Question 1

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) 5,5-Dimethylcycloheptanone 
D) 4,4-Dimethylcycloheptanone 
E) 3,3-Dimethylcycloheptanone 
A) 5,5-Dimethyl-2-heptanone 
B) 5-Ethyl-5,5-dimethyl-methyl-2-octanone 
C) 5,5-Dimethylcycloheptanone 
D) 4,4-Dimethylcycloheptanone 
E) 3,3-Dimethylcycloheptanone

Question 2

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

Accepted Answer

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

Question 3

Which is the proper name for the structure shown?

Accepted Answer

A) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal 
B) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal 
C) 3-Methyl-5-(2,5-dinitrophenyl)pentanal 
D) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde 
E) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde 
A) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal 
B) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal 
C) 3-Methyl-5-(2,5-dinitrophenyl)pentanal 
D) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde 
E) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde

Question 4

The product,E,of the following sequence of reactions   would be:

Accepted Answer

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

Question 5

Which synthesis or syntheses would yield propanal?

Accepted Answer

A)    
B)    
C)    
D) All of these choices. 
E) None of these choices. 
A)    
B)    
C)    
D) All of these choices. 
E) None of these choices.

Question 6

Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group of an aldehyde or ketone?

Accepted Answer

A) I- 
B) H3O+ 
C) AlCl3 
D) BF3 
E) ZnCl2 
A) I- 
B) H3O+ 
C) AlCl3 
D) BF3 
E) ZnCl2

Question 7

Select the structure of the major product in 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

Question 8

Which reagent(s)could be used to carry out the following transformation?

Accepted Answer

A) Zn(Hg),HCl,reflux 
B) LiAlH4,ether 
C) HSCH2CH2SH,BF3; then Raney Ni (H2) 
D) All of these choices. 
E) Two of these choices. 
A) Zn(Hg),HCl,reflux 
B) LiAlH4,ether 
C) HSCH2CH2SH,BF3; then Raney Ni (H2) 
D) All of these choices. 
E) Two of these choices.

Question 9

A compound with formula C5H10O gives two signals only,one a triplet and the other a quartet,in the 1H NMR spectrum.Which of these structures is a possible one for this compound?

Accepted Answer

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

Question 10

Which compound is an acetal?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) All of these choices.

Question 11

Select the structure of the major product in 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

Question 12

Select the structure of the major product in 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

Question 13

The following reduction can be carried out with which reagent(s)?

Accepted Answer

A) Zn(Hg),HCl 
B) i)HSCH2CH2SH,BF3 ; ii)Raney Ni (H2) 
C) NaBH4,CH3OH 
D) Zn(Hg),HCl and i)HSCH2CH2SH,BF3 ; ii)Raney Ni (H2) 
E) Zn(Hg),HCl and NaBH4,CH3OH 
A) Zn(Hg),HCl 
B) i)HSCH2CH2SH,BF3 ; ii)Raney Ni (H2) 
C) NaBH4,CH3OH 
D) Zn(Hg),HCl and i)HSCH2CH2SH,BF3 ; ii)Raney Ni (H2) 
E) Zn(Hg),HCl and NaBH4,CH3OH

Question 14

In the total synthesis of the Cecropia juvenile hormone,the following sequence of reactions were used.Draw the intermediate and final product formed.

Accepted Answer

The answer of In the total synthesis of the Cecropia...

Question 15

The 1H NMR spectrum of a compound with formula C7H14O gives three signals.Which of these structures is a possible one for this compound?

Accepted Answer

A) 2-Heptanone 
B) 3-Heptanone 
C) 2,4-Dimethyl-3-pentanone 
D) 2,2-Dimethyl-3-pentanone 
E) Two of these choices. 
A) 2-Heptanone 
B) 3-Heptanone 
C) 2,4-Dimethyl-3-pentanone 
D) 2,2-Dimethyl-3-pentanone 
E) Two of these choices.

Question 16

What is the correct IUPAC name for the following compound?

Accepted Answer

A) bicyclo[1.1.1]pentan-2-one 
B) bicyclo[1.1.0]pentan-2-one 
C) cyclopentanone 
D) methylenepentan-2-one 
E) bicyclo[1.0.1]pentan-2-one 
A) bicyclo[1.1.1]pentan-2-one 
B) bicyclo[1.1.0]pentan-2-one 
C) cyclopentanone 
D) methylenepentan-2-one 
E) bicyclo[1.0.1]pentan-2-one

Question 17

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

Accepted Answer

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

Question 18

Predict 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

Question 19

What is the correct structure for 4-chloro-3-methylbenzaldehyde?

Accepted Answer

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

Question 20

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

Accepted Answer

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

Exam 16: Aldehydes and Ketones

What is the correct IUPAC name for the following compound?

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

Which is the proper name for the structure shown?

The product,E,of the following sequence of reactions would be:

Which synthesis or syntheses would yield propanal?

Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group of an aldehyde or ketone?

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

Which reagent(s)could be used to carry out the following transformation?

A compound with formula C5H10O gives two signals only,one a triplet and the other a quartet,in the 1H NMR spectrum.Which of these structures is a possible one for this compound?

Which compound is an acetal?

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

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

The following reduction can be carried out with which reagent(s)?

In the total synthesis of the Cecropia juvenile hormone,the following sequence of reactions were used.Draw the intermediate and final product formed.

The 1H NMR spectrum of a compound with formula C7H14O gives three signals.Which of these structures is a possible one for this compound?

What is the correct IUPAC name for the following compound?

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

Predict the major organic product of the following reaction:

What is the correct structure for 4-chloro-3-methylbenzaldehyde?

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

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

A compound with formula C₅H₁₀O gives two signals only,one a triplet and the other a quartet,in the ¹H NMR spectrum.Which of these structures is a possible one for this compound?

The ¹H NMR spectrum of a compound with formula C₇H₁₄O gives three signals.Which of these structures is a possible one for this compound?