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Exam 18: Ketones and Aldehydes

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Question 31

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When a carbonyl is part of a conjugated π-network, the C-O stretch:

A) has a higher frequency than in a nonconjugated system.
B) has a lower frequency than in a nonconjugated system.
C) always occurs at 1710 cm^-1.
D) occurs around 2700 cm^-1.
E) cannot be distinguished from the C-O stretch in a nonconjugated system.

F) A) and B)
G) B) and D)

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Question 32

Multiple Choice

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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?

A) H₂CO < cyclohexanone < CH₃CHO < 2-methylcyclohexanone
B) CH₃CHO < 2-methylcyclohexanone < cyclohexanone < H₂CO
C) cyclohexanone < 2-methylcyclohexanone < H₂CO < CH₃CHO
D) cyclohexanone < 2-methylcyclohexanone < CH₃CHO < H₂CO
E) 2-methylcyclohexanone < cyclohexanone < CH₃CHO < H₂CO

F) All of the above
G) None of the above

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Question 33

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Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.

By which single reaction can benzene be readily converted into acetophenone?

Provide the IUPAC name for the following compound.

Propose a synthesis of 3-heptanone from propanal.

Provide the major organic product which results when PhCH₂CH₂CO₂H is treated with excess butyllithium followed by H₃O⁺.

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

Provide the major organic product of the reaction shown below.

Beginning with 1,3-dithiane, propose a synthesis of 4-heptanone.

Provide the proper IUPAC name for CH₃CHOHCH₂COCH₂C(CH₃)₂CH₂CH₃.

Conversion of aldehydes and ketones to imines is an acid-catalyzed process. Explain why this conversion is actually hindered by the presence of too much acid.

In the mass spectrum of 3,3-dimethyl-2-butanone, the base peak will occur at m/z ________.

Provide the structure of cyclohexanecarbaldehyde.

Oxidation of a 1° alcohol with chromic acid results in the production of ________.

Through what sequence of steps can toluene be converted into PhCH₂PPh₃⁺Br^-?

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

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

Provide the structure of the diethyl acetal of butanal.

Provide the major organic product of the reaction shown below.