Question 1

Provide the structure of trans-1,3-cyclohexanedicarboxylic acid.

Accepted Answer

The answer of Provide the structure of trans-1,3-cyclohexanedicarboxylic acid....

Question 2

The methyl ester of a carboxylic acid can be synthesized directly using ________.

Accepted Answer

A)  SOCl2 
B)  PCl5 
C)  C2O2Cl2 
D)  CH2N2 
E)  CH3NH2 
A)  SOCl2 
B)  PCl5 
C)  C2O2Cl2 
D)  CH2N2 
E)  CH3NH2

Question 3

List the following weak acids in order of increasing acidity (from lowest to highest.).

Accepted Answer

A)  4 < 3 < 2 < 1 < 5 
B)  4 < 1 < 3 < 2 < 5 
C)  5 < 2 < 3 < 1 < 4 
D)  4 < 1 < 2 < 5 < 3 
E)  1 < 2 < 4 < 3 < 5 
A)  4 < 3 < 2 < 1 < 5 
B)  4 < 1 < 3 < 2 < 5 
C)  5 < 2 < 3 < 1 < 4 
D)  4 < 1 < 2 < 5 < 3 
E)  1 < 2 < 4 < 3 < 5

Question 4

Provide the structure of pent-3-ynoic acid.

Accepted Answer

The answer of Provide the structure of pent-3-ynoic acid....

Question 5

Lithium aluminum hydride reduces carboxylic acids to primary alcohols via what intermediate?

Accepted Answer

A)  a ketone 
B)  a methyl ester 
C)  an aldehyde 
D)  a secondary alcohol 
E)  an acid chloride 
A)  a ketone 
B)  a methyl ester 
C)  an aldehyde 
D)  a secondary alcohol 
E)  an acid chloride

Question 6

An ether solution of PhCO2H (A), PhNH2 (B), and PhCH3 (C) is extracted with aqueous NaOH. The ether layer will contain what compound(s) after the extraction?

Accepted Answer

A)  A + B 
B)  A + C 
C)  B + C 
D)  A + B + C 
E)  A only 
A)  A + B 
B)  A + C 
C)  B + C 
D)  A + B + C 
E)  A only

Question 7

Which of the following compounds is the strongest acid?

Accepted Answer

A)  p-nitrobenzoic acid 
B)  p-bromobenzoic acid 
C)  m-methylbenzoic acid 
D)  m-methoxybenzoic acid 
E)  water 
A)  p-nitrobenzoic acid 
B)  p-bromobenzoic acid 
C)  m-methylbenzoic acid 
D)  m-methoxybenzoic acid 
E)  water

Question 8

Which of the following reagents can be used to convert a carboxylic acid directly into its corresponding acid chloride derivative?

Accepted Answer

A)  (COCl)2 
B)  HCl 
C)  CH3Cl 
D)  NaOCl 
E)  CH3COCl 
A)  (COCl)2 
B)  HCl 
C)  CH3Cl 
D)  NaOCl 
E)  CH3COCl

Question 9

How can one prepare ethyl cyclohexyl ketone from cyclohexanecarboxylic acid?

Accepted Answer

1. CH₃CH₂Li

Question 10

Starting with any alkene, how could you make pimelic acid (HOOC(CH2)5COOH)?

Accepted Answer

Treat cycl

Question 11

Provide the major organic product for the following reaction.

Accepted Answer

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

Question 12

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 13

An unknown compound is insoluble in water but dissolves in an aqueous solution of sodium bicarbonate with a release of carbon dioxide bubbles. The compound is almost certainly ________.

Accepted Answer

A)  a carboxylic acid 
B)  an amine 
C)  an aldehyde 
D)  an alkyl chloride 
E)  an alcohol 
A)  a carboxylic acid 
B)  an amine 
C)  an aldehyde 
D)  an alkyl chloride 
E)  an alcohol

Question 14

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 15

Provide a detailed, stepwise mechanism for the methylation of a carboxylic acid with diazomethane.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 16

Provide a mechanism for the reaction shown below.

Accepted Answer

The answer of Provide a mechanism for the reaction shown...

Question 17

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 18

Provide the major organic product for the following reaction.

Accepted Answer

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

Question 19

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 20

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Exam 20: Carboxylic Acids

Provide the structure of trans-1,3-cyclohexanedicarboxylic acid.

The methyl ester of a carboxylic acid can be synthesized directly using ________.

List the following weak acids in order of increasing acidity (from lowest to highest.).

Provide the structure of pent-3-ynoic acid.

Lithium aluminum hydride reduces carboxylic acids to primary alcohols via what intermediate?

An ether solution of PhCO2H (A), PhNH2 (B), and PhCH3 (C) is extracted with aqueous NaOH. The ether layer will contain what compound(s) after the extraction?

Which of the following compounds is the strongest acid?

Which of the following reagents can be used to convert a carboxylic acid directly into its corresponding acid chloride derivative?

How can one prepare ethyl cyclohexyl ketone from cyclohexanecarboxylic acid?

Starting with any alkene, how could you make pimelic acid (HOOC(CH2)5COOH)?

Provide the major organic product for the following reaction.

Provide the major organic product of the following reaction.

An unknown compound is insoluble in water but dissolves in an aqueous solution of sodium bicarbonate with a release of carbon dioxide bubbles. The compound is almost certainly ________.

Which of the following is the strongest acid?

Provide a detailed, stepwise mechanism for the methylation of a carboxylic acid with diazomethane.

Provide a mechanism for the reaction shown below.

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

Provide the major organic product for the following reaction.

Provide the major organic product of the reaction shown below.

Provide the major organic product of the reaction shown below.

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

An ether solution of PhCO₂H (A), PhNH₂ (B), and PhCH₃ (C) is extracted with aqueous NaOH. The ether layer will contain what compound(s) after the extraction?

Starting with any alkene, how could you make pimelic acid (HOOC(CH₂)₅COOH)?