A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent. Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent. Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

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Answer 1

Question

Chapter 14.10A, Problem 14.18P

(a)

Interpretation Introduction

To determine: A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

(b)

Interpretation Introduction

To determine: The products that might be formed by the reaction of mustard gas with bleach.

Interpretation: The products that might be formed by the reaction of mustard gas with bleach are to be stated.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

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9 7 8 C 9 8 200 190 B 5 A -197.72 9 8 7 15 4 3 0: ང་ 200 190 180 147.52 134.98 170 160 150 140 130 120 110 100 90 90 OH 10 4 3 1 2 -143.04 140. 180 170 160 150 140 130 120 110 100 90 CI 3 5 1 2 141.89 140.07 200 190 180 170 160 150 140 130 120 110 100 ៖- 90 129. 126.25 80 70 60 -60 50 40 10 125.19 -129.21 80 70 3.0 20 20 -8 60 50 10 ppm -20 40 128.31 80 80 70 60 50 40 40 -70.27 3.0 20 10 ppm 00˚0-- 77.17 30 20 20 -45.36 10 ppm -0.00 26.48 22.32 ―30.10 ―-0.00

Assign all the carbons

C 5 4 3 CI 2 the Righ B A 5 4 3 The Lich. OH 10 4 5 3 1 LOOP- -147.52 T 77.17 -45.36 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm B -126.25 77.03 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 200 190 180 170 160 150 140 130 120 110 100 90 80 TO LL <-50.00 70 60 50 40 30 20 10 ppm 45.06 30.18 -26.45 22.36 --0.00 45.07 7.5 1.93 2.05 -30.24 -22.36 C A 7 8 5 ° 4 3 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 8 5 4 3 ཡི་ OH 10 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 5 4 3 2 that th 7 I 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 115 2.21 4.00 1.0 ppm 6.96 2.76 5.01 1.0 ppm 6.30 1.00

Answer 2

Question

Chapter 14.10A, Problem 14.18P

(a)

Interpretation Introduction

To determine: A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

(b)

Interpretation Introduction

To determine: The products that might be formed by the reaction of mustard gas with bleach.

Interpretation: The products that might be formed by the reaction of mustard gas with bleach are to be stated.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

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Answer 3

Question

Chapter 14.10A, Problem 14.18P

(a)

Interpretation Introduction

To determine: A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

(b)

Interpretation Introduction

To determine: The products that might be formed by the reaction of mustard gas with bleach.

Interpretation: The products that might be formed by the reaction of mustard gas with bleach are to be stated.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

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Answer 4

Question

Chapter 14.10A, Problem 14.18P

(a)

Interpretation Introduction

To determine: A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

(b)

Interpretation Introduction

To determine: The products that might be formed by the reaction of mustard gas with bleach.

Interpretation: The products that might be formed by the reaction of mustard gas with bleach are to be stated.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

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Answer 5

Chapter 14.10A, Problem 14.18P

(a)

Interpretation Introduction

To determine: A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

(b)

Interpretation Introduction

To determine: The products that might be formed by the reaction of mustard gas with bleach.

Interpretation: The products that might be formed by the reaction of mustard gas with bleach are to be stated.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

Answer 6

Chapter 14.10A, Problem 14.18P

(a)

Interpretation Introduction

To determine: A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

Answer 7

Chapter 14.10A, Problem 14.18P

(a)

Interpretation Introduction

To determine: A mechanism that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Interpretation: A mechanism is to be proposed that explains the fact that mustard gas is an exceptionally potent alkylating agent.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

Answer 8

(b)

Interpretation Introduction

To determine: The products that might be formed by the reaction of mustard gas with bleach.

Interpretation: The products that might be formed by the reaction of mustard gas with bleach are to be stated.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

Answer 9

(b)

Interpretation Introduction

To determine: The products that might be formed by the reaction of mustard gas with bleach.

Interpretation: The products that might be formed by the reaction of mustard gas with bleach are to be stated.

Concept introduction: Mustard gas was used as a poisonous chemical agent in World War I. It is much more toxic than a typical primary alkyl chloride. It is able to alkylate amino groups on important metabolic enzymes. It renders the enzyme inactive. Therefore, it is toxic.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2P Ch. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5P Ch. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8P Ch. 14.5 - Prob. 14.9P Ch. 14.6 - Prob. 14.10P

Solution Summary: The author explains that mustard gas is an exceptionally potent alkylating agent. Sulfur is more nucleophilic than other corresponding oxygen compounds.

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