Question 1

Will acetone be completely deprotonated by potassium tert-butoxide?

Accepted Answer

A)  Yes 
B)  No 
A)  Yes 
B)  No B

Question 2

What are the three steps in the malonic ester synthesis?

Accepted Answer

A)  Deprotonation, alkylation, hydrolysis/decarboxylation 
B)  Hydrogenation, alkylation, deprotonation 
C)  Alkylation, hydrolysis/decarboxylation. hydrogenation 
D)  Hydrolysis/decarboxylation, deprotonation, alkylation 
A)  Deprotonation, alkylation, hydrolysis/decarboxylation 
B)  Hydrogenation, alkylation, deprotonation 
C)  Alkylation, hydrolysis/decarboxylation. hydrogenation 
D)  Hydrolysis/decarboxylation, deprotonation, alkylation A

Question 3

Which is the kinetic enolate of 2-methylcyclohexanone?

Accepted Answer

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

Question 4

Which is the most acidic proton in the following compound?

Accepted Answer

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

Question 5

Which of the following compounds is an enol of compound X drawn below?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  Only I and II 
A)  Only I 
B)  Only II 
C)  Only III 
D)  Only I and II

Question 6

Which is the most stable form of 1,3-cyclohexanedione?

Accepted Answer

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

Question 7

What is the starting material for the following reaction?

Accepted Answer

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

Question 8

It has been found that F1F1F1S1F1F1F10-dicarbonyl compounds have a greater concentration of the enol form over the keto form. This can be explained by:

Accepted Answer

A)  The C=C of the enol is conjugated with the carbonyl group. 
B)  The -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. 
C)  Both A and B above are true. 
D)  None of the choices are true. 
A)  The C=C of the enol is conjugated with the carbonyl group. 
B)  The -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. 
C)  Both A and B above are true. 
D)  None of the choices are true.

Question 9

Which of the following is an enol form of the following compound?

Accepted Answer

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

Question 10

Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?

Accepted Answer

A)  Yes 
B)  No 
A)  Yes 
B)  No

Question 11

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Accepted Answer

A)  An enolate 
B)  An enol 
C)  A tautomer 
D)  An epimer 
A)  An enolate 
B)  An enol 
C)  A tautomer 
D)  An epimer

Question 12

Which of the following compounds would undergo racemization in the presence of a base?

Accepted Answer

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

Question 13

What is the starting material in the following reaction?

Accepted Answer

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

Question 14

What is the missing reagent in the reaction below?

Accepted Answer

A)  Br2/AcOH 
B)  I2/KOH 
C)  I2 
D)  KOH 
A)  Br2/AcOH 
B)  I2/KOH 
C)  I2 
D)  KOH

Question 15

The following molecule is called:

Accepted Answer

A)  a 1,3-diketopentanoate. 
B)  a diethyl malonate. 
C)  an ethyl acetoacetate. 
D)  a F1F1F1S1F1F1F10-keto ester. 
A)  a 1,3-diketopentanoate. 
B)  a diethyl malonate. 
C)  an ethyl acetoacetate. 
D)  a F1F1F1S1F1F1F10-keto ester.

Question 16

If you want to form a kinetic enolate, you want to:

Accepted Answer

A)  Use a strong, non-nucleophilic base such as LDA. 
B)  Use a protic solvent. 
C)  Use a low temperature. 
D)  Both use a strong, non-nucleophilic base such as LDA and use a low temperature. 
A)  Use a strong, non-nucleophilic base such as LDA. 
B)  Use a protic solvent. 
C)  Use a low temperature. 
D)  Both use a strong, non-nucleophilic base such as LDA and use a low temperature.

Question 17

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

Accepted Answer

A)  Sodium hydroxide 
B)  Sodium methoxide 
C)  Sodium tert-butoxide 
D)  Sodium hydride 
A)  Sodium hydroxide 
B)  Sodium methoxide 
C)  Sodium tert-butoxide 
D)  Sodium hydride

Question 18

Which of the following compounds is the most acidic?

Accepted Answer

A)  Ethyl acetoacetate 
B)  2-Butanone 
C)  1-Butanol 
D)  3-Pentanone 
A)  Ethyl acetoacetate 
B)  2-Butanone 
C)  1-Butanol 
D)  3-Pentanone

Question 19

The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation.

Accepted Answer

A)  The nucleophilic enolate requires a reaction center that has a positive charge. 
B)  Hindered alkyl halides do not undergo SN1 reactions. 
C)  Hindered alkyl halides do not undergo SN2 reactions. 
D)  Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate. 
A)  The nucleophilic enolate requires a reaction center that has a positive charge. 
B)  Hindered alkyl halides do not undergo SN1 reactions. 
C)  Hindered alkyl halides do not undergo SN2 reactions. 
D)  Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.

Question 20

Starting with cyclohexanone, how could you prepare the diketone below?

Accepted Answer

A)  Treat cyclohexanone with a base under thermodynamic conditions. 
B)  Hydrogenate cyclohexanone with Raney nickel. 
C)  Convert cyclohexanone into the F1F1F1S1F1F1F10-bromoketone and then react this with the enolate of cyclohexanone. 
D)  Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone. 
A)  Treat cyclohexanone with a base under thermodynamic conditions. 
B)  Hydrogenate cyclohexanone with Raney nickel. 
C)  Convert cyclohexanone into the F1F1F1S1F1F1F10-bromoketone and then react this with the enolate of cyclohexanone. 
D)  Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.

Exam 23: Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Will acetone be completely deprotonated by potassium tert-butoxide?

What are the three steps in the malonic ester synthesis?

Which is the kinetic enolate of 2-methylcyclohexanone?

Which is the most acidic proton in the following compound?

Which of the following compounds is an enol of compound X drawn below?

Which is the most stable form of 1,3-cyclohexanedione?

What is the starting material for the following reaction?

It has been found that -dicarbonyl compounds have a greater concentration of the enol form over the keto form. This can be explained by:

Which of the following is an enol form of the following compound?

Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Which of the following compounds would undergo racemization in the presence of a base?

What is the starting material in the following reaction?

What is the missing reagent in the reaction below?

The following molecule is called:

If you want to form a kinetic enolate, you want to:

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

Which of the following compounds is the most acidic?

The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation.

Starting with cyclohexanone, how could you prepare the diketone below?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

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