Question 1

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 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. 
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 3

Give the IUPAC name for the following compound.

Accepted Answer

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

Question 4

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 5

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 ppm 
A) 1700 cm-1 
B) 180-160 ppm 
C) 2)5-3.0 ppm 
D) 100-80 ppm

Question 6

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 7

Will the following reaction occur?

Accepted Answer

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

Question 8

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. 
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.

Question 9

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 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

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 12

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-1 
A) 2)5 ppm 
B) 2250 cm-1 
C) 3800 cm-1 
D) 1740 cm-1

Question 13

What reagents are necessary to perform the following reaction?

Accepted Answer

A) EtOH,H+ 
B) CH3CH2NH2,DCC 
C) SOCl2 
D) Heat 
A) EtOH,H+ 
B) CH3CH2NH2,DCC 
C) SOCl2 
D) Heat

Question 14

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 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

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 17

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 18

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 19

What reagents are necessary to perform the following reaction?

Accepted Answer

A) EtOH,H+ 
B) CH3CH2NH2,DCC 
C) SOCl2 
D) Heat 
A) EtOH,H+ 
B) CH3CH2NH2,DCC 
C) SOCl2 
D) Heat

Question 20

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

Exam 20: Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

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

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

Give the IUPAC name for the following compound.

Which of the following is a lactam?

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

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

Will the following reaction occur?

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

What is the missing reagent in the reaction below?

What is the product of the following reaction?

Give the IUPAC name for the following compound.

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

What reagents are necessary to perform the following reaction?

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

What is the product of the following reaction?

Which of the following statements about amides is true?

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

What is the product of the following reaction?

What reagents are necessary to perform the following reaction?

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 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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

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

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