Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 10: Q46P (page 538)

Vinyl alcohols are generally unstable, quickly isomerizing to carbonyl compounds. Propose mechanisms for the following isomerizations.

(a)

(b)

c)

Short Answer

Expert verified

a)

b)

c)

Step by step solution

01

Vinyl alcohols

Vinyl alcohols are the simplest enols(CH2CHOH) , also named ethenol. They are unstable compounds and gets quickly isomerizes to carbonyl compounds.

02

Mechanism for the isomerizations in (a)

a) Here, H-A is a generic acid and A-1is the conjugate base. An aldehyde is formed along with H-A.


Mechanism of vinyl alcohol

03

Mechanism for the isomerizations in (b)

b) Here, H-A is a generic acid and A-1 is the conjugate base. A cyclohexanone is formed along with H-A.


The mechanism for the isomerization

04

Mechanism for the isomerizations in (c)

c) Here, the base attacks the cyclic alcohol. A cyclohexanone is formed along with -OH .


The mechanism for the isomerization

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

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

(a) 1-methylcyclohexanol (b) cyclohexylmethanol

(c) 1-(hydroxymethyl)cyclohexanol (d) trans-2-methylcyclohexanol

(e) 2-chloro-1-methylcyclohexanol (f) 1-(phenylmethyl)cyclohexanol

Ever since the Grignard reaction was discovered to react with ethylene oxide, chemists have experimented with other epoxides to test the limits of this reaction (which chemists call the scope of the reaction). The conclusion is that the success of the Grignard reaction is limited by the steric hindrance in the epoxide. One group published results of several Grignard reagents on one epoxide; one of their products is shown here. What Grignard reagent and what epoxide were used to make this compound? Comment on the steric requirements of the epoxide and the stereochemistry of the product.

Determine the structures of compounds A through G, including stereochemistry where appropriate.

A nitro group (-NO2) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:

Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.

Give the IUPAC name of the following alcohols.
See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Chemical Analysis

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