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Geminal diols, or 1,1-diols, are usually unstable,

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 45SP Chapter 10

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 45SP

Geminal diols, or \(\text { 1, 1-diols }\) are usually unstable, spontaneously losing water to give carbonyl compounds. Therefore, geminal diols are regarded as hydrated forms of ketones and aldehydes. Propose a mechanism for the acid-catalyzed loss of water from

\(\text { propane-2,2-diol }\)  to give acetone.

 

Equation Transcription:

 

Text Transcription:

1,1-diols

propane-2,2-diol

CH_3

HO

OH

CH_3

C

propane-2,2-diol

H+  

CH_3

C

CH_3

H2O

Step-by-Step Solution:
Step 1 of 3

Solution 45SP

The mechanism for the acid-catalyzed loss of water from propane -2, 2-diol to give acetone is given below.--

Step 2 of 3

Chapter 10, Problem 45SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Geminal diols, or 1,1-diols, are usually unstable,