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Answers |
Chapter 7 : Stereochemistry |
1. Given that (S)-2-bromobutane has a specific rotation of +23.1o and (R)-2-bromobutane has a specific rotation of -23.1o, what is the optical purity and % composition of a mixture whose specific rotation was found to be +18.4o?
The positive sign indicates that the (S)-isomer is in excess.
Optical purity, % = 100 [a]mixture
/ [a]pure sample
= 100 (+18.4) / +23.1o
= 80% this indicates a 80% excess of S over R!
The 20% leftover, which is optically inactive, must be equal amounts of both (R)- and (S)-bromobutane. The excess 90% is all S so there is a total of 10% (R) and 90% (S).
Answers to Absolute and Relative Configurations:
| Qu 1: | |
| (a) Propene will react to give 1,2-dibromopropane which contains 1 stereocenter at C2, therefore the product will be a racemic mixture of (R)- and (S)-1,2-dibromopropane. | |
| (b) E-2-butene will react to give 2,3-dibromobutane which has 2 stereocenters at C2 and C3. However, the stereospecific nature of the addition in an anti fashion will give meso-2,3- dibromobutane | |
| (c) Z-2-butene, as above, will react to give 2,3-dibromobutane which has 2 stereocenters at C2 and C3. Now the product 1 2 a racemic mixture of (2R, 3R) - 2, 3 - dibromobutane and (2S, 3S) -2, 3 - dibromobutane. | |
| (d) cyclohexene will react to give trans - 1,2-dibromocylcohexane |