ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
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Question
Chapter 5, Problem 5.68P
Interpretation Introduction
Interpretation:
It is to be explained how the results of specific reactions carried out on
Concept introduction:
A chiral compound contains at least one carbon which is bonded to four different atoms or groups. D-sugar is one in which the
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The 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 C
1. Identify the anomeric carbons on sucrose and explain how they are different from lactose and cellulose.
2. On Wikipedia (image pictures below) sucrose is labeled β-D-Fructofuranosyl α-D-glucopyranoside. But the anomeric carbon has the oxygen pointing down and other stereocenters inverted from that of fructose. Did Wikipedia incorrectly name it? Or can you explain why this is the case using structures of sucrose, fructose and glucose…
When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react to form an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of D-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of D-glucose exists in the anhydro form under the same conditions.
Chapter 5 Solutions
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Prob. 5.3PCh. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - Prob. 5.7PCh. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27PCh. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Prob. 5.38PCh. 5 - Prob. 5.39PCh. 5 - Prob. 5.40PCh. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Prob. 5.46PCh. 5 - Prob. 5.47PCh. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.52PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Prob. 5.56PCh. 5 - Prob. 5.57PCh. 5 - Prob. 5.58PCh. 5 - Prob. 5.59PCh. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 - Prob. 5.66PCh. 5 - Prob. 5.67PCh. 5 - Prob. 5.68PCh. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Prob. 5.72PCh. 5 - Prob. 5.73PCh. 5 - Prob. 5.74PCh. 5 - Prob. 5.75PCh. 5 - Prob. 5.76PCh. 5 - Prob. 5.77PCh. 5 - Prob. 5.78PCh. 5 - Prob. 5.79PCh. 5 - Prob. 5.1YTCh. 5 - Prob. 5.2YTCh. 5 - Prob. 5.3YTCh. 5 - Prob. 5.4YTCh. 5 - Prob. 5.5YTCh. 5 - Prob. 5.6YTCh. 5 - Prob. 5.7YTCh. 5 - Prob. 5.8YTCh. 5 - Prob. 5.9YTCh. 5 - Prob. 5.10YTCh. 5 - Prob. 5.11YTCh. 5 - Prob. 5.12YTCh. 5 - Prob. 5.13YTCh. 5 - Prob. 5.14YTCh. 5 - Prob. 5.15YTCh. 5 - Prob. 5.16YTCh. 5 - Prob. 5.17YT
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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 d-allose, the C3 epimer of glucosearrow_forwardCarbohydrates- DRAW the D isomer in both the Fisher (linear) and Hawthorne (cyclical) configuration. Carbons located within the ring in the Hawthorne structure DO NOT need to be labeled but PLEASE LABEL all other atoms in the correct orientation to the plane of the ring, meaning above or below. Also for disaccharides make sure the glycosidic linkage is in the correct orientation above or below the plane. D-glyceraldehyde D-ribose D-xylose D-glucose D-galactose D-fructose lactose sucrose maltose amylose amylopectin glycogen ALSO PLEASE DRAW OUT the amino acid Tripeptide= Three amino acids each linked by a peptide bond LABEL ALL PARTS AND LABEL ALL ATOMS– Peptide backbone atoms and side chains for the amino acid at pH 1, 7 and 13.arrow_forwardAll the glucose units in dextran have six-membered rings. When a sample of dextran is treated with methyl iodide and Ag2O and the product ishydrolyzed under acidic conditions, the final products are 2,3,4,6-tetra-O-methyl-d-glucose, 2,4,6-tri-O-methyl-d-glucose, 2,3,4-tri-O-methyl-d-glucose, and 2,4-di-O-methyl-d-glucose. Draw a short segment of dextran.arrow_forward
- An unknown disaccharide is subjected to methylation with CH3I followed by acid hydrolysis. The reaction yields 2,3,4,6-tetra-O-methyl-D-glucose and 2,3,4-tri-O- methyl-D-glucose. Draw the structure of the unknown disaccharide.arrow_forwardHow many chiral centers are present in d-glucose? in d-ribose?arrow_forwardProvide an explanation for the fact that α-D-mannose is more stable thanβ-D-mannose, whereas the opposite is true for glucose.arrow_forward
- Circle each functional group in glucose (Problem 1.59) and sucrose (Problem 1.60). What compound class is characteristic of each of those functional groups?arrow_forwardWhen a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react toform an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of d-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of d-glucose exists in the anhydro form under the same conditions.arrow_forwardClassify below pair of compounds as enantiomers, epimers, diastereomers but not epimers, or constitutional isomers of each other. D-galactose and D-talosearrow_forward
- In addition to lactose, D-galactose and D-glucose can form different heterodisaccharides. Draw the structures (Haworth projections) of the (i) a-glucose-(1→1) -a-galactose and ii) a- glucose-(1→3)-?-galactose, two examples of heterodisaccharides that can form.arrow_forwardDraw the linear form and formation ring of the monosaccharide fructose. Draw the linear form and formation ring of monosaccharide glucose. Show the dehydration reaction of the two monosaccharide. Draw the structure of oleic acid Draw the Fischer projection formula of the sugar gulose. Draw the enantiomer of the sugar and indicate the D/L designationarrow_forwardDraw d-talose, the C2 epimer of d-galactosearrow_forward
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