ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
Publisher: WILEY
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Chapter 18, Problem 34P

Compound A has the molecular formula C 6 H 12 O 3 and shows a strong IR absorption peak at 1710 c m 1 . When treated with iodine in aqueous sodium hydroxide, A gives a yellow precipitate. When A is treated with Tollens’ reagent ( A g ( N H 3 ) 2 +   H O , a test for an aldehyde or a group that can be hydrolyzed to an aldehyde, Sect. 16.13B), no reaction occurs; however, if A is treated first with water containing a drop of sulfuric acid and then with Tollens’ reagent, a silver mirror (positive Tollens’ test) forms in the test tube. Compound A shows the following 1H NMR spectrum. Write a structure for A.

Singlet δ 2.1

Doublet δ 2.6

Singlet δ 3.2 ( 6 H )

Triplet δ 4.7

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