Question 1

Which product can be obtained via the following generalized reaction?

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 product is finally formed when the initial compound formed from cyclopentanone and piperidine is mixed with benzyl chloride and that product is heated and then hydrolyzed?

Accepted Answer

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

Question 3

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

Accepted Answer

A) Cyclopentanone,ClCH2CH2COOH,AlCl3,heat 
B) Cyclopentanone,(CH3CH2)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,(CH3CH2)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ 
E) Cyclopentanone,(CH3CH2)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,(CH3CH2)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,(CH3CH2)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ 
E) Cyclopentanone,(CH3CH2)2NH,HA,(-H2O); then BrCH2CH2COOC2H5; then OH-,H2O,heat; then H3O+ and 3-(2-hydroxycyclopentyl)propanal,KMnO4,OH-,heat; then H3O+

Question 4

When optically active 2-methyl-1-phenyl-1-butanone undergoes reaction with Br2/H3O+,the product is observed to exhibit no optical activity.Explain clearly.

Accepted Answer

An achiral enol is formed in presence of

Question 5

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

Accepted Answer

A) Ag(NH3)2+ 
B) O3 
C) NaOCl (Cl2 in NaOH) 
D)    
E) Cu2+ 
A) Ag(NH3)2+ 
B) O3 
C) NaOCl (Cl2 in NaOH) 
D)    
E) Cu2+

Question 6

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

Accepted Answer

A) Cyclohexanone,ClCH2COOH,AlCl3,heat 
B) Cyclohexanone,(CH3)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,(CH3)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 7

Which of the compounds listed below is more acidic than 2-pentanol?

Accepted Answer

A) Diethyl malonate 
B) 2-Pentanone 
C) Pentanal 
D) All of these choices. 
E) Two of these choices. 
A) Diethyl malonate 
B) 2-Pentanone 
C) Pentanal 
D) All of these choices. 
E) Two of these choices.

Question 8

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

Accepted Answer

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

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 the following would provide the best synthesis of 3,5-dimethyl-2-hexanone?

Accepted Answer

A) Ethyl acetoacetate + NaOC2H5 + CH3I; then KO-t-Bu + (CH3)3CCH2Br; then NaOH; then H3O+; then heat 
B) Ethyl acetoacetate + NaOC2H5 + (CH3)3CBr; then KO-t-Bu + CH3I; then NaOH; then H3O+; then heat 
C) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2Br; then KO-t-Bu + CH3I; then NaOH; then H3O+; then heat 
D) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2CHBrCH3; then NaOH; then H3O+; then heat 
E) Ethyl acetoacetate + NaOC2H5 + CH3I; then KO-t-Bu + (CH3)2CHBr; then NaOH; then H3O+; then heat 
A) Ethyl acetoacetate + NaOC2H5 + CH3I; then KO-t-Bu + (CH3)3CCH2Br; then NaOH; then H3O+; then heat 
B) Ethyl acetoacetate + NaOC2H5 + (CH3)3CBr; then KO-t-Bu + CH3I; then NaOH; then H3O+; then heat 
C) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2Br; then KO-t-Bu + CH3I; then NaOH; then H3O+; then heat 
D) Ethyl acetoacetate + NaOC2H5 + (CH3)2CHCH2CHBrCH3; then NaOH; then H3O+; then heat 
E) Ethyl acetoacetate + NaOC2H5 + CH3I; then KO-t-Bu + (CH3)2CHBr; then NaOH; then H3O+; then heat

Question 11

Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

Accepted Answer

A) Sodium methoxide 
B) Sodium ethoxide 
C) Sodium hydride 
D) Potassium tert-butoxide 
E) Sodium amide 
A) Sodium methoxide 
B) Sodium ethoxide 
C) Sodium hydride 
D) Potassium tert-butoxide 
E) Sodium amide

Question 12

Compounds with two electron-withdrawing groups attached to the same carbon atom are known as ___ or ___.

Accepted Answer

active hydrogen comp

Question 13

Which of the following would undergo epimerization in base?

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 14

Which of the following is a keto-enol tautomeric pair?

Accepted Answer

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

Question 15

Which of the compounds listed below is more acidic than 2-pentanol?

Accepted Answer

A) Malonic ester 
B) 2-Pentanone 
C) Pentanal 
D) All of these choices. 
E) Two of these choices. 
A) Malonic ester 
B) 2-Pentanone 
C) Pentanal 
D) All of these choices. 
E) Two of these choices.

Question 16

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

Accepted Answer

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

Question 17

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 18

A reaction of a particular $\beta$-dicarbonyl compound that gives substituted or disubstituted acetic acids is called the ___.

Accepted Answer

malonic es

Question 19

Which of the following would undergo racemization in base?

Accepted Answer

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

Question 20

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Accepted Answer

The answer of What is the final product of the...

Exam 18: Reactions at the Α Carbon of Carbonyl Compounds

Which product can be obtained via the following generalized reaction?

What product is finally formed when the initial compound formed from cyclopentanone and piperidine is mixed with benzyl chloride and that product is heated and then hydrolyzed?

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

When optically active 2-methyl-1-phenyl-1-butanone undergoes reaction with Br2/H3O+,the product is observed to exhibit no optical activity.Explain clearly.

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

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 2-pentanol?

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

What would be the major product of the following reaction?

Which of the following would provide the best synthesis of 3,5-dimethyl-2-hexanone?

Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

Compounds with two electron-withdrawing groups attached to the same carbon atom are known as ___ or ___.

Which of the following would undergo epimerization in base?

Which of the following is a keto-enol tautomeric pair?

Which of the compounds listed below is more acidic than 2-pentanol?

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

What would be the major product of the following reaction?

A reaction of a particular β\betaβ -dicarbonyl compound that gives substituted or disubstituted acetic acids is called the ___.

Which of the following would undergo racemization in base?

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

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

When optically active 2-methyl-1-phenyl-1-butanone undergoes reaction with Br₂/H₃O⁺,the product is observed to exhibit no optical activity.Explain clearly.

Compounds with two electron-withdrawing groups attached to the same carbon atom are known as _ or _.

A reaction of a particular $\beta$ -dicarbonyl compound that gives substituted or disubstituted acetic acids is called the ___.