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The lab focuses on conducting a Diels-Alder reaction using anthracene and maleic anhydride, with detailed calculations for reagent amounts and equivalents. The experiment yielded a mass of crystals with a recovery percentage of 132.7%, potentially affected by the use of CaCl2 as a drying agent. NMR analysis indicates specific multiplet patterns in the product's spectrum.

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10 views3 pages

7

The lab focuses on conducting a Diels-Alder reaction using anthracene and maleic anhydride, with detailed calculations for reagent amounts and equivalents. The experiment yielded a mass of crystals with a recovery percentage of 132.7%, potentially affected by the use of CaCl2 as a drying agent. NMR analysis indicates specific multiplet patterns in the product's spectrum.

Uploaded by

abigailjchiu
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Gail Chiu CHM 226

Diels-Alder Reaction:

Purpose statement: The purpose of this lab is to have a Diels-Alder reaction


using anthracene as a diene and maleic anhydride as a dienophile.

Reaction Scheme:

Reagent table:

Anthracene Maleic m-xylene Deuterated


anhydride chloroform
MW (g/mol) 178.23 g/mol 98.06 g/mol
D (g/ml) 1.24 g/mL 1.48 g/mL
Lab Amt 100 mg 55 mg 7 ml 1 ml
Amt Used 107 mg 55 mg 7 ml 1 ml
Mmols 0.69 mmols 0.56 mmols
Equiv. 1.07 equiv. 1 equiv.
Calculations for reagent table:

Mmols Anthracene:

107 mg /1000 = 0.107 g

(0.107 g / 178.23 g/mol)*1000 = 0.60 mmols

Mmols maleic anhydride:

55 mg/1000 = 0.055 g

(0.055 g / 98.06 g/mol)*1000 = 0.56 mmols

Equiv.:

0.60/0.56 = 1.07

Data table:

g Watch g Filter paper Total mass Mass crystals % Recovery


glass
59.920 g 0.184 g 60.177 g 0.073 g (73 132.7%
mg) recovery
Calculations:

Mass crystals:

60.177 g – (59.20 g + 0.184 g) = 0.073 g

% Recovery = 73 mg/ 55 mg = 132.7% recovery

Errors: The percent recovery is high possibly due to the addition of CaCl2 as
a drying agent in the experiment. This could have added weight to the
product.

NMR analysis

Theres a multiplet at 7.12 – 7.41 ppm, a triplet at 4.81 – 4.83 ppm, and a
sextet at 3.51 – 3.55 ppm. The solvent line is at 7.25 ppm.

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