<< Chapter < Page Chapter >> Page >

Experiment 2: aldol condensation reaction

Objective

The purpose of this laboratory exercise is to introduce the concept of the Carbon-Carbon bond forming reaction and the basic mechanism of the aldol condensation reaction.

Background information

A useful carbon-carbon bond-forming reaction is known as the Aldol Reaction or Aldol Condensation. It is an example of electrophilic substitution at the alpha carbon in enols or enolate anions. Traditionally, it is the acid- or base-catalyzed condensation of one carbonyl compounds with the enolate/enol of another, which may or may not be the same, to generate aβ-hydroxy carbonyl compound—an aldol. It is reversible in nature. The reaction may occur between two molecules of aldehyde, two molecules of ketones or one molecule of aldehyde and a molecule of ketone. When two different carbonyl compounds react, it is known as mixed aldol/ Crossed aldol condensation.

Reactions in which a larger molecule is formed from smaller components with the elimination of a very small by-product such as water are termed Condensations. Hence the following examples are properly referred to as aldol condensations. The dehydration step of an aldol condensation is also reversible in the presence of acid and base catalysts. Consequently, on heating with aqueous solutions of strong acids or bases, manyα,β-unsaturated carbonyl compounds fragment into smaller aldehyde or ketones, a process known as the retro-aldol reaction. Below, a few examples of aldol condensation reaction are:

The product has both a carbonyl and an alcohol group; since the chemistry was initially developed with aldehydes the name "Ald-ol" (aldehyde-alcohol) was coined and has been applied to the reaction that forms it. For aldol condensation, the presence ofα-H (acidic hydrogen atom) atom is necessary. In the absence ofα-H atom, it can undergo the Cannizaro reaction. Aldol condensation involves the following steps in the mechanism:

1. Addition phase:

(a) Formation of an enol or enolate anion.

(b) Nucleophilic addition

(c) Proton transfer

2. Dehydration phase (If strong base/acid or some heat is applied)

Using acetone as an example:

Step 1: An acid-base reaction occurs first. Ethoxide functions as a base and removes the acidic-hydrogen giving the reactive enolate.

Step 2: The nucleophilic enolate attacks another molecule of acetone at the electrophilic carbonyl C in a nucleophilic addition type process giving an intermediate alkoxide.

Step 3: An acid-base reaction. The alkoxide deprotonates a solvent molecule (here ethanol) creating hydroxide and the β size 12{β} {} hydroxyaldehydes or aldol product is formed.

There is little difference mechanistically between an acid or base catalyzed mechanism but examples of both have been given for completeness.

In next figure, the actual carbon-carbon bond formation has shown in different color for simplicity.

Acid catalyzed reaction mechanism:

Base catalyzed reaction mechanism:

From the mechanism it is clear that presence of electron withdrawing group in acceptor molecule facilitates the reaction and vice versa.

Questions & Answers

what is Nano technology ?
Bob Reply
write examples of Nano molecule?
Bob
The nanotechnology is as new science, to scale nanometric
brayan
nanotechnology is the study, desing, synthesis, manipulation and application of materials and functional systems through control of matter at nanoscale
Damian
Is there any normative that regulates the use of silver nanoparticles?
Damian Reply
what king of growth are you checking .?
Renato
What fields keep nano created devices from performing or assimulating ? Magnetic fields ? Are do they assimilate ?
Stoney Reply
why we need to study biomolecules, molecular biology in nanotechnology?
Adin Reply
?
Kyle
yes I'm doing my masters in nanotechnology, we are being studying all these domains as well..
Adin
why?
Adin
what school?
Kyle
biomolecules are e building blocks of every organics and inorganic materials.
Joe
anyone know any internet site where one can find nanotechnology papers?
Damian Reply
research.net
kanaga
sciencedirect big data base
Ernesto
Introduction about quantum dots in nanotechnology
Praveena Reply
what does nano mean?
Anassong Reply
nano basically means 10^(-9). nanometer is a unit to measure length.
Bharti
do you think it's worthwhile in the long term to study the effects and possibilities of nanotechnology on viral treatment?
Damian Reply
absolutely yes
Daniel
how to know photocatalytic properties of tio2 nanoparticles...what to do now
Akash Reply
it is a goid question and i want to know the answer as well
Maciej
characteristics of micro business
Abigail
for teaching engĺish at school how nano technology help us
Anassong
Do somebody tell me a best nano engineering book for beginners?
s. Reply
there is no specific books for beginners but there is book called principle of nanotechnology
NANO
what is fullerene does it is used to make bukky balls
Devang Reply
are you nano engineer ?
s.
fullerene is a bucky ball aka Carbon 60 molecule. It was name by the architect Fuller. He design the geodesic dome. it resembles a soccer ball.
Tarell
what is the actual application of fullerenes nowadays?
Damian
That is a great question Damian. best way to answer that question is to Google it. there are hundreds of applications for buck minister fullerenes, from medical to aerospace. you can also find plenty of research papers that will give you great detail on the potential applications of fullerenes.
Tarell
what is the Synthesis, properties,and applications of carbon nano chemistry
Abhijith Reply
Mostly, they use nano carbon for electronics and for materials to be strengthened.
Virgil
is Bucky paper clear?
CYNTHIA
carbon nanotubes has various application in fuel cells membrane, current research on cancer drug,and in electronics MEMS and NEMS etc
NANO
so some one know about replacing silicon atom with phosphorous in semiconductors device?
s. Reply
Yeah, it is a pain to say the least. You basically have to heat the substarte up to around 1000 degrees celcius then pass phosphene gas over top of it, which is explosive and toxic by the way, under very low pressure.
Harper
Do you know which machine is used to that process?
s.
how to fabricate graphene ink ?
SUYASH Reply
for screen printed electrodes ?
SUYASH
What is lattice structure?
s. Reply
of graphene you mean?
Ebrahim
or in general
Ebrahim
in general
s.
Graphene has a hexagonal structure
tahir
On having this app for quite a bit time, Haven't realised there's a chat room in it.
Cied
how did you get the value of 2000N.What calculations are needed to arrive at it
Smarajit Reply
Privacy Information Security Software Version 1.1a
Good
Got questions? Join the online conversation and get instant answers!
Jobilize.com Reply

Get the best Algebra and trigonometry course in your pocket!





Source:  OpenStax, Chem217labsfall07. OpenStax CNX. Oct 16, 2007 Download for free at http://cnx.org/content/col10463/1.4
Google Play and the Google Play logo are trademarks of Google Inc.

Notification Switch

Would you like to follow the 'Chem217labsfall07' conversation and receive update notifications?

Ask