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25. Condensation Chemistry

Aldol Condensation

25. Condensation Chemistry

Aldol Condensation

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General Features

General Features

Johnny Betancourt

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Multiple Choice

What product can be isolated from the following aldol condensation reaction?

Provide the mechanism for the following transformation.

Multiple Choice

Predict the major, organic product for the following reaction.

Multiple Choice

Which of the following will successfully synthesize the given target?

Textbook Question

A student tried to prepare the following compounds using aldol condensations. Which of these compounds was she successful in synthesizing? Explain why the other syntheses were not successful. a.

Textbook Question

Describe how the following compounds can be prepared using an aldol addition in the first step of the synthesis: c.

Textbook Question

Describe how the following compounds can be prepared using an aldol addition in the first step of the synthesis: b.

Textbook Question

Describe how the following compounds can be prepared using an aldol addition in the first step of the synthesis: a.

Textbook Question

Identify A–C. (Hint: A shows three singlets in its 1H NMR spectrum with integral ratios 3 : 2 : 3 and gives a positive iodoform test; see Problem 58.)

Textbook Question

What aldol addition product is formed from each of the following compounds? b.

Textbook Question

What aldol addition product is formed from each of the following compounds? a.

Textbook Question

An aldol addition can be catalyzed by acids as well as by bases. Propose a mechanism for the acid-catalyzed aldol addition of propanal.

Textbook Question

Draw the products of the following reactions: b.

Textbook Question

The following compounds can be synthesized by aldol condensations, followed by further reactions. (In each case, work backward from the target molecule to an aldol product, and show what compounds are needed for the condensation.) (c)

Textbook Question

The following compounds can be synthesized by aldol condensations, followed by further reactions. (In each case, work backward from the target molecule to an aldol product, and show what compounds are needed for the condensation.) (b)

Textbook Question

The following compounds can be synthesized by aldol condensations, followed by further reactions. (In each case, work backward from the target molecule to an aldol product, and show what compounds are needed for the condensation.) (a)

Textbook Question

Predict the products of aldol condensation, followed by dehydration, of the following ketones and aldehydes. (c) cyclohexanone

Textbook Question

Predict the products of aldol condensation, followed by dehydration, of the following ketones and aldehydes. (b) acetophenone

Textbook Question

Predict the products of aldol condensation, followed by dehydration, of the following ketones and aldehydes. (a) butyraldehyde

Textbook Question

Give the expected products for the aldol condensations of (c) pentan-3-one.

Textbook Question

Give the expected products for the aldol condensations of (b) phenylacetaldehyde.

Textbook Question

Give the expected products for the aldol condensations of (a) propanal.

Textbook Question

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.(b) (b)

Textbook Question

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation. (c)

Textbook Question

Propose a mechanism for the aldol condensation of cyclohexanone. Do you expect the equilibrium to favor the reactant or the product?

Textbook Question

Propose a complete mechanism for the acid-catalyzed aldol condensation of acetone.

Textbook Question

Predict the products of the following aldol condensations.

Show the products both before and after dehydration.

(a) <IMAGE of reaction>

Textbook Question

Propose a mechanism for the dehydration of diacetone alcohol

to mesityl oxide

(a) in acid.

(b) in base.

Textbook Question

Show how each compound can be dissected into reagents

joined by an aldol condensation, then decide whether

the necessary aldol condensation is feasible.

(a) <IMAGE>

Textbook Question

Using cyclopentanone as the reactant, show the product of

b. an aldol addition.

c. an aldol condensation.

Textbook Question

Show how each compound can be dissected into reagents

joined by an aldol condensation, then decide whether

the necessary aldol condensation is feasible.

(b) <IMAGE>

Textbook Question

Show how each compound can be dissected into reagents

joined by an aldol condensation, then decide whether

the necessary aldol condensation is feasible.

(c) <IMAGE>

Textbook Question

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts

with an aldehyde or ketone, in the presence of a secondary

amine as a basic catalyst, to produce a new C=C. Show

the starting materials that made each of these

by a Knoevenagel condensation.

(d) <IMAGE>

Textbook Question

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts

with an aldehyde or ketone, in the presence of a secondary

amine as a basic catalyst, to produce a new C=C. Show

the starting materials that made each of these

by a Knoevenagel condensation.

(e) <IMAGE>

Textbook Question

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts

with an aldehyde or ketone, in the presence of a secondary

amine as a basic catalyst, to produce a new C=C. Show

the starting materials that made each of these

by a Knoevenagel condensation.

(f) <IMAGE>

Textbook Question

Predict the products of these reaction sequences. <

Textbook Question

Show how you would use an aldol, Claisen, or another type of condensation to make each compound. (c)

Textbook Question

Propose mechanisms for the reactions shown in

Problems 22-62 parts (a)

Textbook Question

Many of the condensations we have studied are reversible. The reverse reactions are often given the prefix retro-,the Latin word meaning “backward.” Propose mechanisms to account for the following reactions.

(b) <IMAGE of reaction>

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