ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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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This synthesis scheme was designed using the reaction roadmaps. (Reaction roadmaps allow you to "navigate" between the different functional groups and their behavior in chemical reactions.) compound c compound b ● W compound a compound f MAVI compound e m compound d Reagents HBr HBr, H₂O₂, hv a. b. c. H₂O, H₂SO4 d. Br₂ e. Cl₂ f. H₂, Pd Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 #[ ] در g. h. i. j. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If there are alternative structures, draw the most stable one. • If the reaction produces a racemic mixture, draw both stereoisomers. Separate structures with + signs from the drop-down menu. k. I. m. n. O. p. Hg(OAc)2, H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S In this synthesis, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound d. q. r. 2 equivalents of NaNH₂ H2, Lindlar's catalyst Na/NH3 H₂SO4, HgSO4 (sia)2BH then H₂O₂, NaOH 1…
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Chapter 14 Solutions

ORGANIC CHEMISTRY MASTERINGCHEM ACCESS

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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