Exam 11: Nucleophilic Substitution and Elimination Reactions 1: Competition Among Sn2,sn1,e2,and E1 Reactions

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Show the starting material needed to complete the following reaction. Show the starting material needed to complete the following reaction.

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Give the product and mechanism for the following reaction.Be sure to include all mechanism arrows,lone pairs of electrons,and formal charges in your mechanism. Give the product and mechanism for the following reaction.Be sure to include all mechanism arrows,lone pairs of electrons,and formal charges in your mechanism.

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Name two bases that are strong enough to deprotonate the following alkyne. Name two bases that are strong enough to deprotonate the following alkyne.

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NaH and NaNR2

Rank the following leaving groups' ability to leave in an SN1 reaction from worst leaving group to best leaving group. Rank the following leaving groups' ability to leave in an S<sub>N</sub>1 reaction from worst leaving group to best leaving group.

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What is the major product of the following reaction? What is the major product of the following reaction?

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Rank the following nucleophiles in order of weakest to strongest. Rank the following nucleophiles in order of weakest to strongest.

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Show the most likely product of the following reaction. Show the most likely product of the following reaction.

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Which attacking species would favor an E2 reaction over an SN2 reaction? Which attacking species would favor an E2 reaction over an S<sub>N</sub>2 reaction?

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Which mechanism(s)would be favored under the following reaction conditions? Which mechanism(s)would be favored under the following reaction conditions?

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Which mechanism(s)can occur when the following alkyl halide is treated with CH3O? Which mechanism(s)can occur when the following alkyl halide is treated with CH<sub>3</sub>O<font face=symbol><sup></sup></font>?

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Circle the solvent(s)that would speed up an E1 reaction mechanism. Circle the solvent(s)that would speed up an E1 reaction mechanism.

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Which is the best (strongest)nucleophile for an SN2 reaction? Which is the best (strongest)nucleophile for an S<sub>N</sub>2 reaction?

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Which reaction mechanism(s)will be favored by a low concentration of Cl?

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Supply a base that would favor the following elimination product over a substitution product. Supply a base that would favor the following elimination product over a substitution product.

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Which solvent would allow an E2 reaction to occur at the fastest rate?

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A secondary alkyl halide can undergo which of the following mechanisms?

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Which of the following bases would make an E2 reaction occur at the fastest rate? Which of the following bases would make an E2 reaction occur at the fastest rate?

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Supply the product of the following reaction,and name the mechanism responsible for its creation. Supply the product of the following reaction,and name the mechanism responsible for its creation.

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Which of the following is the best leaving group? Which of the following is the best leaving group?

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Which of the following bases would make an E2 reaction occur at the fastest rate? Which of the following bases would make an E2 reaction occur at the fastest rate?

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