Question 1

Suggest a sequence of synthetic steps through which 2-phenylethanol can be prepared from toluene. One of your intermediates must be a carboxylic acid.

Accepted Answer

1) Br₂, hν or NBS 2) NaCN, acet

Question 2

Why are the OH groups of carboxylic acids more acidic than alcohols?

Accepted Answer

A)  resonance stabilization of the carboxylate ion 
B)  inductive electron donating by the carbonyl oxygen 
C)  reduced hydrogen bonding capacity 
D)  because they have lower pKa values 
E)  None of the above - carboxylic acids are not more acidic than alcohols. 
A)  resonance stabilization of the carboxylate ion 
B)  inductive electron donating by the carbonyl oxygen 
C)  reduced hydrogen bonding capacity 
D)  because they have lower pKa values 
E)  None of the above - carboxylic acids are not more acidic than alcohols.

Question 3

Provide the name of the compound shown below.

Accepted Answer

2,5-dimethyl-4-hexen

Question 4

Show how you could make the acid shown below starting with any alcohol:

Accepted Answer

The answer of Show how you could make the acid...

Question 5

The 1H NMR spectrum of an unknown acid has the following peaks:
Δ (ppm) = 12.71 (1H, s), 8.04 (2H, d), 7.30 (2H, d), 2.41 (3H, s)
Which structure best fits this spectral information?

Accepted Answer

A)    
B)    
C)    
D)    
A)    
B)    
C)    
D)

Question 6

How does the O-H stretch in the IR spectrum of a carboxylic acid differ from the O-H stretch of an alcohol?

Accepted Answer

The O-H stretch of a

Question 7

What is the common name for the following compound?

Accepted Answer

A)  γ-hydroxyvaleric acid 
B)  γ-hydroxypentanoic acid 
C)  γ-hydroxy-γ-methylbutyric acid 
D)  δ-hydroxyvaleric acid 
A)  γ-hydroxyvaleric acid 
B)  γ-hydroxypentanoic acid 
C)  γ-hydroxy-γ-methylbutyric acid 
D)  δ-hydroxyvaleric acid

Question 8

Carboxylic acids can be made from Grignards by treating the Grignard reagents with ________.

Accepted Answer

A)  carbon monoxide 
B)  esters 
C)  aldehydes 
D)  diborane 
E)  carbon dioxide 
A)  carbon monoxide 
B)  esters 
C)  aldehydes 
D)  diborane 
E)  carbon dioxide

Question 9

Provide the IUPAC name for the compound shown below.

Accepted Answer

o-hydroxyb

Question 10

What two alkenes, which contain only one double bond, yield exclusively propanoic acid upon oxidation with hot concentrated KMnO4?

Accepted Answer

Question 11

Provide the structure of the major organic compound which results when cyclopentanecarboxylic acid is treated with thionyl chloride and the resulting product is treated with LiAlH[OC(CH3)3]3.

Accepted Answer

Question 12

Show the deprotonation of benzoic acid by hydroxide and draw the important resonance structures of the carboxylate ion.

Accepted Answer

The answer of Show the deprotonation of benzoic acid by...

Question 13

Propose a reasonable synthetic route to prepare cyclohexylacetic acid from methylenecyclohexane.

Accepted Answer

1) HBr, peroxides
2)

Question 14

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 15

The first mechanistic step in the direct reaction of an amine with a carboxylic acid to produce an amide is ________.

Accepted Answer

A)  an acid-base reaction 
B)  nucleophilic attack on the carbonyl carbon 
C)  loss of H2O 
D)  loss of CO2 
E)  loss of N2 
A)  an acid-base reaction 
B)  nucleophilic attack on the carbonyl carbon 
C)  loss of H2O 
D)  loss of CO2 
E)  loss of N2

Question 16

What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence of steps?
1) Mg, Et2O 2. CO2

Accepted Answer

A)  2-methylpropanoic acid 
B)  3-methylpropanoic acid 
C)  2-methylbutanoic acid 
D)  3-methylbutanoic acid 
E)  2-methylhexanoic acid 
A)  2-methylpropanoic acid 
B)  3-methylpropanoic acid 
C)  2-methylbutanoic acid 
D)  3-methylbutanoic acid 
E)  2-methylhexanoic acid

Question 17

In glutaric acid (HOOCCH2CH2CH2COOH), pKa1 is 4.35 while the pKa2 is 5.42. Why is the second carboxylic acid less acidic?

Accepted Answer

The second carboxyl group is much less a

Question 18

Provide the structure of 3-nitrophthalic acid.

Accepted Answer

The answer of Provide the structure of 3-nitrophthalic acid....

Question 19

Carboxylic acids boil at considerably higher temperatures than do alcohols, ketones, or aldehydes of similar molecular weights. This is because they ________.

Accepted Answer

A)  have a greater oxygen content 
B)  are more acidic 
C)  form stable hydrogen-bonded dimers 
D)  are hydrophobic 
E)  none of the above 
A)  have a greater oxygen content 
B)  are more acidic 
C)  form stable hydrogen-bonded dimers 
D)  are hydrophobic 
E)  none of the above

Question 20

The strongest dichlorobutanoic acid is ________.

Accepted Answer

A)  2,2-dichlorobutanoic acid 
B)  2,3-dichlorobutanoic acid 
C)  3,3-dichlorobutanoic acid 
D)  3,4-dichlorobutanoic acid 
E)  4,4-dichlorobutanoic acid 
A)  2,2-dichlorobutanoic acid 
B)  2,3-dichlorobutanoic acid 
C)  3,3-dichlorobutanoic acid 
D)  3,4-dichlorobutanoic acid 
E)  4,4-dichlorobutanoic acid

Exam 20: Carboxylic Acids

Suggest a sequence of synthetic steps through which 2-phenylethanol can be prepared from toluene. One of your intermediates must be a carboxylic acid.

Why are the OH groups of carboxylic acids more acidic than alcohols?

Provide the name of the compound shown below.

Show how you could make the acid shown below starting with any alcohol:

The 1H NMR spectrum of an unknown acid has the following peaks: Δ (ppm) = 12.71 (1H, s), 8.04 (2H, d), 7.30 (2H, d), 2.41 (3H, s) Which structure best fits this spectral information?

How does the O-H stretch in the IR spectrum of a carboxylic acid differ from the O-H stretch of an alcohol?

What is the common name for the following compound?

Carboxylic acids can be made from Grignards by treating the Grignard reagents with ________.

Provide the IUPAC name for the compound shown below.

What two alkenes, which contain only one double bond, yield exclusively propanoic acid upon oxidation with hot concentrated KMnO4?

Provide the structure of the major organic compound which results when cyclopentanecarboxylic acid is treated with thionyl chloride and the resulting product is treated with LiAlH[OC(CH3)3]3.

Show the deprotonation of benzoic acid by hydroxide and draw the important resonance structures of the carboxylate ion.

Propose a reasonable synthetic route to prepare cyclohexylacetic acid from methylenecyclohexane.

Provide the major organic product of the reaction shown below.

The first mechanistic step in the direct reaction of an amine with a carboxylic acid to produce an amide is ________.

What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence of steps? 1) Mg, Et2O 2. CO2

In glutaric acid (HOOCCH2CH2CH2COOH), pKa1 is 4.35 while the pKa2 is 5.42. Why is the second carboxylic acid less acidic?

Provide the structure of 3-nitrophthalic acid.

Carboxylic acids boil at considerably higher temperatures than do alcohols, ketones, or aldehydes of similar molecular weights. This is because they ________.

The strongest dichlorobutanoic acid is ________.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

What two alkenes, which contain only one double bond, yield exclusively propanoic acid upon oxidation with hot concentrated KMnO₄?

Provide the structure of the major organic compound which results when cyclopentanecarboxylic acid is treated with thionyl chloride and the resulting product is treated with LiAlH[OC(CH₃)₃]₃.

What compound is produced when (CH₃)₂CHCH₂Br is subjected to the following sequence of steps? 1) Mg, Et₂O 2. CO₂

In glutaric acid (HOOCCH₂CH₂CH₂COOH), pKa₁ is 4.35 while the pKa₂ is 5.42. Why is the second carboxylic acid less acidic?