Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 19: Q24P (page 946)

Which of the following compounds is easier to decarboxylate?

or

Short Answer

Expert verified

The reactivity of pyridine is low towards an electrophilic substitution reaction because of the presence of an electron withdrawing nitrogen atom.

A pyridine undergoes such a reaction under vigorous conditions. It is more reactive towards a nucleophilic substitution reaction.

Step by step solution

01

Reactivity of pyridine 

The reactivity of pyridine is low towards an electrophilic substitution reaction because of the presence of an electron withdrawing nitrogen atom.

A pyridine undergoes such a reaction under vigorous conditions. It is more reactive towards a nucleophilic substitution reaction.

02

Identifying the compound that is easier to decarboxylate

Compounds

The compound shown on the right is easier to decarboxylate as the electrons left behind when the carbon dioxide is removed can be delocalized into nitrogen, generating a stable neutral species because of the proton donation to nitrogen.

Decarboxylation of the compound on the right

The electrons left behind when the other compound loses the carbon dioxide cannot be delocalized.

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: How do the mechanisms of the following reactions differ?

The chemical shifts of the C-2 hydrogen in the spectra of pyrrole, pyridine, and pyrrolidine are 2.82 ppm, 6.42 ppm, and 8.50 ppm. Match each heterocycle with its chemical shift.

One of the following compounds undergoes electrophilic aromatic substitution predominantly at C-3, and one undergoes electrophilic aromatic substitution predominantly at C-4. Which is which?

What is the major product of the following reaction?

a.Draw the structure of 3-quinuclidinone.

b.What is the approximatepKaof its conjugate acid?

c.Which has a lowerpKavalue, the conjugate acid of 3-bromoquinuclidine or the conjugate acid of 3-chloroquinuclidine?
See all solutions

Recommended explanations on Chemistry Textbooks

Kinetics

Read Explanation

Ionic and Molecular Compounds

Read Explanation

The Earths Atmosphere

Read Explanation

Chemical Reactions

Read Explanation

Making Measurements

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