CHEM 31 NON-DEPARTMENTAL EXAM

1\fULTIPLE CHOICE: Write the CAPITAL LETTER ofthe best answer.

l. Which of the following statements about an sjl
hybridized carbon is TRUE?
(A) It is divalent.
(B) It fonns bonds that are linear.
(C) ft has two p orbitals.
(D) It ahvays fonns double bonds to carbon.
2. Which of the following structures docs NOT have
tetrahedral geometry around any of its central atoms?
(A)
H3C
I .--c:Hs

(B) 0
3. Which of the following statements about the molecule
r _ ..
shonn is TRUE?
(A) The geometry of N is trigonal planar.
(B) The formal charge on 0 is -1.
(C) The hybridization ofN is 8[1.
(D) The formal charge on theN is + 1.
4. What is the total charge of the following species?
CH3 1-1
I_ 1'!.
-y, -N,-CH3
:o: H
(A) +2 (B) +1 (C) 0 (D) -1
5. What type of orbital hybridization and geometry is
used by the two nitrogens in pyrimidine?

ll)
.N
pyrtmidine
(A) sp:! hybridization and trigonal planar
(B) sp
2
hybridization and tetrahedral geometry
(C) sp
3
hybridi7.ation and trigonal planar
(D) sp hybridization and linear geometry
(E) sl hybridization and bent geometry
6. How many resonance structures can be drawn for the
following species?
.

(A) i (B) 2 (C) 3 (D)4
For nos. 7-10. the choices are:
A. I and II D. III only
B. III and IV E. IV only
C. II only
()
0
0 N
I
N
"'
H I
H
H
I.
olpel1dlne
II.
1H-pyrrole
ill.
pyrrole
7. Contains N sp
3
hybrid orbitals
8. Contains a lone pair at p orbital
.. ..
0"1
I. V II. III. 0
9. Contains several interacting p orbitals
10. Contains a highs orbital character
PART ll. Refer to the anion below:
e.oX
0

H
IV. Imidazole
IV.
1. Draw the resonance structures and resonance hybrid of
the anion. (5 points)
2. Rank the resonance structures in order of increasing
energy. (4 points)
3. Wllich atom is MOST likely susceptible to
protonation? Show the protonated structure. (1 point)