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

Provide the major organic product of the reaction shown below.

Accepted Answer

2-acetylcy

Question 3

Provide the sequence of synthetic steps necessary to convert cyclohexanone into the compound shown below.

Accepted Answer

1. NaOCH₂CH

Question 4

Provide the structure of the aldol product that results when 4-methylpentanal is treated with sodium hydroxide.

Accepted Answer

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

Question 5

Starting with cyclohexene and employing a Dieckmann cyclization show how the compound below can be prepared.

Accepted Answer

1. KMnO₄, ^-OH, Δ 2. H⁺

Question 6

What crossed-aldol product results when butanal is heated in the presence of excess benzaldehyde and sodium hydroxide?

Accepted Answer

The answer of What crossed-aldol product results when butanal is...

Question 7

Disregarding stereoisomers, how many different enols can the β-diketone CH3COCH2COCH2CH3 form?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  4 
A)  0 
B)  1 
C)  2 
D)  3 
E)  4

Question 8

Complete the following short synthesis by providing the necessary sequence of reagents.

Accepted Answer

1) I₂ / NaO

Question 9

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

Accepted Answer

Question 10

What product results when malonic ester is treated with the following sequence of reagents:

Accepted Answer

The answer of What product results when malonic ester is...

Question 11

Draw a correct structure of the expected product for the following reaction.

Accepted Answer

The answer of Draw a correct structure of the expected...

Question 12

Name the aldol produced when butanal is treated with NaOH.

Accepted Answer

2-ethyl-3-

Question 13

In the iodoform reaction, a methyl ketone is converted to the ________ upon treatment with excess iodine and hydroxide.

Accepted Answer

A)  carboxylate 
B)  acyl iodide 
C)  primary alkyl iodide 
D)  aldehyde 
E)  primary amide 
A)  carboxylate 
B)  acyl iodide 
C)  primary alkyl iodide 
D)  aldehyde 
E)  primary amide

Question 14

In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a:

Accepted Answer

A)  1,2-fashion. 
B)  1,3-fashion. 
C)  1,4-fashion. 
D)  1,5-fashion. 
E)  Diels-Alder reaction. 
A)  1,2-fashion. 
B)  1,3-fashion. 
C)  1,4-fashion. 
D)  1,5-fashion. 
E)  Diels-Alder reaction.

Question 15

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 16

Provide the structure of the product which results from the base-catalyzed condensation followed by dehydration between benzophenone and propanal.

Accepted Answer

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

Question 17

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 18

Provide the structure of the product that results when diethyl malonate is subjected to the following sequence: 1. NaOCH2CH3  2. CH3CH2CH2CH2I 3. H3O+, D.

Accepted Answer

Question 19

When 2-methylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  5 
A)  0 
B)  1 
C)  2 
D)  3 
E)  5

Question 20

Provide the structure of the product that results when ethyl acetoacetate is subjected to the following sequence: 1. NaOCH2CH3  2. CH3CH2CH2CH2I 3. H3O+, D.

Accepted Answer

Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

The Hell-Volhard-Zelinsky reaction involves:

Provide the major organic product of the reaction shown below.

Provide the sequence of synthetic steps necessary to convert cyclohexanone into the compound shown below.

Provide the structure of the aldol product that results when 4-methylpentanal is treated with sodium hydroxide.

Starting with cyclohexene and employing a Dieckmann cyclization show how the compound below can be prepared.

What crossed-aldol product results when butanal is heated in the presence of excess benzaldehyde and sodium hydroxide?

Disregarding stereoisomers, how many different enols can the β-diketone CH3COCH2COCH2CH3 form?

Complete the following short synthesis by providing the necessary sequence of reagents.

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

What product results when malonic ester is treated with the following sequence of reagents:

Draw a correct structure of the expected product for the following reaction.

Name the aldol produced when butanal is treated with NaOH.

In the iodoform reaction, a methyl ketone is converted to the ________ upon treatment with excess iodine and hydroxide.

In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a:

Complete the following reaction by filling in the necessary reagents.

Provide the structure of the product which results from the base-catalyzed condensation followed by dehydration between benzophenone and propanal.

Provide the major organic product of the reaction shown below.

Provide the structure of the product that results when diethyl malonate is subjected to the following sequence: 1. NaOCH2CH3 2. CH3CH2CH2CH2I 3. H3O+, D.

When 2-methylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound?

Provide the structure of the product that results when ethyl acetoacetate is subjected to the following sequence: 1. NaOCH2CH3 2. CH3CH2CH2CH2I 3. H3O+, D.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Disregarding stereoisomers, how many different enols can the β-diketone CH₃COCH₂COCH₂CH₃ form?

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

In the Michael reaction, addition to theα,β-unsaturated carbonyl occurs in a:

Provide the structure of the product that results when diethyl malonate is subjected to the following sequence: 1. NaOCH₂CH₃ 2. CH₃CH₂CH₂CH₂I 3. H₃O⁺, D.

When 2-methylcyclohexanone is treated with catalytic base in excess D₂O, how many deuterium atoms become incorporated in the organic compound?

Provide the structure of the product that results when ethyl acetoacetate is subjected to the following sequence: 1. NaOCH₂CH₃ 2. CH₃CH₂CH₂CH₂I 3. H₃O⁺, D.