Thestereoisomer whichreacts faster in the elimination reaction on treatment with sodium ethoxide in ethanol is to be predicted. Concept Introduction: > Dehydrohalogenation reaction is the loss of hydrogen and a halogen from adjacent carbon atoms in an alkyl halide to form the most stable alkene by β eliminations. > E 2 elimination reactions are favored whenever an alkyl halide is treated with a strong base. > The difference in the reaction rates between the two stereoisomers results from different degrees of π bond development in the E 2 transition state. > The anti-coplanar arrangement imposes little strain in the E 2 transition state, and elimination occurs readily. An absence of anti-coplanar arrangement increases the strain in the E 2 transition state, and this slows the rate of elimination.

Question

Menthyl chloride and neomenthyl chloride have the structures shown. One of these stereoisomers undergoes elimination on treatment with sodium ethoxide in ethanol much more readily than the other. Which reacts faster, menthyl chloride or neomenthyl chloride? Why?

Answer 1

Question

Chapter 7.16, Problem 26P

Interpretation Introduction

Interpretation:

Thestereoisomer whichreacts faster in the elimination reaction on treatment with sodium ethoxide in ethanol is to be predicted.

Concept Introduction:
>
Dehydrohalogenation reaction is the loss of hydrogen and a halogen from adjacent carbon atoms in an alkyl halide to form the most stable alkene by β eliminations.
>
E2 elimination reactions are favored whenever an alkyl halide is treated with a strong base.
>
The difference in the reaction rates between the two stereoisomers results from different degrees of π bond development in the E2 transition state.
>
The anti-coplanar arrangement imposes little strain in the E2 transition state, and elimination occurs readily. An absence of anti-coplanar arrangement increases the strain in the E2 transition state, and this slows the rate of elimination.

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