Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 51AP
Interpretation Introduction
Interpretation:
Reduction of D-sorbose gives sorbitol.
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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?
(d) Draw the structure of the expected product when monosaccharide B undergo
mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3,
NHẠOH).
он
OH
O.
OH
OH
OH
monosaccharide B
Draw the product formed when CH3CH2CH2CH2CH=CH2 is treated with either(a) H2O, H2SO4; or (b) BH3 followed by H2O2, HO−.
Chapter 25 Solutions
Organic Chemistry
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
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- One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. -OPO3²- Enz-SH H-C-OH ATP CH₂OPO3²- 3-phosphoglycerate O 0-0--0 O ADP CH₂CH3 substitute for 1,3-bisphosphoglycerate C H-C-OH CH₂OPO3²- 1,3-bisphosphoglycerate O=C CH3-SH substitute for Enz-SH H H-C-OH | CH₂OPO3²- PO4³- O. S-Enz H-C-OH glyceraldehyde 3-phosphate Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this intermediate. To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH. CH₂OPO3²- (Enzyme-bound thioester) NADH/H* NAD*,…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_forward5)A certain aerobic organism is able to metabolize the followingglycolipid CH,OH H H OH H HO OH A.Draw the 2 resulting structures that would occur upon initial hydrolysis of the O-glycosidic bond.arrow_forward
- Write down the reactions: D-Glucose + HNO3 →arrow_forward4. Glycolysis is a metabolic pathway that converts glucose into pyruvate while synthesizing high-energy molecules. During one step of Glycolysis, glucose-6-phosphate (an aldose) is converted to fructose-6-phosphate (a ketose) via an ene-diol intermediate. OH OH O OP OH OH ОН ОН glucose-6-phosphate OH OH OH OP OH fructose-6-phosphate Draw arrow pushing mechanism to describe this isomerization. Use B: and HA as surrogates for basic/acidic amino acid residues.arrow_forwardCellulose is not digestible by humans because it contains glucose units linked by -glycosidic bonds. O a-1,6 O a-1,4 O a-1,2 O B-1,4 O B-1,2arrow_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_forwardDraw the ketohexose provided in the B-pyranose form using the pyranose skeleton as a guide. O: H +OH H +OH HO -H HO- HO.arrow_forwardWhich of the following is the correct pair of monosaccharides needed 2 to form the given glycoside? * CH2OH CH-OH CH2OH OH он он OH OH a-D-fructofuranose & B-D-glucopyranose a-D-sorbofuranose & B-D-allopyranose a-D-mannofuranose & B-D-glucopyranose O a-D-sorbofuranose & B-D-galactopyranosearrow_forward
- Draw β-d-psicofuranose :arrow_forwardDraw the products formed when α-D-galactose is treated with each reagent: i. CH3I (excess), Ag2O ii. CH3OH, H3O+ iii. NaOH, H2O iv. Br2, H2Oarrow_forwardRibose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. To determine which ring is formed, ribose is treated with methanol in the presence of an acid catalyst. The products are then isolated and treated with NaIO, then with H₂O*. HO OH OH OH Ribose, C5H10O5 H 9.81 ** MeOH H* A & B isomeric cyclic acetals with formula C6H12O5 Assuming that ribose formed a five-membered ring cyclic hemiacetal, draw the structure of the sodium periodate digestion products. ▼ • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. 1. NalO4, 2. H₂O* MeOH products 4 SIF Previous Nextarrow_forward
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