University:
Emory University
Course:
CHEM 141 | General Chemistry I
Academic year:

2019
Views:

479

Pages:

3
Author:

Marin Mason

Diels-Alder Reaction of Anthracene and Maleic Anhydride Yielding 9,10Dihydroanthracene-9,10-α,β-Succinic Anhydride Supplemental information 9,10-dihydroanthracene-9,10-α,β-succinic anhydride. Anthracene (0.25 g, 1.42 mmol) and meleic anhydride (0.13 g, 1.28 mmol) were added to xylenes (3 mL, 24.30 mmol) with a boiling chip and was heated to reflux with a reflux condenser for 30 minutes. The reaction mixture was allowed to cool to room temperature (~25°C) and then cooled in an ice/water bath. The reaction mixture was transferred to a Hirsch funnel, washed with cold xylenes (1.50 mL), and was filtered using vacuum filtration. The product was purified and filtered to give the pure product as an offwhite crystalline solid (0.15 g, 47%): m.p = 262-264 °C; IR (film) 2960, 1861, 1780, 1770, 1458 cm-1; 1H NMR (300 MHz, CDCl3) δ 7.40 (d, J=3.9 Hz, 4H), 7.22 (t, J=15.9 Hz, 4H), 4.83 (d, J=3.4 Hz, 2H), 3.53 (t, J=2.46 Hz, 2H). Results IR Peaks (cm-1) Functional Group Bond 2950 Alkane C-H 1861, 1780-1771 Carbonyl (Aldehyde) C=O 1458 Aromatics C-C Figure 1. IR Analysis of 9,10-dihydroanthracene-9,10-α,β-succinic anhydride (corresponds to Figure 3) Peak Shift (ppm) Splitting J (Hz) Integration A 7.40 Doublet 3.90 4 B 7.22 Triplet 15.93 4 C 4.83 Doublet 3.36 2 D 3.53 Triplet 2.46 2 Figure 2. NMR Analysis of 9,10-dihydroanthracene-9,10-α,β-succinic anhydride (corresponds to Figure 4) Figure 3. Labeled IR Spectrum of 9,10-dihydroanthracene-9,10-α,β-succinic anhydride 2 Figure 4. Labeled NMR of 9,10-dihydroanthracene-9,10-α,β-succinic anhydride Theoretical Yield: Maleic Anhydride (limiting reagent): 0.1259 𝑔 1 𝑚𝑜𝑙 1 𝑚𝑜𝑙 𝑝𝑟𝑜𝑑𝑢𝑐𝑡 276.29 𝑔 𝑝𝑟𝑜𝑑𝑢𝑐𝑡 ) = 𝟎. 𝟏𝟗𝟓𝟐 𝒈 𝒑𝒓𝒐𝒅𝒖𝒄𝒕 ( )( )( )( 1 𝑚𝑜𝑙 𝑝𝑟𝑜𝑑𝑢𝑐𝑡 1 178.23 𝑔 1 𝑚𝑜𝑙 Pure Yield (after recrystallization): 0.1452 g (measured) Percent Yield: 0.1452 𝑔 ) × 100 = 𝟕𝟒% ( 0.1952 𝑔 Figure 5. Percent Yield Calculations of the Product 9,10-dihydroanthracene-9,10-α,β-succinic anhydride from the Reaction of Maleic Anhydride and Anthracene Crude Yield: 0.3100 g Pure Yield: 0.1452 g Percent Recovery: 0.1452 𝑔 ( ) × 100 = 𝟒𝟕% 0.3100 𝑔 Figure 6. Percent Recovery Calculation from the Purification of 9,10-dihydroanthracene-9,10α,β-succinic anhydride via Recrystallization 3