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Which of the following substrates cannot be used as an immediate precursor to synthesize an ester? Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?   A)  I B)  II C)  III D)  IV


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

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

Correct Answer

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


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

E) None of the above
F) All of the above

Correct Answer

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C

From the list below, pick the compound that does not react with acetyl chloride.


A) Isopropyl alcohol
B) Benzoic acid
C) Ammonia
D) Triethyl amine

E) A) and B)
F) A) and C)

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Which of the following statements about amides is true?


A) Amides react with methyl alcohol in the presence of an acid catalyst to form an ester.
B) Amides are hydrolyzed in acid or base to form carboxylic acids or carboxylate anions.
C) Amides react with thionyl chloride to form the acid chloride.
D) Amides do not react under any conditions. They are inert compounds.

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

Correct Answer

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What is the product of the following reaction (after acidic work-up) ? What is the product of the following reaction (after acidic work-up) ?   A)  I B)  II C)  III D)  IV


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

E) A) and C)
F) None of the above

Correct Answer

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Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution. Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.   A)  I > II > III B)  III > II > I C)  II > III > I D)  III > I > II


A) I > II > III
B) III > II > I
C) II > III > I
D) III > I > II

E) A) and D)
F) A) and C)

Correct Answer

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


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

E) A) and B)
F) B) and C)

Correct Answer

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What is the product of the following reaction? What is the product of the following reaction?   A)  Hexanoic acid B)  1-Hexanamide C)  Hexanal D)  1-Hexanamine


A) Hexanoic acid
B) 1-Hexanamide
C) Hexanal
D) 1-Hexanamine

E) A) and C)
F) C) and D)

Correct Answer

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What is the first step in the general mechanism for nucleophilic acyl substitution?


A) Protonation of the carbonyl
B) Removal of an -proton
C) Addition of the nucleophile to the carbonyl
D) Loss of the leaving group

E) A) and B)
F) A) and C)

Correct Answer

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Will the following reaction occur? Will the following reaction occur?   A)  Yes B)  No


A) Yes
B) No

C) A) and B)
D) undefined

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All of the following contain sp2 hybridized atoms in their functional group except


A) a carboxylic acid
B) a nitrile
C) an aldehyde
D) an anhydride

E) All of the above
F) B) and C)

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What is the IUPAC name for the following compound? What is the IUPAC name for the following compound?   A)  methyl 3-methylbutanamide B)  5-methylhexanamide C)  N-methyl 3-methylhexanamide D)  N-methyl 3-methylbutanamide


A) methyl 3-methylbutanamide
B) 5-methylhexanamide
C) N-methyl 3-methylhexanamide
D) N-methyl 3-methylbutanamide

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

Correct Answer

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Will the following reaction occur? Will the following reaction occur?   A)  Yes B)  No


A) Yes
B) No

C) A) and B)
D) undefined

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What is the IUPAC name for the following compound? What is the IUPAC name for the following compound?   A)  Propionyl phenol B)  Phenyl propanoate C)  Phenol propanoate D)  Phenyl acetate


A) Propionyl phenol
B) Phenyl propanoate
C) Phenol propanoate
D) Phenyl acetate

E) B) and C)
F) A) and D)

Correct Answer

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Which of the following two amides will react more readily with a nucleophile? Why? Which of the following two amides will react more readily with a nucleophile? Why?   A)  I, because it is less hindered B)  II, because it is less hindered C)  I, because it is more strained D)  II, because it is more strained


A) I, because it is less hindered
B) II, because it is less hindered
C) I, because it is more strained
D) II, because it is more strained

E) A) and B)
F) A) and C)

Correct Answer

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Which of the following reaction conditions can be used to synthesize an ester (RCOOR') ?


A) RCOCl + R'NH2 + pyridine
B) RCOOH + R'OH + H+
C) RCOOH + R'OH + OH-
D) RCONH2 + R'OH

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

Correct Answer

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B

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


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

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

Correct Answer

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Why is pyridine included in the reaction of an acid chloride and an amine or alcohol?


A) Pyridine will deprotonate the amine or alcohol, making it a better nucleophile.
B) Pyridine will neutralize the acid by-product of the reaction.
C) Pyridine will protonate the carbonyl of the acid chloride, making it more reactive.
D) Pyridine will absorb the heat of the reaction.

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

Correct Answer

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n-Butanenitrile will undergo all of the following listed reactions except one. Which reaction listed is not true for n-butanenitrile?


A) n-Butane nitrile will react with ethylmagnesium bromide to form an alcohol.
B) n-Butanenitrile with be reduced to butyl amine in the presence of LiAlH4 with an aqueous work-up.
C) n-Butanenitrile is hydrolyzed in the presence of acid to form butanoic acid.
D) n-Butanenitrile is reduced with DIBAL-H to form n-butanal.

E) None of the above
F) A) and B)

Correct Answer

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


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

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

Correct Answer

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A

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