Question 1

Predict the product(s)of the following reaction sequence:

Accepted Answer

A) A mixture of I and II 
B) A mixture of I and III 
C) A mixture of II and III 
D) A mixture of II and IV 
E) A mixture of III and IV 
A) A mixture of I and II 
B) A mixture of I and III 
C) A mixture of II and III 
D) A mixture of II and IV 
E) A mixture of III and IV

Question 2

Jones reagent will fail to give a positive test with?

Accepted Answer

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

Question 3

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1,4-pentanediol from methyl-4-hydroxybutanoate HOCH2CH2CH2COOCH3.

Accepted Answer

Question 4

The following transformation would be considered a(n)?

Accepted Answer

A) reduction 
B) oxidation 
C) addition 
D) elimination 
E) rearrangement 
A) reduction 
B) oxidation 
C) addition 
D) elimination 
E) rearrangement

Question 5

In which of the following series are the compounds arranged in order of decreasing basicity?

Accepted Answer

A) CH3CH2MgBr > NaNH2 > HC$\equiv$CNa > NaOH > CH3CH2ONa 
B) CH3CH2MgBr > NaNH2 > HC$\equiv$CNa > CH3CH2ONa > NaOH 
C) HC$\equiv$CNa > CH3CH2MgBr > NaNH2 > CH3CH2ONa > NaOH 
D) NaNH2 > CH3CH2MgBr > HC$\equiv$CNa > CH3CH2ONa > NaOH 
E) None of these choices. 
A) CH3CH2MgBr > NaNH2 > HC$\equiv$CNa > NaOH > CH3CH2ONa 
B) CH3CH2MgBr > NaNH2 > HC$\equiv$CNa > CH3CH2ONa > NaOH 
C) HC$\equiv$CNa > CH3CH2MgBr > NaNH2 > CH3CH2ONa > NaOH 
D) NaNH2 > CH3CH2MgBr > HC$\equiv$CNa > CH3CH2ONa > NaOH 
E) None of these choices.

Question 6

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)3COH and (CH3)2CHCH2OH?

Accepted Answer

A) NaH 
B) NaOH/H2O 
C) Br2 in CCl4 
D) Cold conc.H2SO4 
E) CrO3 in H2SO4 
A) NaH 
B) NaOH/H2O 
C) Br2 in CCl4 
D) Cold conc.H2SO4 
E) CrO3 in H2SO4

Question 7

When nucleophilic addition to a carbonyl group occurs,the carbon attacked undergoes this hybridization change:

Accepted Answer

A) sp2 $\to$ sp3 
B) sp $\to$ sp2 
C) sp $\to$ sp3 
D) sp3 $\to$ sp2 
E) sp2 $\to$  sp 
A) sp2 $\to$ sp3 
B) sp $\to$ sp2 
C) sp $\to$ sp3 
D) sp3 $\to$ sp2 
E) sp2 $\to$  sp

Question 8

What would be the product,D,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 9

Which of these compounds will not be reduced by LiAlH4?

Accepted Answer

A) CH3CH2CH2CH=CH2 
B)    
C)    
D)    
E)    
A) CH3CH2CH2CH=CH2 
B)    
C)    
D)    
E)

Question 10

Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-2-ol and 2-methyl-5-hexyn-1-ol?

Accepted Answer

A) CrO3 in H2SO4 
B) IR spectroscopy 
C) Br2 in CCl4 
D) Both CrO3 in H2SO4 and IR spectroscopy. 
E) All of these choices. 
A) CrO3 in H2SO4 
B) IR spectroscopy 
C) Br2 in CCl4 
D) Both CrO3 in H2SO4 and IR spectroscopy. 
E) All of these choices.

Question 11

A reaction which increases the oxygen content or decreases the hydrogen content of an organic molecule is called a(n)___.

Accepted Answer

The answer of A reaction which increases the oxygen content...

Question 12

The reagent PCC in dry methylene chloride is successful in the selective oxidation of primary alcohols to aldehydes because:

Accepted Answer

A) PCC is a relatively weak oxidizing agent. 
B) primary alcohols cannot oxidize any further. 
C) hydration of the intermediate aldehyde is unable to take place in dry methylene chloride. 
D) methylene chloride is a reducing agent. 
E) None of these choices. 
A) PCC is a relatively weak oxidizing agent. 
B) primary alcohols cannot oxidize any further. 
C) hydration of the intermediate aldehyde is unable to take place in dry methylene chloride. 
D) methylene chloride is a reducing agent. 
E) None of these choices.

Question 13

What would be the major 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 14

Predict the product(s)of the following reaction sequence:

Accepted Answer

The answer of Predict the product(s)of the following reaction sequence:...

Question 15

How could the following synthesis be accomplished?

Accepted Answer

A) (1)SOCl2,(2)Mg,ether,(3)   then H3O+ 
B) (1)SOCl2,(2)Li,ether,(3)(CH3CH2)2CuLi,(4)KMnO4,OH- 
C) 1)PBr3,(2)Mg,ether,(3)   then H3O+ (4)PCC,CH2Cl2 
D) More than one of these choices. 
E) None of these choices. 
A) (1)SOCl2,(2)Mg,ether,(3)   then H3O+ 
B) (1)SOCl2,(2)Li,ether,(3)(CH3CH2)2CuLi,(4)KMnO4,OH- 
C) 1)PBr3,(2)Mg,ether,(3)   then H3O+ (4)PCC,CH2Cl2 
D) More than one of these choices. 
E) None of these choices.

Question 16

Upon oxidation of a 1S1U1P1$\circ$S1S1P0 or 2S1U1P1$\circ$S1S1P0 alcohol with Jones reagent,the chromium ion goes from ___ to ___.

Accepted Answer

The answer of Upon oxidation of a 1S1U1P1$\circ$S1S1P0 or 2S1U1P1$\circ$S1S1P0...

Question 17

Predict the product(s)of the following reaction sequence:

Accepted Answer

The answer of Predict the product(s)of the following reaction sequence:...

Question 18

Predict the product(s)of the following reaction sequence:

Accepted Answer

The answer of Predict the product(s)of the following reaction sequence:...

Question 19

The final product,E,in the following reaction sequence is,

Accepted Answer

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

Question 20

What is the product,A,that would be obtained from 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

Exam 12: Alcohols From Carbonyl Compounds

Predict the product(s)of the following reaction sequence:

Jones reagent will fail to give a positive test with?

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1,4-pentanediol from methyl-4-hydroxybutanoate HOCH2CH2CH2COOCH3.

The following transformation would be considered a(n)?

In which of the following series are the compounds arranged in order of decreasing basicity?

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)3COH and (CH3)2CHCH2OH?

When nucleophilic addition to a carbonyl group occurs,the carbon attacked undergoes this hybridization change:

What would be the product,D,of the following reaction sequence?

Which of these compounds will not be reduced by LiAlH4?

Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-2-ol and 2-methyl-5-hexyn-1-ol?

A reaction which increases the oxygen content or decreases the hydrogen content of an organic molecule is called a(n)___.

The reagent PCC in dry methylene chloride is successful in the selective oxidation of primary alcohols to aldehydes because:

What would be the major product of the following reaction?

Predict the product(s)of the following reaction sequence:

How could the following synthesis be accomplished?

Upon oxidation of a 1 ∘\circ∘ or 2 ∘\circ∘ alcohol with Jones reagent,the chromium ion goes from ___ to ___.

Predict the product(s)of the following reaction sequence:

Predict the product(s)of the following reaction sequence:

The final product,E,in the following reaction sequence is,

What is the product,A,that would be obtained from the following reaction sequence?

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

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

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

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1,4-pentanediol from methyl-4-hydroxybutanoate HOCH₂CH₂CH₂COOCH₃.

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH₃)₃COH and (CH₃)₂CHCH₂OH?

Which of these compounds will not be reduced by LiAlH₄?

Upon oxidation of a 1^$\circ$ or 2^$\circ$ alcohol with Jones reagent,the chromium ion goes from _ to _.