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- Two sugars differing in configuration at a single asymmetric carbon atom are known as epimers. D-mannose is a C-2 epimer of glucose (Structure I), while D-galactose is a C-4 epimer of glucose. Structure Il and IIl are H- -OH но- -H H OH HO H но- H HO H H -OH H- -OH HO OH H -OH H- -OH H OH HO. HO, OH II II Which of the following represents an aldopentose? OH H O HO O HO H но н HO H но- HO H HO H HO- H OH H OH H OH H OH OH HO Он of но" HO O OH он III IV These are chemical messengers that are secreted by endocrine glands and carried through the bloodstream to target tissues. prostaglandin deoxysugar glycoside hormones Which of the following is NOT correctly paired? cellulose: beta-1,4-glycosidic linkage amylose: alpha-1,4-glycosidic linkage chitosan: alpha-1,4-glycosidic linkage cellubiose: beta-1,4-glycosidic linkageDraw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?H3C-C=C-CH2-CH-CH3 excess H2 ČH3
- TLNEVE-++ACOD n t t G 80. n Tuu 30 BRE 40 20 Oc C d 4000 a b 3600 (a) CH-CH₂-CH₂-CH₂-C=CH (B) CH-CH2-CH2-CH2-CH2-CI (c) CH-CH₂-CH₂-CH₂-CH-CH₂ (d) CH,CH2-CH2-CH2-CH2-CH3 2000 2600 Wa venumberc 2000 1600 1000 600Nemotin is a compound that was first isolated from the fungi Poria tenuis and Poria corticola in the 1940s and was shown to possess potent antibacterial activity. (Org. Biomol. Chem. 2010, 8, 811-821). However, its structure was not verified until it was made in the laboratory much more recently. :ö H H-C-C-H H C=c=C H Nemotin Determine the hybridization state of each carbon atom in nemotin. ミ-0三O-O三Consider the following equilibrium: O || R-C-H + HCN HO OH R-C-H | CN (A) When R = CH3CH2-, Keq = 1. (i) Predict whether Keq should be greater or less than 1 when R = CICH2, and (ii) when R is CH2=CH. Explain. (B) In the case where R is CH2=CH, the cyanohydrin is formed faster but given enough time, another constitutional isomeric C4H5NO product predominates. Explain and write a base-catalyzed mechanism for the formation of the other isomer. Recall that: HO HON N
- (C) (D) PQ-25. Which pair of compounds are enantiomers? CI CI CI CI H- OH HO -H- H- HO- HO H- and and (A) OH Но- -- (B) CI H- CI -H- -H- CI CI ОН ОН OH ОН CI CI H- CI H- HO- H -CI (С) and НО H- H- HO- HO H- and CIFH CI CI ОН OH2H2O, H* X3 OH t°C HBr KCN H;C-CH-CH2-C ОН 1) X4 t°C 2) Но-СH2-С OH t°C 3) H3C-CH-CH2 CH2-C OHLOH HO OH Threitol Threitol is a sugar alcohol derived from Threose by catalytic hydrogenation. Is it chiral or meso? OH OH HO HO ОН ОН Galactitol Galactitol is a sugar alcohol derived from galactose by catalytic hydrogenation. Is it chiral or meso? Oll
- 5-54 Ribose, an essential part of ribonucleic acid (RNA), has the following structure: H H H OH CHO Ribose Но но н но н (a) How many chirality centers does ribose have? Identify them. (b) How many stereoisomers of ribose are there? (c) Draw the structure of the enantiomer of ribose. (d) Draw the structure of a diastereomer of ribose.Br Br2 Br + enantiomer Cl2 H20 но + enantiomer 1) внЗ /THF OH 2) н202 / NaOH HBr (excess) Br Bi + enantiomerPQ-25. Which pair of compounds are enantiomers? CI (A) CI H-OH H-OH CI OH CI- (C) Н -OH CI 애 and and -Н НО НО -H CI о OH н- HO-H CI -CI -OH (B) CIH ОН (D) CI оно 8 I I -ОН H- CI and and НО- CI-H OH o- НО CI- ОН