Question 1

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-1 
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-1

Question 2

What is the product formed by hydrolysis of the following lactone with acid?

Accepted Answer

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

Question 3

What is the structure for ethyl 4-chlorobenzoate?

Accepted Answer

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

Question 4

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 5

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 6

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

Accepted Answer

A) Ethyl acetate 
B) 2-Propanone 
C) 3,3-Dimethyl-2-pentanone 
D) Ethyl 2,2-dimethylpropionate 
A) Ethyl acetate 
B) 2-Propanone 
C) 3,3-Dimethyl-2-pentanone 
D) Ethyl 2,2-dimethylpropionate

Question 7

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 8

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 9

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 10

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 11

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 12

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 13

What is the IUPAC name for the following compound?

Accepted Answer

A) 2-fluorobutanonitrile 
B) 2-fluoropentanonitrile 
C) 3-fluoropentanonitrile 
D) 2-fluorobutylcyanide 
A) 2-fluorobutanonitrile 
B) 2-fluoropentanonitrile 
C) 3-fluoropentanonitrile 
D) 2-fluorobutylcyanide

Question 14

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 15

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 FeCl3. 
A) Heat with hydrochloric acid. 
B) React with thionyl chloride (SOCl2). 
C) React with sodium chloride. 
D) React with Cl2 and FeCl3.

Question 16

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 17

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 18

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 19

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 20

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

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

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

What is the product formed by hydrolysis of the following lactone with acid?

What is the structure for ethyl 4-chlorobenzoate?

What reagents are necessary to perform the following reaction?

What is the product of the following reaction?

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

What is the IUPAC name for the following compound?

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

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

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

What is the product of the following reaction?

What is the product of the following reaction?

What is the IUPAC name for the following compound?

Give the IUPAC name for the following compound.

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

What is the product of the following reaction?

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

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

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

What is the product of the following reaction?

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

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

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