Chapter 5: Q.45 (page 207)
Which group in each pair is assigned the higher priority in R,S nomenclature?
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Short Answer
The following group among the pairs will get the higher priority:
Chapter 5: Q.45 (page 207)
Which group in each pair is assigned the higher priority in R,S nomenclature?
The following group among the pairs will get the higher priority:
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Get started for freeDraw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.
ethambutol
The shrub ma huang (Section 5.4 A) contains two biologically active stereoisomers-ephedrine and pseudoephedrine-with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once popular combination drug used by body builders to increase energy and alertness, while pseudoephedrine is a nasal decongestant.
a. Draw the structure of naturally occurring (–)-ephedrine, which has the 1R,2Sconfiguration.
b. Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2Sconfiguration.
c. How are ephedrine and pseudoephedrine related?
d. Draw all other stereoisomers of (–)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.
e. How is each compound drawn in part (d) related to (–)-ephedrine?
Consider Newman projections (A–D) for four-carbon carbohydrates. How is each pairof compounds related: (a) A and B; (b) A and C; (c) A and D; (d) C and D? Choose fromidentical molecules, enantiomers, or diastereomers.
Amygdalin, a compound isolated from the pits of apricots, peaches, and wild cherries, has been used as an unsanctioned anticancer drug both within and outside of the United States. One hydrolysis product formed from amygdalin is mandelic acid, used in treating common skin problems caused by photo-aging and acne.
a. How many stereogenic centres are present in amygdalin? What is the maximum number of stereoisomers possible?
b. Draw both enantiomers of mandelic acid and label each stereogenic centre as R or S.
c. Pure (R)-mandelic acid has a specific rotation of –154. If a sample contains 60% of the R isomer and 40% of its enantiomer, what is of this solution?
d. Calculate the ee of a solution of mandelic acid having = +50. What is the percentage of each enantiomer present?
Classify each pair of compounds as constitutional isomers or stereoisomers.
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