Question 1

What is the product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and C)
F) B) and D)

Question 2

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

Accepted Answer

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

Question 3

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

Accepted Answer

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) B) and D)
F) None of the above

Question 4

Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) All of the above
F) C) and D)

Question 5

Which of the following is a lactam?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) All of the above
F) B) and C)

Question 6

What is the IUPAC name for the following compound?

Accepted Answer

A)  Methyl 3-methylbutanamide
B)  5-Methylhexanamide
C)  N-Methyl 3-methylhexanamide
D)  N-Methyl 3-methylbutanamideE) B) and C)
F) All of the above

Question 7

What is the product of the following reaction?

Accepted Answer

A)  Hexanoic acid
B)  1-Hexanamide
C)  Hexanal
D)  1-HexanamineE) B) and C)
F) None of the above D

Question 8

Where is the carbonyl absorption found in the IR spectrum of a simple ester?

Accepted Answer

A)  2.5 ppm
B)  2250 cm-1
C)  3800 cm-1
D)  1740 cm-1E) All of the above
F) A) and B)

Question 9

What is the product formed by hydrolysis of the following lactone with acid?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) C) and D)

Question 10

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

Accepted Answer

A)  a carboxylic acid.
B)  a nitrile.
C)  an aldehyde.
D)  an anhydride.E) A) and C)
F) B) and C)

Question 11

You see an absorption at 2250 cm-1 in the IR spectrum of a compound.What kind of functional group is present?

Accepted Answer

A)  A ketone
B)  An aldehyde
C)  An ester
D)  A nitrileE) B) and C)
F) C) and D)

Question 12

Which of the following two amides will react more readily with a nucleophile? Why?

Accepted Answer

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 strainedE) B) and C)
F) A) and B)

Question 13

What is the structure for the compound whose IUPAC name is pentyl 2-methylbutanoate?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and C)
F) A) and B)

Question 14

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

Accepted Answer

A)  RCOCl + R'NH2 + pyridine
B)  RCOOH + R'OH + H+
C)  RCOOH + R'OH + OH-
D)  D. RCONH2 + R'OHE) A) and B)
F) All of the above

Question 15

What is the product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) A) and C) A

Question 16

Draw the structure of N-phenyl acetamide.

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and C)
F) A) and D)

Question 17

What is the IUPAC name for the following compound?

Accepted Answer

A)  4-Fluoro-3-methylbenzoate
B)  4-Fluoro-3-methylbenzoic acid
C)  3-Methyl-4-fluorobenzoic acid
D)  4-Fluoro-5-methylbenzoic acidE) B) and C)
F) All of the above

Question 18

Which of the following peaks would you see in the IR spectrum of a carboxylic acid?

Accepted Answer

A)  A flat line (carboxylic acids are not IR active) 
B)  A sharp line at 2250 cm-1
C)  A broad peak from 3800-2800 cm-1
D)  A broad peak from 800-600 cm-1E) C) and D)
F) None of the above

Question 19

Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?

Accepted Answer

A)  Nitrogen is a better leaving group.
B)  Chloride is a better leaving group.
C)  Nitrogen donates more electron density into the carbonyl.
D)  The amide anion is less basic.E) B) and C)
F) B) and D) C

Question 20

What is the product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) All of the above
F) A) and D)

Exam 22: Carboxylic Acids and Derivatives

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?

Correct AnswerverifiedShow Answer

Which of the following is a lactam?

Correct AnswerverifiedShow Answer

What is the IUPAC name for the following compound?

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedD

Where is the carbonyl absorption found in the IR spectrum of a simple ester?

Correct AnswerverifiedShow Answer

What is the product formed by hydrolysis of the following lactone with acid?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

You see an absorption at 2250 cm-1 in the IR spectrum of a compound.What kind of functional group is present?

Correct AnswerverifiedShow Answer

Which of the following two amides will react more readily with a nucleophile? Why?

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What is the structure for the compound whose IUPAC name is pentyl 2-methylbutanoate?

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

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedA

Draw the structure of N-phenyl acetamide.

Correct AnswerverifiedShow Answer

What is the IUPAC name for the following compound?

Correct AnswerverifiedShow Answer

Which of the following peaks would you see in the IR spectrum of a carboxylic acid?

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Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?

Correct AnswerverifiedC

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

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D

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

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You see an absorption at 2250 cm^-1 in the IR spectrum of a compound.What kind of functional group is present?

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A

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C

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