Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 24, Problem 41P
Treatment of
isomeric products having the molecular formula
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What product is formed when D-Gulose is treated with
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When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose
d-Xylose and d-lyxose are formed when d-threose undergoes a Kiliani–Fischer synthesis. d-Xylose is oxidized to an optically inactive aldaric acid,whereas d-lyxose forms an optically active aldaric acid. What are the structures of d-xylose and d-lyxose?
Chapter 24 Solutions
Organic Chemistry - Standalone book
Ch. 24.2 - Prob. 1PCh. 24.3 - Problem 24.2 Which aldotetrose in the structure...Ch. 24.4 - Prob. 3PCh. 24.4 - Prob. 4PCh. 24.6 - Prob. 5PCh. 24.6 - Prob. 6PCh. 24.7 - Prob. 7PCh. 24.8 - Prob. 8PCh. 24.8 - Prob. 9PCh. 24.9 - Prob. 10P
Ch. 24.10 - Prob. 11PCh. 24.10 - Prob. 12PCh. 24.11 - Prob. 13PCh. 24.12 - Prob. 14PCh. 24.14 - Prob. 15PCh. 24.14 - Prob. 16PCh. 24.14 - Prob. 17PCh. 24.14 - Using Mechanism 24.2 as a guide, write a stepwise...Ch. 24.15 - Prob. 19PCh. 24.17 - Prob. 20PCh. 24.17 - Prob. 21PCh. 24.18 - Prob. 22PCh. 24.18 - Prob. 23PCh. 24.18 - Prob. 24PCh. 24.20 - Prob. 25PCh. 24 - Prob. 26PCh. 24 - Prob. 27PCh. 24 - Prob. 28PCh. 24 - Prob. 29PCh. 24 - Prob. 30PCh. 24 - Prob. 31PCh. 24 - Prob. 32PCh. 24 - Prob. 33PCh. 24 - Prob. 34PCh. 24 - Prob. 35PCh. 24 - Methyl glycosides of 2-deoxy sugars have been...Ch. 24 - Prob. 37PCh. 24 - Prob. 38PCh. 24 - Prob. 39PCh. 24 - Prob. 40PCh. 24 - Treatment of d-mannose with methanol in the...Ch. 24 - Prob. 42PCh. 24 - Prob. 43PCh. 24 - Prob. 44PCh. 24 - Prob. 45DSPCh. 24 - Prob. 46DSPCh. 24 - Prob. 47DSPCh. 24 - Prob. 48DSPCh. 24 - Prob. 49DSP
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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_forwardTreatment of either anomer of fructose with excess ethanol in the presence of a trace ofHCl gives a mixture of the a and b anomers of ethyl-d-fructofuranoside. Draw the startingmaterials, reagents, and products for this reaction. Circle the aglycone in each productarrow_forwardThe cyclic form of this sugar would be A) alpha-anomer as the -CH2OH and the hemiacetal -OH are trans B) beta-anomer as the -CH2OH and the hemiacetal -OH are cis C) beta-anomer as the -CH2OH and the hemiacetal -OH are trans D) alpha-anomer as the -CH2OH and the hemiacetal -OH are cisarrow_forward
- Trehalose, C12H22O11, is a nonreducing sugar that is only 45% as sweet as sugar. When hydrolyzed by aqueous acid or the enzyme maltase, it formsonly d-glucose. When it is treated with excess methyl iodide in the presence of Ag2O and then hydrolyzed with water under acidic conditions, only2,3,4,6-tetra-O-methyl-d-glucose is formed. Draw the structure of trehalose.arrow_forwardPredict the products obtained when d-galactose reacts with each reagent.(a) Br2 and H2O (b) NaOH, H2O (c) CH3OH, H + (d) Ag(NH3) 2+ -OH(e) H2, Ni (f) excess Ac2O and pyridine (g) excess CH3 I, Ag2O (h) NaBH4(i) Br2, H2O, then H2O2 and Fe2(SO4)3 (j) (1) KCN/HCN; (2) H2, Pd/BaSO4; (3) H3O! (k) excess HIO42arrow_forwardWhy is molecule "A" the major acetal formed when d-erythrose reacts with H2SO4 and acetone as opposed to molecule "B"?arrow_forward
- Hyaluronic acid, a component of connective tissue, is the fluid that lubricates joints. It is a polymer of alternating N-acetyl-d-glucosamine and d-glucuronic acid subunits joined by β-1,3'-glycosidic linkages. Draw a short segment of hyaluronic acid.arrow_forwardWhich of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(arrow_forwardDraw all the isomeres of a thioester with molecular formula C4H8OSarrow_forward
- An aldopentose "O", is oxidized with HNO3 to a diacid "P" which is optically active. The compound "O", is also degraded to an aldotetrose "Q" which undergoes another oxidation to an optically inactive diacid "R". Assuming that "O" has the configuration D-(4R); what are the structures of "O" to "R"?arrow_forwardFats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products.arrow_forwardrank the products in the indicated CH2 groups in order of increasing acidity and give reasons why.arrow_forward
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