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 15.43P
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.
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8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below.
(a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle.
(b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle.
(a)
НО.
Carbon a
HO
O OH
Carbon a:
OR
OS
Carbon b
H
N
Carbon b:
R
OS
of
H
Carbon c:
OR
OS
OH OH
Carbon c
F
Carbon d:
R
OS
OH
Carbon d
(b) The two
structures are:
O the same
compound
O stereoisomers
5-54
Ribose, an essential part of ribonucleic acid (RNA), has the following
structure:
H H
H OH
CHO
Ribose
Но
но н но н
(a) How many chirality centers does ribose have? Identify them.
(b) How many stereoisomers of ribose are there?
(c) Draw the structure of the enantiomer of ribose.
(d) Draw the structure of a diastereomer of ribose.
Consider the following pairs of structures. Identify the relationship between them by describing them as
representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound.
H
H3C"
CH3
Br
Hitm
Br
enantiomers
constitutional isomers
diastereomers
H
B
H
F
F
two molecules of the same compound
CH3
H
Ba
CH3
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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- 15-44 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_forward15-26 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. How many stereoisomers are possible for this compound?arrow_forward15-16 Which of the following compounds contain stereocenters? (a) 2-Chloropentane(b) 3-Chloropentane (c) 3-Chloro-l-butene(d) 1,2-Dichloropropanearrow_forward
- 15-17 Which of the following compounds contain stereocenters? Cyclopentanol l-Chloro-2-propanol 2-Methylcyclopentanol 1-Phenyl-l-propanolarrow_forward15-46 Consider Lunesta, a nonbenzodiazepine hypnotic agent (i.e., sleep-inducing drug) that is frequently advertised on TV commercials. Answer the following questions with respect to the given structure: Lunesta Determine the molecular formula for Lunesta. Identify the functional groups present in Lunesta. How many of Lunesta’s rings are aromatic? Fill in the blanks as shown: Lunesta has stereocenter(s) and therefore possible stereoisomer(s). Of the possible stereocenter(s), is/are R and is/are S. Does Lunesta have an enantiomer? Does it have a diastereomer? Which of the following is true about an enantiomer of Lunesta? Identify all that apply: The enantiomer rotates plane-polarized light in the opposite direction as Lunesta. The enantiomer is a mirror image of Lunesta. The enantiomer has the opposite biological effects as Lunesta (i.e., it keeps you awake). Lunesta does not have an enantiomer. Draw an enantiomer of Lunesta. Examine the derivative of the representation of the six-membered ring found in Lunesta. Draw the alternative chair conformations of this ring and label the more stable chair conformation. (Chapter 11)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_forward
- 16-17 Propylamine (bp 48°C), ethylmethylamine (bp 37°C), and trimethylamine (bp 3°C) are constitutional isomers with the molecular formula C3HgN. Account for the fact that trimethylamine has the lowest boiling point of the three and propylamine has the highest.arrow_forward15-10 Define the term “stereoisomer.” Name three types of stereoisomers.arrow_forward15-37 Consider a cyclohexane ring substituted with one hydroxyl group and one methyl group. Draw a structural formula for a compound of this composition that: Does not show cis-trans isomerism and has no stereocenters. Shows cis-trans isomerism but has no stereocenters. Shows cis-trans isomerism and has two stereocenters.arrow_forward
- 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?arrow_forward16-54 Several poisonous plants, including Atropa belladonna, contain the alkaloid atropine. The name “belladonna” (which means “beautiful lady”) probably comes from the fact that Roman women used extracts from this plant to make themselves more attractive. Atropine is widely used by ophthal mologists and optometrists to dilate the pupils for eye examination. Classify the amino group in atropine as primary, secondary, or tertiary. Locate all stereocenters in atropine. Account for the fact that atropine is almost insoluble in water (1 g in 455 mL of cold water) but atropine hydrogen sulfate is very soluble (1 g in 5 mL of cold water). Account for the fact that a dilute aqueous solution of atropine is basic (pH approximately 10.0).arrow_forwardFollowing are stereorepresentations for the four stereoisomers of 3-chloro-2-butanol. (a) Assign an R or S configuration to each chiral center. (b) Which compounds are enantiomers? (c) Which compound are diastereomers?arrow_forward
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