Blackboard Quiz #1 SOLUTION
1. The best way to add a chlorine atom to the benzylic position of toluene is to use:
a. NBS and an organic peroxide.
b. Cl2 and FeCl3.
c. HCl and H2O2.
d. NCS and an organic peroxide.
2. Which of the following statements is not true? (Corrected)
a. 1,3,5-cycloheptatriene can become aromatic by losing a proton.
b. Cyclooctatetraene is a diradical species, with 2 unpaired electrons in antibonding orbitals.
c. 1,3,5-cycloheptatriene can become aromatic by losing a hydride ion.
d. The lone pair on the nitrogen in pyridine is not part of the pi-electron system, and can by used
as a Lewis base.
3. For an electrophilic subsitution reaction to be spontaneous:
a. The electrophile must attach through an atom that is less electronegative than hydrogen.
b. The electrophile must attach through an atom that is more electronegative than
hydrogen.
c. The electrophile should only have a small, partial positive charge.
d. The electrophile should be polar.
4. The correct reagents to add an iodine atom to a benzene ring are:
a. I2, FeI3
b. HI, HNO3
c. HI, AlI3
d. I2, HNO3
5. Which figure below best depicts meso-2,4-pentanediol?
CH3
CH3
CH3
H
OH
HO
H
H
H
H
H
H
HO
HO
H
HO
H
H
CH3
CH3
CH3
H
H
OH
OH
H
OH
H
H
H
CH3
CH3
6. Which of the following best represents the mechanism for electrophilic substitution of benzene?
H
a.
E
+
E
H
B
H
E
E
E
b.
c.
H-
H
E
B
E
7. What is the correct name for:
NO2
a.
b.
c.
d.
m-nitrotoluene
m-nitrophenol
m-methylnitrobenzene
o-nitrotoluene
8. Which compound obeys all rules for aromaticity?
O
O
CH3
O
P
N
9. The maximum number of stereoisomers for the following molecule is:
OH H
N
HO3S
a.
b.
c.
d.
O
OH
OH
24
25
26
27
10. What is the correct name for:
O
Br
a.
b.
c.
d.
SO3H
(2R, 3R, 5S)-5-bromo-2-methoxy-3-benzylhexane
(2R, 4R, 5R)-2-bromo-5-methoxy-4-phenylhexane
(2R, 3R, 5R)-5-bromo-2-methoxy-3-phenylhexane
(2S, 3S, 5S)-5-bromo-2-methoxy-3-phenylhexane