Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Question
Chapter 22, Problem 20P
Interpretation Introduction
Interpretation:
The structural formulas of the given compounds are to be represented.
Concept Introduction:
▸ There are many ways of representing
▸ Fischer’s projection method represents the structure of
▸ The Haworth formulas demonstrate the cyclic form of glucose acetals6-carbon-atom rings. It represents the chirality center of the open-chain form through the cyclic forms. The chair form conformations represent the most accurate conformations of the ring structures.
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Which of the following statements about the monosaccharide shown below is correct?
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
Regarding 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.
Chapter 22 Solutions
Organic Chemistry
Ch. 22 - Prob. 1PPCh. 22 - Prob. 2PPCh. 22 - Prob. 3PPCh. 22 - Prob. 4PPCh. 22 - Prob. 5PPCh. 22 - Prob. 6PPCh. 22 - Prob. 7PPCh. 22 - Prob. 8PPCh. 22 - Practice Problem 22.9 What products would you...Ch. 22 - Prob. 10PP
Ch. 22 - Prob. 11PPCh. 22 - Prob. 12PPCh. 22 - Prob. 13PPCh. 22 - Prob. 14PPCh. 22 - Prob. 15PPCh. 22 - Prob. 16PPCh. 22 - Prob. 17PPCh. 22 - Prob. 18PPCh. 22 - Prob. 19PPCh. 22 - Prob. 20PCh. 22 - Prob. 21PCh. 22 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Prob. 28PCh. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Prob. 37PCh. 22 - Prob. 38PCh. 22 - Arbutin, a compound that can be isolated from the...Ch. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - 22.44 The following reaction sequence represents...Ch. 22 - 22.45
The NMR data for the two anomers...Ch. 22 - Shikimic acid is a key biosynthetic intermediate...Ch. 22 - Prob. 1QCh. 22 - Prob. 2QCh. 22 - Give the structural formula of the monosaccharide...Ch. 22 - Prob. 4QCh. 22 - Prob. 5QCh. 22 - Prob. 6QCh. 22 - Prob. 7QCh. 22 - Prob. 8QCh. 22 - Select the reagent needed to perform the following...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw the structure of: (a) a polysaccharide formed by joining D-mannose units in 1->4-ß-glycosidic linkages; (b) a polysaccharide formed by joining D-glucose units in 1->6-a-glycosidic linkages. The polysaccharide in (b) is dextran, a component of dental plaque.arrow_forwardArabinoxylan is a copolymer of arabinose and xylose-two five-carbon sugars. A portion of the polysaccharide is shown here. (a) Identify and classify each glycosidic linkage. (b) Based on the structure, do you think arabinoxylan functions as a storage polysaccharide or a structural polysaccharide? Explain your reasoning. HOH,C. OH Но OH OH но но OH Но LO. Но HOH,C HOH2C НО OH OH CH,OHarrow_forwardJust little explanation Asap Thanksarrow_forward
- Which statement about the following disaccharide is correct?arrow_forward(A) Identify the glycosidic bond in the following disaccharide (B) Decide whether the compound is a non reducing or reducing sugar (C) Polysaccharide units are usually bonded together with alpha or beta 1,6 or 1,4 linkages. What linkage is used in the disaccharide shown below?arrow_forwardClassify the following monosaccharides as reducing or non reducing sugars?arrow_forward
- (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).arrow_forward(g) Using appropriate prefixes/infixes/suffixes (ketohentese, aldahentase, etc.), classify each of the monosaccharides shown below. СНО CH2OH O: HOI но ОН OH HO H. CH2OH CH2OH I II (h) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. CH2OH CH2OH CH2OH CH2OH O. ОН OH OH OH OH OH ОН OH OH OH ОН OH OH OH OH OH I II III IV | (i) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. VI I CH2OH CH2OH II V OH III ОН IV H OH Harrow_forward14. (a) Identify the acetal and the ketal group in the following disaccharide. (b) Decide whether the compound is a non-reducing or reducing sugar. OH НО HƠ HO Н HO Н НО HO 15. (a) Identify the glycosidic bond in the following disaccharide. (b) Decide whether the compound is a non-reducing or reducing sugar. (c) Polysaccharide units are usually bonded together with a or B 1, 6 or 1, 4 linkages. What linkage is used in the disaccharide shown below? s) НО НО НО HO НО -OH OH -H OH CH2OH 16. Draw the structure for 1,4-B-D-galactopyranosyl-D-glucose. ( но- 17. Assign an R/S designation to each chirality center in the following compound: ( CHO НО -OHarrow_forward
- (d) Use the diagram below to complete the cyclic alpha form of structure V (e) Circle the hemiacetal in cyclic alpha form of structure V. (f) Redraw the cyclic alpha form of structure V but replace the OH group on the anomericcarbon with a methoxy group. Is this modified monosaccharide a reducing sugar or anonreducing sugar?arrow_forwardThis substance, produced by certain soil bacteria as a defensive weapon, is used as an antibiotic. It is derived from monosaccharides. CH3 H NH₂ H₂N CH3 OH HO NH₂ CH3 NH -CH3 OH (a) How many "monosaccharide" residues are present? (b) List one way that these residues differ chemically from the monosaccharides you have I seen so far. (c) Draw an arrow pointing to one glycosidic bond. (d) Can you tell whether the bonds linking the residues have the alpha or beta configuration?arrow_forwardCan you please solve this question for me?arrow_forward
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