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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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.
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
e. C6H5COCl + pyridine
f. The product in (c), then C6H5COCl + pyridine
Which sugar will yield a single alditol upon reduction?
A. Rhamnose
B. Sorbose
C. Xylulose
D. Erythrulose
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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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
- Why is molecule "A" the major acetal formed when d-erythrose reacts with H2SO4 and acetone as opposed to molecule "B"?arrow_forwardWhich one is b-D glucose and which one is a-L glucose ? 2. Which one is b-fructose and which a-L fructose?arrow_forward1. Why is "A" the major acetal formed when d-erythrose reacts with H2SO4 and acetone? 2. Why do carbons 2 and 3 on molecule "A" react with H2SO4 and acetone to form acetal "B", rather than carbons 3 and 4 on molecule "A" forming a different acetal?arrow_forward
- What would be the product if D-allose is reacted witha.. 1.) NH2OH then 2.) (CH3CO)2O, NaOCOCH3 then 3.)NaOCH3, then 4.)HNO3, H2O [note this is a consectutive reaction] b. oxidation using HNO3arrow_forwardDraw the product resulting from the Molisch reaction with D-xylose.arrow_forwardDraw the products formed when α-D-galactose is treated with each reagent: i. CH3I (excess), Ag2O ii. CH3OH, H3O+ iii. NaOH, H2O iv. Br2, H2Oarrow_forward
- Draw the product formed when each monosaccharide is oxidized with Benedict’s reagent.arrow_forward5-Deoxyglucose will close to a?arrow_forwardWhat would be the product if D-mannose is reacted witha.. 1.) NH2OH then 2.) (CH3CO)2O, NaOCOCH3 then 3.)NaOCH3, then 4.)HNO3, H2O [note this is a consectutive reaction] b. oxidation using HNO3arrow_forward
- A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two Daldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?arrow_forwardDraw the products formed when D-arabinose is treated with each reagent: (a) Ag2O, NH4OH; (b) Br2, H2O; (c) HNO3, H2O.arrow_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
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