Chemistry 262 Winter 2014 Exam 3 Practice The following practice exam contains 30 multiple choice questions, one

synthesis problem, and covers chapters 13, 14 and basic EAS. Your exam will contain 29 questions valued at 3 points/question, a synthesis problem valued at 6 points, and an unknown identification problem valued at 6 points Name _________________________________________________

1. How many bonding molecular orbitals are found in 1,3,5-hexatriene?

a. 0 b. 2 c. 3 d. 4 e. 6

2. How many non-bonding molecular orbitals are found in 1,3,5-hexatriene?

a. 0 b. 2 c. 3 d. 4 e. 6

3. What product(s) would you expect from the following reaction?

*
Cl Cl

Cl2 500oC
Cl

Cl

* I
a. I b. II c. III d. IV e. More than one of the above

* II III

* IV

4. Which of the following carbocations would be least stable?

II

III

IV

a. I b. II c. III d. IV e. V

5. Please provide the formal IUPAC name for borneol1

Name: __________________________________________ 6. Please draw the structure for (4S,6E)-4-chloronon-6-en-2-yne

7. Which of the following is a conjugated diene?

I
a. I b. II c. III d. IV e. V

II

III

IV

Harder than you will find on the exam, but you should be comfortable with basic fused ring nomenclature

8. The HOMO of 1,3-cyclopentadiene has how many electrons in its ground state?
a. 1 b. 2 c. 3 d. 4 e. 0

9. Briefly, why is benzene more stable than 1,3,5-hexatriene?

____________________________________________________________________

______________________________________________________________________________ ______________________________________________________________________________

10. Which of the following will act as dienes in a Diels-Alder (DA) reaction? a. b. c. d.

e. None of the above will act as DA dienes

11. Which of the following would produce the DA adduct shown?

H CO2CH3 CO2CH3 H

CO2CH3

CO2CH3 CO2CH3

+
CH3O2C H

+
H

II

CO2CH3

CO2CH3 CO2CH3

+
H CO2CH3

+
H

III

IV

a. I b. II c. III d. IV e. None of the above

12. Which of the following would produce the DA adduct shown?

O N COOCH3 COOCH3

O N + H3CO

O N OCH3 O + H3COOC II COOCH3 NH2 + O

III

O N + H3CO

O + OCH3 O IV V N HN O

a. I b. II c. III d. IV e. V

13. Please name the following compound

NH
2

HO

OH

Name: ____________________________________________________ 14. Please draw the structure for 3-aminoresorcinol

15. The conjugate acid of aniline has a much lower pKa that a typical alkyl amine (4.6 vs. 9.2). Please rationalize this fact in words and pictures

____________________________________________________________________

______________________________________________________________________________ ______________________________________________________________________________

16. Which reagents would act as a simple chemical test to distinguish between benzene and 1-hexene?
a. Br2 in CCl4 b. Aqueous NaOH c. AgNO3 in EtOH d. Aqueous NaHSO3 e. None of the above would distinguish benzene from 1-hexene

17. Why would 1,3-cyclohexadiene undergo dehydrogenation readily?

a. It is easily reduced b. Hydrogen is a small molecule c. 1,3-cyclohexadiene has no resonance energy d. 1,3-cyclohexadiene would gain considerable stability by becoming benzene e. 1,3-cyclohexadiene does not undergo dehydrogenation, it only forms DielsAlder adducts

18. Which dibromobenzene would yield only 1 mononitro derivative?

a. o-dibromobenzene b. m-dibromobenzene c. p-dibromobenzene d. More than one of the above e. None of the above

19. In the molecular orbital model of pyridine, how many electrons are delocalized around the ring?
a. 4 b. 5 c. 6 d. 8 e. 10

20. In the molecular orbital model of pyridine, how many electrons are in bonding molecular orbitals? a. 4 b. 5 c. 6 d. 8 e. 10

21. Which of the following statements regarding the cyclopentadienyl radical is correct? a. The cyclopentadienyl radical is aromatic b. The cyclopentadienyl radical is not aromatic c. The cyclopentadienyl radical obeys Hckels rule d. The cyclopentadienyl radical undergoes reactions characteristic of benzene e. The cyclopentadienyl radical has a closed shell of 6 -electrons 22. How many equivalent resonance structures can be written for the cyclopentadienyl anion? a. 3 b. 4 c. 5 d. 6 e. 7 23. Which of the following would you expect to have significant resonance stabilization energy?

O N

II

III

a. I b. II c. III d. II & III e. All of the above

24. Which of the following is aromatic?

N CH3

B CH3

N H

S O

I
a. I b. II c. III d. IV e. V

II

III

IV

25. Which of the following is aromatic?

O

N CH3
CH3 N

B CH3

N H

S O

II
a. I b. II c. III d. IV e. V

II

III

IV

26. Which of the following would you expect to be antiaromatic?

I
a. I b. II c. III d. IV e. V

II

III

IV

27. Which of the following is aromatic?

NH2 O O N

N H

N H

N H

II

III

IV

a. I b. II c. III d. IV e. V

28. Which of the following reactions could be used to synthesize t-butylbenzene?

H2SO4

a. C6H6 + CH2=C(CH3)2

b. C6H6 + (CH3)3COH

H2SO4

c. C6H6 + (CH3)3CCl d. All of the above e. None of the above

AlCl3

29. Which of the following would be unsuitable as an inert solvent for a FriedelCrafts reaction?
a. Chlorobenzene b. Nitrobenzene c. Acetophenone d. (Trifluoromethyl)benzene e. All of the above are unsuitable

30. A mixture of chlorobenzene (1 mol) and acetanilide (1 mol) is allowed to react with Br2 (0.5 mol) with trace FeBr3 present. What is the principal product of the competing reactions?
a. 1-bromo-4-chlorobenzene b. 1-bromo-2-chlorobenzene c. 1-bromo-3-chlorobenzene d. 4-bromoacetanilide e. 3-bromoacetanilide

Fun with synthesis: Please synthesize compound (I) from 1,3-cyclohexadiene and compound (II)

I OH

OH

O
II