Organic Chemistry I Final Exam

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Organic I

Fall 2010

Final Exam
Please read each question carefully before answering. Answer the questions in ink in the spaces provided inside. If you make changes as you go, please make sure your final answer is clearly indicated. Scratch papers are available at the end. Total points = 150. You have 120 min. Good Luck! ____________________________________________________________

___________

Grading:
Q.# 1. 2. 3. 4. 5. 6. 7. Score (Max)

__________ (60 pts) __________ (18 pts) __________ (17 pts) __________ (13 pts) __________ (18 pts) __________ (12 pts) __________ (12 pts)

Total __________ (150)

Chem. 121

Final Exam Fall 2010

Name_____________________________________

1.

(3 pts each) Please circle one answer for each question.

A. The following compound is named: A. 2,2-dimethyl-4-butanol B. 2-methyl pentanol C. hexanol D. 3,3-dimethyl-butanol E. 4,4-dimethyl-pentanol B. Indicate the hybridization of all of the second row elements in the following compound. A. 1-sp2; 2-sp2; 3-sp3; 4-sp2 B. 1-sp3; 2-sp2; 3-sp3; 4-sp3 C. 1-sp; 2-sp2; 3-sp3; 4-sp3 D. 1-sp; 2-sp ; 3-sp ; 4-sp 3 2 3

OH

3 1 2 4

OH

E. 1-sp; 2-sp2; 3-sp2; 4-sp3 C. Rank the following hydrogens (1, 2, and 3) in order of increasing acidity. A. 1, 2, 3 B. 2, 3, 1 C. 3, 2, 1 D. 3, 1, 2 E. 2, 1, 3 D. Which one of the following compounds has the highest boiling point? A. (CH3CH2)3N B. CH3CHCl(CH2)4CH3 C. CH3(CH2)5CH3 D. CH3(CH2)5NH2 E. CH3(CH2)5Cl H OH

1

3

2

H

Page 2

%

Chem. 121

Final Exam Fall 2010

Name_____________________________________

E.

Consider the molecule below, the nitrogen atom can best act as a A. electrophile B. nucleophile C. base D. acid E. none of the above N

F.

Name the following compound. A. R,S-1,3-dichloro-cyclopentane B. S,S-1,3-dichloro-cyclopentane C. trans-1,3-dichloro-cyclopentane D. A and C E. B and C

Cl

Cl

G.

How many stereogenic centers are in the following molecule? A. 1 B. 2 C. 3 D. 4 E. 5

H.

The following compounds are: A. enantiomers B. diastereoisomers. C. identical. D. meso compounds. E. None of the above.

I.

Which of the following has at least one stereogenic center?

None
A B C
Page 3

D

E
%

J.

What is the correct stereochemical assignment for each of the following alkenes? A. B. C D. E. A = E; B = Z; C = E A = Z; B = E; C = E A = Z; B = Z; C = Z A = E; B = E; C = Z A = E; B = E; C = E

A

B

C

K.

The order of stability of the following conformers is (from stable at left to unstable on right): A. B. C D. E. 4,2,1,3 1,4,2,3 1,3,4,2 4,1,2,3 2,1,4,3 OH OH HO OH

1

2

3

4

L.

What is the IUPAC name of the following alcohol? A. S-2-ethyl-5,5-dimethyl-R-cyclohexanol B. R-2-ethyl-5,5-dimethyl-R-cyclohexanol C. S-2-ethyl-5,5-dimethyl-S-cyclohexanol D. S-6-ethyl-3,3-dimethyl-cyclohexane E. S-3-ethyl-R-6-S-6-dimethyl-cyclohexanol HO

M.

Predict the most likely mechanism(s) for the reaction of cis-3-methyl-chloro-cyclohexane with sodium methoxide (in methanol as the solvent) – circle one option. A. SN2 B. C. D. E. E1 SN1 E2 E2 and SN2

N.

With which reagent is cis-2-methyl-cyclopentanol most likely to undergo rearrangement? A. NaOH in protic solvent B. C. D. E. water Concentrated H2SO4 KOC(CH3)3 in aprotic solvent NaNH2 in aprotic solvent

Chem. 121

Final Exam Fall 2009

Name_____________________________________

O.

The rate equation that describes the reaction shown below is: A. k[A] B. C. D. E. k[C][D] k[B] k[A][B] k([C][D][E]/[A][B]) Br + NaOC(CH3)3 + NaBr + HOC(CH3)3

A

B

C

D

E

P.

The main product of the oxidation of the following compound with KMnO4 is:

OH OH OH

OH OH OH OH

OH

OH

OH

A
Q.

B

C

D

E

The main product of the ozonolysis of the same compound (question 1.P. above) is: O O O

A
O

O

B
O O

C
O O

D
R.

E
O

How many products (including stereoisomers) would you expect to...
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