Orgo 2 Lab 1 - Lab report for Diels-Alder PDF

Preview

Summary

Lab report for Diels-Alder
...

Description

Madison Fisher Malorie Hacker February 6, 2019

Diels-Alder Reaction Objective: The objective of this experiment was to synthesize a bridged polycyclic ring system via Dielscycloaddition reaction, to purify the product by recrystallization, and to characterize the products purity and identify using melting point and IR spectroscopy.

Experimental: Anthracene (0.500g, 0.0028mol), Maleic Anhydride (0.378g, 0.0039 mol) and xylene (3mL) were added to a 10 mL round bottom flask. The mixture turned yellow as it was mixed. The mixture was attached to a condenser and refluxed for 30 minutes, while constantly stirring. After 30 minutes, the mixture was allowed to cool and the crystals were isolated using vacuum filtration. The crystals were washed using xylene and the crude was weighed. The crude product was recrystallized from xylene to afford 9,10- dihydroanthracene 9,10-α,β-succinic acid anhydride (0.544g, 70%) As a white needle-like and powder crystal; mp 262.3-264.5. An IR spectrum was obtained for the pure product.

Results and Discussion: Data: Reagents

MW (g/mol)

mp Co

Amount used (g)

Moles

Equivalents

Limiting Reagent

anthracene

178.23

215.76

0.500

0.0028

1

x

Maleic anhydride

98.06

52.6

0.378

0.0039

1.39

Product

MW (g/mol)

mp Co (Literature)

mp Co (observed)

Theoretical Yield (moles)

Theoretical Yield (g)

Weight (g)

% Yield

9,10dihydroant hracene 9,10-α,βsuccinic acid anhydride

276.29

262-264

262.3 -264.5

0.0028

0.774

0.544

70%

Crude Weight: 0.665g % Recovery after Recrystallization: 82%

University of New Orleans

1

M.Fisher

Madison Fisher Malorie Hacker February 6, 2019

Calculations: 0.500 g 1 mol anthracene × 178.23 g /mol 1 ¿ moles anthracene=0.0028 Theoretical Yield 9,10−dihydroanthracene 9,10−α , β−succinic acid anhydride ¿ 0.0028 g × 276.29 g /mol Theoretical Yield 9,10−dihydroanthracene 9,10−α , β−succinic acid anhydride=0.774 g 0.544 % yield 9,10−dihydroanthracene 9,10−α , β−succinicacid anhydride= 0.774 % yield 9,10−dihydroanthracene 9,10−α , β−succinicacid anhydride=70 % Mass of recrystallization compound , g % Recovery after Recrystallization: Mass of crude compound , g 0.544 =82 % ¿ 0.665 ¿ moles anthracene=

Discussion: 9,10- dihydroanthracene 9,10-α,β-succinic acid anhydride was prepared by the synthesis of a bridged polycyclic ring system via Diels-cycloaddition reaction. the identity of the product was confirmed to be 9,10- dihydroanthracene 9,10-α,β-succinic acid anhydride by IR spectrum And melting point. The IR absorption at 2973.25 corresponds to the C-H functional groups, at 1772.50 corresponds to a C=O Carbonyl and that 1457.50 corresponds to C=C aromatic. The melting point of a pure product was 262.3-264.5 degrees Celsius. does melting point corresponds to the literature melting point range of 262 - 264 degrees Celsius.

Conclusion: 9,10- dihydroanthracene 9,10-α,β-succinic acid anhydride was prepared by the synthesis of a bridged polycyclic ring system via Diels-cycloaddition reaction. 9,10- dihydroanthracene 9,10α,β-succinic acid anhydride Was obtained you're in a 70% yield. IR spectroscopy and melting point confirm the structure and the purity of the product.

University of New Orleans

2

M.Fisher...