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
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…
Chapter 19 Solutions
Introduction To General, Organic, And Biochemistry
Ch. 19.1 - Prob. 19.1QCCh. 19.1 - Prob. 19.2QCCh. 19.2 - Prob. 19.3QCCh. 19.3 - Prob. 19.4QCCh. 19.4 - Prob. 19.5QCCh. 19.5 - Prob. 19.6QCCh. 19 - Prob. 1PCh. 19 - Prob. 2PCh. 19 - Prob. 3PCh. 19 - Prob. 4P
Ch. 19 - Prob. 5PCh. 19 - Prob. 6PCh. 19 - Prob. 7PCh. 19 - Prob. 8PCh. 19 - Prob. 9PCh. 19 - Prob. 10PCh. 19 - Prob. 11PCh. 19 - Prob. 12PCh. 19 - Prob. 13PCh. 19 - Prob. 14PCh. 19 - Prob. 15PCh. 19 - Prob. 16PCh. 19 - Prob. 17PCh. 19 - Prob. 18PCh. 19 - Prob. 19PCh. 19 - Prob. 20PCh. 19 - Prob. 21PCh. 19 - Prob. 22PCh. 19 - Prob. 23PCh. 19 - Prob. 24PCh. 19 - Prob. 25PCh. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - Prob. 28PCh. 19 - Prob. 29PCh. 19 - Prob. 30PCh. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - Prob. 33PCh. 19 - Prob. 34PCh. 19 - Prob. 35PCh. 19 - Prob. 36PCh. 19 - Prob. 37PCh. 19 - Prob. 38PCh. 19 - Prob. 39PCh. 19 - Prob. 40PCh. 19 - Prob. 41PCh. 19 - 6 Where is glycogen stored in the human body?Ch. 19 - Prob. 43PCh. 19 - 8 How is it possible that cows can digest grass...Ch. 19 - 1 Hyaluronic acid acts as a lubricant in the...Ch. 19 - Prob. 46PCh. 19 - Prob. 47PCh. 19 - Prob. 48PCh. 19 - Prob. 49PCh. 19 - Prob. 50PCh. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - Prob. 54PCh. 19 - Prob. 55PCh. 19 - Prob. 56PCh. 19 - Prob. 57PCh. 19 - Prob. 58PCh. 19 - Prob. 59PCh. 19 - Prob. 60PCh. 19 - Prob. 61PCh. 19 - Prob. 62PCh. 19 - Prob. 63PCh. 19 - Prob. 64PCh. 19 - Prob. 65PCh. 19 - Prob. 66PCh. 19 - Prob. 67PCh. 19 - Prob. 68PCh. 19 - Prob. 69PCh. 19 - Prob. 70PCh. 19 - Prob. 71PCh. 19 - Prob. 72PCh. 19 - Prob. 73PCh. 19 - Prob. 74PCh. 19 - Prob. 75P
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- Like glucose, galactose mutarotates when it dissolves in water. The specific rotation ofa-d-galactopyranose is +150.7°, and that of the b anomer is +52.8°. When either ofthe pure anomers dissolves in water, the specific rotation gradually changes to +80.2°.Determine the percentages of the two anomers present at equilibrium.arrow_forwardThe specific rotation of α-d-galactose is 150.7 and that of β-d-galactose is 52.8. When an aqueous mixture that was initially 70% α-d-galactose and 30%β-d-galactose reaches equilibrium, the specific rotation is 80.2. What is the percentage of α-d-galactose and β-d galactose at equilibrium?arrow_forwardThe anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forward
- The specific rotation of a-d-glucose is +112.2. Q.) What is the specific rotation of a-l-glucose?arrow_forwardC2. Subject:- Chemistry please identify the chiral centers and determine the sterechemistry of a compound that contains a cycolhexanearrow_forwardThe specific rotation of S-Ibuprofen is +54.5o. Which direction would a mixture containing 80% S-Ibuprofen and 10% R-ibuprofen rotate plane polarized light? To the left or to the right?arrow_forward
- If a solution of glucose at equilibrium has an observed rotation of +22.5° in a 200 mm polarimeter cell, calculate the concentration of the glucose solution.arrow_forward2) What is the difference between stereoisomers and enantiomers?arrow_forwardIn addition to lactose, D-galactose and D-glucose can form different heterodisaccharides. Draw the structures (Haworth projections) of the (i) a-glucose-(1→1) -a-galactose and ii) a- glucose-(1→3)-?-galactose, two examples of heterodisaccharides that can form.arrow_forward
- a hexose if it has 6 C's, and so forth. ? Explainarrow_forwardThe rod cells in the eyes absorb 498 nm light. What is the energy difference (in Joules) between the HOMO and LUMO of the retinal that absorbs this light?arrow_forwardCarbohydrates. Determination of the extent of branching in glycogen. The amount of branching (number of α 1⟶ 6 glycosidic bonds) in glycogen can be determined by the following procedure. A sample of glycogen is exhaustively methylated-treated with a methylating agent (methyl iodide) that replaces the hydrogen of every sugar hydroxyl with a methyl group, converting –OH to –OCH3. All the glycosidic bonds in the treated sample are then hydrolyzed in aqueous acid, and the amounts of α -D-2,3-di-O-methylglucopyranose and α -D-2,3,6-tri-O-methylglucopyranose formed are measured. 1- Draw the cyclic structure of α-D-glucopyranose, α-D-2,3-di-O-methylglucopyranose and α-D-2,3,6-tri-O-methylglucopyranose, including the numbering of carbon atoms. 2- Which of α-D-2,3-di-O-methylglucopyranose or α-D-2,3,6-tri-O-methylglucopyranose represents a glucose unit in glycogen which was originally carrying a α 1⟶ 6 glycosidic bond? Explain.arrow_forward
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