Solved: Which member of each pair is a better nucleophile

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

Problem 36P Chapter 9

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 36P

Which member of each pair is a better nucleophile in methanol?

a. H2O or HO- c. H2O or H2S e. I- or Br-

b. NH3 or H2O d. HO- or HS- f. Cl- or Br-

Step-by-Step Solution:

Solution 36P

Step 1 of 7</p>

Methanol is a polar protic solvent. It can participate in hydrogen bonding with the nucleophile. The nucleophile is less reactive as its lone pair of electrons interacts with the electron-poor hydrogen atoms of the solvent.

Step 2 of 7</p>

(a)

The charged species are better nucleophiles.

Therefore,  is a better nucleophile?

Step 3 of 7</p>

(b)

The nucleophilicity of the species decreases with increase in electronegativity.

Therefore,  is a better nucleophile.

Step 4 of 7</p>

(c)

The nucleophilicity of the species decreases with increase in electronegativity.

Therefore,  is a better nucleophile.

Step 5 of 7

Chapter 9, Problem 36P is Solved
Step 6 of 7

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

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Solved: Which member of each pair is a better nucleophile

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