(a) Which of the D-aldopentoses will give optically active aldaric acids on oxidation with HNO 3 ?...

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(a) Which of the D-aldopentoses will give optically active aldaric acids on oxidation with HNO3?

(b) Which of the D-aldotetroses will give optically active aldaric acids on oxidation with HNO3?

(c) Sugar X is known to be a D-aldohexose. On oxidation with HNO3 X gives an optically inactive aldaric acid. When X is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine the structure of X.

(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an optically active aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form optically active products?

(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose. Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?

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Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

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