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What is/are the product(s) of the following reaction? What is/are the product(s) of the following reaction?   A)    B) CH<sub>2</sub> <sub> </sub>   CH<sub>2</sub> C)    D) A and B E) A and C


A) What is/are the product(s) of the following reaction?   A)    B) CH<sub>2</sub> <sub> </sub>   CH<sub>2</sub> C)    D) A and B E) A and C
B) CH2 What is/are the product(s) of the following reaction?   A)    B) CH<sub>2</sub> <sub> </sub>   CH<sub>2</sub> C)    D) A and B E) A and C CH2
C) What is/are the product(s) of the following reaction?   A)    B) CH<sub>2</sub> <sub> </sub>   CH<sub>2</sub> C)    D) A and B E) A and C
D) A and B
E) A and C

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What mechanism predominates in the reaction below? What mechanism predominates in the reaction below?   A) S<sub>N</sub>2 B) S<sub>N</sub>1 without rearrangement C) S<sub>N</sub>1 with rearrangement D) E2 E) E1


A) SN2
B) SN1 without rearrangement
C) SN1 with rearrangement
D) E2
E) E1

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Assuming no other changes,what is the effect of doubling both the alkyl halide and the nucleophile concentrations in the above reaction?


A) no change
B) doubles the rate
C) triples the rate
D) quadruples the rate
E) rate is halved

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What is the major product of the following reaction? What is the major product of the following reaction?   A) I B) II C) III D) IV E) V


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

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Give the major product for the following E1 reaction. Give the major product for the following E1 reaction.   A)    B)    C)    D)    E)


A) Give the major product for the following E1 reaction.   A)    B)    C)    D)    E)
B) Give the major product for the following E1 reaction.   A)    B)    C)    D)    E)
C) Give the major product for the following E1 reaction.   A)    B)    C)    D)    E)
D) Give the major product for the following E1 reaction.   A)    B)    C)    D)    E)
E) Give the major product for the following E1 reaction.   A)    B)    C)    D)    E)

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Which of the following can't undergo nucleophilic substitution reactions? Which of the following can't undergo nucleophilic substitution reactions?   A) I B) II C) III D) IV E) V


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

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Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?


A) These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom.
B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects.
C) tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density.
D) tert-Butoxide is more nucleophilic because it is more basic.
E) none of the above

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Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane?


A) Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane? A)    B)    C)    D)    E)
B) Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane? A)    B)    C)    D)    E)
C) Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane? A)    B)    C)    D)    E)
D) Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane? A)    B)    C)    D)    E)
E) Which of the following bases gives the highest anti-Zaitsev product in E2 reactions when reacted with 2-bromo-2,3-dimethylbutane? A)    B)    C)    D)    E)

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Give the best answer for the reaction. Give the best answer for the reaction.   A) CH<sub>3</sub>CH<sub>2</sub>OCH<sub>3</sub> B) CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> E) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3 </sub>


A) CH3CH2OCH3
B) CH3CH2OCH2CH3
C) CH3CH2OCH2CH2CH3
D) CH3CH2CH2OCH2CH2CH3
E) CH3CH2CH2OCH2CH2CH2CH3

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When 1-bromo-2,2-dimethylcyclopentane is heated in ethanol,one of the products which results is shown below.Provide a detailed,stepwise mechanism for the production of this compound,and give the name of the mechanism by which it is produced. When 1-bromo-2,2-dimethylcyclopentane is heated in ethanol,one of the products which results is shown below.Provide a detailed,stepwise mechanism for the production of this compound,and give the name of the mechanism by which it is produced.

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How would you obtain the following product from 1-bromo-1-methylcyclohexane? How would you obtain the following product from 1-bromo-1-methylcyclohexane?

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Provide the major organic product of the following reaction. Provide the major organic product of the following reaction.

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What reaction mechanism predominates when 1-bromo-1-propylcyclopentane is treated with sodium methoxide in methanol?

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Identify the alkyl halide that reacts the fastest in an SN2 reaction.


A) 1-chloropropane
B) 1-bromopropane
C) 1-fluoropropane
D) 1-iodopropane

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Which of the following solvents is aprotic?


A) CH3CH2OH
B) CH3CH2CH2NH2
C) CH3CH2OCH2CH3
D) CH3CH2NHCH3
E) Which of the following solvents is aprotic? A) CH<sub>3</sub>CH<sub>2</sub>OH B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> C) CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub> D) CH<sub>3</sub>CH<sub>2</sub>NHCH<sub>3</sub> E)

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Provide the structure of the major organic product of the following reaction. Provide the structure of the major organic product of the following reaction.

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Which of the following carbocations is the least stable? Which of the following carbocations is the least stable?   A) I B) II C) III D) IV E) V


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

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Give the mechanism including the transition state. Give the mechanism including the transition state.

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Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

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No.All primary iodides are not...

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Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?

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Primary halides cannot undergo...

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