Select the rate law for the following reaction,e.g., CH3CH2CH2CHBrCH3 + OH-$\to$CH3CH2CH2CHOHCH3 + Br - ( RBr )

A) Rate = k [RBr] B) Rate = k [RBr] [OH-] C) Rate = k [RBr]2 [OH-] D) Rate = k [RBr] [OH-]2 E) Rate = k [RBr]2 [OH-]2 A) Rate = k [RBr] B) Rate = k [RBr] [OH-] C) Rate = k [RBr]2 [OH-] D) Rate = k [RBr] [OH-]2 E) Rate = k [RBr]2 [OH-]2

Exam 6: Nucleophilic Reactions

In the S_N2 reaction,the unstable arrangement of atoms in which both the nucleophile and the leaving group are partially bonded to the same carbon atom is called the ___.

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(Short Answer)

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Question 1

Correct Answer:

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transition state

Typically,increasing the concentration of the nucleophile of an S_N1 reaction has no impact on the rate of the reaction.The reason for this is that ___.

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Question 2

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An S_N1 reaction is a multi-step process; the overall reaction rate is determined by the rate of formation of the carbocation intermediate.Since the nucleophile is not involved in the rate-determining step,changes in its concentration typically have no impact on the rate of reaction.

Rank the following in terms of nucleophilic strength:

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(Multiple Choice)

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Question 3

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When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether,the product is analyzed to be C₅H₁₀O.Propose a likely structure for this product,suggesting a reasonable mechanistic pathway for its formation.

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Question 4

Select the rate law for the following reaction,e.g., CH₃CH₂CH₂CHBrCH₃ + OH^- $\to$ CH₃CH₂CH₂CHOHCH₃ + Br ^- ( RBr )

(Multiple Choice)

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Question 5

S_N1 reactions of the following type: Nu:^- + R-X $\to$ R-Nu + :X^- Are favored

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Question 6

S_N1 reactions of the type,Nu^- + RL $\to$ Nu-R + L^-,are favored

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Question 7

Which ion is the strongest nucleophile in an aprotic solvent such as dimethylsulfoxide?

(Multiple Choice)

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Question 8

Consider the S_N2 reaction of 2-iodopentane with CH₃CO₂- ion. Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 2-iodopentane and sodium acetate?

(Multiple Choice)

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Question 9

Which of the following nucleophiles will react the fastest with tert-butyl bromide in ethanol?

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Question 10

Reaction of (R)-2-chloro-4-methylhexane with excess NaI in acetone gives racemic 2-iodo-4-methylhexane.What is the explanation that best describes this transformation?

(Multiple Choice)

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Question 11

Typically alkyl chlorides are slow in S_N2 reactions with sodium methoxide in methanol,however the rate of the reaction can be greatly increased with a small addition of NaI.Explain.

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Question 12

Considering the relative solvation of reactants and the transition states of substitution reactions of these reactants,predict which general type of reaction would be most favored by the use of a polar solvent.

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Question 13

An endergonic S_N2 reaction will have a have a higher energy of activation ( $\Delta$ G^‡)than an exergonic S_N2 reaction.

(True/False)

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Question 14

Draw the potential energy diagram that represents an exothermic reaction between a tertiary alkyl halide and methanol.Briefly explain your rationale.

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Question 15

Consider the reaction of 2-chloro-2-methylpentane with sodium iodide. Assuming no other changes,how would it affect the rate if one simultaneously doubled the concentration of 2-chloro-2-methylpentane and sodium iodide?

(Multiple Choice)

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Question 16

Which of the following would be most reactive in an S_N2 reaction?

(Multiple Choice)

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Question 17

The rate equation for a nucleophilic substitution reaction of a tertiary alkyl bromide (R-Br)with I^- ion would be:

(Multiple Choice)

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Question 18

Which S_N2 reaction would take place most rapidly?

(Multiple Choice)

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Question 19

Which ion is the strongest nucleophile in aqueous solution?

(Multiple Choice)

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Question 20

Showing 1 - 20 of 91

Exam 6: Nucleophilic Reactions

In the SN2 reaction,the unstable arrangement of atoms in which both the nucleophile and the leaving group are partially bonded to the same carbon atom is called the ___.

Typically,increasing the concentration of the nucleophile of an SN1 reaction has no impact on the rate of the reaction.The reason for this is that ___.

Rank the following in terms of nucleophilic strength:

When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether,the product is analyzed to be C5H10O.Propose a likely structure for this product,suggesting a reasonable mechanistic pathway for its formation.

Select the rate law for the following reaction,e.g., CH3CH2CH2CHBrCH3 + OH- →\to→ CH3CH2CH2CHOHCH3 + Br - ( RBr )

SN1 reactions of the following type: Nu:- + R-X →\to→ R-Nu + :X- Are favored

SN1 reactions of the type,Nu- + RL →\to→ Nu-R + L-,are favored

Which ion is the strongest nucleophile in an aprotic solvent such as dimethylsulfoxide?

Consider the SN2 reaction of 2-iodopentane with CH3CO2- ion. Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 2-iodopentane and sodium acetate?

Which of the following nucleophiles will react the fastest with tert-butyl bromide in ethanol?

Reaction of (R)-2-chloro-4-methylhexane with excess NaI in acetone gives racemic 2-iodo-4-methylhexane.What is the explanation that best describes this transformation?

Typically alkyl chlorides are slow in SN2 reactions with sodium methoxide in methanol,however the rate of the reaction can be greatly increased with a small addition of NaI.Explain.

Considering the relative solvation of reactants and the transition states of substitution reactions of these reactants,predict which general type of reaction would be most favored by the use of a polar solvent.

An endergonic SN2 reaction will have a have a higher energy of activation ( Δ\DeltaΔ G‡)than an exergonic SN2 reaction.

Draw the potential energy diagram that represents an exothermic reaction between a tertiary alkyl halide and methanol.Briefly explain your rationale.

Consider the reaction of 2-chloro-2-methylpentane with sodium iodide. Assuming no other changes,how would it affect the rate if one simultaneously doubled the concentration of 2-chloro-2-methylpentane and sodium iodide?

Which of the following would be most reactive in an SN2 reaction?

The rate equation for a nucleophilic substitution reaction of a tertiary alkyl bromide (R-Br)with I- ion would be:

Which SN2 reaction would take place most rapidly?

Which ion is the strongest nucleophile in aqueous solution?

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In the S_N2 reaction,the unstable arrangement of atoms in which both the nucleophile and the leaving group are partially bonded to the same carbon atom is called the ___.

Typically,increasing the concentration of the nucleophile of an S_N1 reaction has no impact on the rate of the reaction.The reason for this is that ___.

When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether,the product is analyzed to be C₅H₁₀O.Propose a likely structure for this product,suggesting a reasonable mechanistic pathway for its formation.

Select the rate law for the following reaction,e.g., CH₃CH₂CH₂CHBrCH₃ + OH^- $\to$ CH₃CH₂CH₂CHOHCH₃ + Br ^- ( RBr )

S_N1 reactions of the following type: Nu:^- + R-X $\to$ R-Nu + :X^- Are favored

S_N1 reactions of the type,Nu^- + RL $\to$ Nu-R + L^-,are favored

Consider the S_N2 reaction of 2-iodopentane with CH₃CO₂- ion. Assuming no other changes,what effect on the rate would result from simultaneously doubling the concentrations of both 2-iodopentane and sodium acetate?

Typically alkyl chlorides are slow in S_N2 reactions with sodium methoxide in methanol,however the rate of the reaction can be greatly increased with a small addition of NaI.Explain.

An endergonic S_N2 reaction will have a have a higher energy of activation ( $\Delta$ G^‡)than an exergonic S_N2 reaction.

Which of the following would be most reactive in an S_N2 reaction?

The rate equation for a nucleophilic substitution reaction of a tertiary alkyl bromide (R-Br)with I^- ion would be:

Which S_N2 reaction would take place most rapidly?