Explain why only a substitution product and no elimination product is obtained when the following Compound reacts with sodium methoxide:

Short Answer

Expert verified

Only substituted product and no elimination product occur because the leaving group and C-H bond are not in anti-periplanar geometry in this compound to undergo elimination.

Step by step solution

01

Definition of substitution reaction

Substitution reaction is a nucleophilic reaction where the Nucleophilic attack and bond breaking between carbon and electronegative group happens either in a step manner or simultaneously.

Example: SN1 and SN2 reaction.

Mechanism of SN2 reaction is given above.

02

Definition of elimination reaction

Elimination reaction is basically a reaction between alkyl bromide and a base in a step-by-step manner or in a concerted mechanism of bond breaking and making. During the elimination reaction, The C-X (X=halogen) and C-H bond should be in anti-periplanar fashion.

Example: E1, E2 E1cB mechanism.

Mechanism of E1 reaction is given above.

03

Explanation of substitution reaction over Elimination

To occur the elimination reaction, The C-X and C-H bond should be in trans periplanar orientation. In the structure given below, The C-Br and C-H bonds are in cis orientation for which elimination doesn’t occur in this case.

So, only substituted product happen in this case.

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 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

See all solutions

Recommended explanations on Chemistry Textbooks

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