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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr
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Propose mechanisms for(a) The acid-catalyzed hydration of

Chapter 12, Problem 17P

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QUESTION:

Problem 17P

Propose mechanisms for

(a) The acid-catalyzed hydration of chloral to form chloral hydrate.

(b) The base-catalyzed hydration of acetone to form acetone hydrate.

Questions & Answers

QUESTION:

Problem 17P

Propose mechanisms for

(a) The acid-catalyzed hydration of chloral to form chloral hydrate.

(b) The base-catalyzed hydration of acetone to form acetone hydrate.

ANSWER:

Solution:

Here we have to propose mechanisms for

(a) The acid-catalyzed hydration of chloral to form chloral hydrate.

(b) The base-catalyzed hydration of acetone to form acetone hydrate

Step 1

(a) The acid-catalyzed hydration of chloral to form chloral hydrate.

Chloral hydrate in presence of acid (H-A) forms an intermediate which has  two resonance structures, it undergoes hydration  and gives chloral hydrate.

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