(a) Interpretation: The appropriate curved arrows for the given reaction are to be drawn. Concept introduction: In the S N 2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the S N 2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

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Answer 1

Question

Chapter 8, Problem 8.66P

Interpretation Introduction

(a)

Interpretation:

The appropriate curved arrows for the given reaction are to be drawn.

Concept introduction:

In the SN2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the SN2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

Interpretation Introduction

(b)

Interpretation:

The reason the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O atoms on methionine is to be suggested.

Concept introduction:

The charge repulsion between the reacting species prevents any negatively charged atom from acting as a nucleophile.

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Answer 2

Question

Chapter 8, Problem 8.66P

Interpretation Introduction

(a)

Interpretation:

The appropriate curved arrows for the given reaction are to be drawn.

Concept introduction:

In the SN2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the SN2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

Interpretation Introduction

(b)

Interpretation:

The reason the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O atoms on methionine is to be suggested.

Concept introduction:

The charge repulsion between the reacting species prevents any negatively charged atom from acting as a nucleophile.

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Answer 3

Question

Chapter 8, Problem 8.66P

Interpretation Introduction

(a)

Interpretation:

The appropriate curved arrows for the given reaction are to be drawn.

Concept introduction:

In the SN2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the SN2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

Interpretation Introduction

(b)

Interpretation:

The reason the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O atoms on methionine is to be suggested.

Concept introduction:

The charge repulsion between the reacting species prevents any negatively charged atom from acting as a nucleophile.

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Answer 4

Question

Chapter 8, Problem 8.66P

Interpretation Introduction

(a)

Interpretation:

The appropriate curved arrows for the given reaction are to be drawn.

Concept introduction:

In the SN2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the SN2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

Interpretation Introduction

(b)

Interpretation:

The reason the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O atoms on methionine is to be suggested.

Concept introduction:

The charge repulsion between the reacting species prevents any negatively charged atom from acting as a nucleophile.

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Answer 5

Chapter 8, Problem 8.66P

Interpretation Introduction

(a)

Interpretation:

The appropriate curved arrows for the given reaction are to be drawn.

Concept introduction:

In the SN2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the SN2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

Interpretation Introduction

(b)

Interpretation:

The reason the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O atoms on methionine is to be suggested.

Concept introduction:

The charge repulsion between the reacting species prevents any negatively charged atom from acting as a nucleophile.

Answer 6

Chapter 8, Problem 8.66P

Interpretation Introduction

(a)

Interpretation:

The appropriate curved arrows for the given reaction are to be drawn.

Concept introduction:

In the SN2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the SN2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

Answer 7

Chapter 8, Problem 8.66P

Interpretation Introduction

(a)

Interpretation:

The appropriate curved arrows for the given reaction are to be drawn.

Concept introduction:

In the SN2 step, the substrate undergoes substitution in which one atom or group of atoms is replaced by another. A nucleophile attacks and forms a bond with the electrophilic carbon atom. A nucleophile forms a bond to the substrate; at the same time, a bond to the leaving group, i.e., the group that is displaced, is broken. In the SN2 step, a curved arrow is drawn from the lone pair of the electron rich atom of the nucleophile to the electron poor atom of the substrate. A second curved arrow is drawn to indicate the breaking of the bond.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The reason the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O atoms on methionine is to be suggested.

Concept introduction:

The charge repulsion between the reacting species prevents any negatively charged atom from acting as a nucleophile.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The reason the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O atoms on methionine is to be suggested.

Concept introduction:

The charge repulsion between the reacting species prevents any negatively charged atom from acting as a nucleophile.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 8 - Prob. 8.1P Ch. 8 - Prob. 8.2P Ch. 8 - Prob. 8.3P Ch. 8 - Prob. 8.4P Ch. 8 - Prob. 8.5P Ch. 8 - Prob. 8.6P Ch. 8 - Prob. 8.7P Ch. 8 - Prob. 8.8P Ch. 8 - Prob. 8.9P Ch. 8 - Prob. 8.10P

Solution Summary: The author explains that the curved arrows for the given reaction are drawn on the basis of movement of electrons from the electron-rich site to the negatively charged O.

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