ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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Chapter 16, Problem 37PP
Interpretation Introduction

Interpretation:

For the 2-ethyl-3-methyl-1,3-cyclohexadiene treated with HBr , the four products and the mechanism that explains the formation of each product are needed to be drawn.

Concept introduction:

Conjugated Dienes undergoes addition reactions with HBr as similar to simple alkenes addition with HBr , but instead of single carbocation intermediate formation of simple alkenes; dienes will form resonance stabilized allylic carbocation as an intermediate.

  • The allylic carbocation is formed as an intermediate by the addition of proton in the HBr ,
  • The Br (nucleophilic) can attacks in either of the two resonance stabilized carbocation’s in the in the allylic intermediate.  

For the Butadiene type dienes, there are four carbons for addition of proton, but at C1 and C4 carbons only forms the allylic carbocation.

To draw: the four products and the mechanism that explains the formation of each product for the 2-ethyl-3-methyl-1,3-cyclohexadiene treated with HBr .

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