Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
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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

Chapter 14 Solutions

Organic Chemistry (9th Edition)

Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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