Journals on Aldol Reaction & Condensation:

A Mixed-Aldol Condensation Reaction with Unknown Aldehydes and Ketones:

Employing Modern Methods To Improve the Learning Process for Second-Year

Undergraduate Organic Chemistry Students. Amy M. Balija and Aileen M. Reynolds,

Journal of Chemical Education2013 90 (8), 1100-1102

The Five Senses of Christmas Chemistry: Derek A. Jackson and Andrew P. Dicks;

Journal of Chemical Education 2012 89 (10), 1267-1273

The Five Senses of Christmas Chemistry : Derek A. Jackson and Andrew P. Dicks;

Journal of Chemical Education2012 89 (10), 1267-1273

A Better Sunscreen: Structural Effects on Spectral Properties: Lawrence

A. Huck and William J. Leigh;

Journal of Chemical Education2010 87 (12), 1384-1387

Use of the Chemical Literature as a Template To Probe Stereoselective Reactions by

NMR: Thomas P. Clausen , Thomas . Green and Benjamin Steiner;

Journal of Chemical Education2008 85 (5), 692

Why Are 1H NMR Integrations Not Perfect? An Inquiry-Based Exercise for Exploring

the Relationship Between Spin Dynamics and NMR Integration in the Organic Lab:

Haim Weizman;

Journal of Chemical Education2008 85 (2), 294

Current Applications of Aldol Condensation:a) Application of the aldol condensation for the synthesis of diaryl-3-hydroxy-2,3,3a,10a-

tetrahydro benzo[b] cycylopenta [e]azepine-4,10(1H,5H)-diones.

b) Synthesis of tetrasubstituted bicyclo[3.2.1]octenes as potential inhibitors of influenza

virus sialidase.

c) Thiophilic ring-opening and rearrangement reactions of epoxyketone natural products

d) Integrated synthesis of dihydroacetone phosphate from Glycerol and its utilization in situ

for diastereo selective aldol additions.

e) Structure-based mutagenesis approaches toward expanding the substrate specificity of

D-2-deoxyribose-5-phosphate aldolase..

f) Stereoselective allyl transfer to chiral α-methoxycarbaldehydes.

g) Sequential aldol condensation for the synthesis of new glycine antagonists

h) Synthesis and biological evaluations of condensed pyridine and condensed pyrimidine-

based HMG-CoA reductase inhibitors.

i) Design and biological evaluation of a series of thiophene-based 3-hydroxy-3-

methylglutaryl coenzyme a reductase inhibitors.

j) Synthesis and antitumoral, antiviral evaluation of chiral spiropyrans.

k) Chemical and Enzymatic Synthesis of Fructose Analogues

Recent Researches on Aldol Condensation:PhD Research: Oxygen Removal and Condensation Reactions of Oxygenates on Solid Acid Catalysts

Stanley Herrmann

University of DelawareB.S. Chemical Engineering (2011)

This research aims to uncover the kinetic mechanism driving aldol-type condensation reactions on solid acid catalysts to increase the viability of biomass feedstocks for liquid fuels and value-added chemical production. Aldol condensation reactions form C-C bonds between molecules that contain a carbonyl function, primarily ketones and aldehydes, and the aldol product is subsequently dehydrated removing one oxygen as H2O. Removing oxygen and elongating carbon chains from oxygenates can be used in a variety of applications such as the synthesis of olefins, aromatics, and most importantly fuel. Solid acid provide an attractive catalyst for this study, specifically zeolites, due to their confining voids which limit the size the products can grow to by limiting the size of the transition state and by limiting the size of molecules that diffuse to the acid site. Once a mechanism for aldol condensation is determined, then the effects of this confining environment will be investigated by varying zeolite framework

Books on Aldol condensation: Modern Aldol Reactions (2 Volume Set) (English) 2 Volume Set Edition by John

Wiley 

Organic Reactions: Article The Aldol Condensation by Arnold T. Nielsen, William J.

Houlihan.

Asymmetric Aldol Reactions by VDM Verlag

Synthesis, Characterization and Application of I /I -oligopeptides: as bifunctional

organocatalysts for the aldol reaction by Vdm Verlag Dr. Mller

Aldol Reactions by Springer

Modern Methods in Stereoselective Aldol Reactions by Wiley-VCH Verlag GmbH

References & Web Sources for Aldol Reaction & Condensation:-

http://isites.harvard.edu/fs/docs/icb.topic93502.files/Lectures_and_Handouts/27- Aldol-1.pdf

http://dept.lamar.edu/chemistry/martincb/chem3412/chem%203412%20lab%20- %20aldol.pdf

http://www.organic-chemistry.org/namedreactions/aldol-condensation.shtm

http://science.uvu.edu/ochem/index.php/alphabetical/a-b/aldol-condensation/

http://www.chem.wisc.edu/areas/reich/chem547/1-carbonyl%7B12%7D.htm

http://guweb2.gonzaga.edu/faculty/cronk/biochem/A-index.cfm?definition=aldolase

www.xula.edu/chemistry/documents/orgleclab/ Aldol _notes. pdf

http://isites.harvard.edu/fs/docs/icb.topic1146159.files/JJB%20Aldol%20Lecture %2021%20Final.pdf

http://chemwiki.ucdavis.edu/Organic_Chemistry/Reactivity_of_Alpha_Hydrogens/ Aldol_Reaction

http://www.srmuniv.ac.in/downloads/MECHANISM_OF_REACTION.pdf

http://www.chemgapedia.de/vsengine/vlu/vsc/en/ch/12/oc/vlu_organik/keto_enol/ aldolkondensation_aehnliche_reaktionen.vlu.html

http://www.personal.kent.edu/~cearley/org52/aldol/aldol.htm

www.chem.ucalgary.ca/courses/351/Carey5th/Ch18/ch18-3-5.html

http://chemwiki.ucdavis.edu/Organic_Chemistry/Reactivity_of_Alpha_Hydrogens/ Aldol_Reaction

http://dept.lamar.edu/chemistry/martincb/chem3412/chem%203412%20lab%20- %20aldol.pdf

http://www2.fiu.edu/~herriott/ch17-carbonyls2.pdf

Recent Literature

An Efficient Method for the Selective Iodination of α,β-Unsaturated KetonesZ. Wang, G. Yin, J. Qin, M. Gao, L. Cao, A. Wu, Synthesis, 2008, 3565-3568.

Organocatalytic Asymmetric Reaction Cascade to Substituted CyclohexylaminesJ. Zhou, B. List, J. Am. Chem. Soc., 2007, 129, 7498-7499.

Aldol Reaction & Condensation Discovery:

The aldol reaction is a means of forming carbon–carbon bonds in organic chemistry. Discovered independently by Charles-Adolphe Wurtz and Alexander Borodin in 1872, the reaction combines two carbonyl compounds (the original experiments used aldehydes) to form a new β-hydroxy carbonyl compound. These products are known asaldols, from the aldehyde + alcohol, a structural motif seen in many of the products. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic. For example, the aldol reaction has been used in the large-scale production of the commodity chemical pentaerythritol and the synthesis of the heart disease drug Lipitor (atorvastatin, calcium salt).

1.2. Charles Adolphe Wurtz was an Alsatian French

chemist. He is best remembered for his decades-long advocacy for the atomic theory and for ideas about the structures of chemical compounds.

3. Born: November 26, 1817, Wolfisheim,

France Died: May 10, 1884, Paris, France Education: University of Giessen Books: The Atomic Theory Awards: Copley Medal

1.

2.3.

Alexander Porfiryevich Borodin was a Russian Romantic composer, doctor and chemist. Borodin lived during the Romantic Era.

4. Born : November 12, 1833, Saint Petersburg,

Russia Died : February 27, 1887, Saint Petersburg,

Russia Compositions : Prince Igor, Polovtsian Dances Film music credits : Supervixens, Fire Maidens

from Outer Space Libretti : Prince Igor

Aldol Reaction & condensation: The aldol reaction unites two relatively simple molecules into a more complex one. Increased complexity arises because up to two new stereogenic centers (on the α- and β-carbonof the aldol adduct, marked with asterisks in the scheme below) are formed. Modern methodology is capable of not only allowing aldol reactions to proceed in high yield but also controlling both the relative and absolute stereochemical configuration of these stereocenters. This ability to selectively synthesize a particular stereoisomer is significant because different stereoisomers can have very different chemical and biological properties

A typical modern aldol addition reaction, shown above, might involve the nucleophilic

addition of a ketone enolate to an aldehyde. Once formed, the aldol product can

sometimes lose a molecule of water to form an α,β-unsaturated carbonyl compound. This is

called aldol condensation. A variety of nucleophiles may be employed in the aldol reaction,

including theenols, enolates, and enol ethers of ketones, aldehydes, and many

other carbonyl compounds

Aldol Condensation:

O

Me Ph

OH

a -hydroxy carbonyl

Acidic:

Basic:

O

R Ph

OHH

H

OH2

O

R Ph

an,-unsaturated carbonyl

O

R Ph

OH

H

–OH

O

R Ph

an,-unsaturated carbonyl

H3O+ E2

E2

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 group is present. The aldol addition product can be dehydrated via two mechanisms; a strong base likepotassium t-butoxide, potassium hydroxide or sodium hydride in an enolate mechanism,[10] or in an acid-catalyzed enol mechanism.

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