OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
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Chapter 25, Problem 25.26P
Interpretation Introduction
Interpretation:
The Fischer projection structures of D-erythrose and D-threose has to be drawn.
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An important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.
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Chapter 25 Solutions
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
Ch. 25.1 - Prob. 25.1PCh. 25.2 - Prob. 25.2PCh. 25.2 - Prob. 25.3PCh. 25.3 - Prob. 25.4PCh. 25.3 - Prob. 25.5PCh. 25.3 - Prob. AQCh. 25.3 - Prob. BQCh. 25.3 - Prob. CQCh. 25.3 - Prob. DQCh. 25.3 - How many stereoisomers would result from the...
Ch. 25.4 - Prob. 25.6PCh. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10PCh. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Prob. 25.24PCh. 25 - Prob. 25.25PCh. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Prob. 25.31PCh. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Prob. 25.34PCh. 25 - In making candy or sugar syrups, sucrose is boiled...Ch. 25 - Prob. 25.36PCh. 25 - Prob. 25.37PCh. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - Prob. 25.41PCh. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Digitalis is a preparation made from the dried...Ch. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Prob. 25.49PCh. 25 - Prob. 25.50P
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- 4. 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_forwardPart 1 Show the complete steps and products of the Haworth Projection structure of the following saccharides. The males have to answer the structure of D-fructose and the females are the structure of D-galactose. Expanded structure of the given molecule Fischer Projection Haworth's structure [show the complete steps] Step 1 Step 2 Step 3 Part 2 Show the synthesis of disaccharide lactose. Give the expanded structure of the reactants. Give the expanded structure of the products. Part 3. Show the chemical reaction of D-ribose. Name the chemical reaction. Show here the chemical equation and name the products. Use the expanded structure. 1. 2. 3.arrow_forwardDraw the structure of the disaccharide maltose (-D-glucopyranosyl (1→4)-D-glucopyranose). Indicate with arrows the reducing end and the acetal functional group.arrow_forward
- d-(-)-Erythrose has the formula HOCH2¬CH(OH)¬CH(OH)¬CHO, and the d in its name implies that it can be degraded to d-(+)-glyceraldehyde. The (-) in its name implies that d-(-)-erythrose is optically active (levorotatory). When d-(-)-erythrose is reduced (using H2 and a nickel catalyst), it gives an optically inactive product of formula HOCH2¬CH(OH)¬CH(OH)¬CH2OH. Knowing the absolute configuration of d-(+)-glyceraldehyde (Section 5-14), determine the absolute configuration of d-(-)-erythrose.arrow_forwardIn 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_forwardThe most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the a or B anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_forward
- 5. Provide suitable responses for questions (a) – (). 6 CH2OH 4 OH OH 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. (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d). (f) Classify the monosaccharide below as a D-sugar or an L-sugar. H. OH O. OH CH,OH OH OHarrow_forwardIllustrate (hand-drawn) the mechanism of intrahemiacetal or intrahemiketal formation in the following monosaccharides and identify/draw the possible products of these reactions. A. D-talose B. D-fructosearrow_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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