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OWLv2 for Bettelheim/Brown/Campbell/Farrell/Torres' Introduction to General, Organic and Biochemistry, 11th Edition, [Instant Access], 1 term (6 months)
11th Edition
ISBN: 9781305106734
Author: Frederick A. Bettelheim; William H. Brown; Mary K. Campbell; Shawn O. Farrell; Omar Torres
Publisher: Cengage Learning US
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Question
Chapter 15, Problem 15.29P
Interpretation Introduction
Interpretation:
The true and false statements should be identified.
Concept Introduction:
An optically active substance has two conditions:
- It should have chiral carbon atom.
- It should not possess plane of symmetry.
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7 For the following compound with two chiral centers assign 'R' and 'S' configurations.
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Classify the following pair of compounds as the same compound, enantiomers, diastereomers,
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Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3S)-2,3-dichloropentane
Compound I: (2S, 3S)-2,3-dichloropentane, Compound II: (2S, 3S)-2,3-dichloropentane
Compound I: (2S, 3R)-2,3-dichloropentane, Compound II: (2S, 3R)-2,3-dichloropentane
Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3R)-2,3-dichloropentane
15-12 Which of the following objects are chiral (assume that there is no label or other identifying mark,?
(a) Pair of scissors(b, Tennis ball(c) Paper clip(d) Beaker(e, The swirl created in water as it drains out of a sink or bathtub
Chapter 15 Solutions
OWLv2 for Bettelheim/Brown/Campbell/Farrell/Torres' Introduction to General, Organic and Biochemistry, 11th Edition, [Instant Access], 1 term (6 months)
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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- 15-30 (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_forwardDiastereomers are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other. OH OH НО Но ÕH ОН How many chiral centers are present in one of the structures above? 1 O 2 O0 Are the structures mirror images of each other (i.e., are ALL of the chiral centers exactly opposite)? no yes I can not tell. How are these two structures related to each other? Diastereomers Non-isomeric (different molecular formulas) O Constitutional (same MF but different connections) Enantiomers (non-superimposable mirror images)arrow_forwardNH2 NH2 of the most important properties of chiral ules in solution is their effect on plane- zed light, this effect is called optical activity. -H 2 COOH HOOC 3 H3C CH3 an enantiomer rotates a plane-polarized light e positive direction or clockwise, it is rotary (+ or d), while for a negative direction unterclockwise, it is levorotary (- or l) (+)-Alanine (-)-Alanine Alanine is a chiral amino acid that has two enantiomers: (+)-alanine and (-)-alanine. These two are optical isomers. 78. Which enantiomer of alanine rotates the plane polarized light clockwise?arrow_forward
- -Tetrahedral representation of the enantiomers of the structure below -tetrahedral representations of both R and S enantiomers of the structure below -what functional groups does the given structure posses?arrow_forward15-11 In what way are constitutional isomers different from stereoisomers? In what way are they the same?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
- 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_forward15-43 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_forwardDraw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?arrow_forward
- 15-7 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_forwardWhat type of stereochemistry, S or R, does the chiral center in this molecule have?arrow_forwardNH2 N CH2 CH2 The stereochemistry around this chiral carbon is: O cannot be determined. O Rand S OR OSarrow_forward
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