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

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 3

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 4

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 5

What reagent would you use for the following transformation?

Accepted Answer

A)  LiAlH4 
B)  DIBAL-H 
C)  NaBH4 
D)  H2, Pd/C 
A)  LiAlH4 
B)  DIBAL-H 
C)  NaBH4 
D)  H2, Pd/C

Question 6

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 7

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 8

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 9

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 10

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 11

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 12

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 13

What is the structure for acetic propanoic anhydride?

Accepted Answer

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

Question 14

Will the following reaction occur?

Accepted Answer

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

Question 15

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 16

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 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

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 20

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

Exam 22: Carboxylic Acids and Derivatives

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

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

What is the product of the following reaction?

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

What reagent would you use for the following transformation?

What is the IUPAC name for the following compound?

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

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

What is the product of the following reaction?

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

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

How can you convert a carboxylic acid into an ester?

What is the structure for acetic propanoic anhydride?

Will the following reaction occur?

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

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

Which of the following is a lactam?

What is the product of the following reaction?

Draw the structure of N-phenyl acetamide.

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 Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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

Lipids

Synthetic Polymers

Filters

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

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?