Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 28, Problem 28.65P
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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Chapter 28 Solutions
Organic Chemistry-Package(Custom)
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 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.23PCh. 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 - Convert each compound to a Fischer projection and...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - Prob. 28.43PCh. 28 - Prob. 28.44PCh. 28 - Prob. 28.45PCh. 28 - Draw both pyranose anomers of each aldohexose...Ch. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - Prob. 28.50PCh. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - What products are formed when each compound is...Ch. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - Prob. 28.58PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 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 - Prob. 28.71PCh. 28 - Prob. 28.72PCh. 28 - Prob. 28.73PCh. 28 - Prob. 28.74PCh. 28 - Prob. 28.75PCh. 28 - Prob. 28.76PCh. 28 - Prob. 28.77PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.79P
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- Deduce the structure of the disaccharide isomaltose from the following data.a. Hydrolysis yields D-glucose exclusively. b. Isomaltose is cleaved with α-glycosidase enzymes. c. Isomaltose is a reducing sugar. d. Methylation with excess CH3I, Ag2O and then hydrolysis with H3O+ forms two products:arrow_forwardWhat reaction is responsible for the conversion of linear d-glucose to cyclic d-glucose? A. Reduction reaction B. Oxidation reaction C. Hydrolysis reaction D. Hemiacetal reactionarrow_forwarda) The D-aldopentose A, C5H1005, reacts with HNO3 to yield an optically active aldaric acid B. Kiliani-Fischer chain extension of A produces a pair of D-aldohexoses C and D. C is converted by HNO3 to an optically active aldaric acid, but D is converted by HNO3 to an optically inactive aldaric acid. Write acyclic Fischer projections for A, B, C, D. b) Disaccharide E is a reducing sugar. It is hydrolyzed by an α-glycosidase enzyme, which means it contains an α- glycoside link. Treatment of E with Ag2O and excess Mel gives an octamethyl derivative F. Hydrolysis of F in dilute aqueous acid gives the pair of molecules shown below. Write the structures of E and F. (If the stereochemistry at a particular carbon is not determined by the above data, indicate this with a wavy line as shown below.) HO OMe OMe MeO MeO MOH OMe mOH OMe OMearrow_forward
- a) The D-aldopentose A, C5H1005, reacts with HNO3 to yield an optically active aldaric acid B. Kiliani-Fischer chain extension of A produces a pair of D-aldohexoses C and D. C is converted by HNO3 to an optically active aldaric acid, but D is converted by HNO3 to an optically inactive aldaric acid. Write acyclic Fischer projections for A, B, C, D.arrow_forwardAmygdalin is a toxic component in the pits of bitter almonds, peaches, and apricots. Q.) Name the two monosaccharide units in amygdalin and describe the glycosidic bond by which they are joined.arrow_forward1arrow_forward
- Sugar X is known to be a d-aldohexose. On oxidation with HNO3, X gives an optically inactive aldaric acid. WhenX is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine thestructure of Xarrow_forwardi need an answer pleaseeeearrow_forwardPropose structural formulas for the following polysaccharides. Q.) Pectic acid is the main component of pectin, which is responsible for the formation of jellies from fruits and berries. Pectic acid is a polymer of d-galacturonic acid in the pyranose form joined by a-1,4-glycosidic bonds.arrow_forward
- Write down the reactions: D-Glucose + HNO3 →arrow_forwardA 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_forwardConsider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine,soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence. a. Is stachyose a reducing sugar?b. What product is formed when stachyose is treated with excess CH3I, Ag2O?c. What products are formed when the product in (e) is treated with H3O+?arrow_forward
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