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  4. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic KOH is

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Q. The total number of alkenes possible by dehydrobromination of $3$-bromo-$3$-cyclopentylhexane using alcoholic $KOH$ is

IIT JEEIIT JEE 2011Haloalkanes and Haloarenes

Solution:

The substrate has three different types of $B - H$, therefore, first three structural isomers of alkenes are expected as :
image
The last two alkenes II and III are also capable of showing geometrical isomerism, hence two geometrical isomers for each of them will be counted giving a total of five isomers.