Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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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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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.
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.
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...
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- Arabinoxylan 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_forwardWhich statement about the following disaccharide is correct?arrow_forwardOne of the cyclic forms of D-ribose has the structure CH2OH OH ОНОН (a) How many anomeric carbon atoms are present in this structure? (b) How many hemiacetal carbon atoms are present in this structure?arrow_forward
- Classify the following monosaccharides as reducing or non reducing sugars?arrow_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_forward
- answer correctly pleasearrow_forwardCan you please solve this question for me?arrow_forwardb) Compounds A and B have the following properties: Compound A (C5H1005) is an optically active D-pentose that exists exclusively as an acyclic molecule. (Hint: that sentence alone completely determines the structure of A! But we generously give you more information.) • Compound A does not react with Br₂/H₂O. • Reduction of A with NaBH4 gives only one product, B (C5H12O5), which is optically active. Write acyclic Fischer projection structures of A and B.arrow_forward
- Which statement about saccharides is correct? (A). Alpha anomers are more common than beta anoomers. (B). Two monosaccharides can form a disaccharide and oxygen. (C). Polysaccharides with alpha or beta glycosidic linkages have the different properties. (D). Disaccharides can be cyclic or acyclic.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_forwardProvide suitable responses for questions (a) – (j). CH2OH 4 OH 2 ОН 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.arrow_forward
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