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Exam 6: Alkyl Halides; Nucleophilic Substitution

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Question 71

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Provide the major organic product of the reaction below.

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Question 72

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Provide the major organic product of the reaction below.

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Question 73

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Provide the major organic product of the reaction below.

Which halide is a better nucleophile, iodide or fluoride? Explain.

Arrange the following substrates in order of their increasing S_N2 reactivity with NaCN: bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

Provide an acceptable name for the compound shown below.

Provide the structure of isopropyl iodide.

Which of the following compounds will undergo an S_N2 reaction most readily?

Circle the aprotic solvents.

Rank the following compounds in order of increasing reactivity in an S_N2 reaction. (Fastest is first, slowest is last.)

If the absolute configuration at an asymmetric carbon does not change during the course of a reaction, the reaction is said to occur with ________ of stereochemistry.

Which of the following solvents could be described as polar and protic?

List the following bromides in order of their increasing reactivity as substrates in S_N2 reactions: PhBr, PhCH₂Br, and PhCH(CH₃)Br.

Rank the following molecules in order of increasing relative rate of S_N1 solvolysis with methanol and heat (slowest to fastest reacting) .

Draw two reasonable resonance structures and the hybrid of the intermediate formed in the following reaction.

Provide the major organic product of the reaction below.

Predict the two most likely mechanisms that occur when iodocyclohexane is heated in methanol.