/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q12P Propose a mechanism for the reac... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 11: Q12P (page 557)

Propose a mechanism for the reaction of

(a) 1-methyl cyclohexanol with HBr to form 1- bromo-1-methylcyclohexane.

(b) 2- cyclohexylethanol with HBr to form 1-bromo-2-cyclohexylethane.

Short Answer

Expert verified

1-methyl cyclohexanol is tertiary alcohol; thus, it will react with HBr by the SN1 mechanism.

Protonation of 1-methyl cyclohexanol converts the hydroxy group to a good leaving group.

Water leaves, forming a carbocation.

Bromide ion attacks the carbocation to form the product 1- bromo-1-methylcyclohexane.

Mechanism of formation of 1- bromo-1-methylcyclohexane

Step by step solution

01

Formation of 1- bromo-1-methylcyclohexane from 1-methyl cyclohexanol

1-methyl cyclohexanol is tertiary alcohol; thus, it will react with HBr by the SN1 mechanism.

Protonation of 1-methyl cyclohexanol converts the hydroxy group to a good leaving group.

Water leaves, forming a carbocation.

Bromide ion attacks the carbocation to form the product 1- bromo-1-methylcyclohexane.

Mechanism of formation of 1- bromo-1-methylcyclohexane

02

 Formation of 1-bromo-2-cyclohexylethane from 2- cyclohexylethanol

2 - cyclohexylethanol is the primary alcohol that reacts with HBr by the SN2 mechanism.

Protonation of 2- cyclohexylethanol converts the hydroxy group to a good leaving group.

Bromide displaces water to give the product 1-bromo-2-cyclohexylethane.

Mechanism of formation of 1-bromo-2-cyclohexylethane

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Classify each reaction as an oxidation, a reduction, or neither.

Predict the major products of the following reactions.

(a)ethyl tosylate+potassium tert-butoxide

(b) isobutyl tosylate + NaI

(c) (R)-2-hexyl tosylate + NaCN

(d) the tosylate of cyclohexylmethanol +excess NH3

When 1-cyclohexylethanol is treated with concentrated aqueous, the major product is 1-bromo-1-ethylcyclohexane.

(a)Propose a mechanism for this reaction.

(b) How would you convert 1-cyclohexylethanol to (1-bromoethyl)cyclohexane in good yield?

Under acid catalysis, tetrahydrofurfuryl alcohol reacts to give surprisingly good yields of dihydropyran. Propose a mechanism to explain this useful synthesis.

Predict the products of the sulfuric acid-catalyzed dehydration of the following alcohols. When more than one product is expected, label the major and minor products.

(a) 2-methylbutan-2-ol (b) pentan-1-ol (c) pentan-2-ol

(d) 1-isopropylcyclohexanol (e) 2-methylcyclohexanol
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Kinetics

Read Explanation

Organic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Making Measurements

Read Explanation

Ionic and Molecular Compounds

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.