Compound U is an aldopentose that can be oxidized to an optically inactive aldaric acid V. Upon Kiliani- Fischer reaction, compound U gives to epimeric aldohexoses, W and X. Both W and X give opically active aldaric acids, when oxidized. On Wohl degradation, compound U gives an aldotetrose Y, which upon oxidation gives an optically active aldaric acid (Z). When Y undergoes Wohl degradation, L- Glyceraldehyde is produced. What are structures U to Z? Show the reagents used for each step.
Compound U is an aldopentose that can be oxidized to an optically inactive aldaric acid V. Upon Kiliani- Fischer reaction, compound U gives to epimeric aldohexoses, W and X. Both W and X give opically active aldaric acids, when oxidized. On Wohl degradation, compound U gives an aldotetrose Y, which upon oxidation gives an optically active aldaric acid (Z). When Y undergoes Wohl degradation, L- Glyceraldehyde is produced. What are structures U to Z? Show the reagents used for each step.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.59P
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![Compound U is an aldopentose that can be oxidized to an optically inactive aldaric acid V. Upon Kiliani-
Fischer reaction, compound U gives to epimeric aldohexoses, W and X. Both W and X give opically active
aldaric acids, when oxidized. On Wohl degradation, compound U gives an aldotetrose Y, which upon
oxidation gives an optically active aldaric acid (Z). When Y undergoes Wohl degradation, L-
Glyceraldehyde is produced. What are structures U to Z? Show the reagents used for each step.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F5973b2e5-a7f4-48c6-9b40-b2392454ffb0%2Ff7353286-2765-4da2-980a-90ffe6281ed5%2Fhzgqkgh_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Compound U is an aldopentose that can be oxidized to an optically inactive aldaric acid V. Upon Kiliani-
Fischer reaction, compound U gives to epimeric aldohexoses, W and X. Both W and X give opically active
aldaric acids, when oxidized. On Wohl degradation, compound U gives an aldotetrose Y, which upon
oxidation gives an optically active aldaric acid (Z). When Y undergoes Wohl degradation, L-
Glyceraldehyde is produced. What are structures U to Z? Show the reagents used for each step.
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