CHEM 204 Lecture Notes - Benzaldehyde, Aldehyde, Ethyl Cinnamate

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31 Jan 2013
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Chemistry 222 Fall 2012
By: Krishnaa Siva
Date: November 28, 2012,
Thursday 1:30-5:30 PM Lab Group
TA: Mathieu Bedard
Experiment 5 (Part 2): Wittig reaction
1. Objective: 1 mark
What is the purpose of this experiment?
To perform the Wittig reaction and synthesize ethyl cinnamate from ylid
and benzaldehyde in the presence of the hexane solvent. Use IR and NMR
Spectroscopy to verify if it is that product that is formed.
2. Introduction: 1 mark
Brief description of the concept/reaction studied – wittig reaction
The Wittig reaction involves the reacting ylide with an aldehyde or
ketone, which is a carbonyl group, to form an olefin/alkene. The
phosphonium ylid can be made through an SN2 reaction between the
triphenyl phosphine and alkyl halide. When a stabilized ylid is used only
alkenes are formed, while if an un-stabilized ylid is used alkenes and
triphenyl phosphine oxide is formed. The Wittig reaction is known to be a
useful reaction since it produces a double in a specific position with no
uncertainty (Hunt, 2011).
3. Reaction Equation: 1 mark
Include proper structures and data for reactants and products [molar
mass, concentration, density, volume, mass, moles, etc – including
theoretical yield]
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