Problems 235
- Butaclamol is a potent antipsychotic that has been used clinically in the treatment of schizophrenia. How many asymmetric
carbons does Butaclamol®have?
- Which of the following objects are chiral?
a. a mug with DAD written on one side e. an automobile
b. a mug with MOM written on one side f. a wineglass
c. a mug with DAD written opposite the handle g. a nail
d. a mug with MOM written opposite the handle h. a screw
- Explain how Rand Sare related to and
- Give the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are obtained.
a. g.
b. h.
c. i.
d. j.
e. k.
f. l.
- a. Draw all possible stereoisomers for the following compound.
b. Which isomers are optically inactive (will not rotate plane-polarized light)?
- Indicate the configuration of the asymmetric carbons in the following molecules:
a. b. c.
- a. Draw all the isomers with molecular formula that contain a cyclobutane ring. (Hint:There are seven.)
b. Name the compounds without specifying the configuration of any asymmetric carbons.
c. Identify:
- constitutional isomers 5. achiral compounds
- stereoisomers 6. meso compounds
- cis–trans isomers 7. enantiomers
- chiral compounds 8. diastereomers
- A compound has a specific rotation of A solution of the compound has an observed rotation of
when placed in a polarimeter tube 10 cm long. What is the percent of each enantiomer in the solution?
- Draw structures for each of the following molecules:
a. (S)-1-bromo-1-chlorobutane d. a chiral isomer of 1,2-dibromocyclobutane
b. (2R,3R)-2,3-dichloropentane e. two achiral isomers of 3,4,5-trimethylheptane
c. an achiral isomer of 1,2-dimethylcyclohexane
- 39.0°. (0.187 g>mL) -6.52°
C 6 H 12
H 3 C CH 2 CH 3
Br
Br
C C H
Br CH O H
CC
HO OH
H
H
CH 2 CH 2 CH 3
CH 2 CH 2 Br
Br C H
OH
HOCH 2 CH CH CHCH 2 OH
OH OH
cis-3-hexene+Br 2 >CH 2 Cl 2 (E)-3,4-dimethyl-3-hexene+H 2 ,Pt>C
trans-3-hexene+Br 2 >CH 2 Cl 2 (Z)-3,4-dimethyl-3-hexene+H 2 ,Pt>C
1-butene+HBr+peroxide (E)-2,3-dichloro-2-butene+H 2 ,Pt>C
1-butene+HCl (Z)-2,3-dichloro-2-butene+H 2 ,Pt>C
trans-2-pentene+Br 2 >CH 2 Cl 2 cis-2-butene+HBr+peroxide
cis-2-pentene+Br 2 >CH 2 Cl 2 3,3-dimethyl-1-pentene+HBr
(+) (-).
OH
H
N
H
Butaclamol
C(CH 3 ) 3
