ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
Question
Book Icon
Chapter 7.7, Problem 7.15TIY

(a)

Interpretation Introduction

Interpretation: The reason behind rate of bimolecular elimination in 1,2,3,4,5,6-hexachlorocyclohexane 7000 times slower than it’s any other stereoisomers should be explained.

Concept introduction: Experimental evidence for E2 mechanism pathway suggests that it readily occurs if the leaving group with respect to the proton is in anti- orientation in stable chair conformation. For instance, when cis-1-bromo-4-(1,1-dimethylethyl)cyclohexane is treated with strong base it leads to faster bimolecular elimination to afford the corresponding alkene relative to trans-1-bromo-4-(1,1-dimethylethyl)cyclohexane . This is because in the transition state for E2 elimination as illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7.7, Problem 7.15TIY , additional homework tip  1

(b)

Interpretation Introduction

Interpretation: The formation of only specific elimination product should be explained.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7.7, Problem 7.15TIY , additional homework tip  2

Concept introduction: Experimental evidence for E2 mechanism pathway suggests that it readily occurs if the leaving group with respect to the proton is in anti- orientation in stable chair conformation. For instance, when cis-1-bromo-4-(1,1-dimethylethyl)cyclohexane is treated with strong base it leads to faster bimolecular elimination to afford the corresponding alkene relative to trans-1-bromo-4-(1,1-dimethylethyl)cyclohexane . This is because in the transition state for E2 elimination as illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 7.7, Problem 7.15TIY , additional homework tip  3

Blurred answer
Students have asked these similar questions
In the drawing area below, draw the major products of this organic reaction: If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. 1. NaH 2. CH3Br ? Click and drag to start drawing a structure. No reaction. : ☐ N
+ Predict the major product of the following reaction. : ☐ + ☑ ค OH H₂SO4 Click and drag to start drawing a structure.
Consider this organic reaction: ... OH CI Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant rate, check the box under the drawing area instead. ☐ No Reaction. Click and drag to start drawing a structure. : а
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning