Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 7: Q 28P (page 369)

Predict the elimination products of the following reactions and label the major products.

  1. Cis-1-bromo-2-methylcyclohexane +in
  2. Trans-1-bromo-2-methylcyclohexane +in

Short Answer

Expert verified

a.

Major Minor

b.

Major

Step by step solution

01

Explanation of part (a)

For E2 elimination to occur, the hydrogen and leaving group, bromine must have trans-diaxial orientation. The cis-isomer has methyl in equatorial position, the NaOCH3 can remove a hydrogen from either C-2 or C-6, giving a mixture of alkenes where the most highly substituted isomer is the major product (Zaitsev product).

Major Minor

02

Explanation of part (b)

Trans-isomer has methyl in the axial position at carbon-2, so no elimination can occur at C-2. The only possible orientation for elimination reaction to occur is toward C-6. Thus, only one alkene is possible which is not more substituted.

Major

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

A graduate student wanted to make methylenecyclobutane, and he tried the following reaction. Propose structures for the other products, and give mechanisms to account for their formation.

Show what happens in step-2 of the example if the solvent acts as a nucleophile (forming a bond to carbon) rather than as a base (removing a proton).

Show that the (S,S) enantiomer of this (R,R) diastereomer of 1-bromo-1,2-diphenylpropane also undergoes E2 elimination to give the cis diastereomer of the product. (We do not expect these achiral reagents to distinguish between enantiomers.)

Question: Give systematic (IUPAC) names of the following alkenes.

(a)

(b)

(c)

(d)

(e)

(f)

(g)

Determine the number of elements of unsaturation in the molecular formula C3H4. Give all three possible structures having this formula. Remember that

a double bond = one element of unsaturation

a ring = one element of unsaturation

a triple bond = two elements of unsaturation
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Chemical Reactions

Read Explanation

The Earths Atmosphere

Read Explanation

Chemical Analysis

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.

Sign-up for free