Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 28, Problem 28.61P
Interpretation Introduction
Interpretation:
The stepwise mechanism to account for the formation of A is to be drawn.
Concept introduction:
The aldehyde group of aldoses oxidizes to carboxyl group on treatment with
Carbohydrates are naturally occurring compounds. Carbohydrates are polyhydroxy
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An aldose A, is reduced by sodium borohydride to an optically inactive alditol B. The Ruff degredation of A forms C. Oxidation of C by nitric acid generates the optically inactive diacid D. The ruff degreation of C forms D-glyceraldehyde. draw the structures for compounds A through D and discuss a mechanism for the reduction step using sodium borohydride
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 MeDgives 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
OH
OMe
Am OH
OMe
OMe
(a) Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(b) Which of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(c) 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 X.(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an opticallyactive aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form opticallyactive products?(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose.Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?
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 - 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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- Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forwardIdentify A, B, C, and D in the preceding problem if D is oxidized to an optically inactive aldaric acid; if A, B, and C are oxidized to optically active aldaric acids; and if interchanging the aldehyde and alcohol groups of A leads to a different sugar.arrow_forwardGive only typing answer with explanation and conclusionarrow_forward
- Please answer d and 4.3arrow_forwardconfiguration of (-)-glyceraldehyde with (+)-lactic acid. Label each compound with its Write bond-line three-dimensional formulas for the starting compound, the product, and all of the intermediates in a synthesis similar to the one just given that relates the PRACTICE PROBLEM 5.31 orarrow_forwardCompound C undergoes a chemical reaction with a reagent, resulting in the formation of two new compounds. Four potential stereoisomers of the product are shown below. e) Name the type of reaction and provide a possible reagent. f) Clearly assign all the stereocentres found in compound D, E, F and G using Cahn-Ingold-Prelog rules. g) Define the relationship between compound D, E, F and G. h) Identify the two stereoisomers which are likely to be formed from compound C.arrow_forward
- 1) How will you describe whether any compound has been oxidized or reduced? Support your answer with suitable examples. 2) A) Define chemo selective reactions with examples.B) Give any two conditions where enol tautomer is more stable than keto tautomer.arrow_forwardTartaric acid is an inexpensive and readily available chiral starting material for the syn- thesis of chiral molecules. In a well-known prostaglandin synthesis, the (S,S)-tartaric acid enantiomer was used to prepare the chiral diol in several steps. The chiral diol was isolated as a synthetic intermediate, and the following reagents are used. Draw the structures of synthetic intermediates A and B. H3C- HO НО HO, Several steps ОН Nal НО ОН A В Pyridine Acetone (S,S)-Tartaric acidarrow_forward(d) With reference to the following reaction scheme: H 22 1. Li, NH3, -78 °C BuOH (1 equiv.) 2. NH4CI H "I 23 (i) Explain why only one of the two C-C double bonds in enone 22 is reduced under these reaction conditions. (ii) Draw a curved arrow mechanism for the transformation of 22 into 23.arrow_forward
- 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 Is is MeO MeO MOH OMe mOH OMe OMearrow_forwardAldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B alsoreacts with warm nitric acid to give an optically active aldaric acid, but A reacts to givean optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, whichgives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D isdegraded to (+)@glyceraldehyde. Deduce the structures of sugars A, B, C, and D, and useFigure 23-3 to determine the correct names of these sugars.arrow_forwardStereochemistry in biological molecules is often denoted by the D- and L- convention, instead of the R- and S- configurations determined by the Cahn-Ingold-Prelog methodology. Historically, the glyceraldehyde enantiomer that rotated plane polarized light clockwise was arbitrarily designated as D and the other enantiomer was designated as the L configuration. The D-glyceraldehyde Fischer projection is shown. D-glyceraldehyde H H- -OH CH₂OH Identify which structures are equivalent to the D-configuration. H CH₂OH 76. OH CH₂OH H- -OH ☐ O H ОН -CH₂OH K H H Incorrect HOCH2 H OH t H OH CH₂OH K.arrow_forward
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