E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn. Concept Introduction: An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step. A strong base favours an E2 reaction. A high concentration of a base favours an E2 reaction. If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

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Answer 1

Question

Chapter 9, Problem 111P

(a)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(b)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(c)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(d)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(e)

Interpretation Introduction

Interpretation:

E2 elimination products of 3-chloro-3-ethyl-2,2-dimethylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

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The Hofmann product is favored by the E2 mechanism when 2-bromo-3-methylbutane is added: A. MeOH B. MeO:- in MeOH C. Nal in acetona D. (CH 3)3 CO:- in (CH 3),COH

When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed

When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutane

Answer 2

Question

Chapter 9, Problem 111P

(a)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(b)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(c)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(d)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(e)

Interpretation Introduction

Interpretation:

E2 elimination products of 3-chloro-3-ethyl-2,2-dimethylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

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Answer 3

Question

Chapter 9, Problem 111P

(a)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(b)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(c)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(d)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(e)

Interpretation Introduction

Interpretation:

E2 elimination products of 3-chloro-3-ethyl-2,2-dimethylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Expert Solution & Answer

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See solution

Answer 4

Question

Chapter 9, Problem 111P

(a)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(b)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(c)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(d)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(e)

Interpretation Introduction

Interpretation:

E2 elimination products of 3-chloro-3-ethyl-2,2-dimethylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Expert Solution & Answer

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Answer 5

Chapter 9, Problem 111P

(a)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(b)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(c)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(d)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

(e)

Interpretation Introduction

Interpretation:

E2 elimination products of 3-chloro-3-ethyl-2,2-dimethylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 6

Chapter 9, Problem 111P

(a)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 7

Chapter 9, Problem 111P

(a)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 8

(b)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 9

(b)

Interpretation Introduction

Interpretation:

E2 elimination products of (2S,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 10

(c)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 11

(c)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3S)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 12

(d)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 13

(d)

Interpretation Introduction

Interpretation:

E2 elimination products of (2R,3R)-2-chloro-3-methylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 14

(e)

Interpretation Introduction

Interpretation:

E2 elimination products of 3-chloro-3-ethyl-2,2-dimethylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 15

(e)

Interpretation Introduction

Interpretation:

E2 elimination products of 3-chloro-3-ethyl-2,2-dimethylpentane drawn.

Concept Introduction:

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

A strong base favours an E2 reaction.

A high concentration of a base favours an E2 reaction.

If one of the reactants is charged, an E2 reaction will be favoured by the least polar solvent that will dissolve the reactant. If neither of the reactant is charged an E2 reaction is favoured by the protic polar solvent.

Answer 16

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Answer 17

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Answer 18

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Answer 19

Ch. 9.1 - Prob. 3P Ch. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8P Ch. 9.2 - Prob. 9P Ch. 9.2 - Prob. 10P Ch. 9.2 - Prob. 11P Ch. 9.2 - Prob. 12P Ch. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P

Solution Summary: The author explains that an E2 reaction is a concerted one-step reaction in which the proton and the halide ion are removed in the same step.

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Chapter 9 Solutions