Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 11, Problem 65P

(a)

Interpretation Introduction

Interpretation:

The respective reactant (methyl substituted piperidine) and respective product (diene) should be given.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate, and this ammonium halide is treating with silver oxide to give ammonium hydroxide salt.

These quaternary ammonium salt under goes an elimination reaction easily.

Organic Chemistry, Chapter 11, Problem 65P , additional homework tip  1

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the Hofmann elimination, abstraction of proton form β- carbon atom which is having more number of hydrogen to result the elimination product.

Organic Chemistry, Chapter 11, Problem 65P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

The respective reactant (methyl substituted piperidine) and respective product (diene) should be given.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the Hofmann elimination, abstraction of proton form β- carbon atom which is having more number of hydrogen to result the elimination product.

Organic Chemistry, Chapter 11, Problem 65P , additional homework tip  3

(c)

Interpretation Introduction

Interpretation:

The respective reactant (methyl substituted piperidine) and respective product (diene) should be given.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination. Proton abstraction is takes place in β- carbon atom which is having more number of hydrogen.

Organic Chemistry, Chapter 11, Problem 65P , additional homework tip  4

(d)

Interpretation Introduction

Interpretation:

The respective reactant (methyl substituted piperidine) and respective product (diene) should be given.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate, and this ammonium halide is treating with silver oxide to give ammonium hydroxide salt.

These quaternary ammonium salt under goes an elimination reaction easily.

Organic Chemistry, Chapter 11, Problem 65P , additional homework tip  5

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the Hofmann elimination, abstraction of proton form β- carbon atom which is having more number of hydrogen to result the elimination product.

Organic Chemistry, Chapter 11, Problem 65P , additional homework tip  6

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Chapter 11 Solutions

Organic Chemistry

Ch. 11.4 - Draw the product of each of the following...Ch. 11.4 - Explain why the following alcohols, when heated...Ch. 11.4 - What stereoisomers are formed in the following...Ch. 11.4 - Prob. 18PCh. 11.4 - What alcohol would you treat with phosphorus...Ch. 11.5 - Prob. 20PCh. 11.6 - Prob. 22PCh. 11.7 - Prob. 24PCh. 11.7 - Would you expect the reactivity of a five-membered...Ch. 11.7 - Prob. 26PCh. 11.7 - What products are obtained from the reaction of...Ch. 11.7 - Prob. 28PCh. 11.7 - Prob. 29PCh. 11.7 - Prob. 30PCh. 11.8 - Prob. 31PCh. 11.8 - Prob. 32PCh. 11.8 - How do the major products obtained from...Ch. 11.8 - Explain why the two arene oxides in Problem 38...Ch. 11.8 - Three arene oxides can be obtained from...Ch. 11.9 - Explain why the half-life (the time it takes for...Ch. 11.10 - Prob. 38PCh. 11.10 - Prob. 39PCh. 11.10 - Prob. 40PCh. 11.10 - Prob. 41PCh. 11.10 - Prob. 42PCh. 11.11 - Using an alkyl halide and a thiol as starting...Ch. 11.11 - The following three nitrogen mustards were studied...Ch. 11.11 - Why is melphalan a good cancer drug?Ch. 11.11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Which compound is more likely to be carcinogenic?Ch. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Write the appropriate reagent over each arrow.Ch. 11 - What alkenes would you expect to be obtained from...Ch. 11 - Prob. 54PCh. 11 - When heated with H2SO4, both...Ch. 11 - What is the major product obtained from the...Ch. 11 - When deuterated phenanthrene oxide undergoes a...Ch. 11 - An unknown alcohol with a molecular formula of...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Propose a mechanism for the following reaction:Ch. 11 - What product would be formed if the four-membered...Ch. 11 - Which of the following ethers would be obtained in...Ch. 11 - Using the given starting material any necessary...Ch. 11 - Prob. 65PCh. 11 - When 3-methyl-2-butanol is heated with...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - How could you synthesize isopropyl propyl ether,...Ch. 11 - When the following seven-membered ring alcohol is...Ch. 11 - Ethylene oxide reacts readily with HO because of...Ch. 11 - Prob. 71PCh. 11 - Propose a mechanism for each of the following...Ch. 11 - Explain why the acid-catalyzed dehydration of an...Ch. 11 - Triethylene glycol is one of the products obtained...Ch. 11 - Prob. 75PCh. 11 - Prob. 76PCh. 11 - When ethyl ether is heated with excess HI for...Ch. 11 - Propose a mechanism for the following reaction:Ch. 11 - Prob. 79PCh. 11 - An ion with a positively charged nitrogen atom in...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - Prob. 82PCh. 11 - The following reaction takes place several times...Ch. 11 - A vicinal diol has OH groups on adjacent carbons....Ch. 11 - Prob. 85PCh. 11 - Prob. 86PCh. 11 - Two stereoisomers are obtained from the reaction...Ch. 11 - Propose a mechanism for each or the following...Ch. 11 - Triethylenemelamine (TEM) is an antitumor agent....
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