Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 14: Q22P (page 733)

Propose mechanisms for the epoxidation and ring-opening steps of the epoxidation and hydrolysis of shown above. Predict the product of the same reaction with.

Short Answer

Expert verified

Answer

Step by step solution

01

Peroxyacid epoxidation

Peroxyacids can be used to convert alkenes to epoxides. The epoxides are known to open to a glycol if the reaction occur in an aqueous medium. For this reason, strong acids are avoided for the synthesis of epoxides.

02

Acid-catalyzed ring opening of epoxides

Epoxides react under both acidic and basic conditions. The products of the acid-catalyzed ring opening depend primarily on the solvent used.

03

Mechanisms 

In water as a solvent, the acid-catalyzed hydrolysis of epoxides forms glycols with anit-stereochemistry. The mechanism involves protonation of oxygen followed by attack by water. The back-side attack of water on the protonated epoxide results in anti-stereochemistry. Lastly, hydrolysis of epoxide occurs to give the glycol.



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. Predict the products of the following reactions.

(a) Sec-butyl isopropyl ether + conc. HBr, heat

(b) 2-ethoxy-2-methylpentane + conc. HBr, heat

(c) di-n-butyl ether + hot conc. NaOH

(d) di-n-butyl ether + Na metal

(e) ethoxybenzene + conc. HI, heat

(f) 1,2-epoxyhexane +

(g) trans-2,3-epoxyoctane +

(h) propylene oxide + methylamine

(i) potassium tert-butoxide + n-butyl bromide

Give a common name (when possible) and a systematic name for each compound

(a) CH3OCH=CH2

(b) CH3CH2OCH(CH3)2

(c) ClCH2CH2OCH3

(d)

e)

f)

g)

h)

i)

Question. Give the structures of the intermediates represented by letters in this synthesis.

Show the rest of the mechanism for formation of cyclized intermediate in figure 14-6.

Role of squalene in the biosynthesis of steroids. The biosynthesis of steroids starts with epoxidation of squalene to squalene-2,3-epoxide. The opening of this epoxide promotes cyclization of the carbon skeleton under the control of an enzyme. The cyclized intermediate is converted to lanosterol and then to other steroids.

Question. Propose a mechanism for the acid-catalyzed condensation of n-propyl alcohol to n-propyl ether, as shown above. When the temperature is allowed to rise too high, propene is formed. Propose a mechanism for the formation of propene and explain why it is favored at higher temperatures.
See all solutions

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Making Measurements

Read Explanation

Chemical Reactions

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