I faced a question like this:
The total number of alkene products possible from the dehydrobromination of 3-bromo-3-cyclopentylhexane is:
The answer is given 5. But I only found 3.
- 3-cyclopentylhex-2-ene
- 3-cyclopentylhex-3-ene
- (hexan-3-ylidene)cyclopentane
I can't find the other 2. Any hint?
Answer
The structures (i) and (ii) have two isomers each,namely E and Z isomers.
For the structure (iii) there is a plane of symmetry (marked in the diagram) so it is not a geometrical isomer.
Thus Number of isomers=2 (of structure i) +2 (of structure ii) + 1(of structure iii)= 5 isomers
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