Organic Chemistry
Chirality
Chirality
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<strong>Organic</strong> <strong>Chemistry</strong> - Ch 11 554 Daley & DaleyHCH 3?BrCH 2 CH 3CH 3 CH 2HBrCH 3(S)-2-BromobutaneSolutionThe structure on the right is rotated clockwise by 90 o compared to thestructure on the left. Converting the structure on the right to a threedimensionalstructure shows it is (R)-2-bromobutane. Thus, they areenantiomers.HHCH 3 CH 2 CH 3CH 3 CH 2 CH 3BrBr(R)-2-Bromobutaneb)CH 2 CH 3Br CH 3?H 3 CCH CH 2BrCH CH 2CH 2 CH 3(R)-3-Bromo-3-methyl-1-penteneSolutionThis molecule is rotated 180 o and thus the two Fischer projections areidentical.Exercise 11.6For each of the following sets of structures, state how the firststructure relates to each of the following structures in the set. Makemodels to help yourself. The relationships may include being the samecompound, a structural isomer, or an enantiomer.a)CH 3CH 3COOHCOOHH NH 2COOHHNH 2COOHNH 2CH 3HHCH 3NH 2b)www.ochem4free.com 5 July 2005
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