/*! 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} Q19P Suggest how you would convert tr... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 20: Q19P (page 1038)

Suggest how you would convert trans-4-methylcyclohexanol to

(a) trans-1-chloro-4-methylcyclohexane.

(b) cis-1-chloro-4-methylcyclohexane.

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

Step 1: Chemical Reaction of Alcohols

Alcohol, while showing their chemical change, act as a 鈥渧ersatile鈥� organic compound. It can act both as a nucleophile (Nu- ) as well as an electrophile(E+ ).

The chemical reaction of Alcohols are of two types:

  • Reaction involving cleavage of O-H bond

  • Reaction involving cleavage of C-OH bond

02

 Conversion of reactant trans-4-methyl cyclohexanol to given products

  1. trans-4-methyl cyclohexanol, when reacting withThionyl chloride (SOCl2), is the best reagent for converting an alcohol to an alkyl chloride and as the by-products (gaseous SO2 and HCl) leave the reaction mixture and ensure there can be no reverse reaction. Thus the trans-4-methyl cyclohexanol has been converted to trans-1-chloro-4-methylcyclohexane when reacted with Thionyl chloride (SOCl2).

Conversion of trans-4-methyl cyclohexanol to trans-1-chloro-4-methylcyclohexane

b. trans-4-methyl cyclohexanol, when reacted with tosyl chloride (TsCl) in the presence of pyridine, forms the tosylate ester. Tosylate ester reacts with sodium chloride (NaCl) shows SN2 displacement of tosylate ion forms the tosylate ester with inversion of configuration leading to the formation of cis 1-chloro-4-methylcyclohexane.

c. Conversion of trans-4-methyl cyclohexanol to cis 1- chloro-4-methylcyclohexane

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

In the presence of 18-crown-6, potassium permanganate dissolves inbenzene to give 鈥減urple benzene鈥� a useful reagent for oxidizing alkenes in an aprotic environment. Use a drawing of the complex to show why dissolves in benzeneand why the reactivity of the permanganate ion is enhanced.

Dimethylamine(CH3) 2 NHhas a molecular weight of 45 and a boiling point of 7.40C. Trimethylamine, (CH3) 3N, has a higher molecular weight (59) but a lower boiling point(3.50C) . Explain this apparent discrepancy.

(a)Hydrogen peroxide (HOOH) has a pKa of 11.6, making it roughly 10,000 times as strong an acid as water (pKa = 15.7). Explain why H2O2is a stronger acid than H2O.

(b) In contrast to part (a), peroxyacetic acid (pKa = 8.2) is a much weakeracid than acetic acid (pka = 4.74) . Explain why peroxyacetic acid is a weaker acid than acetic acid.

(c) Peroxyacetic acid (bp = 105掳 C) has a lower boiling point than acetic acid (bp = 118掳 C) , even though peroxyacetic acid has a higher molecular weight. Explain why peroxyacetic acid is more volatile than acetic acid.

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Circle the isoprene units in geranial, menthol, camphor, and abietic acid.

See all solutions

Recommended explanations on Chemistry Textbooks

Kinetics

Read Explanation

The Earths Atmosphere

Read Explanation

Physical Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Chemistry Branches

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.