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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