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 15.42P
Interpretation Introduction
(a)
Interpretation:
The stereocenters in glucose molecule should be determined.
Concept Introduction:
Glucose is the simplest monosaccharide with molecular formula C6 H12 O6. It can exist as open chain structure and also as Haworth’s projection. Enantiomers are the optically active stereoisomers which are non-super imposable mirror images of each other. Diastereomers are also stereoisomers which have two or more stereocenters but not mirror image of each other.
Interpretation Introduction
(b)
Interpretation:
The number of stereoisomers in glucose molecule should be determined.
Concept Introduction:
Glucose is the simplest monosaccharide with molecular formula C6 H12 O6. It can exist as open chain structure and also as Haworth’s projection. Enantiomers are the optically active stereoisomers which are non-super imposable mirror images of each other. Diastereomers are also stereoisomers which have two or more stereocenters but not mirror image of each other.
Interpretation Introduction
(c)
Interpretation:
Pairs of enantiomers possible for glucose should be determined.
Concept Introduction:
Glucose is the simplest monosaccharide with molecular formula C6 H12 O6. It can exist as open chair structure and also as Haworth’s projection.
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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_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_forward15-16 Which of the following compounds contain stereocenters? (a) 2-Chloropentane(b) 3-Chloropentane (c) 3-Chloro-l-butene(d) 1,2-Dichloropropanearrow_forward
- 15-26 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_forward15-37 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_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_forward
- 15-17 Which of the following compounds contain stereocenters? Cyclopentanol l-Chloro-2-propanol 2-Methylcyclopentanol 1-Phenyl-l-propanolarrow_forward15-21 Answer true or false. For a molecule with two stereocenters, 22 = 4 stereoisomers are possible. For a molecule with three stereocenters, 32 = 9 stereoisomers are possible. Enantiomers, like gloves, occur in pairs. 2-Pentanol and 3-pentanol are both chiral and show enantiomerism. 1-Methylcyclohexanol is achiral and does not show enantiomerism. Diastereomers are stereoisomers that are not mirror images.arrow_forward15-30 (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?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_forward15-7 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_forward15-10 Define the term “stereoisomer.” Name three types of stereoisomers.arrow_forward
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