2. For each pair, predict the stronger nucleophile in the reaction (using an alcohol as thesolvent). Explain your prediction.(a) (CH3CH₂)3N or (CH3CH₂)NH(b) I or Cl(c) (CH3)20 or (CH3)2S(CH3)2CHO or CH3CH₂CH₂O

Answered: 2. For each pair, predict the stronger…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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2. For each pair, predict the stronger nucleophile in the reaction (using an alcohol as the
solvent). Explain your prediction.
(a) (CH3CH₂)3N or (CH3CH₂)NH
(b) I or Cl
(c) (CH3)20 or (CH3)2S
(CH3)2CHO or CH3CH₂CH₂O

Expert Solution

Step 1

The nucleophilicity increases as the electron density of the negative charge increases.

(a) Between ${(C H_{3} C H_{2})}_{3} N$ or $(C H_{3} C H_{2}) N H$ , There's only one factor to decide which is a stronger nucleophile which is the inductive effect. The ethyl $(C H_{3} C H_{2} -)$ groups present to increase the electron density by releasing the electron density through the inductive effect, so the greater the number of ethyl $(C H_{3} C H_{2} -)$ groups stronger will be the nucleophile.

${(C H_{3} C H_{2})}_{3} N$ has three ethyl groups present, so it's a stronger nucleophile than the $(C H_{3} C H_{2}) N H$ .

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