Question 1

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 2

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq. ),ethyl bromide,potassium tert-butoxide,isobutyl chloride,hot aqueous NaOH,HCl,and heat.What is the final product?

Accepted Answer

A)  4-Ethyl-2-methylpentanoic acid 
B)  6-Methylheptanoic acid 
C)  2-Ethyl-3-methylpentanoic acid 
D)  2-Ethyl-4-methylpentanoic acid 
E)  Ethylisobutylmalonic acid 
A)  4-Ethyl-2-methylpentanoic acid 
B)  6-Methylheptanoic acid 
C)  2-Ethyl-3-methylpentanoic acid 
D)  2-Ethyl-4-methylpentanoic acid 
E)  Ethylisobutylmalonic acid

Question 3

The ethyl acetoacetate anion is the synthetic equivalent of the ___________.

Accepted Answer

The answer of The ethyl acetoacetate anion is the synthetic...

Question 4

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...

Question 5

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 6

What is the expected final product when phenylacetonitrile is subjected to the following reaction sequence?

Accepted Answer

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

Question 7

Which is the most acidic hydrogen in the compound shown?

Accepted Answer

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

Question 8

Dissolving a halogen in aqueous sodium hydroxide provides a solution of _____________.

Accepted Answer

sodium hyp

Question 9

Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl malonate?

Accepted Answer

A)  Bromoethane,1-bromopropane,sodium ethoxide,and potassium tert-butoxide 
B)  3-Bromohexane and sodium ethoxide 
C)  3-Bromopentane and sodium ethoxide 
D)  Bromoethane,2-bromopropane,sodium ethoxide,and potassium tert-butoxide 
E)  2-Bromopentane and sodium ethoxide 
A)  Bromoethane,1-bromopropane,sodium ethoxide,and potassium tert-butoxide 
B)  3-Bromohexane and sodium ethoxide 
C)  3-Bromopentane and sodium ethoxide 
D)  Bromoethane,2-bromopropane,sodium ethoxide,and potassium tert-butoxide 
E)  2-Bromopentane and sodium ethoxide

Question 10

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 11

Explain why the following tautomer equilibrium lies far to the right.

Accepted Answer

Conjugated system wi

Question 12

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

Accepted Answer

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

Question 13

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...

Question 14

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...

Question 15

A negative iodoform test will be observed in the case of which of these?

Accepted Answer

A)  Acetone 
B)  Ethanal 
C)  Ethanol 
D)  2-Butanol 
E)  All of these will give a positive test. 
A)  Acetone 
B)  Ethanal 
C)  Ethanol 
D)  2-Butanol 
E)  All of these will give a positive test.

Question 16

What product is finally formed when the initial compound formed from cyclohexanone and pyrrolidine is mixed with allyl 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 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

What is the product,W,of the following reaction sequence?

Accepted Answer

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

Question 19

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 20

What product is finally formed when the initial compound formed from cyclopenatone and piperidine is mixed with allyl 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

Exam 18: Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

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

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq. ),ethyl bromide,potassium tert-butoxide,isobutyl chloride,hot aqueous NaOH,HCl,and heat.What is the final product?

The ethyl acetoacetate anion is the synthetic equivalent of the ___________.

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

What would be the major product of the following reaction?

What is the expected final product when phenylacetonitrile is subjected to the following reaction sequence?

Which is the most acidic hydrogen in the compound shown?

Dissolving a halogen in aqueous sodium hydroxide provides a solution of _____________.

Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl malonate?

What would be the major product of the following reaction?

Explain why the following tautomer equilibrium lies far to the right.

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

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

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

A negative iodoform test will be observed in the case of which of these?

What product is finally formed when the initial compound formed from cyclohexanone and pyrrolidine is mixed with allyl chloride and that product is heated and then hydrolyzed?

What would be the major product of the following reaction?

What is the product,W,of the following reaction sequence?

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.

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

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

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.