Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 15: Q54. (page 570)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

Answer

Mechanism:

Step by step solution

01

N-bromosuccinimide

N-bromosuccinimide is utilized for “selective halogenation” at the allylic carbon, i.e., C-H bond, in the presence of light.

02

Mechanism 

Initiation:

In the presence of light, a weak Na-Br bond is NBS is homolytically cleaved, and the bromine radical is formed.

Initiation reaction

Propagation and Termination:

The bromine radical formed in the initiation step and a proton is abstracted from the C-H bond, and an allylic radical is formed. This radical can undergo resonance.

The allylic radical reacts with Br2 to form the C-Br bond.

The propagation step can occur multiple times.

When two radicals combine, a stable product is formed, which terminates the reaction.

Propagation and termination reactions

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

Question: When two monomers (X and Y) are polymerized together, a copolymer results. An alternating copolymer is formed when the two monomers X and Y alternate regularly in the polymer chain. Draw the structure of the alternating copolymer formed when the two monomers, CH2CCl2 and CH2,=CHC6H5 are polymerized together.

Devise a synthesis of 1-methylcyclohexene oxide from methylcyclohexane. You may use any other required organic or inorganic reagents

Question: Which compounds can be prepared in good yield by allylic halogenation of an alkene?

a.

b.

c.

Question: Draw the products formed when each alkene is treated with NBS + hv .

a.

b.

c.

Question: Which C-H bond is most readily cleaved in linoleic acid? Draw all possible resonance structures for the resulting radical. Draw all the hydroperoxides formed by the reaction of this resonance stabilized radical with O2.
See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Kinetics

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Chemistry Branches

Read Explanation

The Earths Atmosphere

Read Explanation

Nuclear 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