Question 1

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

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

Question 3

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 4

Which of the following compounds will have the lowest frequency for carbonyl absorption in IR spectroscopy?

Accepted Answer

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

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

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 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 product of the following reaction?

Accepted Answer

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

Question 9

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 10

Will the following reaction occur?

Accepted Answer

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

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

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 13

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 14

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 15

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 16

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

Question 17

Will the following reaction occur?

Accepted Answer

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

Question 18

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 19

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 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 22: Carboxylic Acids and Derivatives

What is the IUPAC name for the following compound?

What is the product of the following reaction?

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

Which of the following compounds will have the lowest frequency for carbonyl absorption in IR spectroscopy?

What is the product of the following reaction?

What is the product of the following reaction?

What is the missing reagent in the reaction below?

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

Will the following reaction occur?

What is the product of the following reaction?

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

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

What is the IUPAC name for the following compound?

Which of the following statements about amides is true?

How can you convert a carboxylic acid into an ester?

Will the following reaction occur?

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

What is the structure for ethyl 4-chlorobenzoate?

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

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

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