Lab Report for Tetraphenyl cyclopentadienone PDF

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Lab Report for Tetraphenyl cyclopentadienone...

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Adeyemo 1

Lab Report for Tetraphenyl cyclopentadienone

Oyinda Adeyemo Howard Community College Lab Instructor: Professor Emma Liu Date: March 16, 2021

Adeyemo 2 Objective 1. To synthesize Tetraphenylcyclopentadienone Chem Index Pure Benzil

1,3-diphenyl acetone

Triethylene glycol (TEG)

Benzyl trimethylammonium hydroxide

Methanol

C14H10O2 Molecular weight:

210.23 g/mol

Melting point:

94.8℃

Boiling point:

347℃

C15H14O Molecular weight:

210.28 g/mol

Melting point:

30℃ - 34℃

Boiling point:

330℃

C6H14O4 Molecular weight:

150.17 g/mol

Melting point:

-7℃

Boiling point:

285℃

C10H17NO Molecular weight:

167.25 g/mol

Melting point:

-98℃

Boiling point:

65℃

CH3OH

Adeyemo 3

Tetraphenylcyclopentadienone

Molecular weight:

32.04 g/mol

Melting point:

-97.6 ℃

Boiling Point:

64.7 ℃

C29H20O Molecular weight:

384.5 g/mol

Melting point:

219℃ - 220℃

Boiling Point:

617.13℃

Major Chemical Reactions Procedure ➢ In a reaction tube, add ~42 mg of 1,3-diphenyl acetone, 42 mg of Benzil and ~8 drops of TEG directly into the vial. ➢ Place vial over aluminum block on a water bath. Set water bath to 110℃ ➢ Use thermometer as stirring rod. ➢ Once the reactants have dissolved, add ~10 drops of Triton B drop-wise. ➢ Place solution on water bath and set to 110℃ and stir for 2 minutes. ➢ Add 1.5mL of methanol and 1mL of water to the tube and allow it cool to room temperature. ➢ Place solution in ice bath. ➢ Vacuum and filter out the product. ➢ Place in drawer to fully dry ➢ Clean up work area. Data & Calculation Mass of Benzil:

0.0420 g

Adeyemo 4 Mass of 1,3-diphenyl acetone: 0.0425 g Mass of filter paper:

0.0960g

Mass of funnel:

7.4218 g

Mass of filter paper + funnel + product: 7.4987 g Mass of product:

0.0762 g

Determination of Limiting reagent: 𝑔𝑟𝑎𝑚𝑠 𝑜𝑓 𝑏𝑒𝑛𝑧𝑖𝑙 𝑀 𝑜𝑓 𝑏𝑒𝑛𝑧𝑖𝑙 𝑤

=

0.0420 𝑔 210.23 𝑔/𝑚𝑜𝑙

𝑔𝑟𝑎𝑚𝑠 𝑜𝑓 1,3−𝐷𝑖𝑝ℎ𝑒𝑛𝑦𝑙 𝑎𝑐𝑒𝑡𝑜𝑛𝑒 𝑀 𝑜𝑓 1,3−𝐷𝑖𝑝ℎ𝑒𝑛𝑦𝑙 𝑎𝑐𝑒𝑡𝑜𝑛𝑒 𝑤

1.9978 x 10-4 mol of Benzil

=

=

0.0425 𝑔 210.28 𝑔/𝑚𝑜𝑙

=

2.0211 x 10-4 mol of 1,3- Diphenyl acetone

Benzil is the limiting reagent. Percent Yield: 𝑔𝑟𝑎𝑚𝑠 𝑜𝑓 Tetraphenylcyclopentadienone 𝑀 𝑜𝑓 Tetraphenylcyclopentadienone 𝑤

=

0.0762 𝑔 384.5 𝑔/𝑚𝑜𝑙

=

1.9818 x 10-4 mol of tetraphenyl

cyclopentadienone 1.9818 x 10^−4 1.9978 𝑥 10^−4

x 100% =

99.19%

Result and Discussion The purpose of this experiment was to synthesize Tetraphenylcyclopentadienone, by using 2 reactants Benzil and 1,3-diphenyl acetone, in the presence of TEG, Triton B, methanol, NaOH and Benzyl trimethylammonium hydroxide. From the calculation, the limiting reagent was Benzil, and the yield gotten was 99.19% which was slightly higher than the expected yield. There are quite a few reasons for this yield such as contamination, the product was kept in a drawer for 2 weeks without being covered during that period of time, it is possible that the product must have come in contact with other things

Adeyemo 5 especially since the drawer was a shared one. Another reason for such a high yield might have been using an excessive amount of the required reactants. The melting point was not taken for this experiment, so there was no way to tell if it is pure or not. In order to avoid having such a high yield with a possible probability of product not being pure, the reaction would be carried out in the same tube. The amount of reagent used would not be in excess as it would be weighed more than once for a more accurate result. During the pre-lab, a lot about Tetraphenylcyclopentadienone was learned. It was understood that Tetraphenylcyclopentadienone, is a compound that has a dark purple color that is crystalline as observed during the experiment, which is used in the making of organic compounds since it is a building block that can be easily made. Tetraphenylcyclopentadienone can be really useful in the pharmaceutical industry, as it can be used as a diene in the synthesis of 1,2,3,4-tetraphenylnaphthalene, alongside benzyne as the dienophile in the DielsAlder synthesis...