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Problem 3: Using curly arrows, draw both an acid- and a base-catalysed mechanism for the reaction below:

Problem 3: Using curly arrows, draw both an acid- and a base-catalysed mechanism for the reaction below:

Chemistry
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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Problem 3: Using curly arrows, draw both an acid- and a base-catalysed mechanism for the reaction below: HCI OH NaOH OH A further challenge, dehydrate the hydroxyketone to the alpha beta unsaturated ketone (shown on page 2) using both acidic and basic conditions. Acid conditions? OH Basic contitions?
Transcribed Image Text:Problem 3: Using curly arrows, draw both an acid- and a base-catalysed mechanism for the reaction below: HCI OH NaOH OH A further challenge, dehydrate the hydroxyketone to the alpha beta unsaturated ketone (shown on page 2) using both acidic and basic conditions. Acid conditions? OH Basic contitions?
Expert Solution
Step 1 Aldol condensation

 

with alpha H caronyl compounds in presence of dilute base (or) acid gives beta-hydroxy carbonyl compounds (aldol)  and this beta-hydroxy compounds on dehydration gives alpha-beta unsaturated carbonyl compounds 

In general alpha hydrogens are acidic in nature 

in this reaction one C-C bond is formed 

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