Both bonding electrons remain with one product fragment in this kind of reaction.33%

33%

10%

19%

5%

1. Homolytic bond cleavage

2. Heterolytic bond cleavage

3. Radical reaction

4. More than one of the above is true

5. None of the above

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

Which of the following is not a Lewis base?

N

OCH3OH BCl3

(a) (b) (c) (d)

33%

29%

5%

33%

1. A

2. B

3. C

4. D

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

Which of the following statements is not true about free radical halogenation of alkanes?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

0%

10%

57%

33%

1. Bromination is more selective than chlorination.

2. Chlorination under thermal conditions (with heat) gives a statistical product mixture.

3. Halogenation is more likely to occur at less sterically hindered positions.

4. Hyperconjugation of the radical intermediates helps explain preferred reactivity.

The compound shown:

19%

5%0%

67%

10% 1

2

3

4

5

1. Has R stereochemistry.

2. Has S stereochemistry.

3. Is dextrorotatory.

4. Is levorotatory.

5. It cannot be determined without taking the sample into the lab and measuring it.

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

Which is the most effective method to accomplish the transformation shown?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

OH

0%

38%

57%

5%

1. H3O+

2. (1) Hg(OAc)2, H2O; (2) NaBH4

3. (1) BH3, ether; (2) H2O2, H2O, -OH

4. Any of the above methods will work equally well.

(S)-(-)-Serine

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

5%

0%

90%

5%

1. is racemic.

2. rotates plane polarized light in a clockwise direction.

3. rotates plane polarized light in a counterclockwise direction.

4. is dextrorotatory.

Which of the following intermediates best explains the regiochemistry of the reaction shown?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

HBr, peroxides

. .BrBr

(a) (b) (c) (d)

19%

5%

38%

38%

1. A

2. B

3. C

4. D

Which is the best way to synthesize 2,2-dibromopropane?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

33%

19%

48%

0%

1. propene + Br2

2. propene + Br2, h

3. propyne + 2 HBr

4. propyne + 2 HBr, ROOR

Which of the following intermediates is formed in the first step of the hydroboration/oxidation reaction shown?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

(1) BH3, ether

(2) H2O2, H2O, -OH

B

CH3

H

H OH

BH2

BH2

H

OH

H

CH3

HH H

CH3

H2B

CH3

(a) (b) (c) (d)

5%

43%

19%

33% 1

2

3

4

1. A

2. B

3. C

4. D

What is the reactive intermediate in the reaction of 1,3-butadiene with HBr which results in 1,2- and 1,4- addition?

1 2 3 4

0% 0%

10%

90%1. a cyclic bromonium cation

2. an allylic carbocation

3. an allylic radical

4. a dienophile

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

Which of the following is the most effective way to carry out the

transformation shown?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

30%

15%

5%

50%

1. (1) Br2, h; (2) (CH3CH2)2CuLi

2. (1) NBS, h; (2) CH3CH2MgCl

3. (1) Br2, h; (2) CH3CH2MgCl

4. 1) NBS, h; (2) (CH3CH2)2CuLi

Identify the functional group in the molecule shown.

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

O

5%

86%

0%

10%

1. Aldehyde

2. Ketone

3. Ester

4. Carboxylic acid

What is the hybridization of the nitrogen on cocaine, which has the structure shown below?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

N

O O

OO

14%

48%

38%

1. sp

2. sp2

3. sp3

Which of the following is not true about homolytic bond cleavages?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

24%

10%

19%

48%1

2

3

41. They are exothermic.

2. They are endothermic.

3. You can encourage one to happen by heating or shining light on the sample.

4. More than one of the above statements is untrue.

Which of the following does not involve the interaction of molecules with

electromagnetic radiation?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

33%

19%

33%

14%

1. Mass spectrometry

2. Infrared spectroscopy

3. Ultraviolet-visible spectroscopy

4. Nuclear magnetic resonance spectroscopy

Which is the best method to

accomplish the transformation shown?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

Br

0%

81%

14%

5%

1. HBr

2. HBr, ROOR

3. NBS, h4. Br2, h

What is the formal charge on the nitrogen on the structure shown?

N

O

O

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

5%

48%

19%

24%

5%

1. +2

2. +1

3. 0

4. -1

5. -2

What is the relationship between the following compounds?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

O

H

HO

OH

H

H

OHOHH H

OH

O

H

HO

OH

H

OH

OHHH H

OH

5%

29%

62%

5%

1. Isomers

2. Enantiomers

3. Diasteromers

4. Identical

When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule corresponds to:

1 2 3 4

10%14%

19%

57%1. the amount necessary to

increase molecular motions in functional groups.

2. the amount necessary to excite electrons from one molecular orbital to another.

3. the amount necessary to “flip” the spin of atomic nuclei.

4. the amount necessary to strip a molecule of one electron to generate a radical cation.

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

Loratidine is the active ingredient in the antihistamine Claritin®. Mass spectral analysis of loratidine shows M+ at m/z = 382 and M+ at m/z = 384 in an approximate ratio of 3:1 in intensity. The mass spectral data indicates that loratidine contains:

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 401 2 3 4

5%

24%

14%

57%1. fluorine

2. chlorine

3. bromine

4. nitrogen

1 2 3 4

10%0%

5%

86%

1. 1

2. 2

3. 3

4. 4

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

Which of the following will react most rapidly in an SN2 reaction?

OCH3 Br

Cl

Br

(a) (b) (c) (d)

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

24%

5%

5%

67%

1. A

2. B

3. C

4. D

For the reaction shown below, what is the mechanism?

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

13%

6%

19%

63%

1. SN1

2. SN2

3. E1

4. E2

Br CH3OH,