CHEM 2324
Exam 2
March 25, 2014
Name:
UTEP ID:
1.-4. Predict which compound has the highest or lowest physical property. Answers may be repeated.
b.p. = boiling point, m.p. = melting point
1. Highest b.p.
2. Lowest b.p.
3. Highest m.p.
4. Lowest m.p.
O
OH
a.
OH
OH
O
b.
OH
O
c.
O
d.
5. Based on the method that we learned in class to estimate specific gravities and the following atomic weights, what
O
H3C
carboxylic acid has a density closest to that of water?
a. n = 1
b. n = 2
O
(CH2)n
c. n = 3
H
, C = 12, H = 1, O = 16
d. n = 4
e. not a.-d.
6. The correct answer of question 5 should be?
a. totally miscible (soluble) in water
b. not totally miscible in water
c. cannot be estimated
7. Given the pKow of propan-1-ol is -0.25, starting with 0.5 g of propan-1-ol in 10 mL of octan-1-ol; to nearest tenth of a
gram, how much propan-1-ol would be extracted into 30 mL of water?
a. 0.4
b. 0.3
c. 0.2
d. 0.1
e. not a.-d.
8. Given its pKa is 10, to the nearest whole number what is the pH of a 1 M solution of phenol?
a. 2
b. 4
c. 6
d. 8
e. not a.-d.
9. Given the pKas above the acids and the molarity of reagents below, to the nearest hundreds how much in molarity of
each product will be formed in the following reaction?
0.3
NO2
O
OH Li+
O2N
-
CF3
HO
NO2
a. 0.36
b. 0.47
CF3
NO2
1.0 M
c. 0.53
10. Nucleophiles are? a. donors of electrons
O
-
O Li+
O2N
O
1.0 M
0.2
NO2
d. 0.64
b. recipients of electrons
e. not a.-d.
c. neither a. or b.
d. both a. and b.
11.-15. Predict which compound is most acidic from the following pairs of compounds on the left. Answers may be
repeated.
11. SiH4 or NH3
F
Cl
F
OH or Cl
F
12.
a. the first compound
O
OH
Cl
O
b. the second compound
OH
OH
or
O
13.
O
Cl
Cl
OH
OH
or
O
O
14.
O
c. both compounds have equal acidity
d. cannot be determined
or
15.
.
16.-19. Match each reaction on the left to a reaction classification on the right. Answers may be repeated.
O
O
OH
HO
O
16.
a. addition
O
O
O
OH
17.
H
H
b. elimination
H
N
N
18.
c. substitution
Br
C
19.
d. not a.-c.
20. What is the oxidation state or number of the carbon with the bromine on it from question 19?
a. 1
b. 2
c. 3
d. 4
21. Which reaction is a net oxidation of the carbons from reactant(s) to product?
e. not a.-d.
a. reaction question 16 b. reaction question 17 c. reaction question 18 d. reaction question 19 e. not a.-d.
H
H
22. What is the stereochemistry of the following 8-methylbicyclo[4.3.0]nonane?
a. (1R, 6R)
b. (1R, 6S, 8r)
23. The compound in question 22 is?
c. (1R, 6S, 8s)
d. (1S, 6S)
e. not a.-d.
a. anti
c. exo
d. syn
e. not a.-d.
b. endo
O
24. The following compound is
?
a. E
b. Z
c. not a. or b.
If required, the Exam 2 retake homework will be due Friday, March 28, before 5 pm through http://organic.utep.edu/quiz,
no exceptions or excuses. These sheets will be available in CCSB 2.0702 after 1 pm today. Put your name on these
sheets so that you can recover your class answers. An exam file will also be available from
http://organic.utep.edu/courses/2324/exams. Expect an email from me this evening.