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View Full Version : Oxymercuration demercuration reaction help.


vkash
Oct1-11, 01:02 AM
1. The problem statement, all variables and given/known data

See attachment there is reaction.why --OH attach to 2nd carbon. why not it attach first carbon(from left).

2. Relevant equations

steric hindrance

3. The attempt at a solution

there seems greater steric hindrance in right carbon(2nd from left) than left one.

gabriels-horn
Oct3-11, 07:24 PM
1. The problem statement, all variables and given/known data

See attachment there is reaction.why --OH attach to 2nd carbon. why not it attach first carbon(from left).

2. Relevant equations

steric hindrance

3. The attempt at a solution

there seems greater steric hindrance in right carbon(2nd from left) than left one.

Sterics is not really a factor with this type of a reaction, it is electrophillic addtion, which takes place around the planar sp2 alkene. If a carbocation were formed, a methyl shift would most likely result in the OH moving to the 3 degree carbon, however, the mercuration reaction proceeds via a ring transition state, no carbocation is formed.