Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 9: Q73P (page 451)

Starting with cyclohexene, how could the following compounds be prepared?

a. methoxycyclohexane

b. cyclohexylmethylamine

c. dicyclohexyl ether

Short Answer

Expert verified

c.

Step by step solution

01

How SN1 reaction proceed

1. It is a two step reaction.

2. In this carbocation is formed.

3. In this negative ion will attack from the side where there is less number of bulkier groups.

4. As the carbocation intermediate is formed so the stability order 3° carbocation>2° carbocation>1° carbocation

02

Final answer

A large excess of methylamine will have to be used in the second step in order to minimize the formation of a tertiary Amine and a quarternary ammonium ion.

c.Half of the cyclohexene is converted to bromocyclohexane and half is converted to an alkoxide ion. The ether is formed from the reaction of bromocyclohexane with the alkoxide ion.

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.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

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

How will the rate of the reaction between bromomethane and hydroxide ion be affected if the following changes in concentration are made?

a. The concentration of the alkyl halide is not changed and the concentration of the nucleophile is tripled.

b. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is not changed.

c. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is doubled.

which solvent—ethanol or diethyl ether—would the equilibrium for the following SN2 reaction lie farther to the right?

a. Assuming that the two compounds shown below have the same stability, which one would you expect to be more reactive in an SN1 reaction?

b. Draw the products that each would form when the solvent is ethanol.

Which alkyl halide is more reactive in an SN2 reaction with a given nucleophile?

cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Chemistry Branches

Read Explanation

Making Measurements

Read Explanation

Physical Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Inorganic Chemistry

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.

Sign-up for free