ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 9.13, Problem 23P
Interpretation Introduction

(a)

Interpretation: The products of the given reaction are to be drawn by indicating the stereochemistry at any stereogenic center.

Concept introduction: Alcohols are converted into alkyl tosylates by treatment with p-toluenesulfonylchloride(TsCl) in the presence of pyridine. The overall reaction converts OH (a poor leaving group) into OTs (a good leaving group). The stereochemistry of the reaction is retention of configuration.

Interpretation Introduction

(b)

Interpretation: The products of the given reaction are to be drawn by indicating the stereochemistry at any stereogenic center.

Concept introduction: Alcohols are converted into alkyl tosylates by treatment with p-toluenesulfonylchloride(TsCl) in the presence of pyridine. The overall reaction converts OH (a poor leaving group) into OTs (a good leaving group). The stereochemistry of the reaction is retention of configuration.

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Chapter 9 Solutions

ORGANIC CHEMISTRY

Ch. 9.11 - Problem 9.18 Draw the products of each reaction,...Ch. 9.11 - Problem 9.19 What is the major product formed...Ch. 9.12 - Prob. 19PCh. 9.12 - Prob. 20PCh. 9.12 - Problem 9.22 Draw the organic products formed in...Ch. 9.12 - Problem 9.23 Draw two steps to convert into each...Ch. 9.13 - Prob. 23PCh. 9.13 - Problem 9.25 Draw the products of each reaction,...Ch. 9.13 - Draw the products formed when (S)-butan-2-ol is...Ch. 9.13 - Draw the product formed when (CH3)2CHOH is treated...Ch. 9.14 - What alkyl halides are formed when each ether is...Ch. 9.14 - Explain why the treatment of anisole with HBr...Ch. 9.15 - Name each thiol. a. b. Ch. 9.15 - Draw the product of each reaction. ac b.d.Ch. 9.15 - Give the IUPAC name for each sulfide. a. b. Ch. 9.15 - Draw the product of each reaction. a. b. Ch. 9.16 - Prob. 33PCh. 9.16 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9.16 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 38PCh. 9 - 9.40 Give IUPAC name for each...Ch. 9 - Prob. 40PCh. 9 - Prob. 41PCh. 9 - 9.46 What alkenes are formed when each alcohol is...Ch. 9 - Prob. 46PCh. 9 - Prob. 51PCh. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 53PCh. 9 - 9.59 Draw two different routes to each of the...Ch. 9 - Prob. 55PCh. 9 - 9.61 Draw the products formed when each ether is...Ch. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 59PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - Prob. 64PCh. 9 - Prob. 75P
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