Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 20.6, Problem 12P
a)
Interpretation Introduction
Interpretation:
The product formed from the reduction of D-idose is to be represented.
Concept Introduction:
Sodium borohydride is a strong reducing agent. The carbonyl group in
b)
Interpretation Introduction
Interpretation:
The product formed from the reduction of D-sorbose is to be outlined.
Concept Introduction:
Sodium borohydride is a strong reducing agent. The carbonyl group in aldoses and ketones can be reduced to an alcohol group by the compound sodium borohydride with hydrolysis. The product formed by the reduction is a polyalcohol and also known as alditol.
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What products are obtained from the reduction of a. d-idose? b. d-sorbose?
Draw the products formed when β-D-galactose is treated with each reagent.
a. Ag2O + CH3I
b. NaH + C6H5CH2Cl
c. The product in (b), then H3O+
d. Ac2O + pyridine
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f. The product in (c), then C6H5COCl + pyridine
a. How many stereogenic centers are present in α-D-galactose? b. Label the hemiacetal carbon in α-D-galactose. c. Draw the structure of β-D-galactose. d. Draw the structure of the polyhydroxy aldehyde that cyclizes to α- and β-D-galactose.
Chapter 20 Solutions
Organic Chemistry (8th Edition)
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Prob. 4PCh. 20.3 - Prob. 5PCh. 20.3 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - Prob. 8PCh. 20.5 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.5 - Prob. 11PCh. 20.6 - Prob. 12PCh. 20.6 - Prob. 13PCh. 20.6 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.8 - Prob. 16PCh. 20.9 - Prob. 18PCh. 20.10 - Prob. 20PCh. 20.10 - Prob. 21PCh. 20.10 - Prob. 22PCh. 20.11 - Prob. 23PCh. 20.11 - Prob. 24PCh. 20.12 - Prob. 25PCh. 20.12 - Prob. 26PCh. 20.14 - Prob. 28PCh. 20.15 - Prob. 29PCh. 20.15 - Prob. 30PCh. 20.16 - Prob. 31PCh. 20.17 - Prob. 32PCh. 20.18 - Refer to Figure 20.5 to answer the following...Ch. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 20 - Prob. 50PCh. 20 - Prob. 51PCh. 20 - Prob. 52PCh. 20 - Prob. 53PCh. 20 - Prob. 54PCh. 20 - Prob. 55PCh. 20 - Prob. 56PCh. 20 - Prob. 57PCh. 20 - Prob. 58PCh. 20 - Prob. 59PCh. 20 - Prob. 60PCh. 20 - Prob. 61PCh. 20 - A hexose is obtained when the residue of a shrub...Ch. 20 - Prob. 63PCh. 20 - Prob. 64PCh. 20 - Prob. 65PCh. 20 - Prob. 66PCh. 20 - Prob. 67PCh. 20 - Prob. 68PCh. 20 - Prob. 69PCh. 20 - Prob. 70PCh. 20 - Prob. 71PCh. 20 - Prob. 72PCh. 20 - Prob. 73P
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- In an aqueous solution, d-glucose exists in equilibrium with two six-membered ring compounds. a.Draw the structures of these compounds. b. Which of the six-membered ring compounds will be the major product?arrow_forwardDraw the products formed when B-D-galactose is treated with each reagent. a. Ag,0 + CH3I b. NaH + CgHsCH2CI c. The product in (b), then H30* d. Ac20 + pyridine e. CeHsCOCI + pyridine f. The product in (c), then CgHsCOCI + pyridinearrow_forwardDraw the products formed when ß-D-galactose is treated with each reagent.a. Ag2O + CH3Ib. NaH + C6H5CH2Clc. The product in (b), then H3O+d. Ac2O + pyridinee. C6H5COCl + pyridinef. The product in (c), then C6H5COCl + pyridinearrow_forward
- Consider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine,soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence. a. Is stachyose a reducing sugar?b. What product is formed when stachyose is treated with excess CH3I, Ag2O?c. What products are formed when the product in (e) is treated with H3O+?arrow_forwardDraw the structure of each type of compound. a. a D-aldotriose b. an L-ketohexose c. a four-carbon aldonic acidarrow_forward6. Draw D-Mannose in its pyranose form.arrow_forward
- Which structure of Erythrose is referred to by the given Fischer projection? A. L-Erythrose B. D-Erythrose но- -H HO H CH2OHarrow_forwardWhat reaction is responsible for the conversion of linear d-glucose to cyclic d-glucose? A. Reduction reaction B. Oxidation reaction C. Hydrolysis reaction D. Hemiacetal reactionarrow_forwardDraw the structure of the following:a. D/L-glucose & D/L-fructoseb. α/β-D-glucopyranose & α/β-D-fructopyranosec. α/β-D-glucofuranose & α/β-D-fructofuranosearrow_forward
- a. In an aqueous solution, d-glucose exists in equilibrium with two six-membered ring compounds. Draw the structures of these compounds.b. Which of the six-membered ring compounds will be the major product?arrow_forwardWhich pairs of molecules are interconvertible via mutarotation? O a. D-glucose and D-fructose O b. D-glucose and D-galactose O c. D-glucose and D-glucosamine O d. a-D-glucose and B-D-glucosearrow_forwardD-Arabinose can exist in both pyranose and furanose forms. a. Draw the α and β anomers of D-arabinofuranose. b. Draw the α and β anomers of D-arabinopyranose.arrow_forward
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