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Which of the following statements is not true?


A) Bromine radicals add to the least substituted end of a carbon-carbon double bond of an alkene.
B) The major anti-Markovnikov product obtained upon addition of HBr to alkenes in the presence of a peroxide is formed in a radical termination step.
C) Two radicals combine in radical termination steps.
D) Alkoxy radicals remove a hydrogen atom from HBr to give an alcohol and a bromine atom.

E) B) and C)
F) A) and D)

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) (R) -1-chloro-3-methyl-2-cyclohexene B) (S) -1-chloro-3-methyl-2-cyclohexene C) (R) -3-chloro-1-methylcyclohexene D) (S) -3-chloro-1-methylcyclohexene


A) (R) -1-chloro-3-methyl-2-cyclohexene
B) (S) -1-chloro-3-methyl-2-cyclohexene
C) (R) -3-chloro-1-methylcyclohexene
D) (S) -3-chloro-1-methylcyclohexene

E) B) and D)
F) None of the above

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What is the reactive intermediate in the autooxidation of cyclohexene?


A) an allylic radical
B) a 2 °\degree carbocation
C) a carbocation
D) a diene

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

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A

What type of orbital contains the unpaired electron of the tert-butyl radical?


A) s
B) p
C) sp3
D) sp

E) A) and C)
F) A) and B)

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Provide neatly drawn resonance structures of the key intermediate in the following reaction. Provide neatly drawn resonance structures of the key intermediate in the following reaction.

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How many electrons does the allyl radical have in p orbitals


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

E) B) and C)
F) A) and D)

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What is the characteristic of a radical chain initiation step?


A) radicals are formed
B) substitution products are formed
C) a radical reacts with a molecule to give a new radical and a new molecule
D) two radicals combine to give a molecule

E) B) and C)
F) A) and D)

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What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction? What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction?

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What is the correct assignment of the names of the following compounds? What is the correct assignment of the names of the following compounds? A) 1 = methyl chloride; 2 = chloroform; 3 = methylene chloride B) 1 = trichlor; 2 = chloroform; 3 = methylene chloride C) 1 = methyl chloride; 2 = methylene chloride; 3 = chloroform D) 1 = chloroform; 2 = methylene chloride; 3 = trichlor


A) 1 = methyl chloride; 2 = chloroform; 3 = methylene chloride
B) 1 = trichlor; 2 = chloroform; 3 = methylene chloride
C) 1 = methyl chloride; 2 = methylene chloride; 3 = chloroform
D) 1 = chloroform; 2 = methylene chloride; 3 = trichlor

E) C) and D)
F) All of the above

Correct Answer

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C

What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the presence of peroxides? What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the presence of peroxides? A) only 1 and 2 B) only 1 and 4 C) only 2 and 3 D) a mixture of 1, 2, 3, and 4


A) only 1 and 2
B) only 1 and 4
C) only 2 and 3
D) a mixture of 1, 2, 3, and 4

E) A) and B)
F) A) and C)

Correct Answer

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Which halogen is most useful in the regioselective radical halogenation of alkenes??


A) fluorine
B) chlorine
C) bromine
D) iodine

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

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Provide the IUPAC name of the following compound (shown as a Fischer projection). Provide the IUPAC name of the following compound (shown as a Fischer projection).

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How many p-bonding, non-bonding, and antibonding orbitals does the allyl radical possess?


A) one bonding, one nonbonding, and one antibonding
B) two bonding, no nonbonding, and no antibonding
C) two bonding, one nonbonding, and no antibonding
D) three bonding, no nonbonding, and no antibonding

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

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A

What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) (R) -2-bromo-2-vinylpentane B) (S) -2-bromo-2-vinylpentane C) (S) -3-bromo-3-propyl-1-butene D) (R) -3-bromo-3-methyl-1-hexene


A) (R) -2-bromo-2-vinylpentane
B) (S) -2-bromo-2-vinylpentane
C) (S) -3-bromo-3-propyl-1-butene
D) (R) -3-bromo-3-methyl-1-hexene

E) All of the above
F) B) and C)

Correct Answer

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Which of the following alkenes undergoes allylic bromination to form a single monobrominated product? Which of the following alkenes undergoes allylic bromination to form a single monobrominated product? A) 1 B) 2 C) 3 D) 4


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

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

Correct Answer

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Which of the following statements is not true about the allyl radical


A) the carbon-carbon bond lengths are identical
B) the unpaired electron density is shared between carbons 1 and 2.
C) it undergoes reaction with bromine to give a single product
D) it is formed by abstraction of a hydrogen atom from the methyl group of propene

E) B) and C)
F) All of the above

Correct Answer

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What are the major organic products obtained from the following reaction? What are the major organic products obtained from the following reaction? A) 1 and 2 B) 3 and 4 C) 1 and 3 D) 2 and 4


A) 1 and 2
B) 3 and 4
C) 1 and 3
D) 2 and 4

E) All of the above
F) None of the above

Correct Answer

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction?

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What is the correct order of stability of the following radicals (more stable > less stable) ? What is the correct order of stability of the following radicals (more stable > less stable) ? A) 1 > 2 > 3 B) 2 > 1 > 3 C) 2 > 3 > 1 D) 3 > 2 > 1


A) 1 > 2 > 3
B) 2 > 1 > 3
C) 2 > 3 > 1
D) 3 > 2 > 1

E) C) and D)
F) B) and D)

Correct Answer

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction?

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