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Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein
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Salicin is a natural analgesic present in the bark of

Chapter 24, Problem 24.76

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QUESTION:

Salicin is a natural analgesic present in the bark of willow trees, and it has been used for thousands of years to treat pain and reduce fevers. O HO HO O OH OH OH Salicin (a) Is salicin a reducing sugar? (b) Identify the products obtained when salicin is hydrolyzed in the presence of an acid. (c) Is salicin an a-glycoside or a b-glycoside? (d) Draw the major product expected when salicin is treated with excess acetic anhydride in the presence of pyridine. (e) Would you expect salicin to exhibit mutarotation when dissolved in neutral water?

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QUESTION:

Salicin is a natural analgesic present in the bark of willow trees, and it has been used for thousands of years to treat pain and reduce fevers. O HO HO O OH OH OH Salicin (a) Is salicin a reducing sugar? (b) Identify the products obtained when salicin is hydrolyzed in the presence of an acid. (c) Is salicin an a-glycoside or a b-glycoside? (d) Draw the major product expected when salicin is treated with excess acetic anhydride in the presence of pyridine. (e) Would you expect salicin to exhibit mutarotation when dissolved in neutral water?

ANSWER:

Step 1 of 6

This exercise asks us to consider the molecule kernel salicin. Note that the bond lengths in the following diagrams have been changed for reasons of clarity/ease of drawing; they're not meant to represent the actual bond lengths present in the molecule.

             

We're now asked a series of questions regarding this salicin molecule.

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