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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Textbook Question
Chapter 15, Problem 15.10P
15-10 Define the term “stereoisomer.” Name three types of stereoisomers.
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Following is a structural formula for cortisol (hydrocortisone). Draw a stereo-
representation of this molecule showing the conformations of the five- and
six-membered rings.
CH,OH
C=0
CH OH
HO
H3C
H
Cortisol
(Hydrocortisone)
Consider the following two molecules and answer the following questions.
Molecule A:
HO-
CH-CH3
CH3
Molecule B:
||
H,C-CH,-C-0-CH3
a) What are all of the IMFS present in molecule A?
b) What are all of the IMFS present in molecule B?
c) Which would have the higher boiling point, molecule A or molecule B?
d) What is the relationship between molecules A & B: structural isomers, geometric isomers, identical, or not related?
Answer the following questions based on these structures. Here is the terminology you can use to
describe the relationships. Structural isomers, Enantiomers, Diastereomers, and no relationship.
CHO
CHO
-Н
H-
I
CHO
HO-H
H-
-OH
-OH
CH₂OH
1
I
НО-
OH
I
I
CHO
-H
H
-ОН
-ОН
HO
I
CH₂OH
=0
H
-OH
CH₂OH
2
H
H
но
Но
CHO
НО
H
H
НО
-ОН
-ОН
-H
-H
CH2OH
8
-H
OH
OH
H
CH₂OH
3
I
НО
CH₂OH
7
What is the relationship between 1 and 4?
What is the relationship between 1 and 3?
What is the relationship between 1 and 5?
What is the relationship between 2 and 9?
What is the relationship between 4 and 10?
What is the relationship between 5 and 6?
What is the relationship between 2 and 10?
CH2OH
-ОН
-Н
CH2OH
9
НО
H-
H
CH2OH
0
H
-ОН
ОН
CH2OH
Н-
НО-
НО-
НО
НО
H-
Н-
CH2OH
-0
-ОН
-H
-H
CH2OH
10
H
-OH
ОН
CH2OH
5
Н
НО
НО-
H-
CHO
OH
-Н
H
OH
CH₂OH
6
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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- 17-54 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_forward13-27 Define autoxidation.arrow_forward15-11 In what way are constitutional isomers different from stereoisomers? In what way are they the same?arrow_forward
- 16-54 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_forward15-8 What does the term “chiral” mean? Give an example of a chiral molecule.arrow_forward17-12 Is it possible for the carbon atom of a carbonyl group to be a stereocenter? Explain.arrow_forward
- 13-31 What structural features are common to vitamin E, BHT, and BHA (the three antioxidants presented in Section 13-40?arrow_forward14-52 (Chemical Connections 14B) What was Alfred Nobel’s discovery that made nitroglycerin safer to handle?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_forward
- 17-15 Draw structural formulas for the four aldehydes with the molecular formula C5H10O. Which of these aldehydes are chiral?arrow_forward16-46 Arrange these three compounds in order of decreas ing ability to form intermolecular hydrogen bonds: CH3OH, CH3SH, and (CH3)2NH.arrow_forward14-51 (Chemical Connections 14B) When was nitroglycerin discovered? Is this substance a solid, a liquid, or a gas'arrow_forward
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