Question 1

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 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

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. B

Question 4

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. 
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.

Question 5

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 salt 
A) A nitrile 
B) A carboxylic acid 
C) An amide 
D) A carboxylic acid salt

Question 6

Which of the following is a lactam?

Accepted Answer

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

Question 7

What is the missing reagent in the reaction below?

Accepted Answer

A) Acetic acid 
B) NaOMe 
C) SOCl2 
D) Pyridine 
A) Acetic acid 
B) NaOMe 
C) SOCl2 
D) Pyridine

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

Question 9

Draw the structure of N-phenyl acetamide.

Accepted Answer

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

Question 10

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 11

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 nitrile. 
A) an alkane. 
B) an aldehyde. 
C) an alkene. 
D) a nitrile.

Question 12

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 13

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 14

Will the following reaction occur?

Accepted Answer

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

Question 15

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 16

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 nitrile 
A) A ketone 
B) An aldehyde 
C) An ester 
D) A nitrile

Question 17

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 heat with an alcohol and catalytic acid and deprotonate with a base and react with an alkyl halide. 
E) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alcohol. 
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 heat with an alcohol and catalytic acid and deprotonate with a base and react with an alkyl halide. 
E) Both heat with an alcohol and catalytic acid and deprotonate with a base and react with an alcohol.

Question 18

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

Question 19

Will the following reaction occur?

Accepted Answer

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

Question 20

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

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

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

What is the product of the following reaction?

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

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

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

Which of the following is a lactam?

What is the missing reagent in the reaction below?

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

Draw the structure of N-phenyl acetamide.

What is the product of the following reaction?

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

Which of the following statements about amides is true?

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

Will the following reaction occur?

What is the product of the following reaction?

You see an absorption at 2250 cm-1 in the IR spectrum of a compound.What kind of functional group is present?

How can you convert a carboxylic acid into an ester?

Give the IUPAC name for the following compound.

Will the following reaction occur?

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

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 Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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

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

You see an absorption at 2250 cm^-1 in the IR spectrum of a compound.What kind of functional group is present?