Sp2007 Organic II Exam #3 Ch 20-21 (100 ... amazonaws com
Sp2007 Organic II Exam #3
Ch 20-21
(100 points)
NAME: To not have your graded script placed outside my office please check this box
1)
Name the general class of organic compounds that each of these molecules belong to. (10pts) O R C Cl
O R C R
O R C OH
R N R C R
O + R N N
_ + R N N N
R C N
O
O
R C F
R C O O H
R C NR2
2)
Draw in all the lone pairs on each molecule above. (10pts)
3)
Circle a molecule with an SP hybridized atom. (2pts)
4)
Put a cross through a molecule that could be formed in a reaction using a cyanide ion. (2pts)
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5)
Circle the strongest acid in the following sets. (12pts) F
F CO2H
CO2H (a)
O
O
CO2H
Cl
O
Cl
(b)
Cl
CH3 CO2H
CH3CH2-O-O-H
CH3CH2-O-H
O
O OH
(c)
F
O
OH
F
F
O
O
O
(d)
O
H N
O N H
O
6)
Cl
Circle the more reactive molecule with respect to nucleophilic acyl substitution. (6pts) (a)
CH3
O NH C CH3
CH3CH2 NH2
O (b)
(c)
H3C C O CH 3 O
H3C C O C CH3 O O
O
H H3C C N CH 3 O
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7)
Name the following compounds in IUPAC acceptable terms. (20pts) Br H N
O
O
Cl OH
O O
NH2
O
O
O
O
O
8)
O
Benzoic acid can be made from a wide variety of benzene derivatives. Fill in the missing reagents. (12pts)
CO2H H
O
O
H
CO2H
C OCH CH 2 3
CO2H
Br
CO2H Sp07org2e3
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9)
Provide the five products. (10pts)
1) SOCl2 2) LiAlH(OBu)3
CH2N2
O H3C C OH
CH3CH2OH, H+
CF3CH2OH, H+
1) SOCl2 2) BrCH2CO2K
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10) (10pts) Carboxylic acid derivatives provide excellent examples of nucleophilic acyl substitution mechanistic processes. O
O O
NaOH, H2O
O- +Na
O- +Na
For the above ester: -which is the most electrophilic carbon?
-which carbon has the greatest amount of positive charge?
-which is the weakest covalent bond?
Write the mechanism for this saponification reaction.
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11) VX (shown below) is one of the most toxic nerve agents ever synthesized and used in chemical warfare. (As little as 200 micrograms is enough to kill an average person). However, VX can be safely destroyed by reaction with strongly basic media, as shown below. O
O N
S
P
NaOH, H2O O
N
S- +Na
Na+ -O
P
O
VX
Using your organic knowledge, propose a mechanism for this transformation. (6pts)
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Ch 20-21
(100 points)
NAME: To not have your graded script placed outside my office please check this box
1)
Name the general class of organic compounds that each of these molecules belong to. (10pts) O R C Cl
O R C R
O R C OH
R N R C R
O + R N N
_ + R N N N
R C N
O
O
R C F
R C O O H
R C NR2
2)
Draw in all the lone pairs on each molecule above. (10pts)
3)
Circle a molecule with an SP hybridized atom. (2pts)
4)
Put a cross through a molecule that could be formed in a reaction using a cyanide ion. (2pts)
Sp07org2e3
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5)
Circle the strongest acid in the following sets. (12pts) F
F CO2H
CO2H (a)
O
O
CO2H
Cl
O
Cl
(b)
Cl
CH3 CO2H
CH3CH2-O-O-H
CH3CH2-O-H
O
O OH
(c)
F
O
OH
F
F
O
O
O
(d)
O
H N
O N H
O
6)
Cl
Circle the more reactive molecule with respect to nucleophilic acyl substitution. (6pts) (a)
CH3
O NH C CH3
CH3CH2 NH2
O (b)
(c)
H3C C O CH 3 O
H3C C O C CH3 O O
O
H H3C C N CH 3 O
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7)
Name the following compounds in IUPAC acceptable terms. (20pts) Br H N
O
O
Cl OH
O O
NH2
O
O
O
O
O
8)
O
Benzoic acid can be made from a wide variety of benzene derivatives. Fill in the missing reagents. (12pts)
CO2H H
O
O
H
CO2H
C OCH CH 2 3
CO2H
Br
CO2H Sp07org2e3
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9)
Provide the five products. (10pts)
1) SOCl2 2) LiAlH(OBu)3
CH2N2
O H3C C OH
CH3CH2OH, H+
CF3CH2OH, H+
1) SOCl2 2) BrCH2CO2K
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10) (10pts) Carboxylic acid derivatives provide excellent examples of nucleophilic acyl substitution mechanistic processes. O
O O
NaOH, H2O
O- +Na
O- +Na
For the above ester: -which is the most electrophilic carbon?
-which carbon has the greatest amount of positive charge?
-which is the weakest covalent bond?
Write the mechanism for this saponification reaction.
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11) VX (shown below) is one of the most toxic nerve agents ever synthesized and used in chemical warfare. (As little as 200 micrograms is enough to kill an average person). However, VX can be safely destroyed by reaction with strongly basic media, as shown below. O
O N
S
P
NaOH, H2O O
N
S- +Na
Na+ -O
P
O
VX
Using your organic knowledge, propose a mechanism for this transformation. (6pts)
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