ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
Question
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Chapter 11, Problem 11.66SP

(a)

Interpretation Introduction

To determine: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent.

Interpretation: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent is to be stated.

Concept introduction: Under normal conditions tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it undergoes a migration of the double bond (that is called an allylic shift) and subsequent oxidation of alcohol. Bobbitt’s reagent is helpful in such kind of oxidation reactions.

(b)

Interpretation Introduction

To determine: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent.

Interpretation: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent is to be stated.

Concept introduction: Under normal conditions tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it undergoes a migration of the double bond (that is called an allylic shift) and subsequent oxidation of alcohol. Bobbitt’s reagent is helpful in such kind of oxidation reactions.

(c)

Interpretation Introduction

To determine: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent.

Interpretation: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent is to be stated.

Concept introduction: Under normal conditions tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it undergoes a migration of the double bond (that is called an allylic shift) and subsequent oxidation of alcohol. Bobbitt’s reagent is helpful in such kind of oxidation reactions.

(d)

Interpretation Introduction

To determine: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent.

Interpretation: The expected product of the given 3ο allylic alcohol with Bobbitt’s reagent is to be stated.

Concept introduction: Under normal conditions tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it undergoes a migration of the double bond (that is called an allylic shift) and subsequent oxidation of alcohol. Bobbitt’s reagent is helpful in such kind of oxidation reactions.

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Chapter 11 Solutions

ORGANIC CHEMISTRY

Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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