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The stabilizing effect of alkyl substituents on carbocations can be explained through ___.

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Which of the following statements is (are) true of SN1 reactions of alkyl halides in general?


A) The rate of an SN1 reaction depends on the concentration of the alkyl halide.
B) The rate of an SN1 reaction depends on the concentration of the nucleophile.
C) SN1 reactions of alkyl halides occur faster in polar aprotic solvents (compared to protic solvents) .
D) The rate of an SN1 reaction depends on the concentration of the alkyl halide and SN1 reactions of alkyl halides occur faster in polar aprotic solvents (compared to protic solvents) .
E) The rate of an SN1 reaction depends on the concentration of the alkyl halide and the concentration of the nucleophile,and SN1 reactions of alkyl halides occur faster in polar aprotic solvents (compared to protic solvents) .

F) None of the above
G) C) and D)

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Which is the strongest nucleophile?


A) OH-
B) CH3CH2O-
C) Which is the strongest nucleophile? A) OH<sup>-</sup> B) CH<sub>3</sub>CH<sub>2</sub>O<sup>-</sup> C)    D) CH<sub>3</sub>CH<sub>2</sub>OH E) H<sub>2</sub>O
D) CH3CH2OH
E) H2O

F) A) and C)
G) All of the above

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Which is a polar aprotic solvent?


A) 2-methylhexane
B) CCl4
C) NH3(l)
D) CH3CH2CH2OCH2CH2CH3
E) 2-methyl-2-propanol

F) B) and D)
G) C) and D)

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Which nucleophilic substitution reaction would be unlikely to occur?


A) HO- + CH3CH2-I \to CH3CH2-OH + I-
B) I- + CH3CH2-H \to CH3CH2-I + H-
C) CH3S- + CH3-Br \to CH3S-CH3 + Br-
D) All of these choices would be unlikely to occur.
E) None of these choices would be unlikely to occur.

F) D) and E)
G) A) and B)

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Select the potential energy diagram that represents a single-step endothermic (endergonic) reaction. Select the potential energy diagram that represents a single-step endothermic (endergonic) reaction.   A) I B) II C) III D) IV E) V


A) I
B) II
C) III
D) IV
E) V

F) B) and D)
G) B) and C)

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SN2 reactions of the type,Nu- + RL \to Nu-R + L-, are favored


A) when tertiary substrates are used.
B) by using a high concentration of the nucleophile.
C) by using a solvent of high polarity.
D) by the use of weak nucleophiles.
E) by none of these choices.

F) C) and D)
G) A) and D)

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What product(s) would you expect to obtain from the following SN2 reaction? What product(s) would you expect to obtain from the following S<sub>N</sub>2 reaction?   A) I B) II C) An equimolar mixture of I and II. D) III E) None of these choices.


A) I
B) II
C) An equimolar mixture of I and II.
D) III
E) None of these choices.

F) A) and D)
G) A) and E)

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The hybridization state of the charged carbon in a carbocation is ___.


A) sp4
B) sp3
C) sp2
D) sp
E) s

F) A) and B)
G) B) and E)

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

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The rate equation for a nucleophilic substitution reaction of a secondary alkyl chloride (R-Cl) with I- ion would be:


A) Rate = k [RCl]
B) Rate = k [I-]
C) Rate = k [RCl][I-]
D) Rate = k [RCl]2[I-]
E) Rate = k [RCl][I-]2

F) C) and E)
G) B) and D)

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If the rate of reaction of [0.1 M] sodium cyanide with [0.1 M] 2-bromo-2-methylpropane is 1.2 x 10-3 M/s,what would be the effect on the overall rate if the concentration of sodium cyanide is increased to [0.2 M] and the concentration of the alkyl bromide is decreased to [0.05 M]?


A) the rate will increase by a factor of 2
B) the rate will decrease by a factor of 2
C) the rate will increase by a factor of 10
D) the rate will decrease by a factor of 10
E) the rate will remain unchanged

F) D) and E)
G) C) and D)

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Which nucleophilic substitution reaction would be likely to occur (although probably not in excellent yield,due to competing elimination) ?


A) HO- + CH3CH2CH2CHICH3 \to CH3 CH2CH2CHOHCH3 + I-
B) Cl-+ CH3CH2CH2CH2-OH \to CH3CH2CH2CH2-Cl + OH-
C) CH3S- + CH3CH2CH2-OCH3 \to CH3S-CH2CH2CH3 + OCH3---
D) All of these choices are likely to occur.
E) None of these choices are likely to occur.

F) B) and E)
G) A) and E)

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Which SN2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance.


A) Which S<sub>N</sub>2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance. A)    B)    C)    D)    E)
B)
Which S<sub>N</sub>2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance. A)    B)    C)    D)    E)
C) Which S<sub>N</sub>2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance. A)    B)    C)    D)    E)
D)
Which S<sub>N</sub>2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance. A)    B)    C)    D)    E)
E) Which S<sub>N</sub>2 reaction would you expect to take place most rapidly? Assume that the concentrations of the reactants and the temperature are the same in each instance. A)    B)    C)    D)    E)

F) A) and D)
G) B) and C)

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Which of the following solvents will best promote a nucleophilic reaction between NaCN and 1-bromopropane?


A) H2O/MeOH mixture
B) H2O
C) MeCN
D) HF(aq)
E) running with no solvent

F) All of the above
G) D) and E)

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Which is not a polar aprotic solvent?


A) Which is not a polar aprotic solvent? A)    B)    C)    D)    E)
B) Which is not a polar aprotic solvent? A)    B)    C)    D)    E)
C) Which is not a polar aprotic solvent? A)    B)    C)    D)    E)
D) Which is not a polar aprotic solvent? A)    B)    C)    D)    E)
E) Which is not a polar aprotic solvent? A)    B)    C)    D)    E)

F) A) and B)
G) All of the above

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The major product of the following reaction would be: The major product of the following reaction would be:   A) I B) II C) III D) IV E) An equimolar mixture of I and II.


A) I
B) II
C) III
D) IV
E) An equimolar mixture of I and II.

F) A) and B)
G) C) and D)

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In order for colliding species to react,they must ___ and ___.

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have energy equal/gr...

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

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Racemic mixtures form in SN1 reactions when leaving group departure results in a loss of chirality followed by subsequent attack of the nucleophile.

A) True
B) False

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