Wittig Synthesis of 1,4-diphenyl-1,3-butadiene Devin Roy March 2, 2012 The purpose of this experiment was synthesize 1,4-Diphenyl-1,3-butadiene from

benzyl triphenylphosphonium chloride and pure trans-cinnamaldehyde using Wittig reaction process to convert the carbonyl group in trans-cinnamaldehyde into a carbon carbon double bond. The M.P. was the determining factor as to whether the experiment was a success or not.

Introduction The Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (often called a Wittig reagent) to give an alkene and triphenylphosphine oxide. An ylide is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a hetero atom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. Ylides are thus 1,2-dipolar compounds. They appear in organic chemistry as reagents or reactive intermediates.

Results and Discussion Yield %=(Actual Yield/Theoretical Yield)x100%= (1.21g/2.06g)x100%=58.74%. M.P. was observed at 145-149 degrees celsius in a capillary tube. Conclusion The product was determine to be the (E,E) isomer due to the M.P. being observed at 145-149 degrees celsius which closely matched the 153 degree M.P. outlined in the chemical section for that particular isomer. Experimental Section The wittig synthesis of 1,4-diphenyl-1,3-butadiene was carried out by combining pure transcinnaldehyde, benzyltriphenylphosphoniun chloride, and dichloromethane as a reaction solvent. First the Cl salt was dissolved in CH2Cl2 along with pure trans-cinneamaldehyde. The NaOH was added after the mixture was completely dissolved to prevent separation. A milky color was observed at this point. The NaOH reaccted with the salt which resulted in a yellow-orange coloration at the first step of the reaction synthesis. The rreaction turned mily white after five minutes. The trans-cinnamaldehyde reacted with the ylide in the second step of reaction synthesis. The product was then extracted by taking advantage of solubility, density, and acid-base properties. The mix was dried using MgSO4 to remove any excess H2O. the CH2Cl2 solvent was boiled away using the rotary evap. The product was then purified using 60% ethanol solution to remove the triphenylphosphine oxide and other impurities. the white crystalline solid was removed from the mother liquor using vacuum filtration and air dried on the filter. Product was then weighed and M.P. then observed.