Question 1

What is the product of the following reaction?

Accepted Answer

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

Question 2

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

Question 3

What is the structure for ethyl 4-chlorobenzoate?

Accepted Answer

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

Question 4

What is the product of the following reaction?

Accepted Answer

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

Question 5

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

Question 6

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

Accepted Answer

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

Question 7

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 C)
F) A) and B)

Question 8

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) All of the above

Question 9

What is the product of the following reaction?

Accepted Answer

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

Question 10

Which structure is consistent with the following 1H NMR spectrum? 1H NMR spectrum?   A) Ethyl acetate B) 2-Propanone C) 3,3-Dimethyl-2-pentanone D) Ethyl 2,2-dimethylpropionate" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Ethyl acetate
B)  2-Propanone
C)  3,3-Dimethyl-2-pentanone
D)  Ethyl 2,2-dimethylpropionateE) All of the above
F) A) and B)

Question 11

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

Question 12

Give the IUPAC name for the following compound.

Accepted Answer

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

Question 13

What is the product of the following reaction?

Accepted Answer

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

Question 14

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

Question 15

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

Accepted Answer

A)  Isopropyl alcohol
B)  Benzoic acid
C)  Ammonia
D)  Triethyl amineE) None of the above
F) B) and C)

Question 16

What is the IUPAC name for the following compound?

Accepted Answer

A)  2-fluorobutanonitrile
B)  2-fluoropentanonitrile
C)  3-fluoropentanonitrile
D)  2-fluorobutylcyanideE) A) and D)
F) A) and C)

Question 17

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

Question 18

What is the product of the following reaction?

Accepted Answer

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

Question 20

How can you convert a carboxylic acid into an acid chloride?

Accepted Answer

A)  Heat with hydrochloric acid.
B)  React with thionyl chloride (SOCl2) .
C)  React with sodium chloride.
D)  React with Cl2 and FeCl3.E) B) and D)
F) A) and C)

Exam 20: Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

What is the product of the following reaction?

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What is the product of the following reaction?

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

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What is the product of the following reaction?

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

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How can you convert a carboxylic acid into an acid chloride?

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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 IUPAC name for the following compound?

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Which structure is consistent with the following 1H NMR spectrum?

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What is the IUPAC name for the following compound?

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

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What is the product of the following reaction?

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

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

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What reagents are necessary to perform the following reaction?

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

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What is the structure for ethyl 4-chlorobenzoate?

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Give the IUPAC name for the following compound.

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What is the product of the following reaction?

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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?

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Which structure is consistent with the following ¹H NMR spectrum?

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