Question 1

Show how an enolate can add to a carbonyl.

Accepted Answer

The answer of Show how an enolate can add to...

Question 2

How many Hs in the compound below are replaced by Ds when it is shaken in D2O containing trace hydroxide?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 6 
E) 7 
A) 1 
B) 2 
C) 3 
D) 6 
E) 7

Question 3

Which compound has the lowest pKa?

Accepted Answer

A) (CH3CH2O2
C) 2CH2 
B) CH3CH2O2CCH2CHO 
C) CH3CH2COCH2CHO 
D) PhCOCH2COCH3 
E) (N
C) 2CH2 
A) (CH3CH2O2
C) 2CH2 
B) CH3CH2O2CCH2CHO 
C) CH3CH2COCH2CHO 
D) PhCOCH2COCH3 
E) (N
C) 2CH2

Question 4

Which is the major organic product from the following reaction?

Accepted Answer

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

Question 5

Which of the following routes works best for the preparation of 3-ethylcyclohexanone from cyclohexanone?

Accepted Answer

A) 1)LDA 2.Br2 3.CH3CH2MgBr 
B) 1)Br2,H3O+ 2.KOC(CH3)3 3.(CH3CH2)2CuLi 4.H3O+  
C) 1)Br2,H3O+ 2.CH3CH2OH,Δ 
D) 1)NBS 2.Mg,ether 3.CH3CHO 
E) 1)Br2,hυ 2.NaOH 3.NaOCH2CH3 4.H3O+ 
A) 1)LDA 2.Br2 3.CH3CH2MgBr 
B) 1)Br2,H3O+ 2.KOC(CH3)3 3.(CH3CH2)2CuLi 4.H3O+  
C) 1)Br2,H3O+ 2.CH3CH2OH,Δ 
D) 1)NBS 2.Mg,ether 3.CH3CHO 
E) 1)Br2,hυ 2.NaOH 3.NaOCH2CH3 4.H3O+

Question 6

What is the molecular formula of the major organic product of the following reaction sequence?

Accepted Answer

A) C7H12O 
B) C7H14O 
C) C11H19N 
D) C11H21N 
E) C11H23N 
A) C7H12O 
B) C7H14O 
C) C11H19N 
D) C11H21N 
E) C11H23N

Question 7

Which of the following aldehydes does not undergo an aldol addition when mixed with base?

Accepted Answer

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

Question 8

An enolate attacks an aldehyde and the resulting product is subsequently protonated.What type of reaction is this?

Accepted Answer

A) a Fischer esterification 
B) an acid-catalyzed aldol condensation 
C) a base-mediated aldol condensation 
D) a Hell-Volhard-Zelinsky reaction 
E) a Selman-Jones reaction 
A) a Fischer esterification 
B) an acid-catalyzed aldol condensation 
C) a base-mediated aldol condensation 
D) a Hell-Volhard-Zelinsky reaction 
E) a Selman-Jones reaction

Question 9

Give the major product of the following reaction.

Accepted Answer

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

Question 10

How would you convert cyclohexene to 2-methylcyclohexanone?

Accepted Answer

The answer of How would you convert cyclohexene to 2-methylcyclohexanone?...

Question 11

Which of the following represent the enol form of the following molecule?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of the above 
A) I 
B) II 
C) III 
D) IV 
E) None of the above

Question 12

Provide the major organic product(s)of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product(s)of the reaction...

Question 13

What two molecules were condensed in an aldol reaction to produce PhCH   CHCOPh?

Accepted Answer

The answer of What two molecules were condensed in an...

Question 14

What materials would you use to prepare the following compound using a Robinson Annulation?

Accepted Answer

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

Question 15

Provide the major organic product of the following.

Accepted Answer

The answer of Provide the major organic product of the...

Question 16

Provide a detailed,stepwise mechanism for the base-catalyzed enolization of acetaldehyde.

Accepted Answer

The answer of Provide a detailed,stepwise mechanism for the base-catalyzed...

Question 17

Provide the major organic product(s)of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product(s)of the reaction...

Question 18

What alkyl bromide should be used in the acetoacetic ester synthesis of the following methyl ketone?

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 of the following statements describes the first step in the mechanism of the aldol condensation?

Accepted Answer

A) An alpha hydrogen is abstracted by the base to form an enolate anion. 
B) A nucleophilic base attacks the carbonyl carbon atom. 
C) The carbonyl oxygen is protonated by the base ion. 
D) The alpha hydrogen is abstracted by an acid to the enolate anion. 
E) The carbonyl oxygen of one aldehyde attacks the carbonyl carbon of another. 
A) An alpha hydrogen is abstracted by the base to form an enolate anion. 
B) A nucleophilic base attacks the carbonyl carbon atom. 
C) The carbonyl oxygen is protonated by the base ion. 
D) The alpha hydrogen is abstracted by an acid to the enolate anion. 
E) The carbonyl oxygen of one aldehyde attacks the carbonyl carbon of another.

Question 20

Provide a synthesis of 2-ethylhexanol using butanal as the only source of carbon.

Accepted Answer

@#IMG-DLM& Depending on the conditions e

Exam 17: Reactions at the Α-Carbon

Show how an enolate can add to a carbonyl.

How many Hs in the compound below are replaced by Ds when it is shaken in D2O containing trace hydroxide?

Which compound has the lowest pKa?

Which is the major organic product from the following reaction?

Which of the following routes works best for the preparation of 3-ethylcyclohexanone from cyclohexanone?

What is the molecular formula of the major organic product of the following reaction sequence?

Which of the following aldehydes does not undergo an aldol addition when mixed with base?

An enolate attacks an aldehyde and the resulting product is subsequently protonated.What type of reaction is this?

Give the major product of the following reaction.

How would you convert cyclohexene to 2-methylcyclohexanone?

Which of the following represent the enol form of the following molecule?

Provide the major organic product(s)of the reaction shown below.

What two molecules were condensed in an aldol reaction to produce PhCH CHCOPh?

What materials would you use to prepare the following compound using a Robinson Annulation?

Provide the major organic product of the following.

Provide a detailed,stepwise mechanism for the base-catalyzed enolization of acetaldehyde.

Provide the major organic product(s)of the reaction shown below.

What alkyl bromide should be used in the acetoacetic ester synthesis of the following methyl ketone?

Which of the following statements describes the first step in the mechanism of the aldol condensation?

Provide a synthesis of 2-ethylhexanol using butanal as the only source of carbon.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds: Nomenclature, physical Properties, and Structure

Isomers: the Arrangement of Atoms in Space

Alkenes: Structure,nomenclature,and an Introduction to Reactivity - Thermodynamics and Kinetics

The Reactions of Alkenes - the Stereochemistry of Addition Reactions

The Reactions of Alkynes - Introduction to Multistep Synthesis

Delocalized Electrons: Their Effect on Stability, pka, and the Products of a Reaction - Aromaticity and Electronic Effects: an Introduction to the Reactions of Benzene

Substitution and Elimination Reactions of Alkyl Halides

Reactions of Alcohols, ethers, epoxides, amines and Sulfur-Containing Compounds

Organometallic Compounds

Radicals

Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions of Benzene and Substituted Benzenes

More About Amines - Reactions of Heterocylic Compounds

The Organic Chemistry of Carbohydrates

Amino Acids,peptides,and Proteins

Catalysis in Organic Reactions and in Enzymatic Reactions

The Organic Chemistry of the Coenzymes, compounds Derived From Vitamins

The Organic Chemistry of the Metabolic Pathways

The Organic Chemistry of Lipids

The Chemistry of the Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

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How many Hs in the compound below are replaced by Ds when it is shaken in D₂O containing trace hydroxide?