Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 25: PROBLEM 24.17 (page 1016)

Question: Draw the products of each acid–base reaction. Indicate whether equilibrium favors the reactants or products.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Equilibrium  

The pKa of many protonated amines is 10–11. So, the pKa of the starting acid must be less than 10 for the equilibrium to favor the products.

Amines are thus readily protonated by strong inorganic acids, such as HCl and H2SO4 and by carboxylic acid (organic acid) as well.

02

Explanation

a. The reaction of the butane amine is represented as

pKavalues of HCl is -7

The pKa of the product is 10. Therefore, the product is a weaker acid.

b. The reaction of the piperidine with water does not favor the product, as shown below.

Favored equilibrium

c. The reaction of the given amine is represented a

pKa value of CH3COOH is 4.2

pKa (CH3)2NH2+ is 10.7

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: What nitro compound, nitrile, and amide are reduced to each compound?

a.

b.

c.

Question: Rank the compounds in each group in order of increasing basicity.

a.

b.

Question: Draw the structure that corresponds to each name.

  1. N-isobutylcyclopentanamine
  2. tri-tert-butylamine
  3. N, N-diisopropylaniline
  4. N-methyl pyrrole
  5. N-methylcyclopentanamine
  6. 3-methylhexan-2-amine
  7. 2-sec-butylpiperidine
  8. (S)-heptan-2-amine

Question: Devise a synthesis of each compound from benzene. You may use any other organic or inorganic reagents.

a.

b.

c.

d.

e.

f.

What carbonyl and nitrogen compounds are needed to make each compound by reductive amination? When more than one set of starting materials is possible, give all possible methods.

(a)

(b)

(c)
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

The Earths Atmosphere

Read Explanation

Making Measurements

Read Explanation

Chemical Analysis

Read Explanation

Chemistry Branches

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