CHEM 2322/2325
Exam 2
Version A
Name:
March 21, 2016
UTEP ID #:
If required, the Exam 2 retake homework will be due Thursday, March 24, 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/2325/exams. Expect an email from me this evening.
1. How many ones are in the adjacency matrix of
a. 2
b. 4
?
c. 6
d. 8
e. not a.-d.
c. x4-3x2+1
d. x4-4x2+1
e. not a.-d.
c. both a. and b.
d. not a.-c.
2. What is the determinate of the adjacency matrix of buta-1,3-diene?
a. x4-x2+1
b. x4-2x2+1
3. 6-methylhepta-2,3,5-triene can be?
a. E or Z
b. R or S
4. Which is the pi-energy diagram of cyclopentadiene,
a.
b.
?
c.
d.
e. not a.-d.
d.
e.
5. Which compound has the longest wavelength of absorption?
a.
b.
c.
6. Which compound will give off the second least amount of energy when combusted?
a.
b.
c.
d.
e.
7. Ignoring stereochemistry, what is the major product of the following reaction?
a.
b.
8.
a.
c.
d.
e. not a.-d.
? (Major product, assume chiral products are racemic)
b.
9. What is the major product of
c.
d.
e. not a.-d.
given that chiral products are racemic?
a.
b.
c.
d.
e. not a.-d.
10.-14. Classify the compounds below as: (Answers may be repeated.)
a. aromatic
b. anti-aromatic
10.
11.
c. non-aromatic
12.
d. not a.-c.
13.
14.
(anion)
15. Given the following 3 different resonance structures, what is the longest bond in the overall structure?
16. Which compound would react slowest with HNO3/H2SO4?
a.
b.
c.
d.
e.
17. What position is most likely to be substituted by reacting with Cl2/FeCl3?
18.-22. Starting with benzene, what is the major product of each reaction sequence? Answer may be repeated.
18.
/AlCl3, Cl2/FeCl3, H2NNH2/-OH
19. Cl2/FeCl3,
20.
/AlCl3
b.
/AlCl3, HS(CH2)2SH/H+, H2/Ni, Cl2/FeCl3
21. HNO3/H2SO4,
22.
a.
c.
/AlCl3, H2/Pd, NaNO2/HCl, CuCl
/AlCl3, Zn/HCl, H2SO4, Cl2/FeCl3, H2O
d.
e. not a.-d.
23. Overall this reaction is what type of substitution?
a. benzyne
b. electrophilic aromatic
c. nucleophilic aromatic
d. radical
e. SN1
Do not forget to put your name, ID, and version letter (A or B) on your scantron, and your name and ID on your exam
sheets.