An aromatic imine is formed when 3,5-dihydroxyphenol is treated with ethanenitrile (CH3CN) in HCI in the presence of a ZnCl, catalyst, as shown here. Propose ОН ОН CH3CN a mechanism for this reaction. HCI, ZnCl, HO HO. Но HN

An aromatic imine is formed when 3,5-dihydroxyphenol is treated with ethanenitrile (CH3CN) in HCI in the presence of a ZnCl, catalyst, as shown here. Propose ОН ОН CH3CN a mechanism for this reaction. HCI, ZnCl, HO HO. Но HN

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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Question

An aromatic imine is formed when 3,5-dihydroxyphenol
is treated with ethanenitrile (CH3CN) in HCI in the
presence of a ZnCl, catalyst, as shown here. Propose
ОН
ОН
CH3CN
a mechanism for this reaction.
HCI, ZnCl,
HO
HO.
Но
HN

Expert Solution

Step 1

In the first step, protonation of ethanenitrile with HCl occurs. Protonation makes the ethanenitrile electron poor, and activates it as an electrophile. Zr²⁺ could also act as a Lewis acid catalyst by coordination to the N, activating the nitrile.

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