopentane → 1-pentanol (no chiral carbon)
2-bromopentane → 2-pentanol (one chiral carbon → optically active)
3-bromopentane → 3-pentanol (symmetrical → achiral)

From branched chain isomers:

2-bromo-2-methylbutane → tert-amyl alcohol (no chiral carbon)
1-bromo-3-methylbutane → 3-methyl-1-butanol (no chiral carbon)
2-bromo-3-methylbutane → 3-methyl-2-butanol (chiral → optically active)

1-bromo-2-methylbutane → 2-methyl-1-butanol (chiral → optically active)

Thus, the optically active alcohols formed are:

1. 2-pentanol
2. 3-methyl-2-butanol
3. 2-methyl-1-butanol

Total number of products showing optical isomerism:

= 3

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