ORGANIC CHEMISTRY-EBOOK>I<
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ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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Chapter 25.SE, Problem 70AP
Interpretation Introduction
Interpretation:
Based on the reaction the following answers are discussed.
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5. Provide suitable responses for questions (a) – ().
6 CH2OH
4
OH
OH
3
OH
(a) What is the relative configuration of the above monosaccharide?
(b) Which labeled carbon is the anomeric carbon?
(c) Trace and identify the acetal in the above monosaccharide.
(d) Draw the hemiacetal that results from above acetal.
(e) Draw the open chain equivalent of the sugar in part (d).
(f) Classify the monosaccharide below as a D-sugar or an L-sugar.
H.
OH
O.
OH
CH,OH
OH
OH
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
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
Chapter 25 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
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- Trehalose, C12H22O11, is a nonreducing sugar that is only 45% as sweet as sugar. When hydrolyzed by aqueous acid or the enzyme maltase, it forms only d-glucose. When it is treated with excess methyl iodide in the presence of Ag2O and then hydrolyzed with water under acidic conditions, only 2,3,4,6-tetra-O-methyl-d-glucose is formed. Draw the structure of trehalosearrow_forwardConsider the following compound, which is used by insects and some fungi to store energy:arrow_forward(a) Label compounds A, B, and C as D- or L-sugars. (b) How are compounds A and B related? A and C? B and C? Choose from enantiomers, diastereomers, or constitutional isomers.arrow_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_forwardTrehalose, C12H22O11, is a nonreducing sugar that is only 45% as sweet as sugar. When hydrolyzed by aqueous acid or the enzyme maltase, it formsonly d-glucose. When it is treated with excess methyl iodide in the presence of Ag2O and then hydrolyzed with water under acidic conditions, only2,3,4,6-tetra-O-methyl-d-glucose is formed. Draw the structure of trehalose.arrow_forward(a) meso-hexane-3,4-diol, CH3CH2CH(OH)CH(OH)CH2CH3, draw any diastereomers.arrow_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_forward2) a-Draw the proper flat, Haworth form and most stable chair conformation for the B- anomer of L- glucopyranose b- Write the systematic name of this compound O: HO- НО—н НО H FOH HO-H -O- L-Gulosearrow_forwardRegarding 4-O- (α-D-psychofuranosyl) -β-D-allopyranose. Please indicate the RIGHT alternative: (a) The disaccharide reacts with CH3OH in an acid medium to form a glycoside that cannot be oxidized with HNO3. (b) It is a reducing disaccharide only in basic medium. (c) In the structure there is only one glycosidic bond that is of the type β 1-O-4 ' (d) The hydrolysis products of this disaccharide do not show mutarrotation. (e) The disaccharide structure contains two six-membered rings.arrow_forward
- 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: OHarrow_forwardThe structure of 4 isomers of an aldotetrose carbohydrate are given. 1) select every structure that is a diastereomer of structure D A, B, or C? 2) select every structure that is a enantiomer of structure C D, B, or A? 3) select every structure that is a stereoisomer of structure D A, B, or Carrow_forwardThe structures of 4 isomers of ketopentose are shown. 1) which of the structures are diastereomers of structure A? C, B, or D 2) which of the structures are enantiomers of structure C? B, A, or D 3) which of the structures are stereoisomers of strcuture A?C, D, or Barrow_forward
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