Experiment 14: Hexaphenylbenzene diphenylacetylene is employed since it is far e

Question

Experiment 14: Hexaphenylbenzene diphenylacetylene is employed since it is far easier to separate from the desired product in the purification steps DO NO CALE THIS REACTION! Complete the following data your lab notebook, using the correct quantities to be table, in used in the experiment mp/bp, oc MW density, equiv mmol g compound tetraphenyl cyclopentadienone mp, 220. (solid) XXX (Solid) XXX diphenylacetylene silicone oil Procedure tetraphenylcyclopentadienone and 100 mg of In a small test tube, place 100 mg of diphenylacetylene. Add 1 mL of high-boiling silicone oil. Clamp the test tube at a slight angle, facing away from yourself and others. Bring the mixture gently to a boil over a 3 to 5 minute period by heating the test tube with a moving flame of a Bunsen burner. On melting, the reagen dissolve in the hot oil to yield a dark solution. Continue gently boiling for an the additional minutes during which time color fades and tan crystals of hexaphenylbenzene from the solution. Cool tube room temperature and add 4 mL of hexane wit stirring to dilute the silicone oil. Collect the crude product by vacuum filtration washing with mL of hexane, then two 2-mL portions of cold toluene. the hexaphenylbenzene product and calculate the yield. obtain an IR spectrum of the compound. Interpret the spectrum before attaching it to report Data for Hexaphenylbenzene n Lab Notebook: Mass of Product Show calculation: Theoretical Yield

Explanation / Answer

Compound

mp/bp, °C

MW,

g/mol

equiv

mmol

g

Density,

g/mL

mL

Tetraphenylcyclopentadienone

mp, 220-221

384.48

1

0.26

0.1 g (100 mg)

(solid)

Diphenylacetylene

mp, 61

178.24

2.15

0.56

0.1 g (100 mg)

(solid)

Silicon oil

Milli moles (mmol) = weight of compound (in mg)/ molecular weight (MW)

Tetraphenylcyclopentadienone milli moles = 100 mg/384.48 = 0.26 mmol

Diphenylacetylene milli moles = 100 mg/ 178.24 = 0.56 mmole

Equiv. we have to take calculate with respective to small number of mmol. Small number of mmol, we have to take as 1 mmol.

0.26 mmol is 1 equivalent then 0.56 mmol become 2.15 equivalent.

Compound

mp/bp, °C

MW,

g/mol

equiv

mmol

g

Density,

g/mL

mL

1,3-diphenylacetone

mp, 35

210.28

1

0.475

0.1 g (100 mg)

(solid)

Benzil

mp, 95

210.23

1

0.475

0.1 g (100 mg)

(solid)

Ethanol, 200 proof

Bp, 78

46.068

64.8

30.82

1.42 g (1420 mg)

0.789

1.8

NaOH, 10% (w/v)

40

0.2 g

2 ml

1,3-diphenylacetone milli moles = 100 mg/210.28 = 0.475 mmol

Diphenylacetylene milli moles = 100 mg/ 210.28 = 0.475 mmole

Density = weight (in grams)/ volume (in ml)

Weight = density x volume

Weight of ethanol = 0.789 x 1.8 = 1.42 g

Ethanol mmoles = 1420/46.068 = 30.82 mmol

10% NaOH solution means 10 g of NaOH present in 100 mL of water.

We need only 2 mL of 10% NaOH solution. For this 0.2 g of NaOH is required (0.2 g of NaOH should dissolve in 2 mL of water)

Compound

mp/bp, °C

MW,

g/mol

equiv

mmol

g

Density,

g/mL

mL

Tetraphenylcyclopentadienone

mp, 220-221

384.48

1

0.26

0.1 g (100 mg)

(solid)

Diphenylacetylene

mp, 61

178.24

2.15

0.56

0.1 g (100 mg)

(solid)

Silicon oil

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