December 27, 2024, 10:21:19 PM
Forum Rules: Read This Before Posting


Topic: Cyclohexadiene Isomers  (Read 3478 times)

0 Members and 1 Guest are viewing this topic.

Offline saN

  • Regular Member
  • ***
  • Posts: 62
  • Mole Snacks: +0/-1
  • Gender: Male
Cyclohexadiene Isomers
« on: November 30, 2007, 02:23:54 PM »


This is what I came up with. Isomers 1-4 are when the Bromine is closeby to react faster. The bromine would attach closest to the double bond because it will form a more stable product. Isomers 5-8 are when the Bromine is faraway reacting slower allowing time for a bond to shift (would this be called hydride shift?).


Offline Rico

  • Regular Member
  • ***
  • Posts: 73
  • Mole Snacks: +30/-0
Re: Cyclohexadiene Isomers
« Reply #1 on: December 01, 2007, 02:59:42 PM »
Hey saN

The products you came up with is the right ones, but the mechanisms is totally different. An allyl cation is formed (see resonance forms in jpeg) and the nucleophilic bromide anion can attack the two posetively charged ends of this cation equally well, giving 8 different isomeric products (see jpeg attached).

Rico

Sponsored Links