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Which is a stronger base?a. HS? or HO? c. CH3OH or CH3O?

Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice ISBN: 9781269406772 80

Solution for problem 48P Chapter 2

Organic Chemistry | 7th Edition

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Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice

Organic Chemistry | 7th Edition

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Problem 48P

Which is a stronger base?

a. \(H S^{-} \text {or } H O^{-}\)                c. \(\mathrm{CH}_{3} \mathrm{OH} \text { or } \mathrm{CH}_{3} \mathrm{O}^{-}\)                e. \(\mathrm{CH}_{3} \mathrm{COO}^{-} \text {or } \mathrm{CF}_{3} \mathrm{COO}^{-}\)

b. \(\mathrm{CH}_{3} \mathrm{O}^{-} \text {or } \mathrm{CH}_{3} \overline{\mathrm{N}} H\)                d. \(\mathrm{Cl}^{-} \text {or } \mathrm{Br}^{-}\)                        f. \(\mathrm{CH}_{3} \mathrm{CHClCOO}^{-} \text {or } \mathrm{CH}_{3} \mathrm{CHBrCOO}^{-}\)

Equation Transcription:

Text Transcription:

HS^- or HO^-

CH_3 O^- or CH_3 overline N H

CH_3 OH or CH_3 O^-

Cl^- or Br^-

CH_3 COO^- or CF_3 COO^-

CH_3 CHClCOO^- or CH_3 CHBrCOO^-

Step-by-Step Solution:

Step 1 of 6

Here we have to find out which is stronger base among the given molecules.

It is known that the relative acidity depends on the following two factors:

     1.  Atomic size

     2.  A Stronger base has weaker conjugate acid.

a.   

Here the bases  are formed from its conjugate acid  and . Here  is the stronger acid than that of  due to the presence of S-atom, which has big atomic size than O-atom.

The conjugate base of the strong acid is less basic, thus  is the stronger base than .

__________________________

Step 2 of 6

Chapter 2, Problem 48P is Solved
Step 3 of 6

Textbook: Organic Chemistry
Edition: 7
Author: Paula Yurkanis Bruice
ISBN: 9781269406772

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Which is a stronger base?a. HS? or HO? c. CH3OH or CH3O?