Question 1

What would be 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 2

Which of the following hydrogens is the most acidic?

Accepted Answer

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

Question 3

The conversion of   is accomplished by the use of which oxidizing agent?

Accepted Answer

A) Ag(NH3)2+ 
B) O3 
C) NaOI (I2 in NaOH) 
D)    
E) Cu2+ 
A) Ag(NH3)2+ 
B) O3 
C) NaOI (I2 in NaOH) 
D)    
E) Cu2+

Question 4

Which of the following would not undergo racemization in base?

Accepted Answer

A) (S)-2-phenylbutanal 
B) (S)-3-phenylbutanal 
C) (S)-3-phenyl-2-butanone 
D) (S)-3-methyl-2-phenylbutanal 
E) All of these choices will undergo racemization in base. 
A) (S)-2-phenylbutanal 
B) (S)-3-phenylbutanal 
C) (S)-3-phenyl-2-butanone 
D) (S)-3-methyl-2-phenylbutanal 
E) All of these choices will undergo racemization in base.

Question 5

Which would be formed when 2-methylpropanal is dissolved in D2O containing NaOD?

Accepted Answer

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

Question 6

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 7

What would be 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 8

Which of these compounds would exist primarily in an enol form?

Accepted Answer

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

Question 9

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 10

Which of these halides is predicted to alkylate malonic ester (as the anion)in highest yield?

Accepted Answer

A) CH3I 
B) C6H5Br 
C) (CH3)3CCH2Cl 
D) CH3CHClCH3 
E) All of these choices should be equally effective. 
A) CH3I 
B) C6H5Br 
C) (CH3)3CCH2Cl 
D) CH3CHClCH3 
E) All of these choices should be equally effective.

Question 11

Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

Accepted Answer

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

Question 12

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 13

What would be 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 14

The pKa for protons on the carbon between two carbonyls is about 9-11.This greater acidity (as compared to single carbonyl systems)can be accounted for by ___.

Accepted Answer

resonance delocaliza

Question 15

A compound,C5H10O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these?

Accepted Answer

A)    
B)    
C) CH2=CHCH2CHOHCH3 
D)    
E)    
A)    
B)    
C) CH2=CHCH2CHOHCH3 
D)    
E)

Question 16

Explain why the following tautomer equilibrium lies far to the right.

Accepted Answer

Conjugated system wi

Question 17

What is the product,Z,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 18

When ethyl acetoacetate is treated with one equivalent of ethoxide ion followed by one equivalent of 1,2-dibromoethane compound,X is produced.Treatment of X with a second equivalent of ethoxide,produces Y.Further treatment of this product to conditions of saponification,acidification and heating produced a product,Z,that gives the following spectral data:
1H NMR: 0.88 $\delta$multiplet 13C NMR: Broad Band Decoupled: 10.40,21.17,29.84,
208.30 $\delta$
1.00 $\delta$ multiplet DEPT 90: 21.17 $\delta$
1.96 $\delta$ multiplet DEPT 135: positive signals at 21.17,29.84 $\delta$
2.24 $\delta$ singlet negative signals at 10.40 $\delta$
What is a reasonable structure for Z?

Accepted Answer

The answer of When ethyl acetoacetate is treated with one...

Question 19

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 20

Alkylation of an enolate anion must be done using either a primary,primary allylic or primary benzylic species because the substitution follows an ___ mechanistic pathway.

Accepted Answer

The answer of Alkylation of an enolate anion must be...

Exam 18: Reactions at the Α Carbon of Carbonyl Compounds

What would be the major product of the following reaction sequence?

Which of the following hydrogens is the most acidic?

The conversion of is accomplished by the use of which oxidizing agent?

Which of the following would not undergo racemization in base?

Which would be formed when 2-methylpropanal is dissolved in D2O containing NaOD?

What would be the major product of the following reaction?

What would be the major product of the following reaction sequence?

Which of these compounds would exist primarily in an enol form?

What would be the major product of the following reaction?

Which of these halides is predicted to alkylate malonic ester (as the anion)in highest yield?

Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity:

What would be the major product of the following reaction?

What would be the major product of the following reaction sequence?

The pKa for protons on the carbon between two carbonyls is about 9-11.This greater acidity (as compared to single carbonyl systems)can be accounted for by ___.

A compound,C5H10O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these?

Explain why the following tautomer equilibrium lies far to the right.

What is the product,Z,of the following reaction sequence?

What would be the major product of the following reaction?

Alkylation of an enolate anion must be done using either a primary,primary allylic or primary benzylic species because the substitution follows an ___ mechanistic pathway.

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

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which would be formed when 2-methylpropanal is dissolved in D₂O containing NaOD?

The pK_a for protons on the carbon between two carbonyls is about 9-11.This greater acidity (as compared to single carbonyl systems)can be accounted for by ___.

A compound,C₅H₁₀O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these?