Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 38P
Interpretation Introduction
Interpretation:
On the basis of the information provided, the structure of stachyose is to be deduced.
Concept introduction:
Stachyose is a type of tetrasaccharide compound, which consists of two units of
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Researchers analysed a glycopeptide (a peptide carrying one or several oligosaccharide
groups) and determined both the sequence of the peptide and the sequence of the sugar molecule. The
latter was identified as a diholoside coupled to the peptide by an osidic bond. The systematic name
of this sugar is:
B-D-glucopyranosyl-(1→4)-ß-D-galactopyranose.
: Represent the chemical formula of this diholoside in a way that all oses are
Question 1
represented according to the Haworth convention. Apart from the furane and/or pyrane cycles all
atoms of this molecule must be given.
Treatment of a 258 mg sample of amylopectin by the methylation and hydrolysis procedure described yielded 12.4 mg of 2,3‑di‑O‑methylglucose. Determine what percentage of the glucose residues in amylopectin contained an (α1→6) branch. (Assume that the average molecular weight of a glucose residue in amylopectin is 162 g/mol and the molecular weight of 2,3‑di‑O‑methylglucose is 208 g/mol.)
(
α1→6) branched glucose residues: %
Identify the organic functional group and reaction type for the following reaction.
The reactant is a(n)
- carboxylic acid hexose
- Aldohexose
- aldotetrose
-deoxyhexose
-carboxylic acid tetrose
- ketohexose
The product is a(n)
- carboxylic acid tetrose
- aldotetrose
-alcohol hexose
-aldohexose
-carboxylic acid hexose
- alcohol tetrose
The reaction type is
- hemiacetal formation
-hydrolysis
-oxidation( Benedict’s)
-acetal formation
-reduction( hydrogenation)
- mutarotation
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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- What structural feature is required for a carbohydrate to behave asreducing sugar?arrow_forwardHumans are able to digest amylose, but not cellulose. What structural features of these polysaccharides might be responsible for this? O amylose contains only beta glycosidic bonds where cellulose contains alpha glycosidic bonds O amylose contains only beta glycosidic bonds where cellulose contains alpha glycosidic bonds amylose contains only alpha peptide bonds where cellulose contains beta peptide bonds amylose contains only alpha glycosidic bonds where cellulose contains beta glycosidic bondsarrow_forwardwhat is the structure digested by and how many reducing sugars are present ОН ОН Но OH HO Но HO- OH HO, The trisaccharide pictured could be completely digested (ie into monomers) by a beta-galactosidase and an alpha-glucosidase an alpha-galactosidase and sucrase lactase and sucrase a beta-fructosidase and lactasearrow_forward
- Describe the following sugar. OH HO- OH но OH Ketose, furanose, a Aldose, pyranose, a Ketose, furanose, B Aldose, pyranose, Barrow_forwardcan you please add an explanation.arrow_forward4. An iterative approach to oligosaccharide synthesis involves the use of protected glycals (sugars with C1-C2 double bond) as shown below. The product from the reaction of the first glycal with DMDO under anhydrous conditions is treated with another suitably-protected glycal to form a disaccharide glycal, and the process can be repeated to form a trisaccharide glycal, and so on... Crucial to the success of this approach is the stereoselective formation of the intermediate A in the scheme below. Draw the structure of A. DMDO CH₂Cl2 A OH ZnCl₂, THF OHarrow_forward
- If lactose is first hydrolyzed (by addition of sulfuric acid) into its constituent monosaccharide, and then subjected to complete methylation, what methylated products do you expect?arrow_forwardWhich statement about the following carbohydrate is correct?arrow_forwardC. Trehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. HO НО НО HO Но HO OH Он HO OHOH Но trehalose maltose 1. Malthose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while maltose can be acid-hydrolyzed with ease.arrow_forward
- Suppose you have two simple sugars, D-arabinose and L-tagatose. Both sugars cyclize and form a non-reducing disaccharide with the glycosidic bond oriented in the alpha position relative to each monosaccharide's structure. Give the full biochemical name for this disaccharide.arrow_forwardSugar alcohols (alditols) are formed by chemically reducing aldoses or ketoses. Which one of the following sugars will give a negative Benedict's Test? aldopentoses alditols 2- Ketopentoses an aldose undergoing mutarotation in solutionarrow_forwardIn glycoside formation, the hemiacetal functional group of a cyclic monosaccharide is converted to an acetal group by reaction with a(an)arrow_forward
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