Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 16, Problem 16.58P
16-58 Following is a structural formula of desosamine, a
sugar component of several macrolide antibiotics, including the erythromycins. The configuration shown here is that of the natural product. Erythromycin is produced by a strain of Streptomyces erythreus originally found in a soil sample from the Philippine Archipelago.
ch3
T
Desosamine
- Name all the
functional groups in desosamine. (Chapter 10) - How many stereocenters are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it?
- Draw the alternative chair conformations for desosamine and label which groups are equatorial and which are axial.
(d > Which of the alternative chair conformations for desosamine is more stable?
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Give the structure(s) of the product(s) for the reactions below, and be sure to indicate any relative stereochemistry (you can assume that each of the Diels-Alder reactions will proceed with endo selectivity). Draw out relevant enantiomer(s) if they are expected to form. If no reaction is expected to occur under the indicated conditions, then write "no reaction" or NR, and explain why you would expect nothing to occur. If more than one product is formed, please indicate which one will be the major product or if they will be formed in equal amounts. In all cases, equimolar amounts of both components/reagents are present unless indicated otherwise .
Chapter 16 Solutions
Introduction to General, Organic and Biochemistry
Ch. 16.1 - Problem 16-1 How many hydrogen atoms does...Ch. 16.2 - Problem 16-2 Write a structural formula for each...Ch. 16.2 - Prob. 16.3PCh. 16.4 - Problem 16-4 Select the stronger base from each...Ch. 16.5 - Prob. 16.5PCh. 16 - 16-6 Answer true or false. te/7-Butylamine is a 3°...Ch. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - 16-9 In what way are pyridine and pyrimidine...Ch. 16 - Prob. 16.10P
Ch. 16 - Prob. 16.11PCh. 16 - Prob. 16.12PCh. 16 - 16-13 Classify each amino group as primary,...Ch. 16 - Prob. 16.14PCh. 16 - 16-15 There are eight primary amines with the...Ch. 16 - Prob. 16.16PCh. 16 - 16-17 Propylamine (bp 48°C), ethylmethylamine (bp...Ch. 16 - 16-18 Account for the fact that 1-butanamine (bp...Ch. 16 - 16-19 2-Me thy 1 propane (bp -12°C), 2-propanol...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - 16-26 The p/fb of amphetamine is approximately 3.2...Ch. 16 - 16-27 Guanidine, p/Ca 13.6, is a very strong base,...Ch. 16 - 16-28 Following is the structural formula of...Ch. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - 16*32 Many tumors of the breast are correlated...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16-35 (Chemical Connections 16B ) What is an...Ch. 16 - Prob. 16.36PCh. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - Prob. 16.41PCh. 16 - Prob. 16.42PCh. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - Prob. 16.45PCh. 16 - 16-46 Arrange these three compounds in order of...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - 16-54 Several poisonous plants, including Atropa...Ch. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - Prob. 16.57PCh. 16 - 16-58 Following is a structural formula of...Ch. 16 - Prob. 16.59P
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