1. Give the best product of the following reaction:

HBr excess

A. B. C. D. E. Br Br Br Br Br Br Br

2. What configurations are found in the product(s) of thereaction below:

A. 1R, 2R only.

B. 1S, 2S only.

C. and equal mixture of 1R, 2S and 1S, 2S.

D. and equal mixture of 1R, 2R and 1S, 2S.

E. and equal mixture of 1R, 2R and 1R, 2S.

3. Identify the most stable conformation of butane:

A. anti

B. eclipsed

C. gauche

D. totally eclipsed

E. adjacent

4. How many distinct alkene products are possible when the alkyliodide below undergoes an E2?

A. 1

B. 2

C. 3

D. 4

E. 5

5. The carbon-carbon triple bond of an alkyne is composed of________.

A. three σ bonds

B. two σ bonds and one π bond

C. one σ bond and two π bonds

D. three π bonds

6. Which of the following would have the highest boilingpoint?

A. B. C. D. E.

7. Which of the compounds have bonds that are predominantlyionic?

A. KCl

B. CF4

D. NH3

D. both A and B

E. both B and C

8. How many asymmetric centers are present in the compoundbelow?

O

9. What is the thermodynamic product of the followingreaction?

E.

Cl Cl

Cl

10. Which of the following compounds is the major product when1-hexyne is treated with excess HBr?

A. 1,1-dibromohexane

B. 1,1-dibromohexene

C. 1,2-dibromohexene

D. 1,2-dibromohexane

E. 2,2-dibromohexane

11. Give the best product for the reaction.

Br

2

A. OH B. Br C. HOD. OH E. Br

Br

Br OH BrBr

12. Give the IUPAC name for the following structure:

A. 3-chloro-2-methylcyclohexanol

OH B. 2-methyl-5-chlorocyclohexanol

C. 1-chloro-4-methylcyclohexanol

D. 5-chloro-2-methylcyclohexanol

E. 2-methyl-3-chlorocyclohexanol Cl

13. What is the major organic product of the followingreaction?

A. 2,3-dimethyl-1-hexene

B. 2,3-dimethyl-2-hexene

C. 2-isopropyl-1-pentene

D. (Z)-2,3-dimethyl-3-hexene

Br

E. (E)-2,3-dimethyl-3-hexene

14. Which of the following statements concerning SN2 reactionsof alkyl halides is not correct?

A. The rate of reaction depends on the concentration of thenucleophile.

B. The rate of reaction depends on the concentration of thealkyl halide.

C. The rate of reaction of a particular alkyl bromide depends onthe steric accessibility of the carbon of the C-Br bond.

D. All alkyl iodides react more rapidly than all alkylchlorides.

E. The rate of the reaction depends on the relativenucleophilicity of the nucleophile.

15. Which of the alkyne addition reactions below involves anenol intermediate?

A. hydroboration/oxidation

B. treatment with HgSO4 in dilute H2SO4

C. hydrogenation

D. both A and B

E. both A and C

16. Which of the following is a true statement

A. All chiral molecules possess a plane of symmetry.

B. All achiral molecules are meso.

C. All molecules which possess a single chiral center of the Sconfiguration are levorotatory.

D. A mixture of achiral compounds will be opticallyinactive.

E. All molecules which possesses two or more chiral centers willbe chiral.

17. The reagent needed to convert 2-butyne to cis-2-buteneis:

A. H2/Pt

B. H2/Lindlar's catalyst

C. Li/NH3

D. Na/NH3

E. H+/zinc dust

18. Which compounds shown below is/are the products of thisreaction:

HO-

Br heat

I. II.

A. I only.

B. II only.

C. I and II are of equal yield.

D. I is major, II is minor.

E. I is minor, II is major.

19. Which of the following structures, including formal charges,is correct for diazomethane, CH2N2?

A. B.C.D.E. +3 -3

20. Name the following compound:

OH A. 3-heptyn-6-ol

H2C N N H2C N N H2C N N H2C N N 3

CH3CH2C CCH2CHCH3 B. 3-hepten-6-ol

C. 4-hepten-2-ol

D. 4-heptyn-2-ol

E. 4-heptan-1-ol

21. Which of the following is a correct statement consideringthermodynamic vs. kinetic control of organic reactions?

A. When a reaction is under thermodynamic control, the relativeamounts of products depend on the activation energies of the stepsleading to their formation. B. The kinetic product alwayspredominates when the reaction is reversible.

C. Higher temperatures and longer reaction times typically favorthe kinetic product over the thermodynamic product.

D. When the products are in equilibrium under the reactionconditions, the relative amounts of products depend on theirstabilities, and the reaction is under thermodynamic control. E.None of the above.

22. Which of the following factors has no effect on the rate ofSN1 reactions?

A. the nature of the alkyl halide.

B. the nature of the leaving group.

C. the concentration of the alkyl halide.

D. the concentration of the nucleophile.

E. the value of the rate constant.

23. Identify the pair of compounds:

A. identical

H CH3 H Cl B. conformational isomers C C C C C. constitutionalisomers

BrCl BrCH3 D. configurational isomers

E. none of the above.

24. Choose the enantiomer of the compound below:

H

H3C CH2Cl

Cl

A. B. C. D. E.

CH2Cl CH3 Cl Cl H

H3C H ClH2C CH3

ClH HCl ClH2CH CH3 CH2Cl Cl

H3C ClH2C

25. Which of the following pairs are resonance structures?

I. CH3 CH3 II.CH3 III. CH3 CH3

and and

IV. CH3 V. CH3 CH3

and and

A. I.

B. II.

C. III.

D. IV.

E. V.

26. Provide an IUPAC name for the compound.

CH3 A. N,N,1,1-tetramethylethanamine

H3C C CH3 B. N,N-dimethyl-2-butanamine

C. N,N,2-trimethyl-1-propanamine

H3CCH3 D. N,N,2-trimethylpropanamine

E. N,N,2-trimethyl-2-propanamine

27. Consider the interaction of two hydrogen 1s atomic orbitalsof the same phase. Which of the statements below is an incorrectdescription of this interaction?

A. A sigma bonding molecular orbital is formed.

B. The molecular orbital formed is lower in energy than ahydrogen 1s atomic orbital.

C. The molecular orbital formed has a node between theatoms.

D. The molecular orbital formed is cylindricallysymmetrical.

E. A maximum of two electrons may occupy the molecular orbitalformed.

28. Give the major product for the following E1 reaction:

29. Which is the strongest acid?

A. O B. Cl O C. Cl O D. Cl O E. Cl O

Cl

OHOHOHOHOH

ClCl Cl Cl

Cl

30. Identify the compound with the highest pKa:

A. CH3NH2

B. CH3OH

C. CH3COOH

D. H2O

E. CH3NH3+

31. What is/are the product(s) of the following reaction?

HBr H2C C CHCH3 H

H2C C C CH2 H Br H3C CBr CBrHCH3 H2CBr HC CH CH3 H H

I. II. III.

A. I only.

B. II only.

C. III only.

D. I and II.

E. I and III.

32. Which of the following compounds will undergo SN2 reactionmost readily?

A. (CH3)3CCH2I

B. (CH3)3CCl

C. (CH3)2CHI

D. (CH3)2CHCH2CH2CH2Cl

E. (CH3)2CHCH2CH2CH2I

33. What is the relationship between the two structuresbelow?

A. enantiomers

B. diastereomers

C. configurational isomers

D. identical compounds

E. constitutional isomers

34. Which of the following is the staggered conformation for therotation about the C1-C2 bond in the following structure?

CH3

CH3CHCH2CH3

1 2 3 4

A. H B. CH3 C. H D. H E. H

H3CCH2CH3 H3CCH2CH3 H3CCH3 C2H5H

H

HH H3CH HH HH H3CC2H5 H H H H H

35. What reagents can best be used to accomplish the followingtransformation?

OH

A. 1. BH3 2. HO-, H2O2

B. H+, H2O

C. 1. Hg(OAc)2, H2O/THF 2. NaBH4

D. Hg(O2CCF3)2, CH3OH 2. NaBH4

E. NaOH, H2O

36. What mechanism predominates in the reaction below?

CH

CH2CH3 3OH, heat

Cl

A. SN2

B. SN1 without rearrangement

C. SN1 with rearrangment

D. E2

E. E1

37. What is the IUPAC name for the following compound?

A. 5-methylcyclohexene

B. 4-methylcyclohexene

H3CC. 1-methyl-3-cyclohexene

D. 1-methyl-4-cyclohexene

E. methylcyclohexene

38. Assuming no other changes, what is the effect of doublingonly the concentration of the alkyl halide in an SN2 reaction?

A. no change.

B. doubles the rate.

C. triples the rate.

D. quadruples the rate.

E. rate is halved.

39. Which of the following has two equatorial alkyl substituentsin the most stable conformation?

A. 1,1-dimethylcyclohexane

B. cis-1,2-dimethylcyclohexane

C. cis-1,3-diethylcyclohexane

D. cis-1,4-diethylcyclohexane

E. trans-1,3-diethylcyclohexane

40. Which of the following alkyl halides gives the fastest SN1reaction?

A. Br B. C. D. E.

Br Br

Cl

Cl

41. Which of the following alkenes yield 3-bromo-3-methylpentaneas the major product upon addition of HBr?

I. II. III. IV.

A. I and II only.

B. III only.

C. I, II, and III only.

D. All of them.

E. None of them.

42. Which of the following statements about propene, CH3CH=CH2,is correct?

A. All nine atoms lie in the same plane.

B. The compound has a cis and trans isomer.

C. It generally acts as a Lewis acid.

D. There is a total eight sigma bonds.

E. All the carbon atoms are sp2 hybridized.

43. Which of the following is the most stable carbocation?

A. B. C. D. E.

CH3 CH3 CH3 CH22

44. Which of the following statements is incorrect aboutbenzene?

A. All of the carbon atoms are sp hybridized.

B. It has delocalized electrons.

C. The carbon-carbon bond lengths are all the same.

D. The carbon-hydrogen bond lengths are all the same.

E. All twelve atoms lie in the same plane.

45. Which of the following carbocations is likely torearrange?

H3C CH3 H3C CH3 H3C CH3 H3C 2

I. II. III. IV.

A. I.

B. II.

C. III.

D. IV.

E. II and IV.

46. What is the activation energy for the reaction B --> A inthe following diagram?

A. A

B. B

C. C

D. D

E. E

47. Which of the following groups has the highest priority inthe Cahn-Ingold-Prelog rules?

A. O B. O C. D. E. O

OH OCH3 OHH O

48. Give the best product for the reaction below:

2. CH3CH2Br

A. B. C. D.

49. Name the structure:

A. (Z)-4,5-dimethyl-4-hepten-1-ol

H3CCH2CH2CH2OH B. (E)-4,5-dimethyl-4-hepten-1-ol

C. (E)-3,4-dimethyl-3-hepten-7-ol

H3CH2C CH3 D. (Z)-3,4-dimethyl-3-hepten-7-ol

E. (E)-4,5-dimethyl-4-heptenol

50. Give the major product of the following E2 elimination.

A. B. C. D. E.