Question 1

Provide a detailed, stepwise mechanism to show how PhCHO is formed by the reaction of PhCOCl with LiAlH [O(CH3)3]3.

Accepted Answer

Question 2

An acid which could not be prepared from an organic halide by carboxylation of the Grignard reagent is:

Accepted Answer

A)  benzoic acid. 
B)  2,2-dimethylpropanoic acid. 
C)  propanoic acid. 
D)  4-oxocyclohexanecarboxylic acid. 
E)  2-methylbutanoic acid. 
A)  benzoic acid. 
B)  2,2-dimethylpropanoic acid. 
C)  propanoic acid. 
D)  4-oxocyclohexanecarboxylic acid. 
E)  2-methylbutanoic acid. D

Question 3

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 4

An unknown compound is insoluble in water but dissolves in 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 5

Provide the IUPAC name for the compound shown below.

Accepted Answer

3-hydroxyh

Question 6

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 7

Deduce a reasonable structure for the compound which exhibits the following spectroscopic data.
C5H9ClO2: IR: 2700-3400 cm-1 (broad), 1710 cm-1; 1H NMR: - 1.40 (6H, singlet), 3.60 (2H, singlet), 10.1 (1H, singlet) ppm.

Accepted Answer

Question 8

Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation?

Accepted Answer

A)  addition of water 
B)  removal of water as it is formed 
C)  addition of an inorganic acid as a catalyst 
D)  addition of alcohol 
E)  both B and D 
A)  addition of water 
B)  removal of water as it is formed 
C)  addition of an inorganic acid as a catalyst 
D)  addition of alcohol 
E)  both B and D

Question 9

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 10

Provide the major organic product for the following reaction.

Accepted Answer

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

Question 11

Name the compound shown below.

Accepted Answer

3,3,6-trimethyl-6-he

Question 12

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 13

What reagent is needed to complete the following transformation?

Accepted Answer

The answer of What reagent is needed to complete the...

Question 14

What salt results from the reaction of benzoic acid with potassium hydroxide?

Accepted Answer

The answer of What salt results from the reaction of...

Question 15

LiAl [OC(CH3)3]3H will reduce an acid chloride to an:

Accepted Answer

A)  alcohol. 
B)  alkane. 
C)  acid. 
D)  aldehyde. 
E)  acetal. 
A)  alcohol. 
B)  alkane. 
C)  acid. 
D)  aldehyde. 
E)  acetal.

Question 16

What are the products of the reaction of benzoic acid with thionyl chloride?

Accepted Answer

benzoyl ch

Question 17

After completing the synthesis of 3-methylpentanoic acid, which of the following treatments will neutralize the mineral acids and facilitate the distribution of the organic acid from the organic layer to the aqueous extraction layer?

Accepted Answer

A)  extraction with aqueous NaCl 
B)  extraction with ether 
C)  extraction with aqueous NaHCO3 
D)  extraction with water 
E)  extraction with dilute aqueous HCl 
A)  extraction with aqueous NaCl 
B)  extraction with ether 
C)  extraction with aqueous NaHCO3 
D)  extraction with water 
E)  extraction with dilute aqueous HCl

Question 18

What compound is produced when cyclohexene is treated with concentrated KMnO4?

Accepted Answer

A)  hexanoic acid 
B)  adipic acid 
C)  cyclohexanecarboxylic acid 
D)  benzoic acid 
E)  succinic acid 
A)  hexanoic acid 
B)  adipic acid 
C)  cyclohexanecarboxylic acid 
D)  benzoic acid 
E)  succinic acid

Question 19

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene and in which Grignard chemistry is employed.

Accepted Answer

1. Br₂, hν

Question 20

Beta-keto acids are unusually unstable and will lose the carboxylate group under certain conditions where both a general acid and base are involved. During this process, CO2 is lost and the original beta-keto acid is converted into a ketone. For the following reaction, show a stepwise mechanism, with electron pushing arrows, in the formation of the products. Make special note of any resonance stabilized intermediates in this reaction.

Accepted Answer

Exam 20: Carboxylic Acids

Provide a detailed, stepwise mechanism to show how PhCHO is formed by the reaction of PhCOCl with LiAlH [O(CH3)3]3.

An acid which could not be prepared from an organic halide by carboxylation of the Grignard reagent is:

Provide the major organic product of the following reaction sequence.

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

Provide the IUPAC name for the compound shown below.

Provide the major organic product of the reaction shown below.

Deduce a reasonable structure for the compound which exhibits the following spectroscopic data. C5H9ClO2: IR: 2700-3400 cm-1 (broad), 1710 cm-1; 1H NMR: - 1.40 (6H, singlet), 3.60 (2H, singlet), 10.1 (1H, singlet) ppm.

Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation?

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

Provide the major organic product for the following reaction.

Name the compound shown below.

Provide the major organic product of the reaction shown below.

What reagent is needed to complete the following transformation?

What salt results from the reaction of benzoic acid with potassium hydroxide?

LiAl [OC(CH3)3]3H will reduce an acid chloride to an:

What are the products of the reaction of benzoic acid with thionyl chloride?

After completing the synthesis of 3-methylpentanoic acid, which of the following treatments will neutralize the mineral acids and facilitate the distribution of the organic acid from the organic layer to the aqueous extraction layer?

What compound is produced when cyclohexene is treated with concentrated KMnO4?

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene and in which Grignard chemistry is employed.

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

Provide a detailed, stepwise mechanism to show how PhCHO is formed by the reaction of PhCOCl with LiAlH [O(CH₃)₃]₃.

Deduce a reasonable structure for the compound which exhibits the following spectroscopic data. C₅H₉ClO₂: IR: 2700-3400 cm^-1 (broad), 1710 cm^-1; ¹H NMR: - 1.40 (6H, singlet), 3.60 (2H, singlet), 10.1 (1H, singlet) ppm.

LiAl [OC(CH₃)₃]₃H will reduce an acid chloride to an:

What compound is produced when cyclohexene is treated with concentrated KMnO₄?