Question 1

Provide the structure of the major organic product which results when   
is treated with PPh3 and the resulting salt is reacted with one equivalent of butyllithium.

Accepted Answer

Question 2

When an aldehyde is reacted with HCN in the presence of KCN, what product is formed?

Accepted Answer

A)  cyanohydrin 
B)  acetal 
C)  hydrate 
D)  oxime 
A)  cyanohydrin 
B)  acetal 
C)  hydrate 
D)  oxime

Question 3

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 4

Provide the IUPAC name for the following compound, including stereochemical designators as appropriate.

Accepted Answer

(S,Z)-2-br

Question 5

Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures.

Accepted Answer

The carbonyl carbon of benzald

Question 6

Give an IUPAC name to the following compound. Be sure to include configurational information in the name.

Accepted Answer

(Z)-4-oxo-

Question 7

Provide the structure of the semicarbazone derivative of 3-pentanone.

Accepted Answer

The answer of Provide the structure of the semicarbazone derivative...

Question 8

The following compound has been found effective in treating pain and inflammation (J. Med. Chem. 2007, 4222). Which sequence correctly ranks each carbonyl group in order of increasing reactivity toward nucleophilic addition?

Accepted Answer

A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 1 < 2 
D)  1 < 3 < 2 
A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 1 < 2 
D)  1 < 3 < 2

Question 9

How might one distinguish an aldehyde from a ketone using IR data alone?

Accepted Answer

The aldehyde has two

Question 10

How could you convert cyclohexane to 1-methylcyclohexanol?

Accepted Answer

1) Br₂, light 2) NaOH

Question 11

Which sequence ranks the following carbonyl compounds in order of increasing rate of nucleophilic addition?

Accepted Answer

A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2 
A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2

Question 12

Show how you would perform the following synthesis.

Accepted Answer

1) NaNH₂ 2)

Question 13

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 14

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 15

What intermediate occurs when a ketone undergoes a Wolff-Kishner reduction?

Accepted Answer

A)  a cyanohydrin 
B)  a hydrated aldehyde 
C)  a carboxylate 
D)  a semicarbazone 
E)  a hydrazone 
A)  a cyanohydrin 
B)  a hydrated aldehyde 
C)  a carboxylate 
D)  a semicarbazone 
E)  a hydrazone

Question 16

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 17

Name the following compound.

Accepted Answer

4,7,7-trimethyl2-oct

Question 18

What reagent can be used to convert benzophenone into triphenylmethanol?

Accepted Answer

PhMgBr fol

Question 19

Provide the structure of the diethyl acetal of butanal.

Accepted Answer

The answer of Provide the structure of the diethyl acetal...

Question 20

Which of the following describes a synthesis of an aldehyde?

Accepted Answer

A)  hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst 
B)  reaction of a primary alcohol with Na2Cr2O7 
C)  reaction of a ketone with ozone 
D)  treatment of an alkene with Sia2BH 
E)  none of the above 
A)  hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst 
B)  reaction of a primary alcohol with Na2Cr2O7 
C)  reaction of a ketone with ozone 
D)  treatment of an alkene with Sia2BH 
E)  none of the above

Exam 18: Ketones and Aldehydes

Provide the structure of the major organic product which results when is treated with PPh3 and the resulting salt is reacted with one equivalent of butyllithium.

When an aldehyde is reacted with HCN in the presence of KCN, what product is formed?

Provide the major organic product of the reaction shown below.

Provide the IUPAC name for the following compound, including stereochemical designators as appropriate.

Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures.

Give an IUPAC name to the following compound. Be sure to include configurational information in the name.

Provide the structure of the semicarbazone derivative of 3-pentanone.

The following compound has been found effective in treating pain and inflammation (J. Med. Chem. 2007, 4222). Which sequence correctly ranks each carbonyl group in order of increasing reactivity toward nucleophilic addition?

How might one distinguish an aldehyde from a ketone using IR data alone?

How could you convert cyclohexane to 1-methylcyclohexanol?

Which sequence ranks the following carbonyl compounds in order of increasing rate of nucleophilic addition?

Show how you would perform the following synthesis.

Provide the major organic product of the following reaction.

Provide the major organic product of the reaction shown below.

What intermediate occurs when a ketone undergoes a Wolff-Kishner reduction?

Provide the major organic product of the reaction shown below.

Name the following compound.

What reagent can be used to convert benzophenone into triphenylmethanol?

Provide the structure of the diethyl acetal of butanal.

Which of the following describes a synthesis of an aldehyde?

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 structure of the major organic product which results when is treated with PPh₃ and the resulting salt is reacted with one equivalent of butyllithium.