Exam 9: Nucleophilic Substitution and Beta-Elimination

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Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

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Which of the following reactions corresponds to a substitution?

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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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Which of the following energy diagrams represents the course of an exothermic SN1 reaction? Which of the following energy diagrams represents the course of an exothermic S<sub>N</sub>1 reaction?

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Which of the following energy diagrams represents the course of an exothermic E1 reaction? Which of the following energy diagrams represents the course of an exothermic E1 reaction?

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For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank to the left of the substrate. -______ For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank to the left of the substrate. -______

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The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI on the rate of the reaction?

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

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The rate law for the following reaction would be of the form Rate = k[A][B]. The rate law for the following reaction would be of the form Rate = k[A][B].

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What is the best choice of reagent to perform the following transformation? What is the best choice of reagent to perform the following transformation?

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The first step in the mechanism for the following reaction would be the formation of a secondary carbocation. The first step in the mechanism for the following reaction would be the formation of a secondary carbocation.

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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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Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol leading to elimination? Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol leading to elimination?

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The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction?

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Classify each of the following species ,Place the letter of the choice in the blank to the left of the formula. -________ Classify each of the following species ,Place the letter of the choice in the blank to the left of the formula. -________

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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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Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH3? Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH<sub>3</sub>?

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In the following reaction the cyanide ion is both a nucleophile and a Lewis acid. In the following reaction the cyanide ion is both a nucleophile and a Lewis acid.

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Which of the following represents the transition state of the rate-determining step in the reaction between 2-bromopropane and sodium methoxide leading to elimination? Which of the following represents the transition state of the rate-determining step in the reaction between 2-bromopropane and sodium methoxide leading to elimination?

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Which of the following alkyl bromides reacts the slowest with NaSCH3 in DMF? Which of the following alkyl bromides reacts the slowest with NaSCH<sub>3</sub> in DMF?

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