EP INTRO.TO GENERAL,ORGANIC...-OWL ACCE
12th Edition
ISBN: 9781337915984
Author: Bettelheim
Publisher: Cengage Learning
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Chapter 14, Problem 26P
Interpretation Introduction
Interpretation: This is to be explained how a drug is said to be chiral. Whether a chiral drug will be optically active or rotate the plane of polarized light or not needs to be explained.
Concept Introduction:
A molecule is said to be chiral if it is non-superimposable with its mirror image. For example, left and right hands. These two non-superimposable mirror images of chiral molecules are known as enantiomers.
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6) Assign R or S stereochemistry
to the chiral centers in the
molecule to the right.
Ol
OH
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Cortisone is a compound that is used as an anti-inflammatory drug to treat
2)
diseases like arthritis. Cortisone is a steroid which contains four rings (A, B, C and D), and
has the following structure:
он
"OH
Cortisone
Provide the data to complete each of the following statements:
The total number of chiral carbons (stereocentres) in Cortisone is
The maximum number of stereoisomers possible is:
The degree of unsaturation (IHD) of Cortisone is
The total number of 2° hydrogens is
The ring fusion between rings B and C is trans or cis?
The absolute configuration of the carbon with * in the structure is
The total number of n bonds is
Predict whether the given molecule is a "Chiral" or "Achiral" compound. Indicate the chiral compounds
by an asterisk (*)
он
CH
он
Chapter 14 Solutions
EP INTRO.TO GENERAL,ORGANIC...-OWL ACCE
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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- 5. Describe the importance of optical isomerism in chiral drugs.arrow_forwardWould you expect cholesterol to dissolve in water? Give your reasoning. State which class of alcohol does cholesterol belongs to. Then identify all the chiral centres on the diagram attatched.arrow_forwardWhy are some chiral drugs are sold as a mixture of enantiomers and why some are not? How enantiomers affect the biological activity of the drugs? Explain.arrow_forward
- The structural formula for the open-chain form of D-mannose is CH НО—С—Н Но-с—н Н—С—ОН Н—ҫ—ОН CH-OН (a) Is this molecule a sugar? (b) How many chiral carbons are present in the molecule? (c) Draw the structure of the six-member-ring form of this molecule.arrow_forwardCount the number of chiral carbons in the given compounds and assign each chiral carbon as R or Sarrow_forwardExplain the concept of chirality in organic chemistry, its significance in drug design, and the difference between enantiomers and diastereomers.arrow_forward
- Do any of the following molecules have chiral carbons? If so label them.arrow_forward11. Which of the following is not true about enantiomers? a) They usually differ in biochemical properties. b) They are nonsuperimposable on each other. c) They have different melting points. d) One form may be more physiologically active than a racemic mixture.arrow_forward11. Which carbon atom(s) is/are chiral? How many stereoisomers are possible? OHarrow_forward
- 5. Glycerol, CH2OHCHOHCH2OH, is an important component in the biological synthesis of fats. a) Does glycerol have a plane of symmetry? If so, write a three-dimensional structure for glycerol and indicate where the plane of symmetry lies. b) Is glycerol chiral?arrow_forwardPropranolol is a chiral compound. (R)-Propranolol is used as a contraceptive; (S)-propranolol is used to treat hypertension. Identify the chiral carbon in the structure below. Is this the (R) or the (S) isomer? Draw the other isomer.arrow_forwardGlucose is the most abundant monosaccharide. In energy metabolism it is the most important source of energy for most organisms. Most carbohydrates have several chiral centers. How many chiral centers are present in the straight chain form of glucose? H- ОН НО H- ОН ОН CH,OHarrow_forward
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