EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 10, Problem 74P

(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.

EBK ORGANIC CHEMISTRY, Chapter 10, Problem 74P , 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.

EBK ORGANIC CHEMISTRY, Chapter 10, Problem 74P , 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.

EBK ORGANIC CHEMISTRY, Chapter 10, Problem 74P , 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.

EBK ORGANIC CHEMISTRY, Chapter 10, Problem 74P , 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.

EBK ORGANIC CHEMISTRY, Chapter 10, Problem 74P , 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.

EBK ORGANIC CHEMISTRY, Chapter 10, Problem 74P , additional homework tip  6

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piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substitutedpiperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene?
The rate law for addition of Br2 to an alkene is first orderin Br2 and first order in the alkene. Does this informationsuggest that the mechanism of addition of Br2 to analkene proceeds in the same manner as for addition of HBr?Explain.
(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case?

Chapter 10 Solutions

EBK ORGANIC CHEMISTRY

Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
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