Question 1

Draw the structure of N-phenyl acetamide.

Accepted Answer

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

Question 2

Will the following reaction occur?

Accepted Answer

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

Question 3

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

Accepted Answer

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

Question 4

What is the product of the following reaction?

Accepted Answer

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

Question 5

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

Question 6

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

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) C) and E)
G) D) and E)

Question 8

Which of the following is a lactam?

Accepted Answer

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

Question 9

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

Question 10

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 B)
F) All of the above

Question 11

What is the product of the following reaction?

Accepted Answer

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

Question 12

What is the IUPAC name for the following compound?

Accepted Answer

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

Question 13

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 B)
F) A) and C)

Question 14

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

Question 15

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

Question 16

What is the structure for acetic propanoic anhydride?

Accepted Answer

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

Question 17

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

Question 18

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)

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 C)
F) All of the above

Question 20

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) C) and D)

Exam 22: Carboxylic Acids and Derivatives

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

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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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Draw the structure of N-phenyl acetamide.

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Will the following reaction occur?

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Which of the following is a lactam?

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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 is the product of the following reaction?

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What is the product of the following reaction?

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What is the IUPAC name for the following compound?

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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 structure for acetic propanoic anhydride?

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

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How can you convert a carboxylic acid into an ester?

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

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

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

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