Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 28, Problem 28.62P
Interpretation Introduction
Interpretation: The compounds A-D are to be identified.
Concept introduction: The optically active compounds should not have plane of symmetry and center of symmetry. A point is said to be center of symmetry, if same molecules are present in opposite direction to each other. If plane passes through the center of the molecule and the molecule is divided into two equal halves, then the molecule is said to have plane of symmetry.
Kilani-Fischer synthesis results in the formation of two epimers. Two compounds which are neither superimposable nor mirror images to each other and the configuration of one of their stereogenic centers is different are known as epimers.
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A 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?
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.
A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?
Chapter 28 Solutions
Organic Chemistry
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Label each stereogenic center as R or S. a. b. c....Ch. 28 - Convert the ball-and-stick model to a Fischer...Ch. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Prob. 28.17PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35
Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - 28.40 Convert each compound to a Fischer...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - 28.43 Draw a Haworth projection for each compound...Ch. 28 - Prob. 28.44PCh. 28 - 28.45 Draw both pyranose anomers of each...Ch. 28 - Prob. 28.46PCh. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - 28.50 Draw the products formed when D-altrose is...Ch. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - Prob. 28.54PCh. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.59PCh. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - 28.71 Draw a stepwise mechanism for the following...
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- A D-aldopentose is oxidized by nitric acid to an optically active aldaric acid. A Wohl degradation of the aldopentose leads to a monosaccharide that is oxidized by nitric acid to an optically inactive aldaric acid. Identify the D-aldopentose.arrow_forwardDraw the products formed when β-D-galactose is treated with each reagent. a. Ag2O + CH3I b. NaH + C6H5CH2Cl c. The product in (b), then H3O+ d. Ac2O + pyridine e. C6H5COCl + pyridine f. The product in (c), then C6H5COCl + pyridinearrow_forwardWhat products are obtained from the reduction of a. d-idose? b. d-sorbose?arrow_forward
- Draw the products formed when ß-D-galactose is treated with each reagent.a. Ag2O + CH3Ib. NaH + C6H5CH2Clc. The product in (b), then H3O+d. Ac2O + pyridinee. C6H5COCl + pyridinef. The product in (c), then C6H5COCl + pyridinearrow_forward1. Carbohydrates classification. 2. Write down the reactions: a) α,D-Glucopyranose + C2H5OH → b) D-Glucose + [Ag(NH3)2]+ → c) D-Glucopyranose + (CH3CO)2 O → d) D-Glucopyranose + CH3I → e) D-Glucose + HNO3 → f) D-Glucose + H2 → g) Lactose formation h) Sucrose hydrolysis 3. Write down the formula of β,D-galactopyranosearrow_forwardAn optically active D-aldopentose (A) produced an optically inactive alditol (B) upon treatment with H2/Pt. When the aldopentose (A) was subjected to a Ruff degradation, D-aldotetrose (C) was generated. The aldotetrose (C) gave an optically active aldaric acid (D) upon oxidation with HNO3. D-aldopentose (A) can be prepared from D-threose by a Killani Fischer synthesis. Propose structure of A through D.arrow_forward
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