CHAPTER 9: STEREOCHEMISTRY
WS# 17
1) (9.15) Which of the following structures represent meso compounds?
a)
b)
c)
d)
2) (9.16) Which of the following have a meso form? (Recall that the -ol suffix refers to an alcohol ROH)
a) 2,3-Butanediol
b) 2,3-Pentaediol
c) 2,4-Pentanediol
3) (9.20) What kinds of isomers are the following pairs?
a) (S)-5-Chloro-2-hexene and chlowocyclohexane
b) (2R,3R)-Dibromopentane and (2S,3R)-dibromopentane
4) (9.21) What products are formed from acid-catalyzed hydration of reacemic (+-)-4-methyl-1-hexene? What can you say
about the relative amounts of the products? Is the product mixture optically active?
5) (9.22) What products are formed from hydration of 4-methylcyclopentene? What can you say about the relative
amounts of the products?
6) (9.39) What's the relationship between the specific rotations of (2R,3R)-dichloropentane and (2S,3S)-dichloropentane?
Between (2R,3S)-dichloropentane and (2R,3R)-dichloropentane?
7) (9.44) Assign R or S configurations to the chirality centers in the following molecules:
a)
b)
c)
8) (9.45) Assign R or S configuration to each chirality center in the following molecues:
a)
b)
c)
9) (9.52) Draw tetrahedral representations of the following molecules:
a) (S)-2-Chlorobutane
b) (R)-3-Chloro-1-pentene
10) (9.50) Which of the following pairs of stuctures represent the same enantiomer and which represent different
enantiomers?
a)
b)
d)
d)