5. The enantiomers of 1-amino-2-propanol were separated and recovered as their hydrochloride salts: CH3CHCH2NH3" cr ÓH The sample of (R)-(-)-1-amino-2-propanol hydrochloride had [a]p²s -31.5° (c 0.01; methanol), and that of (S)-(+)-1-amino-2-propanol hydrochloride had [a]p²5 +35° (c 0.01; methanol). (a) Write correct stereochemical formulas for both isomers. (b) Which enantiomer was recovered with the higher purity? (c) Assuming that the optical rotation observed for the enantiomer of higher purity is the correct specific optical rotation for the compound, what is the enantiomeric excess in the sample of the other enantiomer? What is its enantiomeric composition?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.28P
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5. The enantiomers of 1-amino-2-propanol were separated and recovered as their
hydrochloride salts:
CH3CHCH2NH3" cr
ÓH
The sample of (R)-(-)-1-amino-2-propanol hydrochloride had [a]p²s -31.5° (c 0.01; methanol),
and that of (S)-(+)-1-amino-2-propanol hydrochloride had [a]p²5 +35° (c 0.01; methanol).
(a) Write correct stereochemical formulas for both isomers.
(b) Which enantiomer was recovered with the higher purity?
(c) Assuming that the optical rotation observed for the enantiomer of higher purity is the
correct specific optical rotation for the compound, what is the enantiomeric excess in the
sample of the other enantiomer? What is its enantiomeric composition?
Transcribed Image Text:5. The enantiomers of 1-amino-2-propanol were separated and recovered as their hydrochloride salts: CH3CHCH2NH3" cr ÓH The sample of (R)-(-)-1-amino-2-propanol hydrochloride had [a]p²s -31.5° (c 0.01; methanol), and that of (S)-(+)-1-amino-2-propanol hydrochloride had [a]p²5 +35° (c 0.01; methanol). (a) Write correct stereochemical formulas for both isomers. (b) Which enantiomer was recovered with the higher purity? (c) Assuming that the optical rotation observed for the enantiomer of higher purity is the correct specific optical rotation for the compound, what is the enantiomeric excess in the sample of the other enantiomer? What is its enantiomeric composition?
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