Question

Some organic compounds are given below:

Select the correct statement(s) about the above compounds from the following:

• A. Compounds (I) and (III) will reduce Fehling’s solution and will also mutarotate
• B. Compound (IV) will reduce Tollen’s reagent but not mutarotate
• C. Compound (II) will not be reducing but mutarotating
• D. The product(s) of the acid catalysed hydrolysis of both (II) and (III) will be reducing but not mutarotating

Answer 1

Answer: (A), (C)

The correct options are
A Compounds (I) and (III) will reduce Fehling’s solution and will also mutarotate
C Compound (II) will not be reducing but mutarotating

All reducing sugars are muatrotating. Although (IV) is an $\alpha -$hydroxy ketone, it reduces Tollen's reagent but it can not mutarotate as it is not a carbohydrate, can’t form ring.
In (II) the glycosidic linkage is in between two anomeric carbons and hence ring opening can’t occur, thus non–reducing as well as non-mutarotating.