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 15, Problem 15.26P
15-26 For centuries, Chinese herbal medicine has
used extracts oi Ephedra sinica to treat asthma. The asthma-relieving component of this plant is ephedrine, a very potent dilator of the air passages of the lungs. The naturally occurring stereoisomer is levorotatory and has the following structure.
HO ¥ Nhch3
Ephedrine |n|„ = —41°
- Mark each stereocenter in epinephrine with an asterisk.
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Chapter 15 Solutions
Introduction to General, Organic and Biochemistry
Ch. 15.1 - Prob. 15.1PCh. 15.2 - Problem 15-2 Assign priorities to the groups in...Ch. 15.2 - Problem 15-3 Assign an R or S configuration to the...Ch. 15.3 - Problem 15-4 3-Amino-2-butanol has two...Ch. 15.3 - Prob. 15.5PCh. 15.3 - Prob. 15.6PCh. 15 - 15-7 Answer true or false. The cis and trans...Ch. 15 - 15-8 What does the term “chiral” mean? Give an...Ch. 15 - 15-9 What does the term “achiral” mean? Give an...Ch. 15 - 15-10 Define the term “stereoisomer.” Name three...
Ch. 15 - 15-11 In what way are constitutional isomers...Ch. 15 - 15-12 Which of the following objects are chiral...Ch. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - 15-15 Explain why the carbon of a carbonyl group...Ch. 15 - 15-16 Which of the following compounds contain...Ch. 15 - 15-17 Which of the following compounds contain...Ch. 15 - Prob. 15.18PCh. 15 - 15-19 Draw the mirror image for each molecule: OH...Ch. 15 - Prob. 15.20PCh. 15 - 15-21 Answer true or false. For a molecule with...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - 15-26 For centuries, Chinese herbal medicine has...Ch. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - 15-30 (Chemical Connections 15A) What does it mean...Ch. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15-35 Following are structural formulas for three...Ch. 15 - Prob. 15.36PCh. 15 - 15-37 Consider a cyclohexane ring substituted with...Ch. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - 15-41 Compound A(C5Hh, is not optically active and...Ch. 15 - Prob. 15.42PCh. 15 - 15-43 Triamcinolone acetonide, the active...Ch. 15 - 15-44 Consider the structure of the...Ch. 15 - Prob. 15.45PCh. 15 - 15-46 Consider Lunesta, a nonbenzodiazepine...Ch. 15 - Prob. 15.47P
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- 15-43 Triamcinolone acetonide, the active ingredient in Azmacort Inhalation Aerosol, is a steroid used to treat bronchial asthma. Triamcinolone acetonide Label the eight stereocenters in this molecule. How many stereoisomers are possible for it? (Of these, the stereoisomer with the configura tion shown here is the active ingredient in Azmacort.)arrow_forward17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes. (a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility. (b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it? (c) Are there any aromatic components in this molecule? (d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter. (e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal. (f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.arrow_forward16-58 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?arrow_forward
- 15-41 Compound A(C5Hh, is not optically active and cannot be separated into enantiomers. It reacts with bromine in carbon tetrachloride to discharge the purple color of bromine and form Compound B( C.FL Br,). When Compound A is treated with H., in the presence of a transition metal catalyst, it is converted to compound C(C5H10). When treated with HC1, compound A is converted to compound DtC.HyCl). Given this information, propose structural formulas for compounds A B, C, and D. Hint: There are at least three possibilities for Compound A and, in turn, three possibilities for Compounds B. C, and D.arrow_forward15-44 Consider the structure of the immunosuppressant FK-506, a molecule shown to disrupt calcineurin- mediated signal transduction in T-lymphocytes. What is the molecular formula of this immunosuppressant? How manj' stereocenters are present in FK-506? Determine the maximum number of stereoisomers possible. Identify and label the various functional groups present. Consider the two stereocenters in this structure labeled with asterisks (*). Determine the absolute configuration of each stereocenter. FK-506 has been shown to exhibit moderate solubility in various organic solvents. Is this immunosuppressant expected to be soluble in ethanol (CH3CH2OH)? Consider the carbon atom labeled “1." Describe the geometry and approximate bond angles about this carbon atom. Draw the alternative chair conformations of the cyclohexane ring at the lower right of FK-506 and label the more stable conformation. Are there any aromatic components present in FK-506? Patients taking FK-506 have reported several side effects from this medication, including headaches, nausea or diarrhea, and slight shaking. Would you expect the enantiomer of this drug to result in the same side effects?arrow_forward15-17 Which of the following compounds contain stereocenters? Cyclopentanol l-Chloro-2-propanol 2-Methylcyclopentanol 1-Phenyl-l-propanolarrow_forward
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- How many stereoisomers does the following compound have? CH3CHCICH₂CHCICH 3 Select one: Ο Α. Ο OB. 1 OC. 2 OD. 3 OE. 4arrow_forwardIs clozapine chiral? If so, how many of the possible stereoisomers are formed in this synthesis?arrow_forwardFollowing are structural formulas for the enantiomers of carvone. Each has a distinctive odor characteristic of the source from which it is isolated. Assign an R or S configuration to the single chiral center in each enantiomer. Why do they smell different when they are so similar in structure?arrow_forward
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