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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr
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All of the following compounds can react as acids. Without

Chapter 1, Problem 38SP

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QUESTION:

All of the following compounds can react as acids. Without using a table of acidities, rank them in order of increasing acidity. Explain your ranking.

(a)    \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SO}_{3} \mathrm{H}\)

(b)   \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)

(c)   \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\)

(d)   \(\mathrm{CH}_{3} \mathrm{CHCICOOH}\)

(e)   \(\mathrm{CICH}_{3} \mathrm{CH}_{3} \mathrm{COOH}\)

Equation Transcription:

Text Transcription:

CH_3CH_2SO_3H

CH_3CH_2OH

CH_3CH_2COOH

CH_3CHCICOOH

CICH_3CH_3COOH

Questions & Answers

QUESTION:

All of the following compounds can react as acids. Without using a table of acidities, rank them in order of increasing acidity. Explain your ranking.

(a)    \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SO}_{3} \mathrm{H}\)

(b)   \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)

(c)   \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\)

(d)   \(\mathrm{CH}_{3} \mathrm{CHCICOOH}\)

(e)   \(\mathrm{CICH}_{3} \mathrm{CH}_{3} \mathrm{COOH}\)

Equation Transcription:

Text Transcription:

CH_3CH_2SO_3H

CH_3CH_2OH

CH_3CH_2COOH

CH_3CHCICOOH

CICH_3CH_3COOH

ANSWER:

Solution:

Step 1

Among all the acids , ethanesulfonic acid (CH3CH2SO3H) is the strongest acid. Because in its resonating structure  the -ve charge spread over three oxygen atoms. Greater the number of resonating structure stronger will be the acid.

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