CH 318L EXPERIMENT

Aim: To synthesize trans, trans-1, 4-diphenyl-1, 3-butadiene by using the Wittig

Reaction method
Reagents:

dichloro
Benzyltriphenyl methane
phosphonium
chloride

IUPAC Triphenyl(phenylme Dichloro

name
methane
thyl)phosphoniu

Ethanol transSodium Sodium

cinnamaldeh sulphate hydroxide
yde
(anhydrou

s)
Ethanol trans-3Phenyl-2propenal

Sodium Sodium
sulphate hydroxide

m chloride
Mol. Wt.388.87g/mol

84.93
g/mol

46.0684 132.16g/mol 142.04

4 g/mol
g/mol

Density

--

1.33
g/cm

0.789
g/cm

M.P

330 C

-96.7 C

-114 C 94 C(lit.)

B.P

--

39.6 C
78.37
C

39.997
g/mol

1.05 g/cm
2.664g/c 2.13
at 25 C(lit.) m
g/cm

250252 C(lit.)

884 C

318 C

1429 C

1,388 C

Apparatus: pipette, burette, conical flask, beaker, measuring cylinder, magnetic

stirrer, dropper, magnetic stirrer
Theory : The Wittig reaction is an organic chemistry synthesis technique that allows
the creation of a new carbon-carbon bond. A nucleophilic addition reaction
mechanism is adapted for the conversion of aldehydes and ketones into alkenes.

Mechanism of Wittig reaction :

Step1: Ylide formation (Ylide is a neutral dipolar molecule with opposite charges on
adjacent atoms and they function as carbon nucleophiles)
Step2:Betaine formation (Betaine is neutral dipolar molecule with opposite charges
on non-adjacent atoms)
Step3: Oxophosphetane formation (Oxophosphetane is a 4-membered ring with
adjacent oxygen and phosphorous atoms)
Step4: Breakdown of oxophosphetane

Procedure:
Step1: 1.5 g of benzyltriphenylphosphonium chloride and 0.5 mL of transcinnamaldehyde to be added to a 50ml flask containing 10ml of dichloromethane.
Step2: Then add 3ml of freshly prepared 50% NaOH(2.5g of NaOH in 5%ml of
water) and stir the mixture for 30 min.
Step3: Do the work-up in a separating funnel using 20ml of dicholoromethane and
20ml of water. Discard the water layer and dry the dicholoromethane layer using
anhydrous Na2SO4, filter and evaporate on a hot plate.
Step4: Add 35 mL of 50% ethanol, mix and break up large masses with a stir rod
Step5: Collect the precipitate on a filter and wash with 10 mL of 50% ethanol
Step6: Recrystallize the product from 10 mL 95% ethanol.

Budget of the Reaction:

Serial No.

Reagent

Quantity

Price

Benzyltriphenylphophonium
chloride

50gm

2484.34

Trans- cinnamaldehyde

25gm

1288.74

Sodium Hydroxide

500gm

252.00

Dichloromethane

1L

821.22

Ethanol

500ml

1500

Sodium Sulphate

500gm

246.00

Hazards:
Serial No.

Reagent

Hazard Information

Benzyltriphenylphophonium
chloride

Toxic if swallowed

Trans- cinnamaldehyde

Irritating to eyes, skin, respiratory system,

may cause sensitization by skin contact

Sodium Hydroxide

Corrosive, causes severe burns

Dichloromethane

Irritating to eyes, skin, respiratory system,

Ethanol

Highly flammable

Sodium Sulphate

Irritant