Chemistry 212
Name_______________________________
Exam 2
Last, First
Spring 2004
Linda Waldman
I. (30 points, 2 points each) Write your answer in the box to the right of the question.
1. What is the product of the following series of reactions?
O
HNO3
Br2
Zn(Hg)
C
H2SO4
FeBr3
HCl
O2N
NO2
CH2
A)
C)
CH2
Br
Br
O2N
B)
D)
CH2
Br
2.
CH2
Br
NO2
Which reaction sequence below converts para-bromoaniline into para-bromophenol?
NaNO2, HCl
H3PO2
Br
A) H2N
o
H2O, O C
B) H2N
Br
HNO3
NaOH
H2SO4
O
C) H2N
Br
(CH3C)2O
NaOH
pyridine
D) H2N
8.
Br
NaNO2, HCl
o
H2O, O C
H2O
warm
Which of the following has the weakest carbon-chlorine bond?
Cl
CH2Cl
Cl
Cl
CH3
A)
B)
C)
D)
CH3
CH3
Organic Chemistry
EXAM 2
Name________________________
212 LSW S’04
Initials
10. Starting with toluene, which of the following is the best method to make the ether shown
below? (assume you can separate ortho and para isomers). (I’m not sure if this one is applicable to this exam- just
look it over….)
Cl
CH2 O
A)
B)
C)
D)
12.
Reaction of an N,N-dialkylaniline with nitrous acid yields:
A) a diazonium salt.
B) a para-nitroso compound.
C) an N-nitroso compound.
D) an azo compound.
14. Carbon-14 labelled chlorobenzene is reacted with sodium amide in ammonia as shown below. Which of the
following depicts the carbon-14 label in the product(s)?
Cl
A)
NaNH2/NH3
C)
N H2
o
and
D)
and
2
(about 50% of each)
N H2
N H2
-33 C
B)
N H2
N H2
N H2
(about 50% of each)
Organic Chemistry
EXAM 2
Name________________________
212 LSW S’04
Initials
13. Identify the methylaniline product(s) of the following reaction.
CH3
Cl
NaNH2, NH3
-33oC
A) only ortho
15.
B) ortho-and meta-
C) meta- and para
D) ortho- and para-
Which position on the potential energy diagram corresponds to the species shown for the reaction of parafluoro(trifluoromethyl)benzene with sodium methoxide?
A
F
C
CH3O
B
energy
CF3
D
rxn coord
II. Write the correct answer in the space provided.
16. (5 points) Describe a chemical test (not spectroscopic) that provides a simple method of distinguishing between
the two compounds shown below, explain what you would do and see.
C H2O H
OH
and
C H3
18. (2 points) Based on resonance theory, what is the approximate charge on the indicated carbon?
H
CH3
19. (3 points) Circle the carbon(s) where the isotopically labelled carbon atom (*) is located in the product.
OH
O
heat
3
Organic Chemistry
EXAM 2
Name________________________
212 LSW S’04
Initials
20. (3 points) What is the kinetic rate equation for the addition-elimination mechanism of nucleophilic aromatic
substitution between p-nitrochlorobenzene and sodium methoxide?
21. (3 points) Indicate all true statements about the benzyne intermediate.
(A) Benzyne is aromatic.
(B) All the hydrogens of benzyne are equivalent and indistinguishable.
(C) The benzyne molecule has strain energy.
III. Rank the following sets of chemicals as indicated, place your answer in the box provided.
22. (3 points) Rank the following three compounds in order of decreasing acidity.
NH3
A
NH3
NH3
NO2
CH3
B
C
23. (4 points) Rank the following four phenols from least acidic to most acidic.
OH
OH
OH
OH
NO2
O2N
O2N
NO2
CH3
A
B
NO2
C
D
IV. (4 points each) Indicate the major product of the following reactions.
24.
toluene and (CH3)2CHCH2Cl and AlCl3 
27.
O
Cl
OH
NaOH, H2O
4
Organic Chemistry
212 LSW S’04
EXAM 2
Name________________________
Initials
28.
OH
CO2H
NaOH (1 eq)
H2O
CH2OH
V. (5 points each) Indicate the major product of the following reactions.
29.
OH
-
+
2 HNO3
TsCl
C6H5O Na
H2SO4
pyridine
ethanol
H2/Pd
CH3
32.
NO2
Br2
(1) Fe, HCl
FeBr3
NaNO2, HCl
CuCl
o
(2) NaOH
H2O, O C
VI. (4 points each) Indicate the required reagents to complete the following transformations.
34.
O
F
Br
H3C
VII. (4 points each) CHOOSE 3 only from questions 35 through 39!!! Indicate the required reagents to
complete the following transformations.
OH
O
?
5
OH
O
Organic Chemistry
212 LSW S’04
38
EXAM 2
39)
ONa
Name________________________
Initials
OH
+ ?
heat
CO2Na
VIII. (6 points each) Indicate the required reagents to complete the following transformations.
40) make meta-bromobenzoic acid from benzene
IX. (8 points)) Using the spectroscopic evidence provided and your knowledge of reactions predict the product of
the following reaction. Explain your reasoning.
X. (8 points each) Propose a mechanisms for the reactions shown below, including all electrons, formal charges
and correct arrows to show electron flow.
45)
Br2 / FeBr3
Br
6