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Boyd & Morrison, 1992

A carbonyl compound contains a carbon-oxygen double bond. An aldol reaction forms a product with an aldehyde and alcohol group from two carbonyl compounds. For an aldol reaction to occur, the reactants must have an alpha hydrogen or lack an alpha hydrogen. Sodium hydroxide is used as a catalyst, and side products like benzoic acid and monobenzalacetone can form. The objectives are to synthesize, purify, analyze the melting point, and compare dibenzalacetone to the starting materials.

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218 views4 pages

Boyd & Morrison, 1992

A carbonyl compound contains a carbon-oxygen double bond. An aldol reaction forms a product with an aldehyde and alcohol group from two carbonyl compounds. For an aldol reaction to occur, the reactants must have an alpha hydrogen or lack an alpha hydrogen. Sodium hydroxide is used as a catalyst, and side products like benzoic acid and monobenzalacetone can form. The objectives are to synthesize, purify, analyze the melting point, and compare dibenzalacetone to the starting materials.

Uploaded by

Lincoln
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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What is a carbonyl, ketone, aldehyde, alpha hydrogen, enol and aldol condensation

Importance of NaOH, structural requirements for aldol condensation, side products expected in
reaction and how to prevent formation of these side products

Objectives

A carbonyl compound is a compound with a carbonyl group which a carbon and an oxygen
atom double-bonded to each other. An example of this are aldehydes and ketones. Aldehydes
are carbon atoms double-bonded to an oxygen atom with a hydrogen atom while ketones are
carbon atoms double-bonded to an oxygen atom (McMurry & Castellion, 1996). An enol is a
compound where the hydroxyl group is substituted to alkenes (Hunt, 2002). An alkoxide ion is
the conjugate base of OH in the form of OR− (Boyd & Morrison, 1992). In aldol condensation, it
results into an aldol product which is a compound where it has both aldehyde and alcohol
functional groups (chance).

An aldol reaction is a base-catalyzed reaction where two aldehydes or ketones form a


compound where it yields to the beta carbon of the ketone functional group having a hydroxyl
group (McMurry & Castellion, 1996). When an alpha hydrogen reacts with a strong base, it can
form two products, a ketone and an enol. This reaction where there are two products from an
equilibrium reaction is called as keto-enol tautomerism (Farmer & Earley, 2015).The steps for
an aldol condensation is the formation of an enol ion, the enol ion attacking the aldehyde
reactant, protonation of the alkoxide ion due to reaction with water, heating in basic solution to
remove the water forming an alpha, beta-unsaturated aldehyde and lastly, the hydroxide ion is
removed from the product. Since aldol condensation is the addition of the enolate ion of a
ketone to form an aldehyde, there is a need for two moles of the aldehyde to form a
dibenzalacetone (Kilway & Drew, 2007).

Figure 1. Mechanism for keto-enol tautomerism.


In this exercise, NaOH has a hydroxide ion which can serve as a catalyst for aldol
condensation. At low concentrations of a base and at low temperatures, it will produce an aldol
product through aldol reaction but at high concentrations and at high temperatures, it will
produce an alpha, beta-unsaturated aldehyde through aldol condensation. To prevent the
reaction of the two ketones and aldehydes with each other, one reactant shouldn’t have an
alpha-hydrogen so it can only assume an anion acceptor. This is a mixed aldol reaction
(chance).

Figure 2. Mixed aldol reaction of acetone and benzaldehyde

Other side products that can be formed from the reaction is benzoic acid and
monobenzalacetone. This is formed due to the contamination of benzaldehyde from oxidation
and there should be more amounts of benzaldehyde than monobenzalacetone for it to react
properly with the acetone (‘Experiment 5”, n.d.).

The objectives in this exercise is to synthesize dibenzalacetone from benzaldehyde and


acetone, purify the synthesized dibenzalacetone using recrystallization, determine and compare
the melting point of the crude and recrystallized dibenzalacetone and to compare the product
from the starting materials using simple chemical tests.

A carbonyl compound is a compound with a carbonyl group which a carbon and an oxygen
atom double-bonded to each other. An example of this are aldehydes and ketones (McMurry &
Castellion, 1996). Alpha hydrogen atoms are acidic since the formation of a carbanion can
result to a resonance stabilization of the anion due to the presence of the double-bonded
oxygen atom (Kriti, 2017). The acidity of the alpha hydrogens can also be due to the polarity of
oxygen atoms having a partial negative charge and for the alpha carbon to have a partial
positive charge (Ouelette & Rawn, 1996).

An aldol reaction is reaction where a compound with an aldehyde condenses with a ketone to
form an aldehyde and a ketone with a hydroxyl ground. The limitation to this reaction, however,
is that both reactants shouldn’t have a tertiary alpha carbon or in other words, the reactants
should have an alpha hydrogen (McMurry & Castellion, 1996). The steps for an aldol reaction is
the formation of an enol ion, the enol ion attacking the aldehyde reactant, protonation of the
alkoxide ion due to reaction with water, heating in basic solution to remove the water forming an
alpha, beta-unsaturated ketone and lastly, the hydroxide ion is removed to form the product
(Kilway & Drew, 2007).

This reaction can be resonance stabilized causing the the oxygen atom to have a negative
charge, forming an enolate ion and the the anion from the alpha carbon to form a double bond
with the carbon in the carbonyl group, forming a different intermediate. Thus, when an alpha
hydrogen reacts with a strong base, it can form two products, a ketone and an enol. This
reaction where there are two products from an equilibrium reaction is called as keto-enol
tautomerism (Farmer & Earley, 2015). An enol is a compound where the hydroxyl group is
substituted to alkenes (Hunt, 2002).

Figure 1. Mechanism for keto-enol tautomerism

Since aldol condensation is the addition of the enolate ion of a ketone to form an aldehyde,
there is a need for two moles of the aldehyde to form a dibenzalacetone (Kilway & Drew, 2007).
The structural requirement for aldol condensation is for a compound to have an alpha hydrogen,
which is the acetone product and for the other compound to not have an alpha hydrogen which
is the benzaldehyde (McMurry & Castellion, 1996).

Figure 2. Synthesis of dibenzalacetone

Other side products that can be formed from the reaction is benzoic acid and
monobenzalacetone. This is formed due to the contamination of benzaldehyde from oxidation
and there should be more amounts of benzaldehyde than monobenzalacetone for it to react
properly with the acetone (‘Experiment 5”, n.d.).

The objectives in this exercise is to synthesize dibenzalacetone from


benzaldehyde and acetone, purify the synthesized dibenzalacetone using recrystallization,
determine and compare the melting point of the crude and recrystallized dibenzalacetone and to
compare the product from the starting materials using simple chemical tests.

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