Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 22, Problem 8Q
Interpretation Introduction
Interpretation:
The saccharides obtained by the hydrolysis of (+)-sucrose are to be identified.
Concept introduction:
Carbohydrates containing single units of sugar molecule are called monosaccharides while those containing two units of sugar are called disaccharides.
Hydrolysis is the process in which a larger compound breaks into smaller compounds in the presence of water.
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Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is
converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid
F.
What is the structure of compound F?
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
You do not have to explicitly draw H atoms.
If a group is achiral, do not use wedged or hashed bonds on it.
• Show stereochemistry in a meso compound.
• Do not include lone pairs in your answer. They will not be considered in the grading.
Identify monomeric and multimeric (di-,tri-meric, for example) saccharides
from this group. If you come across multimeric polypeptides, state the mono-
mers that form these multimers. State the nature of the bond that links two
units together in each case.
(a) Maltose
(b) Trehalose
(c) Lactose
(d) Sucrose
(e) Cellobiose
(f) Agarose
b) Disaccharide E is a reducing sugar. It is hydrolyzed by an α-glycosidase enzyme, which means it contains an α-
glycoside link. Treatment of E with Ag2O and excess MeDgives an octamethyl derivative F. Hydrolysis of F in
dilute aqueous acid gives the pair of molecules shown below. Write the structures of E and F. (If the
stereochemistry at a particular carbon is not determined by the above data, indicate this with a wavy line as
shown below.)
HO OMe
OMe
MeO
MeO
OH
OMe
Am OH
OMe
OMe
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
- An aldopentose "O", is oxidized with HNO3 to a diacid "P" which is optically active. The compound "O", is also degraded to an aldotetrose "Q" which undergoes another oxidation to an optically inactive diacid "R". Assuming that "O" has the configuration D-(4R); what are the structures of "O" to "R"?arrow_forwardCan you please answer somearrow_forwardBelow are drawn the different chair conformations of the methyl glycoside of galactose. но он но он оМе OMe но- в A OH он (ii) Give the correct full name of compound A (= B) (ii) The name of the compound does not contain information on conformation (only configuration). Give the accepted conformational description for compound A and for compound B. (iv) Draw the Fischer projections of the open form of the corresponding reducing sugars of compound A (= B).arrow_forward
- Will the reduction using NaBH4 of D-glucose and D-galactose give an optically active or inactive compound?Explain why and draw your solution.arrow_forwardb) Disaccharide E is a reducing sugar. It is hydrolyzed by an α-glycosidase enzyme, which means it contains an α- glycoside link. Treatment of E with Ag2O and excess Mel gives an octamethyl derivative F. Hydrolysis of F in dilute aqueous acid gives the pair of molecules shown below. Write the structures of E and F. (If the stereochemistry at a particular carbon is not determined by the above data, indicate this with a wavy line as shown below.) HO OMe OMe Is is MeO MeO MOH OMe mOH OMe OMearrow_forwardThis question is related to the hydrolysis of fatty acids in the ß-oxidation pathway. One of the steps involves the following reaction: COA Compound A COA OH Compound B (a) Indicate the type of reaction occurring in the above figure. (b) Draw a reaction mechanism for this reaction (c) What type of isomers can you find in both compounds? Draw any possible chiral group as hashed-wedge structures (d) Provide Cahn-Ingold-Prelog (CIP) R/S stereoisomer nomenclature for any chiral isomer found (that is identify whether the chiral atom(s) from (c) is/are R or S stereoisomer). (e) What product would result from the hydrolysis of compound B with ATP (f) Propose a mechanism for the reaction described in (e) Sarrow_forward
- Two sugars, A and B, are known to be glucose and galactose, but it is not certain which oneis which. On treatment with nitric acid, A gives an optically inactive aldaric acid, whileB gives an optically active aldaric acid. Which sugar is glucose, and which is galactose?arrow_forwardRuff degradation of d-arabinose gives d-erythrose. The Kiliani–Fischer synthesis converts d-erythrose to a mixture of d-arabinose and d-ribose. Draw out these reactions, andgive the structure of d-ribosearrow_forwardNn.73. Subject :- Chemistryarrow_forward
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