Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 5.6, Problem 14P
Interpretation Introduction
Interpretation:
The stereoisomerism of morphine is to be explained.
Concept introduction:
Morphine is a pain medication of the opiate family which is found naturally in a number of plants and animals. It acts directly on the central nervous system to decrease the feeling of pain. It can be taken for both acute pain and chronic pain.
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What is the configuration of the carbon atom indicated
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The quantitative differences in biological activity between the two enantiomers of a compound are sometimes quite large. For example, the D isomer of the drug isoproterenol, used to treat mild asthma, is 50 to 80times more effective as a bronchodilator than the L isomer. Identify the chiral center in isoproterenol. Why do the two enantiomers have such radically different bioactivity?
Identify the configuration of the chiral centre: (R) or (S).
OH
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O There is no chiral centre.
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Chapter 5 Solutions
Organic Chemistry
Ch. 5.2 - Prob. 1PCh. 5.2 - Prob. 2PCh. 5.2 - Prob. 3PCh. 5.2 - Prob. 4PCh. 5.3 - Is cocaine (Worked Example 5-2) dextrorotatory or...Ch. 5.3 - Prob. 6PCh. 5.5 - Prob. 7PCh. 5.5 - Prob. 8PCh. 5.5 - Prob. 9PCh. 5.5 - Assign R or S configuration to the chirality...
Ch. 5.5 - Draw a tetrahedral representation of...Ch. 5.5 - Prob. 12PCh. 5.6 - One of the following molecules (a)–(d) is...Ch. 5.6 - Prob. 14PCh. 5.6 - Assign R or S configuration to each chirality...Ch. 5.7 - Prob. 16PCh. 5.7 - Which of the following have a meso form? (Recall...Ch. 5.7 - Does the following structure represent a meso...Ch. 5.8 - Prob. 19PCh. 5.8 - Prob. 20PCh. 5.9 - Prob. 21PCh. 5.11 - Prob. 22PCh. 5.11 - Prob. 23PCh. 5.11 - The lactic acid that builds up in tired muscles is...Ch. 5.11 - The aconitase-catalyzed addition of water to...Ch. 5.SE - Which of the following structures are identical?...Ch. 5.SE - Prob. 27VCCh. 5.SE - Prob. 28VCCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 30VCCh. 5.SE - Prob. 31APCh. 5.SE - Which of the following compounds are chiral? Draw...Ch. 5.SE - Prob. 33APCh. 5.SE - Eight alcohols have the formula C5H12O. Draw them....Ch. 5.SE - Draw compounds that fit the following...Ch. 5.SE - Prob. 36APCh. 5.SE - Prob. 37APCh. 5.SE - Prob. 38APCh. 5.SE - What is the stereochemical configuration of the...Ch. 5.SE - Prob. 40APCh. 5.SE - Prob. 41APCh. 5.SE - Prob. 42APCh. 5.SE - Prob. 43APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 46APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configurations to the chirality...Ch. 5.SE - Assign R or S stereochemistry to the chirality...Ch. 5.SE - Prob. 50APCh. 5.SE - Draw examples of the following: (a) A meso...Ch. 5.SE - Prob. 52APCh. 5.SE - Prob. 53APCh. 5.SE - Prob. 54APCh. 5.SE - On reaction with hydrogen gas by a platinum...Ch. 5.SE - Prob. 56APCh. 5.SE - Prob. 57APCh. 5.SE - One of the steps in fat metabolism is the...Ch. 5.SE - The dehydration of citrate to yield cis-aconitate,...Ch. 5.SE - The first step in the metabolism of glycerol,...Ch. 5.SE - One of the steps in fatty-acid biosynthesis is the...Ch. 5.SE - Prob. 62APCh. 5.SE - Draw tetrahedral representations of the two...Ch. 5.SE - The naturally occurring form of the amino acid...Ch. 5.SE - Prob. 65APCh. 5.SE - Prob. 66APCh. 5.SE - Prob. 67APCh. 5.SE - Allenes are compounds with adjacent carbon-carbon...Ch. 5.SE - Prob. 69APCh. 5.SE - Prob. 70APCh. 5.SE - How many stereoisomers of...Ch. 5.SE - Draw both cis- and trans-1,4-dimethylcyclohexane...Ch. 5.SE - Draw both cis- and trans-1,3-dimethylcyclohexane...Ch. 5.SE - cis-1,2-Dimethylcyclohexane is optically inactive...Ch. 5.SE - Prob. 75APCh. 5.SE - Prob. 76APCh. 5.SE - Prob. 77AP
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- The naturally occurring form of the amino acid cysteine (Problem 5-63) has the S configuration at its chirality center. On treatment with a mild oxidizing agent, two cysteines join to give cystine, a disulfide. Assuming that the chirality center is not affected by the reaction, is cystine optically active? Explain.arrow_forwardDraw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?arrow_forwardPayalbenarrow_forward
- 7 For the following compound with two chiral centers assign 'R' and 'S' configurations. Draw enantiomers and diastereomers for the following compound? How many enantiomers and diastereomers are possible. Assign (R) and (S) configurations for all the structures. What are diastereomers? COOH H CI € Br -H CH3arrow_forward3. Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chirality centers as R or S. Ans: OH OH CO₂Harrow_forwardHow many the chirality center(s) can you see in the following compound. 02 none H3C. 03 01 OH Br НО CH3arrow_forward
- Assign the absolute configuration of the two chiral centers as R or S. он он CO₂H Both centers are S The center on the left is R; the center on the right is S Both centers are R The center on the left is S; the center on the right is Rarrow_forwardHow many chiral centers does prostaglandin E2 have? Assign R,S configurations to these centers.arrow_forwardThreonine is one of the two naturally occurring amino acids with two chirality centers, one of the possible stereoisomers is shown below. Assign R or S configurations to the two chiral centers. α-carbon: ball & stick + labels R-group: くarrow_forward
- A well known non steroidal anti inflammation drug NSAID exists in two sterochemical forms. Only one is biologically active. Below is the structure of the biological active form. Identify the chiral center and determine if it is the R- or S- stereoisomer.arrow_forwardThe amino acid threonine has two chiral centers. The stereoisomer found in proteins has the configuration 2S,3R about the two chiral centers. Draw (a) a Fischer projection of this stereoisomer and (b) a three-dimensional representationarrow_forwardIdentify the configuration of the chiral centre in this ring: (R) or (S). TI S There is no chiral centre. Rarrow_forward
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