Problem 5.36 (S)-Lactic acid has a specific rotation of +3.8. (a) If the ee of a solution of lactic acid is 60%, what is [a] for this solution? (b) How much of the dextrorotatory and levorotatory isomers does the solution contain?
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![Problem 5.36
(S)-Lactic acid has a specific rotation of +3.8. (a) If the ee of a solution of lactic acid is
60%, what is [a] for this solution? (b) How much of the dextrorotatory and levorotatory
isomers does the solution contain?](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F689fc72f-cbdc-4540-8cb5-d6f9174c712e%2Fd237c1b6-5be7-4797-b439-d59facd5fdab%2Fgvlj6q_processed.jpeg&w=3840&q=75)
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- Problem 5.27 (a) Label the four stereogenic centers in sorbitol as R or S. (b) How are sorbitol and A related? (c) How are sorbitol and B related? HO H HO H но н но н Н Он Н ОН HO HO но но но н он Н ОН B H OH HO H HO H HO H sorbitol AChemistry 5.66 A mixture contains equal amounts of compounds A-D. D B C A a. Which compounds alone are optically active? b. If the mixture was subjected to fractional distillation, how many fractions would be obtained? c. How many of these fractions would be optically active?Problem 5.25 If the two stereogenic centers of a compound are R,S in configuration, what are the R,S assignments for its enantiomer and two diastereomers?
- Chemistry 5.66 A mixture contains equal amounts of compounds A-D. K D C B A a. Which compounds alone are optically active? b. If the mixture was subjected to fractional distillation, how many fractions would be obtained? c. How many of these fractions would be optically active? SETEL5.57 The shrub ma huang (Section 5.4A) 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, whereas pseudoephedrine is a nasal decongestant. a. Draw the structure of naturally occurring (-)-ephedrine, which has the 1R,2S configuration. b. Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration. c. How are ephedrine and pseudoephedrine related? d. Draw all other stereoisomers of (-)-ephedrine and (+)- pseudoephedrine, and give the R,S designation for all stereogenic centers. e. How is each compound drawn in part (d) related to (-)-ephedrine?Problem 5.37 Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopentane. A B C three stereolsomers of 1,3-dimethylcyclopentane a. How do the boiling points of A and B compare? What about those of A and C? b. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C. c. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?
- Which compounds (B–F) are identical to A? (b) Which compounds (B–F) represent an isomer of A?Problem 5.20 Label the two stereogenic centers in dB re stereoisomers. ne. each compound and draw all possible CI a. rro OH Br CI ne b. B. Problem 5.21 Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A-D) in Figure 5.8 are identical to E and F? im et wihr boe A mot Br omin oldne Br F Br5.75 An acid-base reaction of (R)-sec-butylamine with a racemic mixture of 2- phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products, How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers of each other. OH NH2 2-phenyipropanoic acid (racemic mixture) Rsec-butylamine
- Page 203 Problem 5.29 Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers. a. b. но c.PROBLEM 4.3 How might Kekulé explain the fact that there is only one dibromobenzene with the bromines on adjacent carbon atoms, even though we can draw two different structures, with either a double or a single bond between the bromine-bearing carbons? Br Br Br Br andPROBLEM 4.13 Write the structures of all the alkenes that can be formed by dehydrohalogenation of each of the following alkyl halides. Apply the Zaitsev rule to predict the alkene formed in greatest amount in each case. (a) 2-Bromo-2,3-dimethylbutane (c) 3-Bromo-3-ethylpentane (b) tert-Butyl chloride (d) 2-Bromo-3-methylbutane
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