Organic Chemistry Direct Problem Set Chapter 24: Reactions of Monosaccharides Se

Question

Organic Chemistry Direct Problem Set Chapter 24: Reactions of Monosaccharides Select the best answer for each of the following questions: 1. Penta-O-acetyl-p-D-glucopyranose can be prepared from glucose with the following reagent: ocOCH, 4. In order to convert glucose into the pentamethyl ether, you should react it with: oc? CH,0 one CHON on, ????, -ocOCH, ??????, CH,CO, CH,CO, a. Br, in CH,COOH b. (CH,CO):0 in pyridine c. CH3cOci in CH,OH d. (CH,CO2)2 in CH,OH a. CH?l in pyridine b. c?o in c?,?? c. Ag,0 in aqueous NH, d. Ag:0 and CH?l 2. Treating glucose with HCI in CH,OH will result in the formation of: 5. Reaction of pentaacetyl glucopyranose with HBr results in: ocoCH, CH,co, to * CON CH,CO.Ti VococH, ??,??, . ocacts a. the pentamethyl ether b. the hemiacetal c. the methyl glucopyranoside a. the hydrolysis of the ester linkages b. the formation of the tetraacetyl glucopyranos) bromide c. the formation of the glucopyanosyl bromide d. ring-opening of the hemiacetal d. glucopyranosyl chloride 6. Reaction of an aldopentose with HCN, followed by reduction with H/Pd, and then hydrolysis in dilute acid results in the formation of: 3. When B-D-glugopyranose if treated with HCI in CH,OH: c?,??. ?. HOH 1 ?? H- OH 2 KPG H -OH JH, 3 H,0: -OH - Om-om a. an aldohexose b. a cyanohydrin c. an alditol d. an aldonic acid a. a mixture of a- and B-anomers will be formed b. the B-anomer will be formed c. the a-anomer will be formed d. the B-hemiacetal will be formed

Explanation / Answer

1. (b) (CH3CO)2O as base is needed for abstration of proton

2. (c) methyl glucopyranoside

3. (a) mixture of alpha and beta anomors

4. (a) CH3I in pyridine as base is needed for abstration of proton

5. b) formation of tetraacetyl glycopyranose bromide

6. a) an aldohexose

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