Question 1

The Hell-Volhard-Zelinsky reaction involves

Accepted Answer

A) the α-bromination of carboxylic acids. 
B) the α-bromination of ketones. 
C) the bromination of alcohols. 
D) the oxidation of aldehydes to acids. 
E) none of the above. 
A) the α-bromination of carboxylic acids. 
B) the α-bromination of ketones. 
C) the bromination of alcohols. 
D) the oxidation of aldehydes to acids. 
E) none of the above.

Question 2

Use an asterisk to indicate the most electron-rich carbon in the molecule below.

Accepted Answer

The answer of Use an asterisk to indicate the most...

Question 3

When compound X is heated,PhCOCH(CH3)2 and CO2 are produced.Offer a structure for compound X.

Accepted Answer

Question 4

Give the major product for the following reaction.

Accepted Answer

The answer of Give the major product for the following...

Question 5

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 6

Fill in the empty boxes.

Accepted Answer

The answer of Fill in the empty boxes.  ...

Question 7

Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate.

Accepted Answer

The answer of Provide the structure of the Claisen product...

Question 8

Give the major product for the following reaction.

Accepted Answer

The answer of Give the major product for the following...

Question 9

Provide the major organic product of the following.

Accepted Answer

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

Question 10

Provide a detailed,stepwise mechanism for the α-bromination of acetone in base.

Accepted Answer

The answer of Provide a detailed,stepwise mechanism for the α-bromination...

Question 11

Give the major product for the reaction.

Accepted Answer

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

Question 12

When compared to the keto form,the enol form of which of the following compounds is most stable?

Accepted Answer

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

Question 13

Explain why the following acid cannot be prepared by the malonic ester synthesis.

Accepted Answer

Since bromobenzene is needed to prepare

Question 14

Which of the labeled hydrogen atoms in the following structure is the most acidic?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
E) 5 
A) 1 
B) 2 
C) 3 
D) 4 
E) 5

Question 15

Provide a detailed,stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone,hydroxide and iodine.

Accepted Answer

The answer of Provide a detailed,stepwise mechanism for the formation...

Question 16

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 17

What materials are needed to prepare the following product?

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 student proposed the following synthesis.Why did it fail?

Accepted Answer

A) The use of LDA results in the thermodynamic product instead of the desired kinetic product. 
B) LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate. 
C) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone. 
D) The tertiary bromide is too sterically hindered to be attacked by the enolate. 
E) Instead of 2-methyl-2-bromopentane,2-bromo-3-methylpentane should have been used to anticipate a cationic rearrangement that would occur. 
A) The use of LDA results in the thermodynamic product instead of the desired kinetic product. 
B) LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate. 
C) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone. 
D) The tertiary bromide is too sterically hindered to be attacked by the enolate. 
E) Instead of 2-methyl-2-bromopentane,2-bromo-3-methylpentane should have been used to anticipate a cationic rearrangement that would occur.

Question 19

When the 1,7-diester CH3O2CCH2CH2CH(CH3)CH2CH2CO2CH3 is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid,what kind of compound is the major organic product?

Accepted Answer

A) an acyclic β-diketone 
B) an acyclic β-ketoacid 
C) an acyclic β-diester 
D) a cyclic β-ketoester 
E) a cyclic β-diketone 
A) an acyclic β-diketone 
B) an acyclic β-ketoacid 
C) an acyclic β-diester 
D) a cyclic β-ketoester 
E) a cyclic β-diketone

Question 20

Give the major product for the following reaction.

Accepted Answer

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

Exam 17: Reactions at the Α-Carbon

The Hell-Volhard-Zelinsky reaction involves

Use an asterisk to indicate the most electron-rich carbon in the molecule below.

When compound X is heated,PhCOCH(CH3)2 and CO2 are produced.Offer a structure for compound X.

Give the major product for the following reaction.

Provide the major organic product of the following reaction.

Fill in the empty boxes.

Provide the structure of the Claisen product in the self-condensation of methyl phenylacetate.

Give the major product for the following reaction.

Provide the major organic product of the following.

Provide a detailed,stepwise mechanism for the α-bromination of acetone in base.

Give the major product for the reaction.

When compared to the keto form,the enol form of which of the following compounds is most stable?

Explain why the following acid cannot be prepared by the malonic ester synthesis.

Which of the labeled hydrogen atoms in the following structure is the most acidic?

Provide a detailed,stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone,hydroxide and iodine.

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

What materials are needed to prepare the following product?

A student proposed the following synthesis.Why did it fail?

When the 1,7-diester CH3O2CCH2CH2CH(CH3)CH2CH2CO2CH3 is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid,what kind of compound is the major organic product?

Give the major product for the following reaction.

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

Filters

When compound X is heated,PhCOCH(CH₃)₂ and CO₂ are produced.Offer a structure for compound X.

When the 1,7-diester CH₃O₂CCH₂CH₂CH(CH₃)CH₂CH₂CO₂CH₃ is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid,what kind of compound is the major organic product?