Question 1

What would be the product of the following reaction sequence?

Accepted Answer

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

Question 2

What is the reactant W in the synthesis given below?

Accepted Answer

A) Cyclopentanone 
B) Cyclopentene 
C) Cyclopentanol 
D) Bromocyclopentane 
E) Triphenylphosphine oxide 
A) Cyclopentanone 
B) Cyclopentene 
C) Cyclopentanol 
D) Bromocyclopentane 
E) Triphenylphosphine oxide

Question 3

Which of the reactions listed below would serve as a synthesis of acetophenone,

Accepted Answer

A) 
  
B)    
C)    
D) Two of these choices. 
E) All of these choices. 
A) 
  
B)    
C)    
D) Two of these choices. 
E) All of these choices.

Question 4

What is the correct IUPAC name for the following compound?

Accepted Answer

A) 2,4-dimethyl-2-pentenone 
B) 2,5-dimethylcyclopenten-3-one 
C) 2,4-dimethylcyclopent-2-enone 
D) 3,5-dimethylcyclopent-2-enone 
E) 2-methyl-5-methylcyclopent-2-enone 
A) 2,4-dimethyl-2-pentenone 
B) 2,5-dimethylcyclopenten-3-one 
C) 2,4-dimethylcyclopent-2-enone 
D) 3,5-dimethylcyclopent-2-enone 
E) 2-methyl-5-methylcyclopent-2-enone

Question 5

Explain clearly how you might use 1H NMR to distinguish between 2-phenylacetaldehyde and acetophenone.

Accepted Answer

A quick inspection of ¹H NMR

Question 6

Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-bromobutane.

Accepted Answer

The answer of Suggest a synthetic strategy for the synthesis...

Question 7

Select the structure of the major product in the following reaction.

Accepted Answer

A) 3-Methylhexanal 
B) 4-Methyl-1-hexanol 
C) 4-Methylhexanal 
D) 4,10-Dimethyldodecane-6,7-dione 
E) 4,10-Dimethyldodecane-6,7-diol 
A) 3-Methylhexanal 
B) 4-Methyl-1-hexanol 
C) 4-Methylhexanal 
D) 4,10-Dimethyldodecane-6,7-dione 
E) 4,10-Dimethyldodecane-6,7-diol

Question 8

The product,D,of the following reaction sequence,   would be:

Accepted Answer

A)    
B) CH3CH2COOCH3 
C)    
D) CH3CH=CHCOOH 
E)    
A)    
B) CH3CH2COOCH3 
C)    
D) CH3CH=CHCOOH 
E)

Question 9

What is the correct IUPAC name for the following compound?

Accepted Answer

A) 5,5-Dimethyl-2-heptanone 
B) 5-Ethyl-5,5-dimethyl-methyl-2-octanone 
C) 5-Ethyl-5-methyl-2-hexanone 
D) 5,5-Dimethyl-2-octanone 
E) 3,3-Dimethyl-6-heptanone 
A) 5,5-Dimethyl-2-heptanone 
B) 5-Ethyl-5,5-dimethyl-methyl-2-octanone 
C) 5-Ethyl-5-methyl-2-hexanone 
D) 5,5-Dimethyl-2-octanone 
E) 3,3-Dimethyl-6-heptanone

Question 10

What is the major product of the following reaction sequence?

Accepted Answer

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

Question 11

Which of the following is a synthesis of 3-heptanone?

Accepted Answer

A)    
B)    
C)    
D) 
  
E) All of these choices are syntheses of 3-heptanone. 
A)    
B)    
C)    
D) 
  
E) All of these choices are syntheses of 3-heptanone.

Question 12

The product,C,of the following reaction sequence,   would be:

Accepted Answer

A)    
B) CH3CH2COOCH3 
C)    
D) CH3CH=CHCOOH 
E) None of these choices. 
A)    
B) CH3CH2COOCH3 
C)    
D) CH3CH=CHCOOH 
E) None of these choices.

Question 13

What is the correct IUPAC name for the following compound?

Accepted Answer

A) (1S,4R)-bicyclo[2.2.1]hexan-2-one 
B) (1S,4R)-bicyclo[2.1.2]heptan-2-one 
C) (1S,4R)-bicyclo[2.2.1]heptan-2-one 
D) (1R,4S)-bicyclo[2.1.1]heptan-2-one 
E) (1S,4S)-bicyclo[2.1.2]heptan-2-one 
A) (1S,4R)-bicyclo[2.2.1]hexan-2-one 
B) (1S,4R)-bicyclo[2.1.2]heptan-2-one 
C) (1S,4R)-bicyclo[2.2.1]heptan-2-one 
D) (1R,4S)-bicyclo[2.1.1]heptan-2-one 
E) (1S,4S)-bicyclo[2.1.2]heptan-2-one

Question 14

What would be the product of the following reaction sequence?

Accepted Answer

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

Question 15

Acetals are unstable in the presence of an aqueous solution of which of these?

Accepted Answer

A) HCl 
B) NaOH 
C) KHCO3 
D) Na2CO3 
E) NaCl 
A) HCl 
B) NaOH 
C) KHCO3 
D) Na2CO3 
E) NaCl

Question 16

A good synthesis of

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All of these are equally useful. 
A) I 
B) II 
C) III 
D) IV 
E) All of these are equally useful.

Question 17

Which Wittig reagent would be used to synthesize

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) Either I or II could be used. 
A) I 
B) II 
C) III 
D) IV 
E) Either I or II could be used.

Question 18

Which is the proper name for the structure shown?

Accepted Answer

A) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal 
B) 3-Methyl-5-(4-chlorophenyl)hexanol 
C) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde 
D) 3-Methyl-5-(4-chlorophenyl)hexanaldehyde 
E) 3-Methyl-5-(4-chlorophenyl)hexanal 
A) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal 
B) 3-Methyl-5-(4-chlorophenyl)hexanol 
C) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde 
D) 3-Methyl-5-(4-chlorophenyl)hexanaldehyde 
E) 3-Methyl-5-(4-chlorophenyl)hexanal

Question 19

What is the major product of the following reaction sequence?

Accepted Answer

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

Question 20

Which of these gem-diols is expected to be the most stable?

Accepted Answer

A)    
B) CH3CH(OH)2 
C)    
D) C6H5CH(OH)2 
E) ClCH2CH(OH)2 
A)    
B) CH3CH(OH)2 
C)    
D) C6H5CH(OH)2 
E) ClCH2CH(OH)2

Exam 16: Aldehydes and Ketones

What would be the product of the following reaction sequence?

What is the reactant W in the synthesis given below?

Which of the reactions listed below would serve as a synthesis of acetophenone,

What is the correct IUPAC name for the following compound?

Explain clearly how you might use 1H NMR to distinguish between 2-phenylacetaldehyde and acetophenone.

Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-bromobutane.

Select the structure of the major product in the following reaction.

The product,D,of the following reaction sequence, would be:

What is the correct IUPAC name for the following compound?

What is the major product of the following reaction sequence?

Which of the following is a synthesis of 3-heptanone?

The product,C,of the following reaction sequence, would be:

What is the correct IUPAC name for the following compound?

What would be the product of the following reaction sequence?

Acetals are unstable in the presence of an aqueous solution of which of these?

A good synthesis of

Which Wittig reagent would be used to synthesize

Which is the proper name for the structure shown?

What is the major product of the following reaction sequence?

Which of these gem-diols is expected to be the most stable?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Explain clearly how you might use ¹H NMR to distinguish between 2-phenylacetaldehyde and acetophenone.