Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16, Problem 41P
Interpretation Introduction
Interpretation:
The explanation corresponding to the given statement that
Concept Introduction:
The chair conformers are stable forms of cyclic compounds. In chair conformation, substituent’s prefers to place at equatorial positions. This is due to unwanted interactions between those substituent’s that are placed at axial positions. These interactions cause repulsion and that leads to the un-stability in molecule. The general interactions that occur between axial substituents are
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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 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.
Draw Fischer projections for five aldoses below: glucose, mannose, galactose, arabinose and
xylose. Now draw Fischer projections for the reduced and acetylated derivatives of these
aldoses. From the Fischer drawings, select the meso molecules and redraw them, this time
adding a plane of symmetry. Then select the molecules having an axis of symmetry, this time
adding a line that skewers the middle of the drawing to indicate this symmetry.
The most stable conformation of most aldopyranoses is one in which the largest group, the CH2OH group, is equatorial. However, alpha-D-idopyranose exists primarily in a conformation with an axial CH2OH group. Write formulas for the two chair conformations of a-D-idopyranose (one with the CH2OH group axial and one with the CH2OH group equatorial) and provide an explanation
Chapter 16 Solutions
Essential Organic Chemistry, Global Edition
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.3 - Prob. 4PCh. 16.4 - Prob. 5PCh. 16.4 - Prob. 6PCh. 16.5 - Prob. 7PCh. 16.5 - Prob. 8PCh. 16.6 - Prob. 10PCh. 16.8 - Prob. 12P
Ch. 16.8 - Prob. 14PCh. 16.9 - Prob. 15PCh. 16.10 - Prob. 16PCh. 16.11 - Refer to Figure 16.4 to answer the following...Ch. 16 - Prob. 18PCh. 16 - Prob. 19PCh. 16 - Prob. 20PCh. 16 - Prob. 21PCh. 16 - Prob. 22PCh. 16 - Prob. 23PCh. 16 - Prob. 24PCh. 16 - Prob. 25PCh. 16 - Name the following compounds:Ch. 16 - Prob. 28PCh. 16 - Prob. 29PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Draw the mechanism for the acid-catalyzed...Ch. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41P
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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.arrow_forwardTreatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forwardDraw the structure of alpha-d-glucopyranose in straight chain cyclic, Haworth and cyclohexane-chair format. Draw the structures of two aldohexoses which are diastereomers but not epimersarrow_forward
- A difficult problem in the synthesis of PGF2α is the introduction of theOH group at C15 in the desired configuration. -Label this stereogenic center as R or S.arrow_forwardHow many chiral centers are in B-d-glucopyranose and a-D-galactopyranose? How many stereoisomers of these two aldohexoses can theoretically be drawn?arrow_forwardWhen a crystalline sample of α-glucopyranose is dissolved in water and the specific rotation is measured immediately, the observed rotation is +112°. When the same amount of βglucopyranose is dissolved, the observed rotation is +18.7°. However, over time, at room temperature, both solutions reach a specific rotation of +52.7°. Explain why these two solutions reach the same specific rotation over time.arrow_forward
- How many asymmetric carbons and stereoisomers are there for an aldohexose? For aketohexose?arrow_forwarddoes structure E represent fructofuranose? explainarrow_forward1. 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…arrow_forward
- Classify below pair of compounds as enantiomers, epimers, diastereomers but not epimers, or constitutional isomers of each other. D-allose and L-allosearrow_forwardThe following compound has two asymmetric centers and four stereoisomers. Two of these are d-erythrose and d-threose, which are naturally occurring sugars. The configuration of d-erythrose is (2R,3R), and the configuration of d-threose is (2S,3R). a. Which structure represents d-erythrose? b. Which represents d-threose?arrow_forwardDraw the cyclic hemiacetal forms of d-mannose and d-galactose both as chair conformations and as Haworth projections. Mannose is the C2 epimer of glucose, and galactoseis the C4 epimer of glucose.arrow_forward
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