Compound A has the molecular formula C6H12O3 and shows a strong IR absorption peak at

Chapter 18, Problem 18.34

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Compound A has the molecular formula C6H12O3 and shows a strong IR absorption peak at 1710 cm-1 . When treated with iodine in aqueous sodium hydroxide, A gives a yellow precipitate. When A is treated with Tollens reagent (a test for an aldehyde or a group that can be hydrolyzed to an aldehyde), 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 1 H NMR spectrum: Singlet d 2.1 Doublet d 2.6 Singlet d 3.2 (6H) Triplet d 4.7 Write a structure for A

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