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Chemistry 220
Finale Examination
April 22, 2002
Name:_____________________________ ID#:______________________
Good morning! Do all the questions on this paper. You may use molecular models but
no other aids (including calculators and cheat sheets) are permitted. The point values of
the questions are shown, so budget your time accordingly. Make your answers as clear as
possible. If you change an answer, indicate clearly what is to be marked, otherwise I will
mark the first answer I find. Remember to examine your answers carefully and try to
eliminate careless mistakes. Good luck, and have a great summer!
1. Give the name or structure for the following, as appropriate (1 point each)
(a) p-chlorobenzophenone
(b)
O
N
(c) 2,4-dinitrophenol
(d)
O
O
(e) N,N-diisopropylethylamine
(f)
O
OH
(f)
phenyl benzoate
(g) N,N-dibutyl-N-ethylamine
(h)
(i)
O
OH
F
(j) 2,4-hexadiyne
2. Using the Friedel-Crafts alkylation of benzene with bromopropane, give the
mechanism of electrophilic aromatic substitution. What two complications can arise
in the alkylation reaction?(15 points)
3. Using the chemical shift table given on the next page, interpret the following NMR
spectrum. Put your answer on the blank page which follows the table. In your
answer, clearly explain how your proposed structure accounts for the observed
number of signals, coupling, chemical shift and integration. Simply drawing a
structure, even the correct one, is not sufficient.(10 points)
4.Draw the structures of the compounds A-E in the reaction sequence given below(10
points):
Br
excess NaNH2
NH3
H2O, Hg++, H+
C
B
A
Br
H2, Pd-C
O
Cl
E
D
5. Each of the reaction equations on the next page contains a question mark, which
represents a reactant, a product, or a reaction condition. For each one, replace the
question mark with the appropriate material/condition so as to make a valid reaction.
Your answers should go on the remainder of this page. Do only 8.(3 points each)
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
(j)
(a)
O
Zn (Hg), HCl
?
(b)
+
N2
Cl
?
NH2
O
O
(c)
O
Br2, NaOH, H2O
?
NH2
Na, NH3 (l)
(d)
?
(e)
O
6.
O
Br2, FeBr3
?
(f)
?
O
OH
OH
+
O
(g)
OH
O
?
+
H
O
(h)
HO
OH
O
+
?
(i)
?
H
N
(j)
?
+
H
H
N
+
Cl
6. The compound shown below is used in the preparation of hawthorne blossom
perfume (no, really, it is!). Show how you would prepare this compound from phenol
and alcohols of four carbons or fewer as your only sources of carbon, and anything
else you might need.(10 points)
O
O
7. Show how you would prepare the following compound, using benzene or toluene,
alcohols and/or amines of four carbons or less, and anything else you need. (11
points)
N
F
8. The compound shown below is used as a scent for geranium soaps. Show how this
compound could be prepared using benzene and/or toluene as your only sources of
carbon.(10 points)