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CH 232 Quiz 4
Chapters 18, 19 & 20
Fall 2007
October 30, 2007
Page 2:
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Page 3:
/ 4 + 3 bonus
Page 4:
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Page 5:
/15 + 2 bonus
Page 6:
/14
Page 7:
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Total:
/100
1
:
O
:
Circle the compound below that is the strongest acid. (4 pts)
F
COOH
3)
O
: :
:
:O
O
2)
: :
O
: :
:
:O
:
:O
: :
:
:O
:
The conjugate base of benzoic acid (benzoate) is resonance stabilized. Draw the significant
resonance structures of the benzoate anion. (8 pts)
:
1)
F
F
COOH
COOH
Circle the compound below that is the weakest acid. (4 pts)
COOH
NC
COOH
H3C
2
COOH
F
4)
Circle the correct name of the structure below. (4 pts)
(R)-2-tert-butylbutanal
(R)-3-tert-butylbutanal
O
(R)-4-ethyl-2-methylpentanal
H
(R)-3-ethyl-4-methylpentane
carbaldehyde
(R)-3-ethyl-4-methylpentanal
Extra Credit (3 pts):
NADH serves as a reducing agent, a biological source of hydride. Identify which hydrogen atom of
NADH (below) would be delivered as hydride in a reaction.
NH2
HO OH
N
NH2
O
N
O
O
P
P
O OOO
O
H
O N
H
HO OH
3
N
O
N
5)
Propose a mechanism for the following transformation. Use proper curved arrow notation and be
sure to show all steps and all intermediates. (23 pts)
N
O
H2O / H+
+
H2N
H+
:
H
N
:
N
H
:O H
H N
H
O H
H+
H
H
H N
O
+
H2N
+
H2N
O
4
H
O:
:
H N
H
O
6)
Predict the products for the following reactions. Be sure to write all products for reactions with
more than one likely product and show stereochemistry where appropriate. (15 pts)
a)
O
H2O
H+
OCH3
HO
H
O
+ CH3OH
Bonus: Is the product optically active? (2 pts) NO
b)
O
OH
1) LiAlH4
2) H3O+ workup
c)
N
H
O
, H+
N
+ H2O
5
OH
7)
Predict the products for the following reactions. Be sure to write all products for reactions with
more than one likely product and show stereochemistry where appropriate. (10 pts)
a)
H
OH
PCC
O
(PCC = pyridinium chlorochromate)
b)
SH
S
1) NaH
2) CH3CH2Br
8)
Identify the functional groups in the compound below (an insecticide) (4 pts).
arene
ether
O
CH3
O
S
O
(or acetal)
ether
6
sulfoxide
9)
Propose a mechanism for the following transformation. Use proper curved arrow notation and be
sure to show all steps and all intermediates. (28 pts)
HO
OH
H+
O O
O
HO
O O
OH
:O:
H+
: :
H
O O
HO
OH
O
H
O
:
H
O
HO
HO
HO
:
O
HO
O
HO
:
HO
H O
H
H+
7