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Chemistry / Organic Chemistry 2 / Chapter 20 / Problem 20.59

Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein

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Treatment of catechol with formaldehyde in the presence of

Chapter 20, Problem 20.59

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QUESTION:

Treatment of catechol with formaldehyde in the presence of an acid catalyst produces a compound with molecular formula C7H6O2. Draw the structure of this product. OH OH Catechol

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QUESTION:

Treatment of catechol with formaldehyde in the presence of an acid catalyst produces a compound with molecular formula C7H6O2. Draw the structure of this product. OH OH Catechol

ANSWER:

Step 1 of 2

Catechol reacts with formaldehyde in the presence of acid catalyst to form the following compound:

This reaction combines a source of hydroxyl groups, a ketone/aldehyde, and an acidic catalyst. These are all the components necessary for acetal formation. The two hydroxyl groups on the benzene ring serve as the source of the oxygen atoms in the final product which, despite its unusual appearance, is just a simple acetal.

The reaction as follows:

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