Quiz_2_answer

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Key
 
 
 
 
 
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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 NO 2 OMe 
 NO 2 
 




C
 


A



 










B
 
 2. Name
the
following
using
IUPAC
nomenclature:
 
 
 
 NO2 
 
 











D
 
 Answer:
B,
A,
D,
C
 Answer:
para­nitrotoluene;
p­nitrotoluene;
4­nitrotoluene

 3. Provide
the
compound
for
each
transformation:
 O O Br Cl OMe 1 eq Br2 FeBr3 OMe 
 Cl O 1. Benzene, AlCl3 2. Zn(Hg), HCl, Heat O 
 3. SOCl2 4. AlCl3 5. HNO3, H2SO4 O2N 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:
 A Cl + 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 NH2 H NH2 Cl NH2 CH3 CH3 A NH3 A CH3 NH2 NH3 Cl- B B NH2 NH3 
 
 
 NH2 
 O O H H Cl O AlCl3, heat AlCl3 H2O O H Cl O H O H H O H2O AlCl3 O H H Cl OH2 O OH O H3O+ H H O O H O OH H HCl O ClAlCl3 O H O H OH HCl O H Cl AlCl3 O H O HCl 
 
 
 
 
 AlCl3 
 ...
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