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Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

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Question 61

Multiple Choice

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Methylamine reacts with acetophenone to yield the:

A) iminium salt.
B) imine.
C) acetal.
D) amide
E) enamine.

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Question 62

Multiple Choice

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An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of reaction is this?

A) a Fischer esterification
B) an acid-catalyzed aldol condensation
C) a base-mediated aldol condensation
D) a Hell-Volhard-Zelinsky reaction
E) a Selman-Jones reaction

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Question 63

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Provide a detailed, stepwise mechanism for the base-catalyzed enolization of acetaldehyde.

Provide the major organic product of the following reaction.

Provide the structure of the Claisen product in the self condensation of methyl phenylacetate.

The reaction of LDA with acetophenone produces:

Provide the structure of lithium diisopropylamide.

Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt?

Which of the following is a nucleophile that does conjugate additions?

When aldehydes are subjected to the same conditions that α-halogenate ketones (i.e., X₂ and aqueous acid or base) , they are:

The relationship between ketones and their corresponding enols is one of:

What name is given to the alpha substitution of a carbonyl compound where the electrophilic component is another carbonyl compound?

What two organic starting materials are required to produce cinnamaldehyde (PhCH=CHCHO) via a crossed aldol condensation followed by dehydration?

A Claisen condensation results in a β-ketoester. Explain why a second ester enolate does not add to this

What reagents are needed to complete the following synthesis?

Provide the structure of the enol of 2,2,4-trimethyl-3-pentanone.

In theory a poorly planned crossed aldol reaction can produce how many different aldol regioisomers?

Provide the major organic product of the following reaction.

What product is formed in the crossed Claisen condensation between methyl benzoate and cyclohexanone?

What organic compounds are produced when 2-pentanone undergoes the haloform reaction upon treatment with HO^- and excess Br₂?