Question 1

Which is the weakest nucleophile in polar protic solvents?

Accepted Answer

A)  I-
B)  Br-
C)  Cl-
D)  F-
E)  All of these choices are equally strong nucleophiles,regardless of the type of solvent used.F) D) and E)
G) None of the above

Question 2

A reaction in which the nucleophile is a molecule of the solvent is referred to as a ___ reaction.

Accepted Answer

The answer of A reaction in which the nucleophile is...

Question 3

The relative nucleophilicity of the halide ions in polar aprotic solvents is observed to be markedly different from that in protic solvents.Explain briefly.

Accepted Answer

The smaller,more highly electronegative ...

Question 4

Identify the nucleophile in the following reaction: 2R'OH + RX  →	o→  ROR' + [R'OH2]+ + X-

Accepted Answer

A)  X-
B)  [R'OH2]-
C)  ROR'
D)  R'OH
E)  RX F) A) and D)
G) All of the above

Question 5

Which of the following is not a good leaving group?

Accepted Answer

A)  C2H5O-
B)  Cl-
C)  Isup>-
D)  CH3CO2-
E)  All of these choices are good leaving groups.F) B) and E)
G) B) and C)

Question 6

Which alkyl chloride,though primary,is essentially unreactive in SN2 reactions?

Accepted Answer

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G) A) and E)

Question 7

Which of these species,acting in a protic solvent,exhibits greater nucleophilic activity than expected on the basis of its basicity?

Accepted Answer

A)  OH-
B)  CH3O-
C)  SH-
D)  Cl-
E)  H2OF) B) and C)
G) A) and E)

Question 8

Which SN2 reaction will occur most rapidly in aqueous acetone solution? Assume concentrations and temperature are the same in each instance.

Accepted Answer

A)  HO- + CH3-Cl  →	o→  CH3OH + Cl-
B)  HO- + CH3CH2-Cl  →	o→  CH3CH2OH + Cl-
C)  HO- + (CH3) 2CH-Cl  →	o→  (CH3) 2CHOH + Cl-
D)  HO- + (CH3) 3C-Cl  →	o→  (CH3) 3COH + Cl-
E)  HO- + (CH3) 3CCH2-Cl  →	o→   (CH3) 3CCH2OH + Cl- F) All of the above
G) B) and D)

Question 9

As we go down Group 7A of the periodic table,the size of the halogen atom increases; accordingly,the carbon-halogen bond length gets ___ and the bond strength gets ___.

Accepted Answer

The answer of As we go down Group 7A of...

Question 10

Which of the following is a feasible substitution reaction?

Accepted Answer

A)  CH3CH2Cl + NaBr  →	o→   CH3CH2Br + NaCl
B)  CH3CH3 + NaCN  →	o→   CH3CH2CN + NaH
C)  CH3CH2Cl + NaOH  →	o→  CH2=CH2 + H2O + NaCl
D)  More than one of these choices.
E)  None of these choices. F) A) and D)
G) A) and C)

Question 11

Which of the following statements is (are) true of an SN2 reaction of (R) -2-bromobutane with hydroxide ion?

Accepted Answer

A)  Doubling the hydroxide ion concentration would double the rate of the reaction.(Assume that all other experimental conditions are unchanged.) 
B)  The major product would be (S) -2-butanol.
C)  Doubling the concentration of (R) -2-bromobutane would double the rate of the reaction.(Assume that all other experimental conditions are unchanged.) 
D)  All of these choices.
E)  Two of these choices.F) C) and D)
G) A) and E)

Question 12

The relative nucleophilicities of species do not necessarily parallel the relative basicities of the same species because

Accepted Answer

A)  not all nucleophiles are bases,and vice versa.
B)  experimental measurements of sufficient accuracy are not available to make the comparisons.
C)  nucleophilicity is a thermodynamic matter; basicity is a matter of kinetics.
D)  basicity is a thermodynamic matter; nucleophilicity is a matter of kinetics.
E)  Actually,the relative values do parallel one another.F) B) and E)
G) D) and E)

Question 13

What final product is likely to be obtained through the following series of reactions?

Accepted Answer

The answer of What final product is likely to be...

Question 14

Increasing the concentration of either of the reactants of an SN2 reaction increases the rate of the reaction.The primary reason for this is that increasing the concentration increases ___.

Accepted Answer

the frequency of collisions be...

Question 15

Which SN2 reaction will occur most rapidly in a mixture of water and ethanol?

Accepted Answer

A)  I- + CH3CH2-Br  →	o→  CH3CH2-I + Br-
B)  I- + CH3CH2-Cl  →	o→  CH3CH2-I + Cl-
C)  I- + CH3CH2-F  →	o→  CH3CH2-I + F-
D)  Br- + CH3CH2-Cl  →	o→  CH3CH2-Br + Cl-
E)  Br- + CH3CH2-F  →	o→  CH3CH2-Br + F- F) B) and E)
G) A) and B)

Question 16

Consider the substitution reaction that takes place when (R) -3-bromo-3-methylhexane is treated with methanol.Which of the following would be true?

Accepted Answer

A)  The reaction would take place only with inversion of configuration at the stereogenic center.
B)  The reaction would take place only with retention of configuration at the stereogenic center.
C)  The reaction would take place with racemization.
D)  No reaction would take place.
E)  The alkyl halide does not possess a stereogenic center.F) A) and B)
G) B) and E)

Question 17

Identify the leaving group in the following reaction. 3OH B) CH3OH2+ C) CH3OCH3 D) H2O E) None of these choices." class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  CH3OH
B)  CH3OH2+
C)  CH3OCH3
D)  H2O
E)  None of these choices.F) D) and E)
G) All of the above

Question 18

Which alkyl halide would you expect to react most slowly when heated in aqueous solution?

Accepted Answer

A)  (CH3) 3C-F
B)  (CH3) 3C-Cl
C)  (CH3) 3C-Br
D)  (CH3) 3C-I
E)  All of these choices would react at the same rate.F) A) and B)
G) A) and C)

Question 19

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

Accepted Answer

A)  by the use of tertiary substrates (as opposed to primary or secondary substrates) .
B)  by increasing the concentration of the nucleophile.
C)  by increasing the polarity of the solvent.
D)  by use of a strong base.
E)  by more than one of these choices. F) B) and E)
G) All of the above

Question 20

A nucleophile in an SN2 reaction must approach from the ___ of the carbon atom attached to the leaving group since the electrons in the nucleophile's HOMO begins to overlap with the ___ of the carbon atom attached to the leaving group.

Accepted Answer

Exam 6: Nucleophilic Reactions

What final product is likely to be obtained through the following series of reactions?

Correct AnswerverifiedShow Answer

Increasing the concentration of either of the reactants of an SN2 reaction increases the rate of the reaction.The primary reason for this is that increasing the concentration increases ___.

Correct Answerverifiedthe frequency of collisions be...View AnswerShow Answer

A reaction in which the nucleophile is a molecule of the solvent is referred to as a ___ reaction.

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which is the weakest nucleophile in polar protic solvents?

Correct AnswerverifiedShow Answer

Which of the following statements is (are) true of an SN2 reaction of (R) -2-bromobutane with hydroxide ion?

Correct AnswerverifiedShow Answer

A nucleophile in an SN2 reaction must approach from the ___ of the carbon atom attached to the leaving group since the electrons in the nucleophile's HOMO begins to overlap with the ___ of the carbon atom attached to the leaving group.

Correct AnswerverifiedShow Answer

Which of the following is not a good leaving group?

Correct AnswerverifiedShow Answer

The relative nucleophilicities of species do not necessarily parallel the relative basicities of the same species because

Correct AnswerverifiedShow Answer

The relative nucleophilicity of the halide ions in polar aprotic solvents is observed to be markedly different from that in protic solvents.Explain briefly.

Correct AnswerverifiedThe smaller,more highly electronegative ...View AnswerShow Answer

Which of the following is a feasible substitution reaction?

Correct AnswerverifiedShow Answer

Which alkyl chloride,though primary,is essentially unreactive in SN2 reactions?

Correct AnswerverifiedShow Answer

Which of these species,acting in a protic solvent,exhibits greater nucleophilic activity than expected on the basis of its basicity?

Correct AnswerverifiedShow Answer

Identify the nucleophile in the following reaction: 2R'OH + RX →\to→ ROR' + [R'OH2]+ + X-

Correct AnswerverifiedShow Answer

As we go down Group 7A of the periodic table,the size of the halogen atom increases; accordingly,the carbon-halogen bond length gets ___ and the bond strength gets ___.

Correct AnswerverifiedShow Answer

Which SN2 reaction will occur most rapidly in a mixture of water and ethanol?

Correct AnswerverifiedShow Answer

Which SN2 reaction will occur most rapidly in aqueous acetone solution? Assume concentrations and temperature are the same in each instance.

Correct AnswerverifiedShow Answer

Identify the leaving group in the following reaction.

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Which alkyl halide would you expect to react most slowly when heated in aqueous solution?

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Consider the substitution reaction that takes place when (R) -3-bromo-3-methylhexane is treated with methanol.Which of the following would be true?

Correct AnswerverifiedShow Answer

Correct Answer
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Increasing the concentration of either of the reactants of an S_N2 reaction increases the rate of the reaction.The primary reason for this is that increasing the concentration increases ___.

Correct Answer
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the frequency of collisions be...
View Answer

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

Correct Answer
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Which of the following statements is (are) true of an S_N2 reaction of (R) -2-bromobutane with hydroxide ion?

Correct Answer
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A nucleophile in an S_N2 reaction must approach from the _ of the carbon atom attached to the leaving group since the electrons in the nucleophile's HOMO begins to overlap with the _ of the carbon atom attached to the leaving group.

Correct Answer
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The smaller,more highly electronegative ...
View Answer

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Which alkyl chloride,though primary,is essentially unreactive in S_N2 reactions?

Correct Answer
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Identify the nucleophile in the following reaction: 2R'OH + RX $\to$ ROR' + [R'OH₂]⁺ + X^-

Correct Answer
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As we go down Group 7A of the periodic table,the size of the halogen atom increases; accordingly,the carbon-halogen bond length gets _ and the bond strength gets _.

Correct Answer
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Which S_N2 reaction will occur most rapidly in a mixture of water and ethanol?

Correct Answer
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Which S_N2 reaction will occur most rapidly in aqueous acetone solution? Assume concentrations and temperature are the same in each instance.

Correct Answer
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Correct Answer
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