1. Which labeled atom(s) in the following compound is (are) in violation of the octet rule? (3 pts)
2. Complete the following table by suppling the number of protons, electrons, neutrons, chemical symbol, and/or mass number as appropriate. (3 points)
Symbol:
52Mn2+
Protons:
Neutrons:
108
Electrons:
72 (Neutral atom)
Mass number:
52
3. Determine how many carbons in the following compound lie in the same plane: (3 pts)
4. Classify the following compounds as cis or trans structures. Write NA if the molecule cannot be classified as a sis or a trans structure. (3 pts)
5. Using the nomenclature guidelines given in class, give the correct IUPAC names for the following compounds: (6 pts)
6. Classify the following compounds as primary (1o), secondary (2o), or tertiary (3o) amines: (3 pts)
7. Classify the following compounds as primary (1o), secondary (2o), or tertiary (3o) alcohol. (3 pts)
8. Classify the labeled carbons in the following compounds as primary (1oC), secondary (2oC), or (3oC) tertiary carbons. (3 pts)
9. For the compound shown below, identify functional groups (A) – (L). (4 pts)
10. Rank the following compounds in order of increasing (lowest to highest) boiling point. (3 pts)
11. Rank the following compounds in order of increasing solubility in hexane. (3 pts)
12. Draw Lewis structures for the following compounds: (6 pts)
13. Which resonance structure in each of the following pairs is more stable? Why ? (3 pts)
14. Used curved arrows to show the movement of electrons in structures I and II only. (3 pts)
15. Determine formal charge of each labeled atom in the following structure: (3 pts)
16. Draw a condensed structural formula and a line-angle formula for the compound shown below. (3 pts)
17. Please refer to the Newman projections shown below to when answering questions (a) – (f). (6 pts)
(a) Which conformation has the greatest steric strain?
(b) Which conformation has the greater torsional strain, IV or V?
(c) Which conformation is higher in energy, II or IV?
(d) Identify two conformations with no torsional strain.
(e) Which conformation has the lowest overall energy?
(f) What is the IUPAC name of this compound?
18. Classify the following substances as nucleophiles (NU) or electrophiles (E+). (3 pts)
19. Determine the hybridization and the approximate bond angle of the labeled atom in the following molecule: (3 pts)
20. Decide which compound in each of the following pairs is more soluble in methanol. (3 pts)
21. Draw the most stable chair conformation for the compound shown below. (3 pts)
22. Rank the following compounds in order of increasing solubility in hexane: (3 pts)
23. Which conformation in each of the following pairs has the greater torsional strain? (3 pts)
24. Which conformation in each of the following pairs is more stable? (3 pts)
25. Decide which compound in each of the following pairs is more basic: (3 pts)
26. Calculate the percentage of the cyclohexane derivative that has the substituent in the axial position. (3 pts)
27. Calculate the ring strain for cycloundecane in kcal/mol. Assume for the purposes of this calculation that the strain-free value for each methylene group is -3.89 kcal/mol and that the heat of formation for this molecule is -41.4 kcal/mol. (3 pts)
28. Estimate the bond angles (B.A.) for planar cycloundecane. (3 pts)
29. Draw the form of the following compound that will predominate at pH 13. (3 pts)
30. Draw the Newman projection for all staggered and eclipsed conformers that result from the rotation (60o) about the C1-C2 bond of 1,2-dibromopentane. Identify the most stable conformer and the most unstable conformer. (6 pts)
HN
I II III
O
Cl
H
O
Br
IV V VI
Br
OH
I II III
NH
2
H
N
N
I II III
OH
HO
OH
OH
N
a
b
c
H
N
HO
O
C
O
O
a
b
c
O
O
N
SH
O
NH
O
OHO
L
d
e
f
g
h
I
J
k
I II III
OH
O
(a)
I II III
(b)
CH
2
CH
3
CH
2
CH
2
CH
2
CH
3
(c)
I II III
O
O
O
OH
O
I II III
O
O(a)
OH
I II III
O
O
O
(b)
(c)
I II III
CH
3
O
O
O
O
NO
3
PBr
3
_
(a)
(b)
(c)SiS
2
O
O
I or II
(a)
CH
3
O
CH
3
O
(b)
I or II
CH
2
O
CH
2
O
(c)
I or II
CH
2
O
CH
2
O
(a)
(b)
II III
O
O
CH
2
CH
2
(c)
NSC
S
CN
O
N
a
b
c
d
e
f
H
CSHCH
2
C
CH
3
C
S
B
a
b
c
d
e
f
g
h
HH
C
C
H
C
HC
C
H
HH
H
H
HH
CC
OH
H
C
Cl
Cl
Cl
F
CH
2
CH
3
H
CH
2
CH
2
CH
3
HH
F
HCH
2
CH
3
CH
2
CH
2
CH
3
HH
I
CH
2
CH
3
H
F
CH
2
CH
2
CH
3
HH
CH
2
CH
3
FH
CH
2
CH
2
CH
3
HH
H
F
H
3
CH
2
C
CH
2
CH
2
CH
3
HH
V
IV
III
II
I II III IV V VI
HS
H
H
HC
CH
2
H
HN
CH
3
H
HB
CH
3
H
HN
CH
2
H
OH
OS
P
CC
H
H
H
a
b
c
d
e
f
(a)
III
COOH
COOH
or
(b)
OH
OH
or
III
(c)
NH
3
+
Cl
–
or
O
III
II
OHCCH
3
CH
2
CH
2
CH
2
NH
2
CH
3
O
III
I
(a)
H
H
H
H
H
H
I or II
H
H
H
H
HH
HH
I or II
H
H
H
H
H
HH
H
HH
H
H
(b)
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Cl
O
H
N
I or II
H
3
C
CH
3
CH
3
H
3
C
(a)
(b)
CH
2
CH
2
CH
3
H
3
C
CH
3
H
3
CH
2
CH
2
C
I or II
(a)
N
H
N
I
II
or
(b)
I
II
or
NH
2
OH
Y
X
Keq = 1.74
NH
2
O
OH
pKa9.13
pKa1.84
Br
1,2-dibromopentane
Br
I II III IV
HH
ClH
ClH
Cl
V
Cl
Cl
Cl
Cl
H
H
VI
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