Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 26: Q18P (page 1337)

Propose a mechanism for the reaction of phenyl isocyanate with methanol.

Short Answer

Expert verified

Complete mechanism for the reaction

Step by step solution

01

Urethanes (or carbamate ester)

They are commonly made by treating an isocyanate with an alcohol or a phenol. The reaction is highly exothermic and it gives a quantitative yield of carbamate ester.

02

Mechanism for the reaction of phenyl isocyanate with methanol

In this reaction, nucleophilic addition of methanol takes place in a concerted way across the nitrogen double bond carbon (N=C) of the phenyl isocyanate. Another methanol molecule adds to the reaction as a result of which a protonated methyl alcohol is formed. The double bond around N=C gets rearranged to give the final product as methyl-N-phenylcarbanate .

Complete mechanism for the reaction

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

Draw the important resonance forms of the stabilized anion formed in the anionic polymerization of methyl acrylate.

The mechanism given for cationic polymerization of isobutylene (Mechanism 26-2) shows that all the monomer molecules add with the same orientation, giving a polymer with methyl groups on alternate carbon atoms of the chain. Explain why no isobutylene molecules add with the opposite orientation.

. (a) Draw the structure of gutta-percha, a natural rubber with all its double bonds in the trans configuration.

(b) Suggest why gutta-percha is not very elastic, even after it is vulcanized.

(a) Nomex®, a strong fire-resistant fabric, is a polyamide made from meta-phthalic acid and meta-diaminobenzene. Draw the structure of Nomex.

(b) Kevlar®, made from terephthalic acid (para-phthalic acid) and para-diaminobenzene, is used in making tire cord and bulletproof vests. Draw the structure of Kevlar.

See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Chemistry Branches

Read Explanation

Physical Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Making Measurements

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