5. structure in aqueous solution. H H-C=O H-C-OH CH₂OH (a) (b) (c) An aldohexose (e.g., Glucose) can occur in three forms: two cyclic forms and one open-chain OH ОН aldotriose H HO H-C-OH н-с-он H-C-OH CH₂OH OH OH OH OH aldopentose Draw the corresponding structures of aldohexoses (c.f., aldotriose and aldopentose). aldohexose Draw the reaction forming two cyclic forms from the open-chain structure How many asymmetric carbon atoms (chiral centers) are there in three forms, respectively?

5. structure in aqueous solution. H H-C=O H-C-OH CH₂OH (a) (b) (c) An aldohexose (e.g., Glucose) can occur in three forms: two cyclic forms and one open-chain OH ОН aldotriose H HO H-C-OH н-с-он H-C-OH CH₂OH OH OH OH OH aldopentose Draw the corresponding structures of aldohexoses (c.f., aldotriose and aldopentose). aldohexose Draw the reaction forming two cyclic forms from the open-chain structure How many asymmetric carbon atoms (chiral centers) are there in three forms, respectively?

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Similar questions

4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОН
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 linkage
Lactose is a disaccharide in which a glycosidic linkage connects the monosaccharides galactose and glucose. OH НО OH (a) Identify the glycosidic linkage and the acetal carbon in lactose. (b) What type of glycosidic linkage does lactose have (i.e., is it 1,1'-, 1,2'-, etc., and is it a or B)? (c) People who are lactose intolerant are deficient in the enzyme lactase, and therefore cannot efficiently break down the disaccharide into its monosaccharides. When lactose is treated with aqueous acid, however, this hydrolysis can take place, though relatively slowly. Draw the complete, detailed mechanism and the products of the acid-catalyzed hydrolysis of lactose. Но ОН НО ОН ОН Lactose
Classify the structures as being either an enantiomer, diastereomer or diastereomer/epimer of D-glucose. Structure A: CH H- -OH Structure B: но- H- H- OH Structure C: H- он H- -H D-Glucose: OH || CH CH CH он H- он но -H H- он но он но но- H- но H- OH OH но -- H- -H H -Ç-H Structure A: OH Structure B: OH Structure C: OH
OH ОН Which monosaccharide has a greater heat of combustion, B-D-glucopyranose or B-D-allopyranose? Explain. но НО Но OH OH OH OH OH B-D-Glucopyranose B-D-Allopyranose
(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 B
N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Ne
tion 6 of 17 > The structures of four isomers of a ketopentose are shown. OH کر کو 3 E D C 80 OH H-C-H 0=C HOLC-H HOC CH H-C-H OH A Dc $ 4 D B D D A Which of the structures are diastereomers of A? R F A DOD F4 H-C-H V OH C=0 HICIOH Но..C.....H HOLC-H HOCH H-C-H OH Which of the structures are stereoisomers of C? % 5 B T G H-C-H Es C=0 B H-C-H OH 6 C FG Y H & 7 OH H-C-H N 0=C HOLC…H HICIOH H-C-H 99 U OH D J * 8 M Which of the structures are enantiomers of C? - Ов OD A DII FB ( - 0 9 K DD FO H O < ) -O L command J F10 P A. : c F11 { [ option + ? 11 I 1 Attempt 5 F12 } 1 delete
One pathway for the metabolism of D-glucose 6-phosphate is its enzyme-catalyzed conversion to D-fructose 6-phosphate. Show that this transformation can be accom- plished as two enzyme-catalyzed keto-enol tautomerisms. СНО CH,OH C=0 enzyme catalysis Но Но H OH H H. O- H- -HO- ČH,OPO, ČH,OPO, D-Glucose 6-phosphate D-Fructose 6-phosphate
(h) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. VI I CH2OH O. CH2OH II H V ОН, IV H III OH OH H (i) The monosaccharide below is a(n) (d-aldopentose, R-aldopentose, S- aldopentose, L-aldopentose, D-aldopentose).
Classify each of the following sugars. (For example, glucose is an aldohexose.) CH2OH CH2OH C=0 Но H- HO- C=0 H- H- CH2OH HỌ H- но -H Но ČH;OH ČH2OH CH2OH
Cellulose is not digestible by humans because it contains glucose units linked by -glycosidic bonds. O a-1,6 O a-1,4 O a-1,2 O B-1,4 O B-1,2