Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 11, Problem 11.47P
During the synthesis of the antiasthmatic drug montelukast (Singulair), a silyl ether protecting group is used to mask the reactivity of an OH group. The silyl group chosen is the tert-butyldimethylsilyl (TBS) group. Draw the product of the following transformation, assuming the TBS-Cl reagent reacts only once with the starting material. Briefly explain your answer.
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Analyze the following reaction by looking at the electron configurations given below each box.
Put a number and a symbol in each box to show the number and kind of the corresponding atom or ion.
Use the smallest integers possible.
cation
anion
+
+
Shell 1: 2
Shell 2: 8
Shell 3: 1
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None
IV.
Show the detailed synthesis strategy for the following compounds.
a. CH3CH2CH2CH2Br
CH3CH2CCH2CH2CH3
Chapter 11 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 11.2 - Write IUPAC and common names for these ethers. (a)...Ch. 11.3 - Arrange these compounds in order of increasing...Ch. 11.4 - Show how you might use the Williamson ether...Ch. 11.4 - Show how ethyl hexyl ether might be prepared by a...Ch. 11.5 - Account for the fact that treatment of tert-butyl...Ch. 11.5 - Draw structural formulas for the major products of...Ch. 11.6 - Prob. 11.7PCh. 11.8 - Draw the expected products of Sharpless...Ch. 11.9 - Prob. AQCh. 11.9 - Prob. BQ
Ch. 11.9 - Prob. CQCh. 11.9 - Prob. DQCh. 11 - Write names for these compounds. Where possible,...Ch. 11 - Prob. 11.11PCh. 11 - Each compound given in this problem is a common...Ch. 11 - Account for the fact that tetrahydrofuran (THF) is...Ch. 11 - Prob. 11.14PCh. 11 - Write equations to show a combination of reactants...Ch. 11 - Propose a mechanism for this reaction.Ch. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Ethylene oxide is the starting material for the...Ch. 11 - Prob. 11.22PCh. 11 - Predict the structural formula of the major...Ch. 11 - The following equation shows the reaction of...Ch. 11 - Propose a mechanism to account for this...Ch. 11 - Acid-catalyzed hydrolysis of the following epoxide...Ch. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Propose a mechanism for the following...Ch. 11 - Show reagents and experimental conditions to...Ch. 11 - Starting with cis-3-hexene, show how to prepare...Ch. 11 - Show reagents to convert cycloheptene to each of...Ch. 11 - Show reagents to convert bromocyclopentane to each...Ch. 11 - Prob. 11.35PCh. 11 - Starting with acetylene and ethylene oxide as the...Ch. 11 - Following are the steps in the industrial...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Aldehydes and ketones react with one molecule of...Ch. 11 - Prob. 11.42PCh. 11 - Write the products of the following sequences of...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - During the synthesis of the antiasthmatic drug...Ch. 11 - Prob. 11.48P
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