/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q-21-21-5P Predict the products of the foll... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Predict the products of the following nucleophilic acyl substitution reactions:

Short Answer

Expert verified

The products of each reaction are as shown below:

Step by step solution

01

Subpart (a)

When methylacetate undergoes hydrolysis in presence of a strong base like NaOH, then nucleophilic acyl substitution takes place. The product formed in this reaction is acetic acid.

The chemical equation of the reaction is as shown below:

02

Subpart (b)

The nucleophilic acyl substitution will convert a chloride to an amide. There is a formation of a tetrahedral intermediate. The product formed during this reaction is shown below:

03

Subpart (c)

The acetic anhydride will undergo nucleophilic acyl substitution for the formation of methyl acetate and ester. The weaker base will replace a stronger base. The replacement of leaving the group in the nucleophilic fragment to predict the product of nucleophilic acyl substitution.

04

Subpart (d)

The product of nucleophilic acyl substitution can be obtained by replacing the leaving group attached to acyl carbon which follows atom-to-atom transfer. The thioester to amino compound using nucleophilic acyl substitution.

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.

Over 30 million students worldwide already upgrade their learning with 91Ó°ÊÓ!

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

The step-growth polymer nylon 6 is prepared from caprolactam. The reaction involves the initial reaction of caprolactam with water to give an intermediate open-chain amino acid, followed by heating to form the polymer. Propose a mechanism for both steps, and show the structures of nylon 6.

21-70 Treatment of a carboxylic acid with trifluoroacetic anhydride leads to anunsymmetrical anhydride that rapidly reacts with alcohol to give an ester.
R−C∥O−OH→(CF3CO)2OR−C∥O−O−C∥O−CF3→R'OHR−C∥O−OR'+CF3CO2H
(a) Propose a mechanism for the formation of the unsymmetrical anhydride.
(b) Why is the unsymmetrical anhydride unusually reactive?
(c) Why does the unsymmetrical anhydride react as indicated ratherthan giving a trifluoroacetate ester plus carboxylic acid?

If the following molecule is treated with acid catalyst, an intramolecular esterification reaction occurs. What is the structure of the product? (Intramolecular means within the same molecule.)

What ester and what Grignard reagent might you start with to prepare the following alcohols?

a.

b.

c.

21-75 One frequently used method for preparing methyl esters is by reactionof carboxylic acids with diazomethane, CH2N2

The reaction occurs in two steps: (1) protonation of diazomethane bythe carboxylic acid to yield methyldiazonium ion,, CH3N2+plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+.
(a) Draw two resonance structures of diazomethane, and account forstep 1.
(b) What kind of reaction occurs in step 2?

See all solutions

Recommended explanations on Chemistry Textbooks

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.