Free Printable Organic II Review

1.

What type of reaction is this?

a)

nucleophilic addtion

b)

nucleophilic substitution

c)

electrophilic addition

d)

electrophilic substitution

2.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

3.

Which substituents would deactivate benzene toward electrophilic aromatic substitution reactions?

a)

I, II, III

b)

I and II only

c)

I and III only

d)

II only

4.

Which reagents would be best for this transformation?

a)

Cl₂ with FeCl₃

b)

Cl₂ in CCl4

c)

Cl₂ with UV light

d)

NaCl with H₂SO₄

5.

Which is the best description for the mechanism of this reaction?

a)

It takes place in one step with no ionic intermediate

b)

It takes place in two steps: elimination, then addition

c)

It takes place in two steps: addition, then elimination

d)

It takes place in three steps and involves a carbocation intermediate

6.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

7.

Which intermediate shows why halogens are ortho/para directors?

a)

A

b)

B

c)

C

d)

D

8.

What is the main product of this reaction?

a)

A

b)

B

c)

C

d)

D

9.

Which structure is an intermediate in this reaction?

a)

A

b)

B

c)

C

d)

D

10.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

11.

Which radical is least stable?

a)

A

b)

B

c)

C

d)

D

12.

Which structure is an intermediate in this reaction?

a)

A

b)

B

c)

C

d)

D

13.

Which reaction is the best way to give the indicated product?

a)

A

b)

B

c)

C

d)

D

14.

At which of the indicated positions would the bromine radical react at the fastest rate?

a)

A

b)

B

c)

C

d)

D

15.

What is the best reagent for this transformation?

a)

A

b)

B

c)

C

d)

D

16.

Which reagents would best accomplish this transformation?

a)

A

b)

B

c)

C

d)

D

17.

Which diol is cleaved by periodic acid?

a)

A

b)

B

c)

C

d)

D

18.

Which conditions are best for the following transformation?

a)

A

b)

B

c)

C

d)

D

19.

What is the product of the reaction?

a)

A

b)

B

c)

C

d)

D

20.

What are the best conditions for this reaction?

a)

A

b)

B

c)

C

d)

D

21.

Which conditions would best accomplish this conversion?

a)

A

b)

B

c)

C

d)

D

22.

Which compound matches best with the IR spectrum below?

a)

A

b)

B

c)

C

d)

D

23.

Which structure is most consistent with this IR spectrum?

a)

A

b)

B

c)

C

d)

D

24.

a)

A

b)

B

c)

C

d)

D

25.

How many different NMR signals would be expected for the following compound?

a)

3

b)

4

c)

5

d)

6

26.

Which compound is consistent with this NMR spectrum?

a)

A

b)

B

c)

C

d)

D

27.

Which compound is consistent with this IR spectrum?

a)

A

b)

B

c)

C

d)

D

28.

For an S_N2 reaction, what happens when the concentration of the nucleophile is cut in half and the concentration of the substrate is doubled?

a)

no change in rate of reaction

b)

reaction speeds up by 2x

c)

reaction slows down by 2x

d)

reaction speeds up by 4x

29.

What is the product of the following reaction?

a)

A

b)

B

c)

C

d)

D

30.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

31.

What is the product of the following reaction?

a)

A

b)

B

c)

C

d)

D

32.

What would the major product of the E2 reaction (dehydrohalogenation) of 2-chloropentane by KOH?

a)

A

b)

B

c)

C

d)

D

33.

Which of the following is the weakest nucleophile?

a)

A

b)

B

c)

C

d)

D

34.

Which reaction would produce phenyl propyl ether?

a)

A

b)

B

c)

C

d)

D

35.

Which two compounds would generate the same carbocation?

a)

1 and 2

b)

1 and 4

c)

2 and 3

d)

3 and 4

36.

What type of intermediate is involved in the following reaction?

a)

A

b)

B

c)

C

d)

D

37.

What is the major product of the reaction below?

a)

A

b)

B

c)

C

d)

D

38.

What is the major product of this reaction?

a)

A

b)

B

c)

C

d)

D

39.

What is the major product of the reaction of 1-butene with Br₂ in Ethanol?

a)

A

b)

B

c)

C

d)

D

40.

What is the major product of the Diels-Alder reaction shown?

a)

A

b)

B

c)

C

d)

D

41.

What is the best reagent for this transformation?

a)

A

b)

B

c)

C

d)

D

42.

What are the best conditions for this transformation?

a)

A

b)

B

c)

C

d)

D

43.

What is the major kinetic product of this reaction?

a)

A

b)

B

c)

C

d)

D

44.

What is the major product of the following reaction?

a)

A

b)

B

c)

C

d)

D

45.

What is the major product of this reaction?

a)

A

b)

B

c)

C

d)

D

46.

What is the major product of the following reaction?

a)

A

b)

B

c)

C

d)

D

47.

The reaction shown is best classified as

a)

a nucleophilic substitution

b)

an electrophilic subsitution

c)

a nucleophilic addition

d)

an electrophilic addition

48.

What are the best conditions for this conversion?

a)

D₂O, with HCl as catalyst

b)

NaBD₄ in EtOH with an aqueous workup

c)

NaOD in CH₃H₂OD with an aqueous workup

d)

D₂O₂ in Acetic Acid

49.

Which reagent will give the product shown?

a)

CH₃I

b)

CH₃Li

c)

CH₃MgBr

d)

(CH₃)₂CuLi

50.

What is the product of this reaction sequence?

a)

A

b)

B

c)

C

d)

D

51.

What is the major product of this reaction?

a)

A

b)

B

c)

C

d)

D

52.

What is a reasonable intermediate for this reaction?

a)

A

b)

B

c)

C

d)

D

53.

What are the best conditions for this transformation?

a)

A

b)

B

c)

C

d)

D

54.

What are the best conditions for this transformation?

a)

A

b)

B

c)

C

d)

D

55.

What is the product of this reaction sequence?

a)

A

b)

B

c)

C

d)

D

56.

Which would be hydrolyzed most slowly with aqueous NaOH?

a)

A

b)

B

c)

C

d)

D

57.

What is the product formed from this reaction?

a)

A

b)

B

c)

C

d)

D

58.

What are the products of this reaction?

a)

A

b)

B

c)

C

d)

D

59.

Which reaction sequence would best accomplish this transformation?

a)

A

b)

B

c)

C

d)

D

60.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

61.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

62.

Which reagents would accomplish this transformation?

a)

A

b)

B

c)

C

d)

d

63.

An aldol reaction can produce an addition product or a further dehydration product. What factor favors the formation of the dehydrated product?

a)

excess aldehyde

b)

excess base

c)

no α-hydrogen atoms

d)

stabilization by conjugation

64.

Which of these will not undergo the haloform reaction (iodoform test)?

a)

A

b)

B

c)

C

d)

D

65.

If this carboxylic acid is heated, which carboxyl group will easily be lost as carbon dioxide?

a)

A

b)

B

c)

C

d)

D

66.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

67.

What is the product of this reaction?

a)

A

b)

B

c)

C

d)

D

68.

What is the IUPAC name for this compound?

a)

1-methyl-4-ethyl-1-pentanol

b)

1,4-dimethyl-1-hexanol

c)

3-methyl-6-heptanol

d)

5-methyl-2-heptanol

69.

What is the IUPAC name for this compound?

a)

3,3,6-trimethyloctane

b)

3,6,6-trimethyloctane

c)

2-ethyl-5,5-dimethylheptane

d)

6-ethyl-3,3-dimethylheptane

70.

What is the IUPAC name of this compound?

a)

(E)-3-ethyl-5-methyl-2-hexene

b)

(Z)-3-ethyl-5-methyl-2-hexene

c)

(Z)-2-ethyl-1-methyl-2-isobutylethylene

d)

(E)-2-methyl-4-ethyl-hexene

71.

Which compound is (E)-1,2-dibromo-2-pentene?

a)

A

b)

B

c)

C

d)

D

72.

Which of the molecules below contain amide, ketone, ester, and ether functional groups?

a)

A

b)

B

c)

C

d)

D

73.

Which structure would have bromine assigned a formal charge of +2?

a)

A

b)

B

c)

C

d)

D

74.

What are the hybridizations of the atoms labeled 1-4?

a)

A

b)

B

c)

C

d)

D

75.

What hybrid orbitals are used to form the sigma bond between the atoms labeled 1 and 2, respectively?

a)

sp and sp³

b)

sp² and sp³

c)

sp and sp²

d)

sp² and sp

76.

Which structure is equivalent to the condensed formula (CH₃)₂CH(CH₂)₄Br?

a)

A

b)

B

c)

C

d)

D

77.

Which carbocation is the most stable?

a)

A

b)

B

c)

C

d)

D

78.

What factor is responsible for a greater heat of combustion per CH₂ for cyclobutane than the heat of combustion per CH₂ for cyclohexane?

a)

Cyclohexane has a different hydrogen-to-carbon atom ratio than cyclobutane

b)

Cyclohexane is a strained ring relative to cyclobutane

c)

Cyclobutane is a strained ring relative to cyclohexane

d)

Cyclohexane has more carbon atoms than cyclopropane

79.

Which pair consists of resonance structures?

a)

A

b)

B

c)

C

d)

D

80.

Which is the weakest base?

a)

A

b)

B

c)

C

d)

D

81.

For which carbocation can the most resonance forms be written that show the delocalization of the carbocation?

a)

A

b)

B

c)

C

d)

D

82.

What is the correct order of acid strength from WEAKEST acid to STRONGEST acid?

a)

1 < 2 < 3 < 4

b)

1 < 3 < 2 < 4

c)

4 < 2 < 3 < 1

d)

4 < 3 < 2 < 1

83.

What is the correct order of acidity from strongest to weakest?

a)

4 > 1 > 3 > 2

b)

2 > 3 > 1 > 4

c)

1 > 2 > 3 > 4

d)

2 > 3 > 4 > 1

84.

Which carboxylate is the strongest base?

a)

A

b)

B

c)

C

d)

D

85.

Which of the indicated protons have the smallest pKa value?

a)

A

b)

B

c)

C

d)

D

86.

Which statement about the acids shown are correct?

a)

1 is most acidic; 3 is least

b)

1 is most acidic; 2 is least

c)

2 is most acidic; 3 is least

d)

3 is most acidic; 2 is least

87.

Which of these compounds is most acidic?

a)

A

b)

B

c)

C

d)

D

88.

Which property of the two enantiomers of 1-phenylethanethiol would you expect to be different, even though it would be challenging to measure?

a)

melting point

b)

boiling point

c)

density

d)

strength of interaction with L-Tyrosine

89.

Which of the indicated carbons is a stereocenter?

a)

A

b)

B

c)

C

d)

D

90.

What would be stereochemical classification of the major product of this reaction?

a)

R-enantiomer

b)

S-enantiomer

c)

achiral

d)

racemic

91.

Which of these molecules are meso isomers?

a)

A only

b)

A and C only

c)

A and B only

d)

B and C only

92.

Which statement is true?

a)

Compounds with R stereocenters always rotate plane-polarized light counterclockwise

b)

All other things being equal, solutions of R and S enantiomers rotate plane-polarized light equally, but in opposite directions

c)

Racemic mixtures can rotate plane-polarized light either clockwise or counterclockwise.

d)

Meso compounds can rotate plane-polorized light either clockwise or counterclockwise depending on the size of the compound.

93.

Upon hydrogenation with H₂/Pt, which product would be a racemic mixture?

a)

A

b)

B

c)

C

d)

D

94.

Which reaction would give a meso product?

a)

A

b)

B

c)

C

d)

D

95.

How many stereocenters does the following molecule have?

a)

1

b)

2

c)

3

d)

4

Organic II Review

Total questions: 95

Worksheet time: 3hrs 10mins

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