Introduction To General, Organic, And Biochemistry
12th Edition
ISBN: 9781337571357
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Question
Chapter 14, Problem 25P
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.
Expert Solution & Answer
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Students have asked these similar questions
Classify the following pair of compounds as the same compound, enantiomers, diastereomers,
constitutional isomers, or not isomeric. Also, select the correct IUPAC name, including the correct (R) or
(S) designation, for each.
H
÷
||I
The correct IUPAC names are:
||
J
k
CI
same compound
enantiomers
diastereomers
constitutional isomers
not isomeric
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
Draw a structural formula of the S configuration of the compound shown below.
• Use the wedge /hash bond tools to indicate stereochemistry where it exists.
Include H atoms at chiral centers only.
• Ifa group is achiral, do not use wedged or hashed bonds on it.
CH3
CH3
CH;CHCHCN
CH,CH,CH,CHCH,CH,
CH2NH2
Draw a structural formula of the RS configuration of the compound shown below.
Use the wedge /hash bond tools to indicate stereochemistry where it exists.
• Include H atoms at chiral centers only.
If a group is achiral, do not use wedged or hashed bonds on it.
ÇI
1
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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Similar questions
- 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_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 is the maximum number of stereoisomers for the following molecule? 00 X √6 CH3 CH3arrow_forward5a 5barrow_forward
- Draw the correct structure for (2S,3R)-2,3-diiodopentane. Show stereochemistry clearly. To ensure proper grading, explicitly draw all four groups, including wedge/dash bonds, around a chirality center. Indicate whether the compound could exist in an optically active form. 5 Draw (2S,3R)-2,3-diiodopentane. Select / ||| ||| / Draw Templates C H More Can (2S,3R)-2,3-diiodopentane exist in an optically active form? Erase Q2Qarrow_forwardIdentify the stereochemical configuration of this cyclic compound. CI R Osarrow_forwardIdentify the stereochemistry of this molecule.arrow_forward
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