LL ORG CHEM
6th Edition
ISBN: 9781264840083
Author: SMITH
Publisher: MCG
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Chapter 26, Problem 64P
Interpretation Introduction
Interpretation: The D-aldopentose which on oxidation produces optically active aldaric acid and that undergoes Wohl Degradation to yield D-aldotetrose which on oxidation produces optically active aldaric acid is to be predicted.
Concept introduction: Carbohydrates containing
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D-Aldopentose A is oxidized to an optically inactive aldaric acid. On Wohl degradation, A forms an aldotetrose B that is oxidized to an optically active aldaric acid. What are the structures of A and B?
Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a D-aldotetrose that is oxidized to an optically active aldaric acid?
Aldohexoses A and B are formed from aldopentose C via a Kiliani–Fischer synthesis. Nitric acid oxidizes A to an optically active aldaric acid, B to an optically inactive aldaric acid, and C to an optically active aldaric acid. Wohl degradation of C forms D, which is oxidized by nitric acid to an optically active aldaric acid. Wohl degradation of D forms (+)-glyceraldehyde. Identify A, B, C, and D.
Chapter 26 Solutions
LL ORG CHEM
Ch. 26.2 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Label each stereogenic center as R or S. a. b. c....Ch. 26.2 - Convert the ball-and-stick model to a Fischer...Ch. 26.2 - Prob. 5PCh. 26.2 - Prob. 6PCh. 26.3 - Prob. 7PCh. 26.3 - Prob. 8PCh. 26.4 - Prob. 9PCh. 26.4 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Draw a stepwise mechanism for the following...Ch. 26.7 - Prob. 18PCh. 26.8 - Prob. 19PCh. 26.9 - Prob. 20PCh. 26.9 - Prob. 21PCh. 26.9 - Draw the products formed when D-arabinose is...Ch. 26.9 - Prob. 23PCh. 26.10 - Prob. 24PCh. 26.10 - Prob. 25PCh. 26.10 - Prob. 26PCh. 26.10 - Prob. 27PCh. 26.11 - Prob. 28PCh. 26.11 - Prob. 29PCh. 26.12 - Prob. 30PCh. 26.12 - Prob. 31PCh. 26.13 - Prob. 32PCh. 26.13 - Prob. 33PCh. 26.13 - Problem-28.35
Draw the structures of the...Ch. 26.13 - Prob. 35PCh. 26 - 28.37 Convert each ball-and-stick model to a...Ch. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - 28.40 Convert each compound to a Fischer...Ch. 26 - Prob. 40PCh. 26 - Prob. 41PCh. 26 - 28.43 Draw a Haworth projection for each compound...Ch. 26 - Prob. 43PCh. 26 - 28.45 Draw both pyranose anomers of each...Ch. 26 - Prob. 45PCh. 26 - 28.50 Draw the products formed when D-altrose is...Ch. 26 - 28.58 Draw a stepwise mechanism for the following...Ch. 26 - Prob. 62PCh. 26 - Prob. 63PCh. 26 - Prob. 64PCh. 26 - Prob. 65PCh. 26 - Prob. 66PCh. 26 - Prob. 67PCh. 26 - Prob. 68PCh. 26 - Prob. 69PCh. 26 - Prob. 70P
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- Draw the structures of the individual mutarotating a and b anomers of maltose.arrow_forwardTreatment with sodium borohydride converts aldose A to an optically inactive alditol. Wohl degradation of A forms B, whose alditol is optically inactive. Wohl degradation of B forms d-glyceraldehyde. Identify A and B.arrow_forwardA D-aldohexose A is formed from an aldopentose B by the Kiliani-Fischer synthesis. Reduction of A with NABH4 forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?arrow_forward
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- 1.Explain what is anomeric effect and why it happens? 2.Explain how a glycosyl acetimidate can loss its glycosyl donor activity?arrow_forwardThere are four d-aldopentoses (Table 25.1). If each is reduced with NaBH4, which yield optically active alditols? Which yield optically inactive alditols?arrow_forwardThe cyclic hemiacetal is more stable than the open-chain form, so very little of the open-chain form is present atequilibrium. Will an aqueous solution of glucose reduce Tollens reagent and give a positive Tollens test? Explain.arrow_forward
- does structure E represent fructofuranose? explainarrow_forward(a) Label all the O atoms that are part of a glycoside in rebaudioside A. Rebaudioside A, marketed under the trade name Truvia, is a sweet glycoside obtained from the stevia plant, which has been used for centuries in Paraguay to sweeten foods. (b) The alcohol or phenol formed from the hydrolysis of a glycoside is called an aglycon. What aglycon and monosaccharides are formed by the hydrolysis of rebaudioside A?arrow_forwardDraw an electron pushing mechanism for proline racemization. Draw a reaction coordinate diagram of the uncatalyzed and catalyzed reaction.arrow_forward
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