Question 1

What reagent can be used to convert benzophenone into triphenylmethanol?

Accepted Answer

PhMgBr followed by hydrolysis

Question 2

By which single-step process can benzene be readily converted into acetophenone?

Accepted Answer

CH₃COCl, AlCl₃ - a Friedel-Crafts acylation reaction

Question 3

What is the major organic product of the following reaction?

Accepted Answer

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

Question 4

Which of the following amines will react with cyclopentanone to form an enamine?

Accepted Answer

A) CH3CH2CH2CH2NH2 
B) (CH3)3N 
C) pyridine 
D) (CH3)3CNH2 
E) none of the above 
A) CH3CH2CH2CH2NH2 
B) (CH3)3N 
C) pyridine 
D) (CH3)3CNH2 
E) none of the above

Question 5

Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions?

Accepted Answer

A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. 
B) Aldehydes are more sterically hindered than esters. 
C) Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups. 
D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized. 
E) Once the nucleophile adds to an aldehyde, neither H- nor R- can be eliminated since they are strongly basic. 
A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. 
B) Aldehydes are more sterically hindered than esters. 
C) Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups. 
D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized. 
E) Once the nucleophile adds to an aldehyde, neither H- nor R- can be eliminated since they are strongly basic.

Question 6

Provide the structure of the hydrate that results when 4-heptanone is treated with dilute aqueous acid.

Accepted Answer

The answer of Provide the structure of the hydrate that...

Question 7

Give the product for the following reaction.

Accepted Answer

A)    
B) CH3CH2CH2OH 
C) CH3CH2CH3 
D)    
E) HOCH2CH2CH2OH 
A)    
B) CH3CH2CH2OH 
C) CH3CH2CH3 
D)    
E) HOCH2CH2CH2OH

Question 8

Which of the following compounds is benzaldehyde?

Accepted Answer

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

Question 9

What is the common name for the following compound?

Accepted Answer

A) chloroaldehyde 
B) α-chloroacetaldehyde 
C) β-chloroacetaldehyde 
D) 2-chloroethanal 
E) α-chloroethanal 
A) chloroaldehyde 
B) α-chloroacetaldehyde 
C) β-chloroacetaldehyde 
D) 2-chloroethanal 
E) α-chloroethanal

Question 10

Identify the product for the reaction.

Accepted Answer

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

Question 11

Provide the structure of the diethyl acetal of butanal.

Accepted Answer

The answer of Provide the structure of the diethyl acetal...

Question 12

Give the product of the following reaction.

Accepted Answer

The answer of Give the product of the following reaction....

Question 13

What is the major organic product of the following reaction?

Accepted Answer

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

Question 14

The compound shown below can form a hemiacetal by reacting with itself in solution.   What is the structure of this hemiacetal?

Accepted Answer

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

Question 15

Give the product for the following reaction.

Accepted Answer

A) CH3CH2NHCH3 
B) CH3CH2CH2OH 
C)    
D) CH3CH2CH2NHCH3 
E) CH3CH2CH2N(CH3)2 
A) CH3CH2NHCH3 
B) CH3CH2CH2OH 
C)    
D) CH3CH2CH2NHCH3 
E) CH3CH2CH2N(CH3)2

Question 16

Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.

Accepted Answer

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

Question 17

Which carbonyl is more susceptible to nucleophilic attack, that of cyclohexanone or that of hexanal? Provide two reasons for your choice.

Accepted Answer

Hexanal. The partial positive charge on

Question 18

Provide the structure of cyclohexanone oxime.

Accepted Answer

The answer of Provide the structure of cyclohexanone oxime....

Question 19

Provide the structure of the imine that results when 4-heptanone is treated with CH3CH2CH2NH2 in the presence of an acid catalyst.

Accepted Answer

Question 20

Propose a synthesis of 3-methyl-4-heptyn-3-ol from 1-butyne.

Accepted Answer

1) NaNH₂ 2)

Exam 17: Reactions of Aldehydes and Ketones

What reagent can be used to convert benzophenone into triphenylmethanol?

By which single-step process can benzene be readily converted into acetophenone?

What is the major organic product of the following reaction?

Which of the following amines will react with cyclopentanone to form an enamine?

Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions?

Provide the structure of the hydrate that results when 4-heptanone is treated with dilute aqueous acid.

Give the product for the following reaction.

Which of the following compounds is benzaldehyde?

What is the common name for the following compound?

Identify the product for the reaction.

Provide the structure of the diethyl acetal of butanal.

Give the product of the following reaction.

What is the major organic product of the following reaction?

The compound shown below can form a hemiacetal by reacting with itself in solution. What is the structure of this hemiacetal?

Give the product for the following reaction.

Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.

Which carbonyl is more susceptible to nucleophilic attack, that of cyclohexanone or that of hexanal? Provide two reasons for your choice.

Provide the structure of cyclohexanone oxime.

Provide the structure of the imine that results when 4-heptanone is treated with CH3CH2CH2NH2 in the presence of an acid catalyst.

Propose a synthesis of 3-methyl-4-heptyn-3-ol from 1-butyne.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Substitution Reactions of Alkyl Halides

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions at the Alpha Carbon of Carbonyl Compounds

Reactions of Benzene and Substituted Benzenes

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Provide the structure of the imine that results when 4-heptanone is treated with CH₃CH₂CH₂NH₂ in the presence of an acid catalyst.