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

Do the electrons on the OH participate in resonance with the ring through a p orbital? How many pi electrons are in the ring, 4 (from the two double bonds) or 6 (including the electrons on the O)?

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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Do the electrons on the OH participate in resonance with the ring through a p orbital? How many pi electrons are in the ring, 4 (from the two double bonds) or 6 (including the electrons on the O)?

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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.