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How many distinct alkyl chlorides can be obtained from monochlorination of 2,3-dimethylpentane?


A) 5
B) 8
C) 10
D) 12
E) 16

F) B) and D)
G) B) and C)

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How many monochlorinated products would be obtained from 2-methylbutane? Show the structures and give their IUPAC names.

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Would chlorination or bromination of 2,5-dimethylhexane produce a greater yield of 1-halo-2,5-dimethylhexane?

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Provide the reagents necessary for carrying out the transformation of 2-methylheptane to 2-methyl-2-heptene.

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1. Br2, hυ
...

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Give the best product for the reaction. Give the best product for the reaction. A) B) C) D) E)


A) Give the best product for the reaction. A) B) C) D) E)
B) Give the best product for the reaction. A) B) C) D) E)
C) Give the best product for the reaction. A) B) C) D) E)
D) Give the best product for the reaction. A) B) C) D) E)
E) Give the best product for the reaction. A) B) C) D) E)

F) A) and E)
G) B) and E)

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The following molecule contains how many 1°, 2°, and 3° hydrogens? The following molecule contains how many 1°, 2°, and 3° hydrogens?

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How many distinct dichlorination products can result when isobutane is subjected to free radical chlorination?


A) 1
B) 2
C) 3
D) 4
E) 6

F) B) and E)
G) A) and D)

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What reagent can best be used to convert cyclopentene to 3-bromocyclopentene in a single step?


A) Br2, hυ
B) NBS, Δ
C) HBr
D) HBr with peroxide
E) none of the above

F) A) and B)
G) A) and C)

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What sequence of reagents can be used to convert 3,3-dimethylpentane into 3,3-dimethyl-2-pentanone?

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1. Br2, hν
...

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Which of the following is a step in the mechanism of the reaction shown? Which of the following is a step in the mechanism of the reaction shown? A) B) C) D) E)


A) Which of the following is a step in the mechanism of the reaction shown? A) B) C) D) E)
B) Which of the following is a step in the mechanism of the reaction shown? A) B) C) D) E)
C) Which of the following is a step in the mechanism of the reaction shown? A) B) C) D) E)
D) Which of the following is a step in the mechanism of the reaction shown? A) B) C) D) E)
E) Which of the following is a step in the mechanism of the reaction shown? A) B) C) D) E)

F) C) and D)
G) C) and E)

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Write a detailed, stepwise mechanism for the following reaction. Write a detailed, stepwise mechanism for the following reaction.

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Given the bond dissociation energies below (in kcal/mol) , estimate the ΔH° for the propagation step Given the bond dissociation energies below (in kcal/mol) , estimate the ΔH° for the propagation step CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>-H 98 (CH<sub>3</sub>) <sub>2</sub>CH-H 95 Cl-Cl 58 H-Cl 103 CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>-Cl 81 (CH<sub>3</sub>) <sub>2</sub>CH-Cl 80 A) -22 kcal/mol B) +22 kcal/mol C) -40 kcal/mol D) +45 kcal/mol E) -45 kcal/mol CH3CH2CH2-H 98 (CH3) 2CH-H 95 Cl-Cl 58 H-Cl 103 CH3CH2CH2-Cl 81 (CH3) 2CH-Cl 80


A) -22 kcal/mol
B) +22 kcal/mol
C) -40 kcal/mol
D) +45 kcal/mol
E) -45 kcal/mol

F) C) and D)
G) A) and E)

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Consider the reaction: CH3CH2 ∙ + Br2 → CH3CH2Br + Br ∙. Given that this reaction has an activation energy of +6 kcal/mol and a ΔH° of -22 kcal/mol, sketch a reaction-energy profile for this reaction. Label the axes and show Ea and ΔH° on your drawing.

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Given the bond dissociation energies below (in kcal/mol), calculate the overall ΔH° for the following reaction: (CH3)3CH + Br2 → (CH3)3CBr + HBr (CH3)3C-H 91 (CH3)3C-Br 65 Br-Br 46 H-Br 88 CH3-Br 70

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Provide the major organic product of the following reaction. Provide the major organic product of the following reaction.

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Which of the following is not an intermediate or product in the reaction of Which of the following is not an intermediate or product in the reaction of A) I B) II C) III D) IV E) V Which of the following is not an intermediate or product in the reaction of A) I B) II C) III D) IV E) V


A) I
B) II
C) III
D) IV
E) V

F) A) and E)
G) A) and B)

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Calculate the percentage of 2-chloro-2-methyl butane in the following reaction. Calculate the percentage of 2-chloro-2-methyl butane in the following reaction. A) 11.56% B) 27.77% C) 23.14% D) 35.18% E) 13.88%


A) 11.56%
B) 27.77%
C) 23.14%
D) 35.18%
E) 13.88%

F) A) and E)
G) All of the above

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How many distinct monochlorinated products, including stereoisomers, can result when the alkane below is heated in the presence of Cl2? How many distinct monochlorinated products, including stereoisomers, can result when the alkane below is heated in the presence of Cl<sub>2</sub>? A) 2 B) 4 C) 5 D) 6 E) 8


A) 2
B) 4
C) 5
D) 6
E) 8

F) None of the above
G) A) and E)

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Identify the most stable radical.


A) Identify the most stable radical. A) B) C) D) E)
B) Identify the most stable radical. A) B) C) D) E)
C) Identify the most stable radical. A) B) C) D) E)
D) Identify the most stable radical. A) B) C) D) E)
E) Identify the most stable radical. A) B) C) D) E)

F) A) and E)
G) A) and D)

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Calculate the percentage of 2-chloro-3,4-dimethylheptane formed in the following reaction. Calculate the percentage of 2-chloro-3,4-dimethylheptane formed in the following reaction. A) 6) 70 B) 11.16 C) 16.96 D) 22.32 E) 26.80


A) 6) 70
B) 11.16
C) 16.96
D) 22.32
E) 26.80

F) A) and C)
G) A) and D)

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