FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry & Biochemistry CHM 2210-U02 ORGANIC CHEMISTRY I Fall 2012

PRACTICE EXAM III

Dr. Keller

Practice Exam IV, Page 2

FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry PRACTICE EXAM IV CHM 2210-U01 Fall 2011

CHM 2210-U02, Fall 2012 Dr. Keller PRACTICE EXAM III, Page 2

1.

What is the major product of the following reaction?

H2O H+

3.

What is the major product from this sequence of reactions?

1. B2H6 2. H2O2/HO-/H2O

a. OH b. OH

c. OH

a. OH c.

b.

OH

d. OH OH e. OH
d. OH

OH e. OH (both cis and trans)

4.

What is the major product from this reaction?

2.

What is the major product of the following reaction?

Cl2
HCl

H2O Cl a. c. OH Cl b. d. OH OH OH OH OH

a. Cl

b. Cl

c. Cl

d. Cl

e.

Cl

CHM 2210-U02, Fall 2012 PRACTICE EXAM III, Page 3 CHM 2210-U01, Fall 2011
Practice Exam IV, Page 3 5. The following sets of reactions involve first an addition, then an elimination. Which sequence of events explains the formation of the product?

8.

Which of the following carbocations is likely to rearrange?

CH3 CH3 CH3 CH3

Ph C C H

H Ph

Br2

CH3CH2O Na

Ph C C Br

Ph H

I CH3 CH3

II CH3 CH2

a. b c. d.

An anti addition, then a syn elimination. A syn addition, then a syn elimination. An anti addition, then an anti elimination. A syn addition, then an anti elimination.

III

IV

6.

Which alkene reaction(s) proceed(s) with anti addition? a. b. c. d. e. acid-catalyzed hydration chlorination hydroboration-oxidation both a and b both b and c 9.

a. I d. IV

b. II c. III e. both III and IV

7.

What is the major organic product from the following?

H3PO4/! OH

Which statement is true concerning the formation of alcohols by the hydroboration method? a. Overall, the process results in syn addition and anti-Markovnikov orientation. b. Overall, the process results in anti addition and anti-Markovnikov orientation. c. Overall, the process results in syn addition and Markovnikov orientation. d. Overall, the process results in anti addition and Markovnikov orientation. e. The stereochemistry and orientation are unpredictable.

10. Which reagents would be appropriate for this chemical transformation:

H OH CH2

a.

b.

c.

CH3

CH3

CH CH3

CH3 CH3

CH3 CH3

d.

e. OPO3H2

a. b. c. d. e.

H2O, H2SO4 BH3, then H2O2, HO Hg(OAc)2, H2O, then NaBH4 NaBH4, CH3OH KOH, H2O

CHM 2210-U02, Fall 2012 CHM 2210-U01, Fall PRACTICE EXAM III,2011 2011 CHM 2210-U01, Fall Page 4 Practice Exam IV, Practice Exam IV, Page 4 Page 4
11. is the is the major product of the 13. Addition of bromine to E-3-hexene will 11. Which Whichmajor product of the base- base13. Addition of bromine to E-3-hexene will give give induced elimination from meso-2,3induced elimination of HBrof HBr from meso-2,3dibromobutane? dibromobutane?
Br C H CH3

Br Br

Br

C C C H H H CH3 CH CH3 3
Br

HCH2CHCH2CH3 Br2 3 C C C C H CH3CHCH3CH2H 2

H

Br2

Br H C H H C CH3

a. onea. one meso compound meso compound b. oneb. one enantiomers pair of pair of enantiomers c. twoc. two meso compounds meso compounds

CH3 a. H

CH3 3 CH3 CH3CH CH3CH CH H C a. C C C c. c. C C C H Br CH3 Br C

CH H 3

Br Br
d.

H CH3 d.C H

H H CH3 H
C C CH H 3

CH3 b. H

d. four stereoisomers d. four stereoisomers

14. What major product(s) is (are) is (are) expected from 14. What major product(s) expected from the reaction shown below? below? the reaction shown
HBr HBr ? CH3 (excess)(excess)

Cb. C C

CH3

12. What is the major product from the following 12. What is the major product from the following series of reactions? series of reactions?
1. Cl2 1. Cl2 CH CH2 CH2 CH 2. 2NaNH2 2. 2NaNH2 3. H2O3. H2O

CH3

C 3 C 3 CH C CH C

?
Br Br

H a. C a. CH3 Br b.

H Br
C C CH CH3 3

Br C c. CH3 Br

Br H CH3 3 CH H Br

H c. H C C Br C C CH3 Br

CH3 H

Br Br

a.

a.

c. C CHCl CHCl C H H

c.

C Cl

CHC 2

CH2

Cl

b. C C C C d. CH3 CH3 3 CH3 CH

H d. C H C C Br C Br CH3 CH3 3 CH3 CH

e. moree. more than one of the above than one of the above

b.

b.

C H

CHNHCHNH C 2 d. 2

d.

CHC 2

H
C CH C

NH2

NH2

15. 15. the Index of Hydrogen Deficiency in CH2 What isWhat is the Index of Hydrogen Deficiency in the following molecule? the following molecule? C14H13F314H13F3N2O C N2 O

e.

e.

CH

a. b. c. d. e.

a. b. c. d. e.

3 5 7 8 10

3 5 7 8 10

CHM 2210-U02, Fall 2012 CHM 2210-U01, Fall 2011 PRACTICE EXAM III, Page 5 Practice Exam IV, Page 5
16. Indicate the expected major product of the following reaction: 18. Which of the following rearrangements would you not expect the carbocation below to undergo to any significant extent?

Cl CH3 CH3

NaOEt

OEt a. CH3 CH3 c.

CH3 CH3

a.

b.

c.

CH3 b. CH3 d.

CH3 OEt CH3

d. Two of the above would not occur to a significant extent. e. All of the above would be significant.

e.

CH2 CH3

19. Which of the following structures represents (Z)-3-fluoro-3-octen-2,5-diol?

17. Predict the product of the following reaction:

CH2CH3 CH3

HO HO OH F H HO a. c. HO F OH d. H HO H e. H F H OH

H2/Pt

CH2CH3 a. CH3 CH2CH3 b. CH3 e. Equal amounts of a and b d. c.

CH2CH3 CH3

F b. HO

CH2CH3 CH3

HO

CHM 2210-U02, Fall 2012 CHM 2210-U01, Fall 2011 PRACTICE EXAM III, Page 6
Practice Exam IV, Page 6 20. Which of the reagents below would best accomplish the following transformation? 22. A chiral compound, C5H8, upon catalytic hydrogenation yields an achiral compound. What is the IUPAC name of the former? a. b. c. d. e. 1-Methylcyclobutene 3-Methylcyclobutene 1,2-Dimethylcyclopropene Cyclopentene None of the above

OH

OH

a. b. c. d. e.

H2O/H O3, then Zn/HOAc cold, dilute KMnO4 OsO4, then NaHSO3 More than one of the above.

23. Which of the following starting materials is most likely to give the product shown under the given reaction conditions?
O

?
21. What would be the major organic product of the following reaction?
a.

1. O3 2. (CH3)2S

10
O

CH3 H HCl H3C C C CH3 CH2 CH3 H CH3 C

a.

c.

?
b.
Cl H

d.

C CH2Cl

CH3 C
c.

C CH3

CH3 H CH3 Cl

CH3 CH3 ClCH2 H C CH3

e.

CH3 C
b.

C CH3

CH3 C
d.

CH3 H

CH3 H

e. CH3

CH3 Cl C C CH2Cl CH3 H

24. Based on your knowledge of the mechanisms of addition reactions, which of the reagents would you expect to accomplish the following reaction?(think through the mechanism!)
CH3

?
OH O

a. H2/Pd + d. H

b. Br2 c. Cold KMnO4 e. CH2N2/light

CHM 2210-U02, Fall 2012 CHM 2210-U01, Fall Page PRACTICE EXAM III,2011 7
Practice Exam IV, Page 7 25. Reaction with ozone, followed by treatment with Zn/HOAc, of which of the following would not yield any CH3CHO? H CH3 CH3 CH3 C C C C a. c. H CH3 H CH3 28. What is the major product expected from the following reaction sequence?
C C H
1. NaNH2 2. CH3CH2I 3. Lindlar's catalyst/H2

H d.

H C C CH3

CH3
a.

CH2CH3 c.

b. C C CH3 CH3

H
b. d.

e. Both b and d

26. Which of the following are (Z) isomers?

CH3 Cl CH3 H Br CH3 CO2H CH3 H CH3
5

e.

H CH3 CH3 Ph CHO CO2H

N(CH3)2 CH3 CO2H H

29. What would be the product of the following reaction?

CH3 C H C CH3 Br C C CH3 Br H C H d. CH3 CH3 H e. C C CH2Br H CH3 c. H

Br2

a. 1 & 5 b. 2 & 5 c. 3 & 5 d. 2 & 3 e. 2,4 & 5

H Br CH C CH3 Br C Br H C H CH2 H

27. Which reagent would you expect to best accomplish the following reaction?
OH

a.

CH3 Br C CH3 b.

a. b. c. d. e.

BH3 then H2O2/HO Hg(OAc)2 then NaBH4 H2O/H+ KMnO4/H2O, cold More than one of the above.

CH3

CHM 2210-U02, Fall 2012 CHM 2210-U01, Fall 2011 PRACTICE EXAMPagePage 8 Practice Exam IV, III, 8

30. What reagent(s) might cause the following conversion:

33. Predict the product of the following reaction:

?
CH3 H CH3

OH H

H Ph C

H CH3

C Br

Ph

NaNH2

a. b. c. d. e.

Hg(OAc)2/H2O/THF; then NaBH4 H2/Lindlars catalyst conc. H2SO4; then H2O/heat B2H6; then H2O2/NaOH Br2/H2O

H a. Ph C

Ph c.

Ph C H Ph d. H C C C

Ph

CH3 NH2

CH3 CH3

Ph

31. Which of the following alkenes of the formula C5H10 would you expect to be the most stable?
a. c.

b. Ph

NH2

CH3 H e. No reaction

Ph

34. What reagent(s) would be required to accomplish this process:

b.

d.

?
C CH3CH2

CH2CH3 C

e.

32. What reagent(s) would be required to accomplish the following transformation:

a. HBr, then NaOH b. NaNH2 c. d. e.

Br2, then excess Br2, then NaOH + catalytic H NaNH2, then H2O

?
C C CH3 C H

H C CH3

35. What is the Index of Hydrogen Deficiency for the following molecule?

a. b. c. d. e.

H2/Pt H2/Lindlars catalyst Li in liq. NH3 NaBH4 None of these would work.

HO

a. 2

b. 3

c. 5

d. 6

e. 7