ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Chapter 9.12, Problem 19P
Interpretation Introduction

Interpretation: The stereochemistry of the alkyl chloride formed by the reaction of (R)-butan-2-ol with (SOCl2) and pyridine is to be stated.

Concept introduction: Alkyl chlorides are obtained by the reaction of 1οor2ο alcohols with thionyl chloride (SOCl2), and pyridine. The reaction yields SO2, and HCl as by-products. The mechanism of the reaction involves two steps. The first step is conversion of the OH group into a good leaving group. The second step is nucleophilic attack by Cl through an SN2 reaction. This SN2 reaction results inversion of stereochemistry at stereogenic center.

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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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