a) Interpretation: The above substitution reaction belongs to S N 1 type. Concept introduction: S N 1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Question

Predict whether each of the following substitution reactions is likely to be SN1 or SN. Briefly explain your answer.

Answer 1

Question

Chapter 11.5, Problem 13P

Interpretation Introduction

a)

Interpretation:

The above substitution reaction belongs to S_N1 type.

Concept introduction:

S_N1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Interpretation Introduction

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

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Answer 2

Question

Chapter 11.5, Problem 13P

Interpretation Introduction

a)

Interpretation:

The above substitution reaction belongs to S_N1 type.

Concept introduction:

S_N1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Interpretation Introduction

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

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Answer 3

Question

Chapter 11.5, Problem 13P

Interpretation Introduction

a)

Interpretation:

The above substitution reaction belongs to S_N1 type.

Concept introduction:

S_N1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Interpretation Introduction

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

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Answer 4

Question

Chapter 11.5, Problem 13P

Interpretation Introduction

a)

Interpretation:

The above substitution reaction belongs to S_N1 type.

Concept introduction:

S_N1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Interpretation Introduction

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

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Answer 5

Chapter 11.5, Problem 13P

Interpretation Introduction

a)

Interpretation:

The above substitution reaction belongs to S_N1 type.

Concept introduction:

S_N1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Interpretation Introduction

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

Answer 6

Chapter 11.5, Problem 13P

Interpretation Introduction

a)

Interpretation:

The above substitution reaction belongs to S_N1 type.

Concept introduction:

S_N1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Answer 7

Chapter 11.5, Problem 13P

Interpretation Introduction

a)

Interpretation:

The above substitution reaction belongs to S_N1 type.

Concept introduction:

S_N1 reaction occurs mostly in acidic condition. The OH group is first protonated by HCl. Spontaneous dissociation of the protonated alcohol occurs in a slow, rate determining step to yield a carbocation intermediate. The carbocation intermediate reacts with the chloride ion to yield the chloride product.

Answer 8

Interpretation Introduction

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

Answer 9

Interpretation Introduction

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

Answer 10

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Answer 11

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Answer 21

Ch. 11.1 - Prob. 1P Ch. 11.2 - Prob. 2P Ch. 11.2 - Prob. 3P Ch. 11.3 - Prob. 4P Ch. 11.3 - Prob. 5P Ch. 11.3 - Rank the following compounds in order of their...Ch. 11.3 - Organic solvents like benzene, ether, and...Ch. 11.4 - Prob. 8P Ch. 11.4 - Prob. 9P Ch. 11.4 - Prob. 10P

Solution Summary: The author explains that the above substitution reaction belongs to S N 1 type. The substrate yields a secondary carbocation intermediate.

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.

Chapter 11 Solutions

Solution Summary: The author explains that the above substitution reaction belongs to S N 1 type. The substrate yields a secondary carbocation intermediate.

b) Interpretation: The above substitution reaction belongs to SN2 type. Concept introduction: SN2 reaction occurs rapidly in polar aprotic solvents. The CH3CN is polar aprotic solvent. The Br- is a best leaving group which stabilizes the transition state.

Chapter 11 Solutions

b)

Interpretation:

The above substitution reaction belongs to S_N2 type.

Concept introduction:

S_N2 reaction occurs rapidly in polar aprotic solvents. The CH₃CN is polar aprotic solvent. The Br^- is a best leaving group which stabilizes the transition state.