Question 1

Which of the following could be used to synthesize the following substance in good yield?

Accepted Answer

A) Cyclohexanone,ClCH2COOH,AlCl3,heat 
B) Cyclohexanone,(CH3CH2)2NH,HA,(-H2O); then BrCH2COOC2H5; then OH-,H2O,heat; then H3O+ 
C) Cyclohexylacetic acid,KMnO4,OH-,heat; then H3O+ 
D) Two of these choices. 
E) All of these choices. 
A) Cyclohexanone,ClCH2COOH,AlCl3,heat 
B) Cyclohexanone,(CH3CH2)2NH,HA,(-H2O); then BrCH2COOC2H5; then OH-,H2O,heat; then H3O+ 
C) Cyclohexylacetic acid,KMnO4,OH-,heat; then H3O+ 
D) Two of these choices. 
E) All of these choices.

Question 2

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 3

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 4

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 5

Explain why acylation of active methylene compounds must be carried out in aprotic solvents,typically using NaH to generate the enolate anion: why can sodium ethoxide/ethanol not be used in these reactions?

Accepted Answer

Acylating agents such as acyl halides an

Question 6

Which reagent would best serve as the basis for a simple chemical test to distinguish between m-chloroacetophenone and m-chloropropiophenone?

Accepted Answer

A) NaOI (I2 in NaOH) 
B) Br2/CCl4 
C) CrO3/H2SO4 
D) NaHCO3/H2O 
E) Ag(NH3)2+ 
A) NaOI (I2 in NaOH) 
B) Br2/CCl4 
C) CrO3/H2SO4 
D) NaHCO3/H2O 
E) Ag(NH3)2+

Question 7

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

Accepted Answer

Enol tautomer is the

Question 8

What is the product,W,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 the compounds listed below is more acidic than 1-butanol?

Accepted Answer

A) Diethylmalonate 
B) 2-Butanone 
C) Ethyl pentanoate 
D) All of these choices. 
E) Two of these choices. 
A) Diethylmalonate 
B) 2-Butanone 
C) Ethyl pentanoate 
D) All of these choices. 
E) Two of these choices.

Question 10

Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl malonate?

Accepted Answer

A) Bromoethane,1-bromopropane,sodium ethoxide,and potassium tert-butoxide 
B) 3-Bromohexane and sodium ethoxide 
C) 3-Bromopentane and sodium ethoxide 
D) Bromoethane,2-bromopropane,sodium ethoxide,and potassium tert-butoxide 
E) 2-Bromopentane and sodium ethoxide 
A) Bromoethane,1-bromopropane,sodium ethoxide,and potassium tert-butoxide 
B) 3-Bromohexane and sodium ethoxide 
C) 3-Bromopentane and sodium ethoxide 
D) Bromoethane,2-bromopropane,sodium ethoxide,and potassium tert-butoxide 
E) 2-Bromopentane and sodium ethoxide

Question 11

Which of the following would not undergo racemization in base?

Accepted Answer

A) (R)-3-methyl-4-heptanone 
B) (R)-3-methyl-2-heptanone 
C) (R)-4-methyl-2-heptanone 
D) (R)-2,4-dimethyl-3-heptanone 
E) All of these choices will undergo racemization in base. 
A) (R)-3-methyl-4-heptanone 
B) (R)-3-methyl-2-heptanone 
C) (R)-4-methyl-2-heptanone 
D) (R)-2,4-dimethyl-3-heptanone 
E) All of these choices will undergo racemization in base.

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

Which of the following could be used to synthesize the following substance in good yield?

Accepted Answer

A) Cyclopentanone,ClCH2CH2COOH,AlCl3,heat 
B) Cyclopentanone,(CH3)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ 
C) 3-(2-Hydroxycyclopentyl)propanal,KMnO4,OH-,heat; then H3O+ 
D) Cyclopentanone,ClCH2CH2COOH,AlCl3,heat and cyclopentanone,(CH3)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ 
E) Cyclopentanone,(CH3)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ and 3-(2-hydroxycyclopentyl)propanal,KMnO4,OH-,heat; then H3O+ 
A) Cyclopentanone,ClCH2CH2COOH,AlCl3,heat 
B) Cyclopentanone,(CH3)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ 
C) 3-(2-Hydroxycyclopentyl)propanal,KMnO4,OH-,heat; then H3O+ 
D) Cyclopentanone,ClCH2CH2COOH,AlCl3,heat and cyclopentanone,(CH3)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ 
E) Cyclopentanone,(CH3)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ and 3-(2-hydroxycyclopentyl)propanal,KMnO4,OH-,heat; then H3O+

Question 14

Which of the compounds listed below is more acidic than 1-butanol?

Accepted Answer

A) Malonic ester 
B) 2-Butanone 
C) Ethyl pentanoate 
D) All of these choices. 
E) Two of these choices. 
A) Malonic ester 
B) 2-Butanone 
C) Ethyl pentanoate 
D) All of these choices. 
E) Two of these choices.

Question 15

The ethyl acetoacetate anion is the synthetic equivalent of the ___.

Accepted Answer

The answer of The ethyl acetoacetate anion is the synthetic...

Question 16

Which of the following would undergo epimerization in acid?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) Both III and IV 
A) I 
B) II 
C) III 
D) IV 
E) Both III and IV

Question 17

Which would be formed when 2-methylpropanal is dissolved in T2O containing NaOT?

Accepted Answer

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

Question 18

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 19

Which compound would be formed when 2-methylbutanal is treated with a solution of NaOD in D2O?

Accepted Answer

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

Question 20

The kinetic enolate (the less highly substituted double bond)is favored when ___ is used as a base.

Accepted Answer

LDA or lit

Exam 18: Reactions at the Α Carbon of Carbonyl Compounds

Which of the following could be used to synthesize the following substance in good yield?

What would be the major product of the following reaction?

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

What would be the major product of the following reaction?

Explain why acylation of active methylene compounds must be carried out in aprotic solvents,typically using NaH to generate the enolate anion: why can sodium ethoxide/ethanol not be used in these reactions?

Which reagent would best serve as the basis for a simple chemical test to distinguish between m-chloroacetophenone and m-chloropropiophenone?

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

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

Which of the compounds listed below is more acidic than 1-butanol?

Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl malonate?

Which of the following would not undergo racemization in base?

What would be the major product of the following reaction?

Which of the following could be used to synthesize the following substance in good yield?

Which of the compounds listed below is more acidic than 1-butanol?

The ethyl acetoacetate anion is the synthetic equivalent of the ___.

Which of the following would undergo epimerization in acid?

Which would be formed when 2-methylpropanal is dissolved in T2O containing NaOT?

What would be the major product of the following reaction?

Which compound would be formed when 2-methylbutanal is treated with a solution of NaOD in D2O?

The kinetic enolate (the less highly substituted double bond)is favored when ___ is used as a base.

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 T₂O containing NaOT?

Which compound would be formed when 2-methylbutanal is treated with a solution of NaOD in D₂O?