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Zoya Ashraf (Aldol Condensation)
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CENTRAL BORAD
OF
SECONDAY EDUCATION
ALL INDIA SENIOR SECONDARY
CERTIFICATE EXAMINATION
(2021-22)
CHEMISTRY PROJECT WORK
Topic- Aldal
Name : ZOYA ASHRAF
Class/sec 3 XII-A
Class roll no.4: 45 |
Board roll no. , : 1900204 i
Subject Teacher : Mrs. Shipra Mahapatra
Head of The Institution: Father Charles K.C hha
i
School : De Paul School, VindhyanagarACKNOWLEDGEMENT
| would take this opportunity to gxpress
my sincere thanks and gratitude to my
chemistry teacher Mrs. Shipra Mahapatra
for her vital support and guidaneg in
completing this project.
I would also like to gxtend my gratitude
and thanks to our lab assistant |
[Link] Jha, who has helped m¢ in
sucegssful completion of my project.%
Why.a project?
Since is an organized and dynamic form of knowledge
about the object and phenomenon of nature
Generally, students are able to explore
only the theoretical concepts with a little amount of
practical. The students find it difficult to relate with real
their studies with real world.
i.
[Link] circumstance, project plays a
significant role as in a project, not only the combination
of practical and theoretical knowledge is there but also a
student can sibel scientific approach and go for
research work so thos he/she finds applications of the
theory, practical and concept in real world and gets the
logic behind the concepts.CONTENT
Acknowledgement
Introduction
Fundamental steps
Mechanism
Applications
Cross Adol Condensation
Types of condensation
Cannizzaro reaction
Declaration
ue
{
aIntroduction
The aldol condensation reaction is an organic
reaction introduced by Charles Wurtz, who
first prepared the B-hydroxy aldehyde from
acetaldehdye in 1872. In an aldol condensation,
an enolate ion reacts with a carbonyl compound
in the presence of acid/base catalyst to form a
B-hydroxy aldehyde or B-hydroxy ketone,
followed by dehydration to give a conjugated
enone. It is a useful carbon-carbon bond-
forming reaction.
eeFundamental steps:
The fundamental steps of the aldol
condensation reaction are:
[Link] (aldehyde + alcohol) reaction —
Reaction of aldehyde (or ketone) enolate
with another molecule of the aldehyde (or
ketone) in the presence of NaOH or KOH to
form B-hydroxy aldehyde (or ketone).
g seit oe
RH)C—C—H —*) RHC-C-H —» H-C-CH-CH
R CHR
2,Dehydration/Elimination reaction —
Involves removal of a water molecule from
the B-hydroxy aldehyde (or ketone) to form
an Q,B-unsaturated aldehyde or an a,B-
unsaturated ketone.Mechanism
The first part of this reaction is an aldol
reaction, the second part a dehydration—
an elimination reaction (Involves removal of
a water molecule or an alcohol molecule).
Dehydration may be accompanied
by decarboxylation when an activated carboxyl
eroup is present. The aldol addition product
can be dehydrated via two mechanisms; a
strong base like potassium
butoxide, potassium hydroxide or sodium
hydride deprotonates the product to an enolate,
which eliminates via the E1cB
mechanism,“ while dehydration in acid
proceeds via an E1 reaction mechanism.
Depending on the nature of the desired
product, the aldol condensation may be carried
out under two broad types of conditions: kinetic
'
4
oJontrol or De eer zie control.
coarse wn reaction (shown using “OCH; as base)
at
Sey
{oststom enolate
Base catalyzed S... rn written as @ vi step)
ae 20H fs 20:
ree toses “OH
2s f rae
eer Ris RR ROR
Enolate of aldol a1,p-unsaturated
(shown as carbanion) aldehyde
(Lost ‘shown for clarity)
4
f
¥
;Acid catalyzed aldotheaction
aN H Protonated
H
0: carbonyl
mi (Glectrophilc) He,
ral"
on on 0: :OH
RR
Enol a Aldol
(nucleophilic)
Acid catalyzed dehydration
0: 10:
oy Ha, a He -.0 1
mre
. a,f-unsaturated
(Lost H shown for ee, aldehyde
h
ep
ne
Fy
©
‘APPLICATIONS
ae Aldol condensation reaction can be used
or the following syntheses:
i Enzymatic synthesis of fatty acids.
- Highly concise total synthesis of epothilone
. Preparation of (E)-6-(2,2,3-trimethyl-
cyclopent-3-enyl)-hex-4-en-3-one-
. Synthesis of high polymers of
poly(glutaraldehyde).
. Stereoselective synthesis of (+)-ephedrine.
. Synthesis of numerous macrolide and
ionophore antibiotics (natural products).
. Total synthesis of distomadines A and B,
two structurally unique tetracyclic
quinolones.LA Dieckmann Diaper n,
: CO.
ester oroun. :
: grou 8,
cyclic Molecule
enry "eaction involves ana
an aliphatic Ditro com ‘ound
n eNSation ;
OD Inyo},
A NVolves two
Molecule and Jields a
Idehyde and
gage ina Michael reaction prior
ondensation,22
- In the Guerbet reaction, an aldehyde,
formed in sity from an alcol
to the dimerized alcohol.
+ In the Japp—Maitland condensation water is
removed not by an elimination reaction but
by a nucleophilic displacement
to the aldol ¢
hol, selfcondenses
FSi:
~.. .