Tara Bhatnagar

Modified Wittig Lab Report

February 27, 2024

Mechanism

Calculations

Weight of empty vial = 9.113 g

Vial weight with sample = 9.676 g
Sample weight = (Vial weight with sample) – (Weight of empty vial) = 9.676 g - 9.113 g = 0.563 g
Percent yield = (sample weight/ Theoretical yield) * 100 = (0.563/ 1.79)*100 = 31.99%

Results Data Table

Compound Sample Molecular Moles Theoretical Yield Melting

weight (g) weight (g/mol) yield (g) percent Point (C)
 E,E-1,4-diphenyl- 0.563 206.28 ~0.003 1.76 31.99% 152.7
1,3-butadiene ~0.009 mol

Discussion

The goal of this was to synthesize E,E-1,4-diphenyl-1,3-butadiene using the Horner-Wadsworth-Emmons

modified Wittig reaction that reacts an aldehyde with a phosphonate ester. This goal was met.

The melting temperature was experimentally found to be around 152.7 C using the melt temp apparatus.
This is around the literature value of 152C -153C, showing that the product formed was quite pure.

Despite the good quality of the product the yield was quite low: 31.99%. During the color changing
process, a spatula was used to move the power around to sure that the color changing process was even.
This could have caused some of the product to seep pass the filter and into the by product. Finally, because
very large plated were formed in the Hirsch funnel it was hard to put all of it into the vial and some of the
product fell out and was lost. These were the two reasons why the yield was low.

Answers to document questions

1.
2. The aldehyde shouldn’t have any free carboxylic acids because the acid will protonate the
negatively charged carbon and lower the yield and will not react with the carbonyl of the
aldehyde.

3. A.
B. DMF is a highly polar solvent and since like dissolves like it dissolves reactant easily. Also,
since it is aprotic it will not donate a proton.
4.

5.