Question 1

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 D

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 A

Question 3

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. C

Question 4

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 5

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 6

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 7

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 8

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 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 acid 
A) 4-Fluoro-3-methylbenzoate 
B) 4-Fluoro-3-methylbenzoic acid 
C) 3-Methyl-4-fluorobenzoic acid 
D) 4-Fluoro-5-methylbenzoic acid

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

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 12

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

Question 13

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 14

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

Accepted Answer

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

Question 15

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 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

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 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

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 20

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.

Exam 22: Carboxylic Acids and Derivatives

What is the product of the following reaction?

What is the product of the following reaction?

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

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

Draw the structure of N-phenyl acetamide.

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

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

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

What is the IUPAC name for the following compound?

What is the product of the following reaction?

What is the IUPAC name for the following compound?

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

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

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

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

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

Which of the following is a lactam?

What is the product of the following reaction?

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

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

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

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

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

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