Name:
Answer
Key
 
 
 
 
 
 
 
 






February
18,
2011




SID:____________________________________








Discussion
Section:

9:00am




11:00am




12:00pm

Chem
30C
 
 
 
 
 
 
 
 









(please
circle)

Quiz
2



1. Predict
the
trend
in
acidity
for
the
following
substituted
phenols.

Rank
by
increasing
acidity

and
explain.

OH OH OH OH

NO2

OMe NO2 






A



 










B
 




C
 











D
 
 Answer:
B,
A,
D,
C



2. Name
the
following
using
IUPAC
nomenclature:





 NO2 
 
 Answer:
para­nitrotoluene;
p­nitrotoluene;
4­nitrotoluene




3. Provide
the
compound
for
each
transformation:

O O
Br
1 eq Br2
Cl OMe FeBr3 Cl OMe 

O
1. Benzene, AlCl3
2. Zn(Hg), HCl, Heat
O
3. SOCl2 O2N
4. AlCl3
5. HNO3, H2SO4
O
O 



4. Devise
a
reasonable
synthesis
for
the
following
compounds
from
reagents
you
are
familiar

with
and
the
starting
material
provided.



O

Cl Cl
1. AlCl3

2. FeCl3, Cl2
3. N2H4, KOH, Heat


note:
Clemmenson
Reduction
also
works
to
remove
benzylic
ketone











5. Provide
Conditions
for
the
Following:


Cl A
+
AlCl3

B
+
AlCl3
Cl

C
+
H3PO4

D
+ OH
H2SO4





6. Propose
a
detailed
mechanism
to
explain
the
following
reactions:



CH3 CH3 CH3

NH2
KNH2
+
liquid NH3
H NH2

Cl NH2
NH2

CH3
CH3

A NH3
A
CH3
NH2
NH3
B
B NH2
Cl-
NH2
NH3








 O
O
H H
Cl
O
AlCl3, heat

AlCl3
O H2O
H O
Cl
O H
H H
H2O O
AlCl3
O
H
H OH2
Cl
O
OH
O
H H3O+
H
O
O
H
O
OH
H
HCl
O
ClAlCl3
O
H
O
H OH

O HCl
H
O
Cl AlCl3
H

O
HCl AlCl3