Question 1

What is the product of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV A

Question 2

What is the product of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV C

Question 3

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)  RCONH2 + R'OH 
A)  RCOCl + R'NH2 + pyridine 
B)  RCOOH + R'OH + H+ 
C)  RCOOH + R'OH + OH- 
D)  RCONH2 + R'OH B

Question 4

Will the following reaction occur?

Accepted Answer

A)  Yes 
B)  No 
A)  Yes 
B)  No

Question 5

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 strained 
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 strained

Question 6

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 amine 
A)  Isopropyl alcohol 
B)  Benzoic acid 
C)  Ammonia 
D)  Triethyl amine

Question 7

What is the product of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 8

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

Accepted Answer

A)  Protonation of the carbonyl 
B)  Removal of an F1F1F1S1F1F1F10-proton 
C)  Addition of the nucleophile to the carbonyl 
D)  Loss of the leaving group 
A)  Protonation of the carbonyl 
B)  Removal of an F1F1F1S1F1F1F10-proton 
C)  Addition of the nucleophile to the carbonyl 
D)  Loss of the leaving group

Question 9

What is the product of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 10

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. 
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.

Question 11

What is the product of the following reaction?

Accepted Answer

A)  Hexanoic acid 
B)  1-Hexanamide 
C)  Hexanal 
D)  1-Hexanamine 
A)  Hexanoic acid 
B)  1-Hexanamide 
C)  Hexanal 
D)  1-Hexanamine

Question 12

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 
A)  a carboxylic acid 
B)  a nitrile 
C)  an aldehyde 
D)  an anhydride

Question 13

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. 
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.

Question 14

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-methylbutanamide 
A)  methyl 3-methylbutanamide 
B)  5-methylhexanamide 
C)  N-methyl 3-methylhexanamide 
D)  N-methyl 3-methylbutanamide

Question 15

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

Accepted Answer

A)  I > II > III 
B)  III > II > I 
C)  II > III > I 
D)  III > I > II 
A)  I > II > III 
B)  III > II > I 
C)  II > III > I 
D)  III > I > II

Question 16

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)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 17

What is the product of the following reaction (after acidic work-up)?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 18

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. 
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.

Question 19

Will the following reaction occur?

Accepted Answer

A)  Yes 
B)  No 
A)  Yes 
B)  No

Question 20

What is the IUPAC name for the following compound?

Accepted Answer

A)  Propionyl phenol 
B)  Phenyl propanoate 
C)  Phenol propanoate 
D)  Phenyl acetate 
A)  Propionyl phenol 
B)  Phenyl propanoate 
C)  Phenol propanoate 
D)  Phenyl acetate

Exam 22: Carboxylic Acids and Derivatives

What is the product of the following reaction?

What is the product of the following reaction?

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

Will the following reaction occur?

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

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

What is the product of the following reaction?

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

What is the product of the following reaction?

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

What is the product of the following reaction?

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

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

What is the IUPAC name for the following compound?

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

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

What is the product of the following reaction (after acidic work-up)?

Which of the following statements about amides is true?

Will the following reaction occur?

What is the IUPAC name for the following compound?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

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