Question 1

Provide the proper IUPAC name for CH3OCH2CH2CH(CH3)CHO.

Accepted Answer

4-methoxy-

Question 2

In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about ________.

Accepted Answer

A)  20 ppm 
B)  40 ppm 
C)  60 ppm 
D)  120 ppm 
E)  200 ppm 
A)  20 ppm 
B)  40 ppm 
C)  60 ppm 
D)  120 ppm 
E)  200 ppm

Question 3

Show how you would perform the following synthesis.

Accepted Answer

A)  1. O3 2. (CH3)2S 
B)  KMnO4, cold, basic 
C)  OsO4 
D)  1. mCPBA 2. potassium dichromate 
A)  1. O3 2. (CH3)2S 
B)  KMnO4, cold, basic 
C)  OsO4 
D)  1. mCPBA 2. potassium dichromate

Question 4

When the carbonyl group of a neutral ketone is protonated ________.

Accepted Answer

A)  the resulting species becomes more electrophilic 
B)  the resulting species is activated toward nucleophilic attack 
C)  subsequent nucleophilic attack on the resulting species is said to occur under acid-catalyzed conditions 
D)  the resulting species has a positive charge 
E)  all of the above 
A)  the resulting species becomes more electrophilic 
B)  the resulting species is activated toward nucleophilic attack 
C)  subsequent nucleophilic attack on the resulting species is said to occur under acid-catalyzed conditions 
D)  the resulting species has a positive charge 
E)  all of the above

Question 5

Provide the single reagent necessary for the conversion of cyclobutanone to the compound shown below.

Accepted Answer

The answer of Provide the single reagent necessary for the...

Question 6

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 7

An ylide is a molecule that can be described as a ________.

Accepted Answer

A)  carbanion bound to a negatively charged heteroatom 
B)  carbocation bound to a positively charged heteroatom 
C)  carbocation bound to a carbon radical 
D)  carbocation bound to a diazonium ion 
E)  carbanion bound to a positively charged heteroatom 
A)  carbanion bound to a negatively charged heteroatom 
B)  carbocation bound to a positively charged heteroatom 
C)  carbocation bound to a carbon radical 
D)  carbocation bound to a diazonium ion 
E)  carbanion bound to a positively charged heteroatom

Question 8

Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing Keq for this equilibrium?

Accepted Answer

A)  H2CO 3CHO 3CHO 2CO 
C)  cyclohexanone 2CO 3CHO 
D)  cyclohexanone 3CHO 2CO 
E)  2-methylcyclohexanone 3CHO 2CO 
A)  H2CO 3CHO 3CHO 2CO 
C)  cyclohexanone 2CO 3CHO 
D)  cyclohexanone 3CHO 2CO 
E)  2-methylcyclohexanone 3CHO 2CO

Question 9

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 10

Provide the major organic product which results when PhCHO is treated with the following sequence of reagents:

Accepted Answer

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

Question 11

Propose a synthesis of 4-phenylbutan-2-ol from 3-phenylpropanal.

Accepted Answer

The answer of Propose a synthesis of 4-phenylbutan-2-ol from 3-phenylpropanal....

Provide the proper IUPAC name for CH₃OCH₂CH₂CH(CH₃)CHO.

In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about ________.

Show how you would perform the following synthesis.

When the carbonyl group of a neutral ketone is protonated ________.

Provide the single reagent necessary for the conversion of cyclobutanone to the compound shown below.

Provide the major organic product of the reaction shown below.

An ylide is a molecule that can be described as a ________.

Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing K_eq for this equilibrium?

Provide the major organic product of the reaction shown below.

Provide the major organic product which results when PhCHO is treated with the following sequence of reagents:

Propose a synthesis of 4-phenylbutan-2-ol from 3-phenylpropanal.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Exam 18: Ketones and Aldehydes

Provide the proper IUPAC name for CH3OCH2CH2CH(CH3)CHO.

In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about ________.

Show how you would perform the following synthesis.

When the carbonyl group of a neutral ketone is protonated ________.

Provide the single reagent necessary for the conversion of cyclobutanone to the compound shown below.

Provide the major organic product of the reaction shown below.

An ylide is a molecule that can be described as a ________.

Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing Keq for this equilibrium?

Provide the major organic product of the reaction shown below.

Provide the major organic product which results when PhCHO is treated with the following sequence of reagents:

Propose a synthesis of 4-phenylbutan-2-ol from 3-phenylpropanal.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide the proper IUPAC name for CH₃OCH₂CH₂CH(CH₃)CHO.

Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing K_eq for this equilibrium?