Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 10: PROBLEM 10.53 (page 422)

Question: Which alkene reacts faster with HBr? Explain your choice

Short Answer

Expert verified

Answer

B

Step by step solution

01

Reactivity of alkene  

The reactivity of an alkene depends on resonance stabilization. If the alkene forms a resonance stabilized carbocation on reaction with HBr, it will react faster.

02

Explanation

Compound B reacts with HBr to give the benzyl carbocation on either side of the double bond. The benzyl carbocation is the most stable because it undergoes resonance.

Therefore, compound B reacts faster than A.

Resonance stabilization of B

Compound A reacts with HBr does not give more stable carbocation. Therefore, there is no resonance stabilization and compound A reacts slow.

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: Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oil tree (Aleurites fordii), a deciduous tree native to China.

(a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid.

(b) Draw the structure of a stereoisomer that has a lower melting point.

Question: Explain why A is a stable compound but B is not.

Question: Draw the products of each reaction and indicate their stereochemistry.

Question: What alkylborane is formed from hydroboration of each alkene?

Question: Label each carbon-carbon double bond in 11-cis-retinal as E or Z. As we will learn in Section 21.11, the isomerization of one double bond in this compound to a less crowded stereoisomer takes place when light strikes the retina of the eye.
See all solutions

Recommended explanations on Chemistry Textbooks

Making Measurements

Read Explanation

Kinetics

Read Explanation

Nuclear Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Physical 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