CHEM 2324
May 11, 2010
Exam 4
Version A
Name:
UTEP ID #:
1.
Given that all the atoms in the square of the following structure are chiral centers, how many atoms have an (R)-configuration?
P N
Si S
O a. 0
H
C
2.
H is? a. chiral
OH
H
3.
OH and a.
equivalent
HO
OH
H are? b. enantiomers
OH
OH
OH b. 1 b. meso c. diastereomers c. 2 d. 3 c. achiral but not meso d. constitutional isomers e. 4 d. not a.-c. e. not a.-d.
4.
OH
and
O
5.
O O
and
H
H
H have the same boiling point?
H
O have the same biological activity? a. true a. true b. false b. false
6.
O O has how many diastereomers? a. 0
O b. 1 c. 2 d. 3 e. not a.-d.
H OH
HO H
7.
OH
is for sure? a. d b. D c. l d. L e. not a.-d.
8.
Given that a 4:1 mixture of enantiomers has a specific rotation of -60°, what is the specific rotation of the pure enantiomers? a.
±65° b. ±75° c. ±85° d. ±95° e. not a.-d.
9.-13. How many 13 C NMR signals does each of the following compounds have? Answers may be repeated.
9.
a.
2
10.
b. 3
11. c. 4
12. d. 5
13. e. not a.-d.

14.-18. What is the topicity relation between the hydrogens on the carbons indicated with an asterisk * in each of the following compounds? Answer may be repeated.
*
14.
* a.
equivalent
15.
* b. enantiotopic
*
16.
*
* c. diastereotopic
17.
*
*
18. d. constitutional heterotopic
*
* e. not a.-d.
19.-23. Match each set of peaks of the following 1 H NMR to the hydrogens on the carbons indicated with letters a.-e. of 5,5dichloro-6-methylheptan-3-one, shown inset.
24. Match one of the following compounds to the spectrum below. An infrared table is given on the back. a.
OH b.
N c.
O
d.
N e.
O
The Exam 4 retake homework will be due Friday, May 14, by 1:00 p.m., through http://organic.utep.edu/quiz, no excuses or exceptions! These exam sheets will be available for you to pickup after 2:00 p.m. today or during normal business hours, thereafter, from PSCI 202. A fresh copy will also be available through http://organic.utep.edu/courses/2324/exams .