Question 1

What two features are prominent in the infrared spectrum of a carboxylic acid?

Accepted Answer

The carbonyl stretch

Question 2

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 3

What products result from the reaction of sodium propanoate with hydrobromic acid?

Accepted Answer

propanoic

Question 4

Which of the reagents listed below would work best in the following reaction?

Accepted Answer

A)  NaBH4 
B)  LiAlH4 
C)  BH3 -THF 
D)  LiAl[(OC(CH3)3]3H 
E)  none of the above 
A)  NaBH4 
B)  LiAlH4 
C)  BH3 -THF 
D)  LiAl[(OC(CH3)3]3H 
E)  none of the above

Question 5

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 6

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 7

The conversion of butanoic acid to 2-pentanone is best accomplished with:

Accepted Answer

A)  1. thionyl chloride; 2. methylmagnesium bromide. 
B)  methyllithium. 
C)  1. methanol, sulfuric acid; 2. methyllithium. 
D)  1. thionyl chloride; 2. methanol. 
E)  1. sulfuric acid; 2. methanol. 
A)  1. thionyl chloride; 2. methylmagnesium bromide. 
B)  methyllithium. 
C)  1. methanol, sulfuric acid; 2. methyllithium. 
D)  1. thionyl chloride; 2. methanol. 
E)  1. sulfuric acid; 2. methanol.

Question 8

Provide the IUPAC name for the compound shown below.

Accepted Answer

o-hydroxyb

Question 9

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 10

Esters and amides are most easily made by nucleophilic acyl substitution reactions on:

Accepted Answer

A)  alcohols. 
B)  acid anhydrides. 
C)  carboxylates. 
D)  carboxylic acids. 
E)  acid chlorides. 
A)  alcohols. 
B)  acid anhydrides. 
C)  carboxylates. 
D)  carboxylic acids. 
E)  acid chlorides.

Question 11

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 12

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 13

Are carboxylic acids of more than 10 carbons more soluble in polar or nonpolar solvents?

Accepted Answer

The answer of Are carboxylic acids of more than 10...

Question 14

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

Accepted Answer

1. HBr, peroxides
2.

Question 15

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 16

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 17

Which of the following is the strongest acid?

Accepted Answer

A)  (CH3)2CHCO2H 
B)  CH3CH2CO2H 
C)  CH3OCH2CO2H 
D)  PhCH2CO2H 
E)  O2NCH2CO2H 
A)  (CH3)2CHCO2H 
B)  CH3CH2CO2H 
C)  CH3OCH2CO2H 
D)  PhCH2CO2H 
E)  O2NCH2CO2H

Question 18

Provide the major organic product for the following reaction.

Accepted Answer

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

Question 19

Acid chlorides can be prepared from carboxylic acids by treatment with ________.

Accepted Answer

A)  (COCl)2 
B)  SOCl2 
C)  KCl 
D)  both A and B 
E)  both B and C 
A)  (COCl)2 
B)  SOCl2 
C)  KCl 
D)  both A and B 
E)  both B and C

Question 20

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Exam 20: Carboxylic Acids

What two features are prominent in the infrared spectrum of a carboxylic acid?

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

What products result from the reaction of sodium propanoate with hydrobromic acid?

Which of the reagents listed below would work best in the following reaction?

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction sequence.

The conversion of butanoic acid to 2-pentanone is best accomplished with:

Provide the IUPAC name for the compound shown below.

Provide the major organic product of the following reaction sequence.

Esters and amides are most easily made by nucleophilic acyl substitution reactions on:

Provide the major organic product of the following reaction sequence.

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

Are carboxylic acids of more than 10 carbons more soluble in polar or nonpolar solvents?

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

Provide the major organic product of the reaction shown below.

Provide the major organic product of the reaction shown below.

Which of the following is the strongest acid?

Provide the major organic product for the following reaction.

Acid chlorides can be prepared from carboxylic acids by treatment with ________.

Provide the major organic product of the following reaction sequence.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

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