Thursday 14 May 2015

organic chemistry - Dehydrobromination of 3-bromo-3-cyclopentylhexane and number of possible alkene products



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.



  1. 3-cyclopentylhex-2-ene

  2. 3-cyclopentylhex-3-ene

  3. (hexan-3-ylidene)cyclopentane



I can't find the other 2. Any hint?



Answer



solution re


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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