CHEM 2325
July 16, 2013
Exam 1
Name:
UTEP ID:
1.-5. Starting with (R)-2-bromobutane, what would be the major product reacting with the following reagents?
means racemic mixture. Answers may be repeated.
1. Hydroiodic acid
a.
2. Hydroiodic acid with heating
b.
I
3. Potassium tertiary-butoxide with heating
c.
I
4. Sodium iodide in acetone
5. Sodium hydroxide with heating
d.
e. not a.-d.
6.-10. What mechanism is involved in reactions 1 through 5 above? Answers may be repeated.
6.
7.
8.
9.
10.
Mechanism of question 1?
Mechanism of question 2?
Mechanism of question 3?
Mechanism of question 4?
Mechanism of question 5?
a. E1
b. E2
c. SN1
d. SN2
e. not a.-d.
11.-14. Match each “rule” with its mnemonic (memory aid)? Answers may be repeated.
11.
12.
13.
14.
Anti-Markovnikov
Hoffman
Markovnikov
Saytzeff
15.-19. Match each of the reagents on the left, all reacting with
chiral products are racemic. Answers may be repeated.
a. the poor get poorer
b. the poor get richer
c. the rich get poorer
d. the rich get richer
e. not a.-d.
, to its major product on the right. Assume
HO
15. B2H6 followed by NaOOH
a.
16. H3O+
OH
b.
17. H2O, Hg2+ followed by NaBH4
OH
c.
Cl
HO
O
18.
O OH
followed by H3O+
d.
HO
19. OsO4 followed by H2S
e.
OH
OH
20. Which “rule” applies to question 3?
a. Saytzeff
b. Markovnikov
c. Hoffman
d. Anti-Markovnikov
e. not a.-d.
21.-24. Match each of the reagents on the left, all reacting with
, to its major product on the right. Assume
chiral products are racemic. The line
means that a mixture of stereocenters is possible. Answers may be
repeated.
21. HBr
Br
a.
HO
O
O
O O
22. HBr and
Br
b.
Br
23. Br2
c.
Br
24. Br2 in H2O
d.
e. not a.-d.
Br
25. The reaction of oct-4-yne with Na in ammonia followed by diiodomethane and zinc makes mostly? Assume any
necessary workup after each step.
a.
I
b.
I
c.
I
d.
I
e. not a.-d.
26. The reaction of oct-4-yne with excess hydrogen bromide makes mostly? Assume chiral products are racemic.
Br
a.
Br
b.
Br
Br
c.
Br
d.
Br
Br
e. not a.-d.
27.-29. Match each sequence of reactions on the left to a major product on the right. Answers may be repeated.
Assume any necessary workup between steps.
27. oct-4-yne reacting with H2 and Lindlar’s catalyst followed by O3/Zn
a.
28. but-1-yne reacting with dicyclohexylborane followed by NaO2H
29. but-1-yne reacting with Hg++/H2SO4/H2O
O
b.
O
c. O
d. not a.-c.
The Exam 1 retake homework is due Thursday, July 18, before 5:00 p.m. via http://organic.utep.edu/quiz. You may work
together on this homework but everyone is responsible for submitting his or her own answers via the online form and
you should not consult with anyone outside of class. Turn in your homework as long before the due date and time as
possible. No excuses for late entries!