Question 1

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 2

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 3

When HOCH2CH2CH2CH2COCH2CH2CH2CH2OH is heated in the presence of an acid catalyst, a reaction occurs. This product has the formula C9H16O2. Provide the structure of this product.

Accepted Answer

Question 4

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 5

Treatment of a nitrile with a Grignard reagent followed by hydrolysis results in ________.

Accepted Answer

A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  an alcohol 
A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  an alcohol

Question 6

What would be the product of the following reaction?

Accepted Answer

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

Question 7

Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH2CH2OH) to produce an acetal.

Accepted Answer

Question 8

Provide the proper IUPAC name for CH3CHBrCH2COCH2CHO.

Accepted Answer

5-bromo-3-

Question 9

In the mass spectrum of 3,3-dimethyl-2-butanone, the base peak will occur at m/z ________.

Accepted Answer

A)  43 
B)  58 
C)  84 
D)  85 
E)  100 
A)  43 
B)  58 
C)  84 
D)  85 
E)  100

Question 10

What organic compound is generated when PhCOCl is treated with

Accepted Answer

The answer of What organic compound is generated when PhCOCl...

Question 11

Which of the following compounds is most soluble in water?

Accepted Answer

A)  acetone 
B)  cyclohexanone 
C)  2-butanone 
D)  3-octanone 
E)  benzophenone 
A)  acetone 
B)  cyclohexanone 
C)  2-butanone 
D)  3-octanone 
E)  benzophenone

Question 12

Provide the preferred reagent pair to synthesize 3-ethylpent-2-ene via a Wittig reaction.

Accepted Answer

CH₃CH₂COCH₂CH

Question 13

How might one prepare 4-heptanone from CH3CH2CH2CN in two steps?

Accepted Answer

Question 14

Provide the major organic product which results when   
is treated with

Accepted Answer

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

Question 15

When H2NCH2CH2CH2CH2COCH3 is heated in the process of an acid catalyst, a reaction occurs. The product has the formula C6H11N. Provide the structure of this product.

Accepted Answer

Question 16

Provide the proper IUPAC name for CH3CHOHCH2COCH2C(CH3)2CH2CH3.

Accepted Answer

2-hydroxy-

Question 17

Why do acetal-forming reactions that use ethylene glycol have more favorable equilibrium constants than those using methanol?

Accepted Answer

A)  Ethylene glycol reacts more rapidly. 
B)  They are more favorable on entropy grounds. 
C)  They are more favorable on enthalpy grounds. 
D)  Ethylene glycol is acidic and catalyzes the reaction. 
E)  The ethylene acetal can serve as a protecting group. 
A)  Ethylene glycol reacts more rapidly. 
B)  They are more favorable on entropy grounds. 
C)  They are more favorable on enthalpy grounds. 
D)  Ethylene glycol is acidic and catalyzes the reaction. 
E)  The ethylene acetal can serve as a protecting group.

Question 18

The proton NMR spectrum of an unknown compound contains a triplet at   Which of the following could be this unknown?

Accepted Answer

A)  (CH3)3CCHO 
B)  CH3CH2CH2CO2H 
C)  CH3CH2CH2CHO 
D)  CH3CO CH2Ph 
E)  PhCHO 
A)  (CH3)3CCHO 
B)  CH3CH2CH2CO2H 
C)  CH3CH2CH2CHO 
D)  CH3CO CH2Ph 
E)  PhCHO

Question 19

Provide the structure of the compound which results when HCN adds to pentanal.

Accepted Answer

The answer of Provide the structure of the compound which...

Question 20

Which of the following compounds would show only one triplet in its off resonance decoupled   spectrum?

Accepted Answer

A)  acetone 
B)  butanal 
C)  pentanal 
D)  2-pentanone 
E)  3-pentanone 
A)  acetone 
B)  butanal 
C)  pentanal 
D)  2-pentanone 
E)  3-pentanone

Exam 18: Ketones and Aldehydes

Provide the major organic product of the reaction shown below.

Provide the major organic product of the reaction shown below.

When HOCH2CH2CH2CH2COCH2CH2CH2CH2OH is heated in the presence of an acid catalyst, a reaction occurs. This product has the formula C9H16O2. Provide the structure of this product.

Provide the major organic product of the reaction shown below.

Treatment of a nitrile with a Grignard reagent followed by hydrolysis results in ________.

What would be the product of the following reaction?

Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH2CH2OH) to produce an acetal.

Provide the proper IUPAC name for CH3CHBrCH2COCH2CHO.

In the mass spectrum of 3,3-dimethyl-2-butanone, the base peak will occur at m/z ________.

What organic compound is generated when PhCOCl is treated with

Which of the following compounds is most soluble in water?

Provide the preferred reagent pair to synthesize 3-ethylpent-2-ene via a Wittig reaction.

How might one prepare 4-heptanone from CH3CH2CH2CN in two steps?

Provide the major organic product which results when is treated with

When H2NCH2CH2CH2CH2COCH3 is heated in the process of an acid catalyst, a reaction occurs. The product has the formula C6H11N. Provide the structure of this product.

Provide the proper IUPAC name for CH3CHOHCH2COCH2C(CH3)2CH2CH3.

Why do acetal-forming reactions that use ethylene glycol have more favorable equilibrium constants than those using methanol?

The proton NMR spectrum of an unknown compound contains a triplet at Which of the following could be this unknown?

Provide the structure of the compound which results when HCN adds to pentanal.

Which of the following compounds would show only one triplet in its off resonance decoupled spectrum?

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

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

When HOCH₂CH₂CH₂CH₂COCH₂CH₂CH₂CH₂OH is heated in the presence of an acid catalyst, a reaction occurs. This product has the formula C₉H₁₆O₂. Provide the structure of this product.

Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH₂CH₂OH) to produce an acetal.

Provide the proper IUPAC name for CH₃CHBrCH₂COCH₂CHO.

How might one prepare 4-heptanone from CH₃CH₂CH₂CN in two steps?

When H₂NCH₂CH₂CH₂CH₂COCH₃ is heated in the process of an acid catalyst, a reaction occurs. The product has the formula C₆H₁₁N. Provide the structure of this product.

Provide the proper IUPAC name for CH₃CHOHCH₂COCH₂C(CH₃)₂CH₂CH₃.