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

PRACTICE EXAM II

Dr. Keller

CHM 2210-U02 Fall 2012 Practice Exam II, Page 2 FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry Dr. Keller 1. PRACTICE EXAM II CHM 2210-U02 Fall 2012 How are the following compounds related?
CH3 Br H CH3 Br H Br Br H CH3 CH3

The most stable conformation of 2,3dimethylpentane, viewed through the C2-C3 bond, (i.e., C2 in front, C3 in the back) is:

3.

CH3 CH3 H
a.

H
c.

CH3 CH3

CH3 CH H 3

CH2CH3

H CHCH3 CH3 CH3 CH3 H CH3

a. b. c. d. e. 4.

b.

CH3 H CH3
e.

CH H 2CH3
d.

CH3CH2 CH3 H

diastereomers enantiomers meso compounds same compound not related

CH3 CHCH3 CH3

A racemic mixture of enantiomers will rotate plane-polarized light: a. b. c. d. 0 degrees 180 degrees need more information to know. there is no such thing as a racemic mixture of enantiomers. e. none of the above

2.

Which of the following will have the same energy after undergoing a ring flip?
Cl
c.

5.

a.

HO

OH

trans-1,2-dibromocyclohexane is represented by which structure(s)?

Br Br H H H Br

b.

Br F CH2CH3
e.

HO
d.

CH3 CH3

I
H Br H Br

Br

II

CH2CH3

III

a. I b. II d. II and III

c. III e. I and II

CHM 2210-U02 Fall 2012 Practice Exam II, Page 3 6. The following Newman projection represents which molecule? 9. The following Newman projection represents which molecule?

H H CH3CH2 H CH2CH3 H

CH3 CH3CH2CH2 H CH3 CH2CH3 CH2CH2CH3

a. Pentane b. Butane c. 3-Ethylbutane d. Hexane 7. e. 3-Methylpentane

a. c. CH3 b. d. CH3

Optically pure (S)-glutamic acid has a specific rotation of +24. What specific rotation would (R)-glutamic acid of 50% optical purity have? a. +24 b. -24 +18 c. -18 d. -12 e.

e.

8.

What would be the complete name of the following?

CH3 H CH3 C CH2 Br C H CH3

a. b. c. d. e. (2R,4S)-2-Bromopentane (R)-2-Bromo-4-methylpentane (S)-4-Bromo-4-methylpentane (2R,4R)-2-Bromo-2-methylpentane (S)-2-Bromo-4-methylpentane

10. Which would be the most stable conformation of trans-1-methyl-3isopropylcyclohexane?

CH(CH3)2 H H a. CH3 CH(CH3)2 CH3 b. H H CH3 e. H CH(CH3)2 H d. H CH3 c. CH3 H CH(CH3)2 H CH(CH3)2 H

CHM 2210-U02 Fall 2012 Practice Exam II, Page 4 11. Consider the potential energy diagram below for rotation about the C2-C3 bond in pentane. The position marked A most likely corresponds to which of the following Newman projections? 13. What would be the proper name of the following molecule?
CH3 CH3 CH3 CH3 C H H

a. b. c.
H H a. H CH3 CH3 H b. H H d. H CH2CH3 CH3 H e. H H H CH3 H H H CH2CH2CH3 H c. H H H CH2CH3 CH3 H CH3 CH2CH3 H

d. e.

cis-1-t-butyl-4-methylcyclohexane trans-1-t-butyl-4-methylcyclohexane axial,equatorial-1-t-butyl-4methylcyclohexane cis-1-isopropyl-4-methylcyclohexane trans-1-isopropyl-4-methylcyclohexane

14. Which of the following statements about conformations of methylcyclohexane is true?

CH3

CH3

12. Although five- and six-membered rings are generally the most stable, why is cyclopentane somewhat less stable than cyclohexane? a. b. c. d. e. The angles in cyclopentane deviate significantly from the tetrahedral angle. Five-membered rings have diaxial interactions. Five-membered rings have hydrogen atoms that eclipse one another. Planar cyclohexane has bond angles closer to 109. Larger rings are always more stable than smaller rings.

a. There is not enough energy at room temperature to allow these conformations to interconvert. b. The two conformations are in equilibrium and are present in equal amounts at room temperature. c. The two conformations are not in equilibrium but are present in equal amounts at room temperature. d. The two conformations are in equilibrium but are not present in equal amounts at room temperature. e. The two conformations are not in equilibrium and are not present in equal amounts at room temperature.

CHM 2210-U02 Fall 2012 Practice Exam II, Page 5 15. Which of the following structures represent cis-1,4-dimethylcyclohexane?
H CH3 H H CH3 H CH3

18. How would you most accurately describe the relationship between the following two molecules?
CH3 H H H F OH I CH3 I HO F CH3 H H H CH3

I
H CH3

II

CH3

III
a. I and II b. I and III

CH3

a. b. c. d. e.

enantiomers diastereomers meso compounds they are the same compound both b and c

c. II and II 19. How are the following compounds related?

d. all of the above

e. none of the above

COOH C HO HO H C H COOH C H OH C OH

16. The following two molecules may be described as:

COOH

COOH

a. constitutional isomers c. enantiomers b. diastereomers d. conformations e. none of the above. 17. What R or S stereochemistry is proper for the following molecule?
H
1

a. b. c. d. e.

diastereomers enantiomers meso compounds they are the same compound they are not related at all

20. How many chirality centers are present in the following molecule?
3

C H

Br

CH3 2 C Cl

H
5

CH3

CH2CH3
4

H
a. (2R,3R) c. (2S,3S) b. (2R,3S) d. (2S,3R) e. none of the above. a. none

H
d. three e. four

b. one c. two

CHM 2210-U02 Fall 2012 Practice Exam II, Page 6 21. An unknown compound has been isolated in pure form and found to exhibit a [] = +15. Which of the following might be the structure of the compound:
H H a. c. H CH3 H

23. Which of the following is not true for a meso compound? a. b. c. d. e. It is achiral It will rotate plane polarized light. It may be cyclic or acyclic. It is a stereoisomer. It possesses a plane of symmetry.

CH3 CH3 CH3 b. H CH3 d. CH3

24.

Select the reagents necessary to convert cyclopentene into cyclopentane. a. b. c. d. e. H2 and Pd H2 O Heat + Zn and H3O Light

CH3 H CH3
OH e. OH

25.

Which of the following statements is not true? a. b. c. Enantiomers have identical properties except in chiral environments or with plane polarized light. Reactions involving achiral materials must produce either achiral or racemic products. Diastereomers may have different properties, but always rotate plane polarized light. Enantiomers always exhibit equal and opposite optical rotations. All of the above are true.

22. Which of the following molecules represents a meso compound?

Br CH3 c. CH3 C H Br b. Br CO2H H e. HO OH H CO2H d. Br CH3 C Br H

d. e.

a.

26. 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

CHM 2210-U02 Fall 2012 Practice Exam II, Page 7 27. How many chirality centers are there in Lovastatin ( Mevacor : a cholesterollowering drug)? 29. What would be the major product of the following reaction?

HO O O

CH3
O

C CH3CH2

H Br

Na

CN

DMSO

CH3 a.
Lovastatin

CH3 H CN c. CH3CH2 C CN H

CH3CH2

a. b. c. d. e. 28.

4 5 6 7 8 Which of the following molecules has (have) the S configuration?

H F Br H (CH3)3C

CH3 C b. CH3CH2 N C H d.

CH3 C N C H

CH3CH2 CH3 C H

e. CH3CH

CH3

30. Which of the following would you expect to react fastest with the nucleophile I (iodide)?

I
Cl Et Me iPr Ph H

II

a. CH3CH2CH2Br b. CH3CH2CH2Cl
O C H

c. (CH3)2CHCH2Br d. (CH3)2CHCH2Cl e. (CH3)3CCH2Br

III
a. b. c. d. e. I and II I and III III and IV I, II, and IV They are all S.

IV

CHM 2210-U02 Fall 2012 Practice Exam II, Page 8 31. Arrange the following in order of increasing nucleophilicity (increasing left to right) 34. Which of the following statements is (are) not true of an SN1 reaction: a. b. c. d. follows a first order rate law typically is stereospecific the slowest step is the rate-determining step the carbocation intermediate adopts a trigonal planar geometry e. all of the above

NH2

NH3

OH

H2O

NH4

a. b. c. d.

NH4 NH4 NH2 NH4

H2O OH OH NH3 H2O

OH NH2 NH3 H2O NH3

NH3 H2O H2O NH2 OH

NH2 NH3 NH4 OH NH2

35. Predict the major product of the following SN1 reaction>

e. NH 4

Br Ph

CH3CH2OH 25

32. The major product of the following reaction conditions will result from which mechanism:
CH3CH2 CH3 Br CH3OH

CH3CH2O Ph a. c. Ph

Ph

?
Ph OCH2CH3 d. CH3CH2O Ph e. (racemic)

a. SN2

b. SN1

b.

e. There is no way to know.

33. Which of the following is not normally a good leaving group? a. b. c. d. e. Br OCH3 Cl OSO2R I
-

36. Which of the following can be used to synthesize (R)-2-cyanopentane from (R)-2-bromopentane? a. NaBr b. NaCN c. NaCN, then HI d. NaI followed by KCN e. This reaction cannot occur.

CHM 2210-U02 Fall 2012 Practice Exam II, Page 9 37. The SN2 substitution of secondary halides is often complicated by E2 elimination. Which of the nucleophiles below would you choose to get the highest yield in an SN2reaction with menthyl bromide? 40. If the alkyl halide in each of these reactions was an alkyl chloride instead of the bromide,
OH, H2O

CH3CH2CH2Br

CH3CH2CH2OH

Br

SH, RSH CH3CH2CH2Br

CH3CH2CH2SH

Br

Nu Br SN2 Nu

Menthyl Bromide

a. the reaction rate would decrease. b. a better leaving group would be involved. c. the activation energy would be decreased. d. two of the above would be true. e. all of the above would be true.

a. CH3O _ Na
-

+ +

c. (CH3)3N d. (CH3)3CO K
+ +

b. CH3CO2 Na

e. CH3CH2S Na

Consider the pair of reactions below to answer the next 4 questions:

38. The least reactive compound in an SN2 reaction would be.

!

Br

KI acetone
KI acetone

+ KBr

Br

+ KBr

II

III

IV

a. I

b. II

c. III

d. IV

41. The alkyl bromide starting materials in these reactions are classified as: a. 3 b. 2 c. 1 d. 4

e. They would all have the same reactivity. 39. The best nucleophile in a substitution reaction at a primary carbon would be:

!
I II III IV

42. The solvent in these reactions is: a. nonpolar aprotic b. polar aprotic c. polar protic d. nonpolar protic

a. I

b. II

c. III

d. IV

e. They would all have the same reactivity.

CHM 2210-U02 Fall 2012 Practice Exam II, Page 10 43. The nucleophile in these reactions is: a. K+ b. alkyl group c. Brd. I44. The mechanism for these reactions is: a. SN1 b. SN2 c. Either mechanism, depending on reaction conditions d. Cant tell from the information given.