Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 10: PROBLEM 10.57 (page 423)

Question: Draw a stepwise mechanism for the following reaction, which results in ring expansion of a six-membered ring to a seven-membered ring.

Short Answer

Expert verified

Answer

Step by step solution

01

Generation of carbocation  

The carbocations generated by the addition of acids to alkenes may undergo shifting (1,2-hydrogen or 1,2-methyl), depending upon their stability.

The stability order of the carbocations is3°>2°>1° .

02

1,2-hydrogen and methyl shift

The stability of carbocations enables 1,2-hydrogen and methyl shift. After the shifting of methyl and hydrogen to adjacent positions, which is the most stable carbocation.

03

Explanation

The reaction of the given compound with water and sulfuric acid proceeds via 1,2-bond shift to generate a carbocation. The carbocation gives a tertiary alcohol product.

The mechanism is shown below:

Reaction mechanism

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 buta-1,3-diene (CH2=CH-CH=CH2) is treated with HBr, two constitutional isomers are formed CH3CHBr-CH=CH2and Br-CH2CH=CHCH2. Draw a stepwise mechanism that accounts for the formation of both products.

Question: Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O,H2SO4; or [2] BH3followed by H2O2,HO-.

Question: (a) Draw the structure of (1E,4R)-1,4-dimethylcyclodecene. (b) Draw the enantiomer and name it, including its E,Z and R,S prefixes. (c) Draw two diastereomers and name them, including the E,Z and R,S prefixes.

Question: What product is formed when each alkene is treated with HCl?

Question: What stereoisomers are formed when pent-1-ene is treated with H2O and H2SO4?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Nuclear Chemistry

Read Explanation

Physical Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Organic 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