Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Question
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Chapter 11, Problem 54P

(a)

Interpretation Introduction

Interpretation:

The major products formed under the given reaction conditions should be identified.

Concept introduction:

SN1 reaction:

The alcohols reacts with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable and won’t undergo SN1 substitution reaction

(b)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

SN2 reaction:

The alcohols reacts with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes SN2 substitution reaction than secondary alcohol than tertiary alcohol because SN2 reaction is simultaneous reaction.

(c)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  1

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

Chromic Acid:

Chromic Acid (H2CrO4) is used as an oxidizing agent, primary alcohol oxidized in to acid, secondary alcohol oxidized in to ketone.

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  2

(e)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  3

In the presence of acid catalyst, this reaction takes place through partial SN1 and partial SN2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  4

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(f)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  5

In the presence of acid catalyst, this reaction takes place through partial SN1 and partial SN2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  6

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(g)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

Tosylation reaction:

The alcohol is treated with any tosyl chloride (methane sulfonyl chloride) which yields tosylated product this reaction is called as alkyl tosylate and which is shown below,

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  7

SN2 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms which is bearing alcohol group which yield the corresponding inversion product.

(h)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

Oxidation of alcohol:

Alcohols reaction with hypochlorous (oxidizing agent) in the presence of acetic acid which yields the corresponding aldehyde and ketones.

Primary alcohols gives aldehyde, secondary alcohols gives ketone.

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  8

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  9

(i)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quartnary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

For elimination reaction quartnary ammonium halide can be converted in to quartnary ammonium hydroxide by using aqueous silver oxide.

Organic Chemistry, Chapter 11, Problem 54P , additional homework tip  10

Hofmann elimination:

Quartnary 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 54P , additional homework tip  11

(j)

Interpretation Introduction

Interpretation:

The major products formed under the given conditions should be identified.

Concept introduction:

SN1 reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on one reactant. First step is the formation of more stable carbocation which is followed by the attack of nucleophile. Formation of more stable carbocation and the leaving group present in the substrate plays very important role in the reactivity of SN1 reaction.

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes SN1 substitution reaction

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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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