Consider all the structural isomers with molecular formula 
are separately treated with 
to give respective substitution products, without any rearrangement. The number of products which can exhibit optical isomerism from these is 
.
Text Solution
Verified by Experts3
(3)
For 
structural isomers to show optical isomerism after KOH substitution 
, the resulting product must have a chiral center (asymmetric carbon with four different groups).
Possible carbon skeletons: n-pentane, 2-methylbutane, 2,2-dimethylpropane.
Analysis of isomers:
2-bromopentane 
: C 2 bonded to 
, and 
(chiral).
3-bromopentane 
: C 3 bonded to 
chiral).
3-bromo-2-methylbutane 
: Chiral center present.
1-bromo-3-methylbutane 
: C 2 bonded to 
, and 
(chiral).
2,2-dimethylpropane derivatives: No chiral centers possible.
Compounds giving chiral products: 2-bromopentane, 3-bromo-2-methylbutane, and 1-bromo-3-methylbutane. Total 
.
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