Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 23.6, Problem 23.15P
Interpretation Introduction
Interpretation: The information regarding the formation of
Concept introduction: Reduction of
To determine: The structure of
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What is the product (from the image below) of the starting material D-glyceraldehyde which will
(1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3
(2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3
3a.
3b.
3c
3d.
3e.
CO₂
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List all possible D-2-ketohexoses. One of these D-2-ketohexoses is called sorbose. When sorbose is treated with sodium borohydride it produces a mixture of glucitol and iditol. What is the structure of sorbose? Another D-2-ketohexose, psychosa produces a mixture of alitol and altritol when reduced with sodium borohydride, which is the structure of psychose
Chapter 23 Solutions
Organic Chemistry (9th Edition)
Ch. 23.2 - Prob. 23.1PCh. 23.3A - Prob. 23.2PCh. 23.3A - Prob. 23.3PCh. 23.3B - Draw and name the enantiomers of the sugars shown...Ch. 23.3B - Prob. 23.5PCh. 23.3C - Prob. 23.6PCh. 23.4 - Draw the Haworth projection for the cyclic...Ch. 23.4 - Prob. 23.8PCh. 23.4 - Prob. 23.9PCh. 23.4 - Prob. 23.10P
Ch. 23.4 - Prob. 23.11PCh. 23.5 - Prob. 23.12PCh. 23.5 - Prob. 23.13PCh. 23.6 - Prob. 23.14PCh. 23.6 - Prob. 23.15PCh. 23.7 - Prob. 23.16PCh. 23.7 - Prob. 23.17PCh. 23.7 - Two sugars, A and B, are known to be glucose and...Ch. 23.7 - Prob. 23.19PCh. 23.8 - Prob. 23.20PCh. 23.8 - Prob. 23.21PCh. 23.8 - Prob. 23.22PCh. 23.8 - Prob. 23.23PCh. 23.8 - Prob. 23.24PCh. 23.9 - a. Show the product that results when fructose is...Ch. 23.9 - Prob. 23.26PCh. 23.9 - Prob. 23.27PCh. 23.9 - Prob. 23.28PCh. 23.10 - Prob. 23.29PCh. 23.10 - Prob. 23.30PCh. 23.10 - Prob. 23.31PCh. 23.11 - Prob. 23.32PCh. 23.11 - The Wohl degradation, an alternative to the Ruff...Ch. 23.11 - Prob. 23.34PCh. 23.11 - Prob. 23.35PCh. 23.12A - Prob. 23.36PCh. 23.12A - Give an equation to show the reduction of Tollens...Ch. 23.12A - Prob. 23.38PCh. 23.12B - Prob. 23.39PCh. 23.12C - Prob. 23.40PCh. 23.12C - Prob. 23.41PCh. 23.13A - Prob. 23.42PCh. 23.15 - Cytosine, uracil, and guanine have tautomeric...Ch. 23.15 - a. An aliphatic aminoglycoside is relatively...Ch. 23.16C - Prob. 23.45PCh. 23 - Prob. 23.46SPCh. 23 - Prob. 23.47SPCh. 23 - Prob. 23.48SPCh. 23 - Prob. 23.49SPCh. 23 - Prob. 23.50SPCh. 23 - Prob. 23.51SPCh. 23 - Prob. 23.52SPCh. 23 - Prob. 23.53SPCh. 23 - Prob. 23.54SPCh. 23 - Prob. 23.55SPCh. 23 - Prob. 23.56SPCh. 23 - Prob. 23.57SPCh. 23 - Prob. 23.58SPCh. 23 - Prob. 23.59SPCh. 23 - Prob. 23.60SPCh. 23 - Prob. 23.61SPCh. 23 - Prob. 23.62SPCh. 23 - Prob. 23.63SPCh. 23 - Draw the structure of a four-residue segment of...Ch. 23 - Retroviruses like HIV, the pathogen responsible...Ch. 23 - Prob. 23.66SPCh. 23 - Prob. 23.67SP
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- (a) Provide (Draw) products for the following reactions OH OH 1. PCC 2. t-BuPh₂SiCl DMAP,CH₂Cl2arrow_forwardThe following observations are obtained after a D-hexose was made to react with several reagents: (1) The reactions of a D-hexose with (a) to (d) below yields an aldaric acid (a) NH₂OH, (b) (CH3CO)₂O, NaOCOCH 3, and, (c) NaOCH3, and then, (d) HNO3, H₂O (2) HNO3 oxidation of the same D-hexose gives an aldaric acid. Predict the structures of the three (3) possible hexoses that can undergo the above reactions?arrow_forwardConsider the ring structure of β-D-glucose. It will give a positive test as a reducing sugar. Describe how can that happen in a pH = 7 solution such as Fehlings'?arrow_forward
- The first step in the catabolism of most amino acids is the removal of the nitrogen atom by transfer to an a-keto acid, a reaction catalyzed by an enzyme called a transaminase. The a-keto acid acceptor is often a-ketoglutarate. Modify the structures in the product to show the products of the transamination of cysteine. Be sure to show functional groups with the charge and number of attached hydrogen atoms appropriate for pH 7.4. transaminase + O=C H₂N-CH + CH₂ CH₂ CH₂ SH Incorrect H₂N || CH | CH₂ | CH₂ I || O || n | CH₂ T SHarrow_forwardKojibiose is a reducing sugar that forms D-glucose on hydrolysis with aqueous acid. Reaction of kojibiose with iodomethane and Ag20 yields an octamethyl derivative, which can be hydrolyzed with aqueous acid to give one equivalent of 2,3,4,6-tetra-O- methyl-D-glucopyranose and one equivalent of 3,4,6-tri-O-methyl-D-glucopyranose. If kojibiose is hydrolyzed by alpha-glucosidases but not beta-glucosidases, what is its structure?arrow_forwardWrite a reaction and mechanism for the formation of osazone when D-erythrose reacts with excess of phenylhydrazine. Apply Fischer projections. сно H. HO- O- CH2OH D-erythrosearrow_forward
- Write the equation of reactions of Glucose+Cu(OH)2(heat) Glucose+HNO3 a-D-glucopyranose+(CH3CO)2O a-D-glucopyronase+CH3Iarrow_forward1mL of Benedict's reagent is added to 1mL of the test solution. The mixture is then heated for 5 minutes in water bath. Appearance of reddish-brown precipitates indicates the presence of a reducing sugar. Glucose and Fructose give a positive result. Sucrose on the other hand gives a negative result. Explain why sucrose give a negative result when subjected to a Benedict's test.arrow_forwardPredict the products formed when the following sugars react with excess acetic anhydrideand pyridine.(a) a-d-glucopyranosearrow_forward
- Which one of the following (Figure 19) is a structure of a phosphatidic acid? CH2OC(CH2)4CH3CH2OC(CH2H4CH3 CH2OC(CH2)4CH3 CH2OH CHOC(CH2H16CHS CHOLI(CH₂/18CHS CHOH 3 CHOH 产 CH2OP(OH)2 CH2OC(CH2)4CH3 CH₂OP(OH)2 ! !! I II III H2OP(OH)2 IVarrow_forwardUnder acidic conditions (catalytic amount of acid) in anhydrous methanol, D-galactose can be converted to the methyl galactopyranoside X on the right side of the reaction arrow. Write a detailed mechanism for the reaction. OH H+ HO HO `Me MeOH HO 'OH HO "OH OH OH Xarrow_forwardAn important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.arrow_forward
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