Stereochemistry Problem Set

1) Indicate whether the following structures are chiral or achiral (no asymmetric centers or meso); if chiral then assign R or S to each stereogenic center.

Br H R Br
CO2H
a) R
h) OH n) HO CHO R
R
H OH R
H Br H Cl Me HO H S
b) i) S Me
S
R R H
HO H H H
HO Br H OH
Br Cl Me
c) S j) S R R o) not chiral
R H
HO H Br H
OH
S S
d) not chiral
p)
HO H H OH CHO
k) H OH R HO
R H OH R
e)
not stereogenic Me
HO Br H Me HO H
S S
CO2H q)
f) Br S S
l) OH
H OH S carbon w/ Cl has higher
HO H H OH HO Cl R priority than CO2H
H
g) CO2H
H OH S CHO Me OH
m) S
Br H R HO H S r)
not stereogenic not stereogenic
CHO H H HO H
H OH R
Me

2) Draw structures which correspond to the following names: More than one picture may be correct.
OH
Br Br
a) (R) 2-bromobutane OR f) meso -1,2-dihydroxycyclohexane
OH

I
b) (S) 2-iodopentane g) (R) 3-bromononane
Br
Br
c) (2R, 3S) 2-bromo-3-iodoheptane h) (S) 4-ethyldecane
I

d) (S) 3-methylhexane i) meso- 1,3-dimethylcyclohexane

NO2
OH
e) (3S, 5S) 3-hydroxy-5-methyloctane j) (S) 2-nitropentane (nitro = NO2)
(hydroxy = OH)

3) Draw i) an enantiomer; ii) a diastereomer, for each of the following H H HO

OH
CH2Cl Br Br Me Me
a) H Cl b) H Me Me H c) H H
d)
HO
OH
H Me Me H O
Cl H CN CN OH OH O
Me enantiomer enantiomer enantiomer
CH2Cl
CH2Cl Me H OH
Cl H H Me
Cl H Me one one
Cl H H Br diastereomer diastereomer
OH OH
H Cl Me CN
H O
Me one one
enantiomer diastereomer diastereomer
4) You have a sample of the enantiomerically pure (3S)-3-chloro-1-butene and carry out the non-stereospecific addition reaction shown below.
H Cl H Cl Me Me
a) What happens to the absolute configuration of the existing stereocenter? unchanged RXN
b) Draw Fisher projection(s) of the product(s). HO H H OH
c) How many product spots would you expect to see by TLC? 2 OH H Cl H Cl
d) Which of the compounds corresponding to the TLC spots would be optically active? both Me Me