Exam (elaborations)
GOC Assignment 3
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Include questions related to the calculation of optical purity, R/S configuration and assigning pairs of compounds as enantiomers, and diastereomers.
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CHM 1321AAssignment 3 Answers
1) Identify each of the following pairs as constitutional isomers, diastereomers, enantiomenrs, meso
compound, same compound or conformers as appropriate.
Br Br Br
a) d)
Br
diastereomers diastereomers
b) Br Br Br
e)
Br
constitutional isomers
constitutional isomers
b) f) Br Br Br
Br
same compound
same compound
(conformers)
2) Identify the hybridization of the indicated atoms in each of the following:
sp3
sp2
O sp2 H
N S
a) b)
O N
O
sp3 OH
O
sp3 sp
sp2
sp2
sp2 O N
N
c) O d) sp3 N
H
O sp2 N
O
sp3 HO2C O
HO OH sp3
sp3 HO sp2
sp3
3) Draw each structure below along with its mirror image. Indicate whether the compound is chiral or
achiral.
a) cis-1,2-dimethylcyclopentane. b) trans-1,2-dimethylcyclopentane
c) cis-1,3-dimethylcyclohexane d) trans-1,3-dimethylcyclohexane
1
, g) CH3CClBrH h) (CH3)2CHOH i) CH3CH2CHOHCH3 j)CH3CH2CHOHCH2CH3
4) Identify the chirality centres in the following molecules:
a. fexofenadine (Allegra):
b. Indinavir (Crixivan):
2
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