Question 1

Which of the following compounds can undergo an Aldol with itself?

Accepted Answer

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

Question 2

What is an intramolecular Claisen reaction called?

Accepted Answer

A) Michael reaction 
B) Robinson reaction 
C) Hoffman reaction 
D) Dieckmann reaction 
A) Michael reaction 
B) Robinson reaction 
C) Hoffman reaction 
D) Dieckmann reaction

Question 3

Why is the Aldol reaction often called an Aldol condensation?

Accepted Answer

A) The initially formed b-hydroxy carbonyl compound loses a hydroxyl group. 
B) The initially formed b-hydroxy carbonyl compound loses an oxygen atom. 
C) The initially formed b-hydroxy carbonyl compound loses a hydrogen atom. 
D) The initially formed b-hydroxy carbonyl compound loses water. 
A) The initially formed b-hydroxy carbonyl compound loses a hydroxyl group. 
B) The initially formed b-hydroxy carbonyl compound loses an oxygen atom. 
C) The initially formed b-hydroxy carbonyl compound loses a hydrogen atom. 
D) The initially formed b-hydroxy carbonyl compound loses water.

Question 4

Which is the unsaturated carbonyl compound formed in the dehydration of the following b-hydroxy carbonyl compound?

Accepted Answer

A) I 
B) II 
C) I and II 
D) None of the choices 
A) I 
B) II 
C) I and II 
D) None of the choices

Question 5

In the correct order,what are the three general steps in the mechanism of a Claisen reaction?

Accepted Answer

A) Enolate formation,elimination,nucleophilic addition 
B) Enolate formation,nucleophilic addition,elimination 
C) Elimination,enolate formation,nucleophilic addition 
D) Nucleophilic addition,enolate formation,elimination 
A) Enolate formation,elimination,nucleophilic addition 
B) Enolate formation,nucleophilic addition,elimination 
C) Elimination,enolate formation,nucleophilic addition 
D) Nucleophilic addition,enolate formation,elimination

Question 6

When is a crossed Claisen reaction between two different esters synthetically useful?

Accepted Answer

A) When only one of the esters has a hydrogen atoms 
B) When both esters have a hydrogen atoms 
C) When only one of the esters has b hydrogen atoms 
D) When both esters lack a hydrogen atoms 
A) When only one of the esters has a hydrogen atoms 
B) When both esters have a hydrogen atoms 
C) When only one of the esters has b hydrogen atoms 
D) When both esters lack a hydrogen atoms

Question 7

What is the major product of the following reaction?

Accepted Answer

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

Question 8

Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

Accepted Answer

A) I 
B) II 
C) III 
D) None of the choices 
A) I 
B) II 
C) III 
D) None of the choices

Question 9

What is the major product of the following reaction?

Accepted Answer

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

Question 10

What are the names for the two parts of the mechanism in a Robinson annulation?

Accepted Answer

A) Michael addition and intramolecular Claisen reaction 
B) Michael addition and intramolecular aldol reaction 
C) Claisen reaction and intramolecular aldol reaction 
D) Aldol reaction and intramolecular Claisen reaction 
A) Michael addition and intramolecular Claisen reaction 
B) Michael addition and intramolecular aldol reaction 
C) Claisen reaction and intramolecular aldol reaction 
D) Aldol reaction and intramolecular Claisen reaction

Question 11

Which of the following statements about Aldol reactions with either aldehydes or ketones is true?

Accepted Answer

A) Equilibrium favors the products with aldehydes; equilibrium favors the starting materials with ketones. 
B) Equilibrium favors the starting materials with aldehydes; equilibrium favors the products with ketones. 
C) Equilibrium favors the products with both aldehydes and ketones. 
D) Equilibrium favors the starting materials with both aldehydes and ketones. 
A) Equilibrium favors the products with aldehydes; equilibrium favors the starting materials with ketones. 
B) Equilibrium favors the starting materials with aldehydes; equilibrium favors the products with ketones. 
C) Equilibrium favors the products with both aldehydes and ketones. 
D) Equilibrium favors the starting materials with both aldehydes and ketones.

Question 12

What is the product of the following Claisen reaction?

Accepted Answer

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

Question 13

What is the general name for the reaction product formed in an aldol addition reaction?

Accepted Answer

A) a-Hydroxy carbonyl compound 
B) b-Hydroxy carbonyl compound 
C) g-Hydroxy carbonyl compound 
D) a,b-Hydroxy carbonyl compound 
A) a-Hydroxy carbonyl compound 
B) b-Hydroxy carbonyl compound 
C) g-Hydroxy carbonyl compound 
D) a,b-Hydroxy carbonyl compound

Question 14

In a Michael reaction,what is the name given to the a,b-unsaturated carbonyl component?

Accepted Answer

A) Michael donor 
B) Michael enolate 
C) Michael nucleophile 
D) Michael acceptor 
A) Michael donor 
B) Michael enolate 
C) Michael nucleophile 
D) Michael acceptor

Question 15

Of the carbonyl compounds; (1)benzaldehyde,(2)acetophenone and (3)dicyclohexyl ketone,which compound has noa-hydrogens?

Accepted Answer

A) Benzaldehyde 
B) Acetophenone 
C) Acetone 
D) All of these compounds contain a-hydrogens. 
A) Benzaldehyde 
B) Acetophenone 
C) Acetone 
D) All of these compounds contain a-hydrogens.

Question 16

What is the name given to the Claisen reaction between two different esters?

Accepted Answer

A) Multiple Claisen reaction 
B) Differential Claisen reaction 
C) Crossed Claisen reaction 
D) Versatile Claisen reaction 
A) Multiple Claisen reaction 
B) Differential Claisen reaction 
C) Crossed Claisen reaction 
D) Versatile Claisen reaction

Question 17

What is the product of the self-condensation of ethanal (acetaldehyde),shown below?

Accepted Answer

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

Question 18

Would this crossed Aldol reaction work well? Why or why not?

Accepted Answer

A) Yes,the diketone is significantly more acidic,so this enolate can be formed selectively. 
B) Yes,the aldehyde is significantly more acidic,so this enolate can be formed selectively. 
C) No,the aldehyde is significantly more acidic,so this enolate cannot be formed selectively. 
D) No,the diketone is significantly more acidic,so this enolate cannot be formed selectively. 
A) Yes,the diketone is significantly more acidic,so this enolate can be formed selectively. 
B) Yes,the aldehyde is significantly more acidic,so this enolate can be formed selectively. 
C) No,the aldehyde is significantly more acidic,so this enolate cannot be formed selectively. 
D) No,the diketone is significantly more acidic,so this enolate cannot be formed selectively.

Question 19

What reaction type is a Claisen reaction?

Accepted Answer

A) Electrophilic addition 
B) Electrophilic substitution 
C) Nucleophilic addition 
D) Nucleophilic substitution 
A) Electrophilic addition 
B) Electrophilic substitution 
C) Nucleophilic addition 
D) Nucleophilic substitution

Question 20

If a Claisen condensation reaction is run using methyl propanoate as the reactant,NaOCH3 is the ideal base.Why is it important to use NaOCH3 and not NaOCH2CH3?

Accepted Answer

A) NaOCH3 is a stronger base than NaOCH2CH3,and this reaction requires a stronger base. 
B) NaOCH3 is a weaker base than NaOCH2CH3,and this reaction requires a weaker base. 
C) Transesterfication can occur when esters react,and this transesterfication would result in a mixture of products. 
D) NaOCH3 is more soluble than NaOCH2CH3 in organic solvents,and this reaction requires a full equivalent of base to proceed.A full equivalent of NaOCH2CH3 would not dissolve,so the reaction would not proceed. 
A) NaOCH3 is a stronger base than NaOCH2CH3,and this reaction requires a stronger base. 
B) NaOCH3 is a weaker base than NaOCH2CH3,and this reaction requires a weaker base. 
C) Transesterfication can occur when esters react,and this transesterfication would result in a mixture of products. 
D) NaOCH3 is more soluble than NaOCH2CH3 in organic solvents,and this reaction requires a full equivalent of base to proceed.A full equivalent of NaOCH2CH3 would not dissolve,so the reaction would not proceed.

Exam 22: Carbonyl Condensation Reactions

Which of the following compounds can undergo an Aldol with itself?

What is an intramolecular Claisen reaction called?

Why is the Aldol reaction often called an Aldol condensation?

Which is the unsaturated carbonyl compound formed in the dehydration of the following b-hydroxy carbonyl compound?

In the correct order,what are the three general steps in the mechanism of a Claisen reaction?

When is a crossed Claisen reaction between two different esters synthetically useful?

What is the major product of the following reaction?

Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

What is the major product of the following reaction?

What are the names for the two parts of the mechanism in a Robinson annulation?

Which of the following statements about Aldol reactions with either aldehydes or ketones is true?

What is the product of the following Claisen reaction?

What is the general name for the reaction product formed in an aldol addition reaction?

In a Michael reaction,what is the name given to the a,b-unsaturated carbonyl component?

Of the carbonyl compounds; (1)benzaldehyde,(2)acetophenone and (3)dicyclohexyl ketone,which compound has noa-hydrogens?

What is the name given to the Claisen reaction between two different esters?

What is the product of the self-condensation of ethanal (acetaldehyde),shown below?

Would this crossed Aldol reaction work well? Why or why not?

What reaction type is a Claisen reaction?

If a Claisen condensation reaction is run using methyl propanoate as the reactant,NaOCH3 is the ideal base.Why is it important to use NaOCH3 and not NaOCH2CH3?

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 Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

If a Claisen condensation reaction is run using methyl propanoate as the reactant,NaOCH₃ is the ideal base.Why is it important to use NaOCH₃ and not NaOCH₂CH₃?