Concept explainers
Interpretation:
The starting material, reagents and products for the reaction of anomer of fructose with excess ethanol in the presence of a trace of
Concept introduction:
Carbohydrates are naturally occurring organic compounds. As the name implies carbohydrates are hydrates of carbon and have general formula of
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Organic Chemistry (9th Edition)
- Treatment of methyl b-d-glucopyranoside with benzaldehyde forms a six-membered cyclic acetal. Draw the most stable conformation of this acetal. Identify each new chiral center in the acetal.arrow_forward5. Which two D-pentose sugars give optically active alditols when reduced with NABH4 CHO н— он CH2OH D-glyceraldehyde. Сно CHO H HOH H HOH CH2OH „D-erythrose HO H H HOH ČH2OH D-threose CHO CHO CHO CHO -OH HO-H H OH Но -O- H +OH но -H но- H- HFOH CH2OH H- -OH H +OH H FOH CH2OH CH2OH ČH2OH D-ribose D-arabinose D-хylose D-lyхose CHO CHO CHO CHO Сно CHO CHO CHO HO-H HO-H HO-H H HOH но—н но—н H FOH H HOH H +OH HO-H H FOH H- -O- HO-H но- H OH H- -O- но но—н H FOH HO-H H +OH CH2OH H HOH H -OH H HOH H FOH но FH HHOH ČH2OH HHOH ČH2OH H- -OH H -OH H- -OH -OH ČH2OH ČH2OH CH2OH CH2OH ČH2OH D-allose D-altose D-glucose D-mannose D-gulose D-idose D-galactose D-talosearrow_forwardDraw the product formed when pentanal (CH3CH2CH2CH2CHO) is treated with each reagent. With some reagents, no reaction occurs.arrow_forward
- Draw the products formed when α-D-gulose is treated with below reagent CH3I, Ag2Oarrow_forwardDraw the product formed when (CH3CH2CH2CH2)2CuLi is treated withattached compound. In some cases, no reaction occurs.arrow_forwardPredict the products obtained when d-galactose reacts with each reagent. (h) NaBH4(i) Br2, H2O, then H2O2 and Fe2(SO4)3arrow_forward
- (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 Barrow_forwardDraw the product formed when (CH3CH2CH2CH2)2CuLi is treated with each compound. In some cases, no reaction occurs.arrow_forwardDraw the products formed when α-D-gulose is treated with below reagent Ac2O, pyridinearrow_forward
- The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the a or ß anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_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_forward1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.arrow_forward