Find study content
Learning Materials

Discover learning materials by subject, university or textbook.

Explanations

Textbooks

Exams
All Subjects

Anthropology

Archaeology

Architecture

Art and Design

Bengali

Biology

Business Studies

Greek

Chemistry

Chinese

Combined Science

Computer Science

Economics

Engineering

English

English Literature

Environmental Science

French

Geography

German

History

Hospitality and Tourism

Human Geography

Italian

Japanese

Law

Macroeconomics

Marketing

Math

Media Studies

Medicine

Microeconomics

Music

Nursing

Nutrition and Food Science

Physics

Polish

Politics

Psychology

Religious Studies

Sociology

Spanish

Sports Sciences

Translation

All Subjects

Biology

Business Studies

Chemistry

Combined Science

Computer Science

Economics

English

Environmental Science

Geography

History

Math

Physics

Psychology

Sociology

EXAM TYPES

GCSE

IGCSE

AS

A Level

International A Level

University Admissions Tests

GCSE SUBJECTS

GCSE 1

GCSE 2

GCSE 3

GCSE 4

GCSE 5

SOME-TEXT

IGCSE SUBJECTS

IGCSE 1

AS SUBJECTS

AS 1

A Level SUBJECTS

A Level 1

International A Level SUBJECTS

International A Level 1

University Admissions Tests SUBJECTS

University Admissions Tests 1
Features
Features

Discover all of these amazing features with a free account.

Flashcards

Vaia AI

Notes

Study Plans

Study Sets
What’s new?

Flashcards
Study your flashcards with three learning modes.

Study Sets
All of your learning materials stored in one place.

Notes
Create and edit notes or documents.

Study Plans
Organise your studies and prepare for exams.
Resources
Discover

All the hacks around your studies and career - in one place.

Find a job

Find a degree

Student Deals

Magazine

Mobile App
Featured

Magazine
Trusted advice for anyone who wants to ace their studies & career.

Job Board
The largest student job board with the most exciting opportunities.

Vaia Deals
Verified student deals from top brands.

Our App
Discover our mobile app to take your studies anywhere.

Go to App

Learning Materials

Features

Discover

Chapter 19: Q42 (page 759)

Which carboxylic acid has the lower ${pK}_{a}$ , pyruvic acid $({CH}_{3} COCOOH)$ or acetoacetic acid $({CH}_{3} {COCH}_{2} COOH)$ ? Explain your choice.

Short Answer

Expert verified

Pyruvic acid is the carboxylic acid that has a lower ${pK}_{a}$ value.

Step by step solution

01

Meaning of pKa

The ${pK}_{a}$ value is determines the acidic strength of the acids. Higher the value of ${pK}_{a}$ , lower will be the acidity of the compound.

The acidic strength increases due to the presence of the electron-withdrawing groups. The acidic strength also increases if the conjugate base is resonance stabilized.

02

Comparison of the acidic strength of pyruvic acid and acetoacetic acid

The structure of pyruvic acid is as follows:

Pyruvic acid

The structure of acetoacetic acid is as follows:

Acetoacetic acid

The acidic strength of acetoacetic acid is lower as compared to pyruvic acid. The pKa of acetoacetic acid is 3.58, whereas the pKa of pyruvic acid is 2.50. This implies that pyruvic acid is a stronger acid than acetoacetic acid.

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

Match the ${pK}_{a}$ values to the appropriate compound. ${pK}_{a}$ values: 0.28, 1.24, 2.66, 2.86, and 3.12. Compounds: (a) ${FCH}_{2} COOH$ ; (b) ${CF}_{3} COOH$ ; (c) $F_{2} CHCOOH$ ; (d) ${ICH}_{2} COOH$ ; (e) ${BrCH}_{2} COOH$

Question: Match each of the following ${pk}_{a}$ values (3.2, 4.9, and 0.2) to the appropriate carboxylic acid:

(a) ${CH}_{3} {CH}_{2} COOH; [b] {CF}_{3} COOH; [c] {ICH}_{2} COOH$

Question: Give the IUPAC name for each compound.

a.

b.

c.

d.

Rank the compounds in each group in order of increasing acidity.

a.

b.

Question: Using the ${pk}_{a}$ table in Appendix A, determine whether each of the following bases is strong enough to deprotonate the three compounds listed below. Bases: [1] ${OH}^{-}; [2] {CH}_{3} {CH}_{2}^{-}; [3] {NH}_{2}^{-} [4] CH \equiv C^{-}$

a.

b.

c.

See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Making Measurements

Read Explanation

Inorganic Chemistry

Read Explanation

Nuclear Chemistry

Read Explanation

Organic 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