Question 1

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) None of the above
F) All of the above

Question 2

Which of the following is a lactam?

Accepted Answer

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

Question 3

Where do the carbonyl signals appear in the 13C NMR spectrum of carboxylic acid derivatives?

Accepted Answer

A)  1700 cm-1
B)  180-160 ppm
C)  2) 5-3.0 ppm
D)  100-80 ppmE) B) and D)
F) All of the above

Question 4

Give the IUPAC name for the following compound.

Accepted Answer

A)  R-3-methoxybutanoyl chloride
B)  S-3-methoxybutanoyl chloride
C)  R-2-methoxy-4-butanoyl chloride
D)  S-2-methoxy-4-butanoyl chlorideE) C) and D)
F) A) and B)

Question 5

What is the product of the following reaction?

Accepted Answer

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

Question 6

Which of the following statements about amides is true?

Accepted Answer

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

Question 7

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

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

Question 9

Give the IUPAC name for the following compound.

Accepted Answer

A)  Butyl ethanoate
B)  Ethyl butanoate
C)  4-hexanoate
D)  3-hexanoateE) C) and D)
F) B) and D)

Question 10

What reagents are necessary to perform the following reaction? + B) CH3CH2NH2,DCC C) SOCl2 D) Heat" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  EtOH,H+
B)  CH3CH2NH2,DCC
C)  SOCl2
D)  HeatE) B) and D)
F) B) and C)

Question 11

What reagents are necessary to perform the following reaction? + B) CH3CH2NH2,DCC C) SOCl2 D) Heat" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  EtOH,H+
B)  CH3CH2NH2,DCC
C)  SOCl2
D)  HeatE) A) and B)
F) All of the above

Question 12

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

Accepted Answer

A)  Protonation of the carbonyl
B)  Removal of an a-proton
C)  Addition of the nucleophile to the carbonyl
D)  Loss of the leaving groupE) C) and D)
F) B) and C)

Question 13

What is the direct product of the base-promoted hydrolysis of an ester?

Accepted Answer

A)  A nitrile
B)  A carboxylic acid
C)  An amide
D)  A carboxylic acid saltE) All of the above
F) B) and D)

Question 14

What is the product of the following reaction?

Accepted Answer

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

Question 15

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

Question 16

Why doesn't nucleophilic acyl substitution stop at the tetrahedral intermediate?

Accepted Answer

A)  The nucleophile is too basic.
B)  Reforming the carbonyl is energetically favorable.
C)  The leaving group is unstable and wants to be negatively charged.
D)  There is no tetrahedral intermediate.E) A) and B)
F) A) and C)

Question 17

Will the following reaction occur?

Accepted Answer

A)  Yes
B)  NoC) A) and B)
D) undefined

Question 18

Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

Accepted Answer

A)  I 
B)  III 
C)  II 
D)  III < I < IIE) C) and D)
F) A) and D)

Question 19

What is the missing reagent in the reaction below? 2 D) Pyridine" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Acetic acid
B)  NaOMe
C)  SOCl2
D)  PyridineE) A) and C)
F) A) and D)

Question 20

What is the product of the following reaction?

Accepted Answer

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

Exam 20: Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Give the IUPAC name for the following compound.

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

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Where do the carbonyl signals appear in the 13C NMR spectrum of carboxylic acid derivatives?

Correct AnswerverifiedShow Answer

Why doesn't nucleophilic acyl substitution stop at the tetrahedral intermediate?

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What reagents are necessary to perform the following reaction?

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What is the IUPAC name for the following compound?

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Which of the following statements about amides is true?

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What is the product of the following reaction?

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Give the IUPAC name for the following compound.

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

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What is the product of the following reaction?

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What reagents are necessary to perform the following reaction?

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

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What is the product of the following reaction?

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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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Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

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Which of the following is a lactam?

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Will the following reaction occur?

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What is the missing reagent in the reaction below?

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What is the direct product of the base-promoted hydrolysis of an ester?

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Where do the carbonyl signals appear in the ¹³C NMR spectrum of carboxylic acid derivatives?

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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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