Introduction To General, Organic, And Biochemistry
Introduction To General, Organic, And Biochemistry
12th Edition
ISBN: 9781337571357
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 19, Problem 24P
Interpretation Introduction

Interpretation:

Whether the specific rotation of a-L-glucose dissolved in water changes and to what values should be determined.

Concept Introduction:

Similar to D-glucose, L-glucose also contains aldehyde and hydroxyl groups and due to its structure it forms either five or six membered fused hemiacetal.

There are two possible isomers of each of five membered and six membered fused hemiacetal. Those isomers are a and ß isomers.

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The specific rotation of a-d-glucose is +112.2. Q.) When a-d-glucose is dissolved in water, the specific rotation of the solution changes from +112.2 to +52.7. Does the specific rotation of a-l-glucose also change when it is dissolved in water? If so, to what value?
How many chiral centers does prostaglandin E2 have? Assign R,S configurations to these centers.
Aswer all parts of the question. A freshly prepared solution of αα ‑D‑glucose shows a specific rotation of +112°.+112°. Over time, the rotation of the solution gradually decreases and reaches an equilibrium value corresponding to [?]25 °CD=+52.5°.[α]D25 °C=+52.5°. In contrast, a freshly prepared solution of ?β‑D‑glucose has a specific rotation of +19°.+19°. The rotation of this solution increases over time to the same equilibrium value as that shown by the ?α anomer. A solution of one enantiomer of a given monosaccharide rotates plane‑polarized light to the left (counterclockwise) and is the levorotatory isomer, designated (−). The other enantiomer rotates plane‑polarized light to the same extent but to the right (clockwise) and is the dextrorotatory isomer, designated (+). An equimolar mixture of the (+) and (−) forms does not rotate plane‑polarized light. The optical rotation, the number of degrees by which plane‑polarized light rotates on passage through a given path length of a…

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Introduction To General, Organic, And Biochemistry

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