Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 7: PROBLEM 7.49 (page 291)

Question: Which of the following nucleophilic substitution reactions will take place?

a.

b.

Short Answer

Expert verified

ANSWER

a.

b.

Step by step solution

01

Leaving group ability

The leaving group is the one that readily takes up the electrons when a bond is broken. So, it is a weak Lewis base and should have a low pKa values.

02

Explanation of (a)

a. In this reaction, the leaving group in the substrate molecule is NH2- . The nucleophile is an iodide ion. But NH2- is a poor leaving group and its conjugate acid NH3 has a value pKaof 35. So, this reaction is not feasible easily.

03

Explanation of (b)

b. In this reaction, the leaving group in the substrate molecule is I-. The nucleophile is a methoxide ion. The iodide ion is one of the best leaving groups, and its conjugate acid has pKavalue of -9. So, this reaction is feasible easily.

Thus, the answer is option (b).

Nucleophilic substitution 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

Question: Give the IUPAC name for each compound.

a.

b.

c,

d.

e.

f.

Question: Diphenhydramine, the antihistamine in Benadryl, can be prepared by the following two-step sequence. What is the structure of diphenhydramine?

Question: Why is the amine N atom more nucleophilic than the amide N atom CH3CONHCH2CH2CH2NHCH3?

Question: Fluticasone, the chapter-opening molecule, can be prepared by the following reaction. Draw a stepwise mechanism for this reaction.

Question: For each reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction

a.

b.

c.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation

Making Measurements

Read Explanation

The Earths Atmosphere

Read Explanation

Physical Chemistry

Read Explanation

Nuclear 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