Introduction to General, Organic and Biochemistry
12th Edition
ISBN: 9780357391594
Author: Frederick A. Bettelheim; William H. Brown; Mary K. Campbell
Publisher: Cengage Learning US
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Chapter 14, Problem 33P
15-37 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.
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Chapter 14 Solutions
Introduction to General, Organic and Biochemistry
Ch. 14.1 - Prob. 14.1QCCh. 14.2 - Problem 15-2 Assign priorities to the groups in...Ch. 14.2 - Problem 15-3 Assign an R or S configuration to the...Ch. 14.3 - Problem 15-4 3-Amino-2-butanol has two...Ch. 14.3 - Prob. 14.5QCCh. 14.3 - Prob. 14.6QCCh. 14 - 15-7 Answer true or false. The cis and trans...Ch. 14 - 15-8 What does the term “chiral” mean? Give an...Ch. 14 - 15-9 What does the term “achiral” mean? Give an...Ch. 14 - 15-10 Define the term “stereoisomer.” Name three...
Ch. 14 - 15-11 In what way are constitutional isomers...Ch. 14 - 15-12 Which of the following objects are chiral...Ch. 14 - Prob. 7PCh. 14 - Prob. 8PCh. 14 - Prob. 9PCh. 14 - Prob. 10PCh. 14 - 15-15 Explain why the carbon of a carbonyl group...Ch. 14 - 15-16 Which of the following compounds contain...Ch. 14 - 15-17 Which of the following compounds contain...Ch. 14 - Prob. 14PCh. 14 - 15-19 Draw the mirror image for each molecule: OH...Ch. 14 - Prob. 16PCh. 14 - 15-21 Answer true or false. For a molecule with...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Prob. 21PCh. 14 - 15-26 For centuries, Chinese herbal medicine has...Ch. 14 - Prob. 23PCh. 14 - Prob. 24PCh. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - Prob. 27PCh. 14 - Prob. 28PCh. 14 - Prob. 29PCh. 14 - Prob. 30PCh. 14 - 15-35 Following are structural formulas for three...Ch. 14 - Prob. 32PCh. 14 - 15-37 Consider a cyclohexane ring substituted with...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - Prob. 36PCh. 14 - 15-41 Compound A(C5Hh, is not optically active and...Ch. 14 - Prob. 38PCh. 14 - 15-43 Triamcinolone acetonide, the active...Ch. 14 - 15-44 Consider the structure of the...Ch. 14 - Prob. 41PCh. 14 - 15-46 Consider Lunesta, a nonbenzodiazepine...Ch. 14 - Prob. 43PCh. 14 - Prob. 44P
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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_forward15-43 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_forward16-17 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_forward
- 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_forward15-16 Which of the following compounds contain stereocenters? (a) 2-Chloropentane(b) 3-Chloropentane (c) 3-Chloro-l-butene(d) 1,2-Dichloropropanearrow_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_forward
- 15-17 Which of the following compounds contain stereocenters? Cyclopentanol l-Chloro-2-propanol 2-Methylcyclopentanol 1-Phenyl-l-propanolarrow_forward14-22 Arrange these compounds in order of increasing boiling point. Values in °C are —42, 78, 117, and 198 CH3CH2CH2CH2OH CH3CH2OH HOCH2CH2OH ch3ch2ch3arrow_forward15-7 Answer true or false. The cis and trans stereoisomers of 2-butene are achiral. The carbonyl carbon of an aldehyde, ketone, carboxylic acid, or ester cannot be a stereocenter. Stereoisomers have the same connectivity of their atoms. Constitutional isomers have the same connectivity of their atoms. An unmarked cube is achiral. A human foot is chiral. Every object in nature has a mirror image. The most common cause of chirality in organic molecules is the presence of a tetrahedral carbon atom with four different groups bonded to it. If a molecule is not superposable on its mirror image, the molecule is chiral.arrow_forward
- 16-6 Answer true or false. te/7-Butylamine is a 3° amine. In an aromatic amine, one or more of the groups bonded to nitrogen is an aromatic ring. In a heterocyclic amine, the amine nitrogen is one of the atoms of a ring. The Lewis structures of both NH4~ and CH4show the same number (eight) of valence electrons, and the VSEPR model predicts tetrahedral geometry for each. There are four constitutional isomers with the molecular formula CgH^N.arrow_forward12-77 Show how to convert cyclopentene into these compounds. 1,2-Dibromocyclopentane Cyclopentanol Iodocyclopentane Cyclopentanearrow_forward17-27 Pentane, 1-butanol, and butanal all have approximately the same molecular weights but different boiling points. Arrange them in order of increasing boiling point. Explain the basis for your ranking.arrow_forward
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