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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Chapter 23 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- 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_forwardHyaluronic 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_forward
- Draw the product formed when pentanal (CH3CH2CH2CH2CHO) is treated with each reagent. With some reagents, no reaction occurs.arrow_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
- Draw the products formed when α-D-gulose is treated with below reagent CH3I, Ag2Oarrow_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_forward
- Draw the products formed when α-D-gulose is treated with below reagent Ac2O, pyridinearrow_forwardThe 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_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
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