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 15.30P
15-30 (Chemical Connections 15A) What does it mean to say that a drug is chiral? If a drug is chiral, will it be optically active? That is, will it rotate the plane of polarized light?
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15-12 Which of the following objects are chiral (assume that there is no label or other identifying mark,?
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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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- 15-8 What does the term “chiral” mean? Give an example of a chiral molecule.arrow_forward15-9 What does the term “achiral” mean? Give an example of an achiral molecule.arrow_forward14-52 (Chemical Connections 14B) What was Alfred Nobel’s discovery that made nitroglycerin safer to handle?arrow_forward
- 17-74 Glucose, C6H12O6, contains an aldehyde group but exists predominantly in the form of the cyclic hemiacetal shown here. We will discuss this cyclic form of glucose in Chapter 20. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. (a) Which carbon in glucose provides the —OH group and which provides the —CHO group? (b) Draw the alternative chair confirmations of D-glucose and state which of the two is the more stable.arrow_forward15-11 In what way are constitutional isomers different from stereoisomers? In what way are they the same?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_forward15-35 Following are structural formulas for three of the drugs most widely prescribed to treat depression. Label all stereocenters in each and state the number of stereoisomers possible for each. Fluoxetine (Prozac!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
- 14-51 (Chemical Connections 14B) When was nitroglycerin discovered? Is this substance a solid, a liquid, or a gas'arrow_forward15-17 Which of the following compounds contain stereocenters? Cyclopentanol l-Chloro-2-propanol 2-Methylcyclopentanol 1-Phenyl-l-propanolarrow_forward17-14 Following are structural formulas for two steroid hormones. (a) Name the functional groups in each. (b) Mark all stereocenters in each hormone and state how many stereoisomers are possible for each.arrow_forward
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