Question 1

What is the product of the following reaction?

Accepted Answer

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

Question 2

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 C)
F) None of the above

Question 3

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

Question 4

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

Question 5

Will the following reaction occur?

Accepted Answer

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

Question 6

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 B)
F) None of the above

Question 7

How can you convert a carboxylic acid into an ester?

Accepted Answer

A)   Heat with an alcohol and catalytic acid
B)   Deprotonate with a base and react with an alcohol
C)   Deprotonate with a base and react with an alkyl halide
D)   Both (a)  heat with an alcohol and catalytic acid and (c)  deprotonate with a base and react with an alkyl halide
E)   Both (a)  heat with an alcohol and catalytic acid and (b)  deprotonate with a base and react with an alcoholF) A) and B)
G) None of the above

Question 8

What is the structure for acetic propanoic anhydride?

Accepted Answer

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

Question 9

What is the product of the following reaction?

Accepted Answer

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

Question 10

Which of the following is a lactam?

Accepted Answer

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

Question 11

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 D)
F) A) and C)

Question 12

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 FeCl3E) B) and D)
F) A) and B)

Question 13

An unknown compound has a sharp, medium peak at 2250 cm-1. The unknown compound is probably

Accepted Answer

A)   an alkane
B)   an aldehyde
C)   an alkene
D)   a nitrileE) A) and B)
F) C) and D)

Question 14

Draw the structure of N-phenyl acetamide.

Accepted Answer

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

Question 15

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) None of the above
F) All of the above

Question 16

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 C)

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) None of the above

Question 18

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

Question 19

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

Accepted Answer

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

Question 20

What reagent would you use for the following transformation? 4 B)  DIBAL-H C)  NaBH4 D)  H2, Pd/C" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   LiAlH4
B)   DIBAL-H
C)   NaBH4
D)   H2, Pd/CE) All of the above
F) C) and D)

Exam 22: Carboxylic Acids and Derivatives

Draw the structure of N-phenyl acetamide.

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

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

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

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What is the product of the following reaction?

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An unknown compound has a sharp, medium peak at 2250 cm-1. The unknown compound is probably

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What is 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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Which of the following is a lactam?

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How can you convert a carboxylic acid into an ester?

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

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What is the product of the following reaction?

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What is the product of the following reaction?

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What reagent would you use for the following transformation?

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

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What is the structure for acetic propanoic anhydride?

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

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What is the IUPAC name for the following compound?

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Will the following reaction occur?

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

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An unknown compound has a sharp, medium peak at 2250 cm^-1. The unknown compound is probably

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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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