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Danielle Colon-Carreras U75338393 CHM2211L-014 TA Sami Abdulkadir Experiment #2: Diels-Alder Reaction: Synthesis of 9,10-dihydroanthracene-9,10-end-alpha, beta-succinic anhydride Introduction Through the use of anthracene and maleic anhydride, a Diels-Alder reaction can be performed,

thus

synthesize

a

Diels-Alder

product

such

as

9,10-dihydroanthracene-9,10-endo-alpha, beta-succinic anhydride, which is the objective of this experiment [1]. A Diels-Alder reaction undergoes a one-step or concerted mechanism with a dienophile and diene [1]. In this experiment in order to facilitate the reaction, the reactants used are diene (anthracene) and dienophile (maleic anhydride) [1]. The dienophile is the reactant that contains the electron withdrawing group whereas, the diene is the reactant that contains the contributing group of electrons [1]. In a Diels-Alder mechanism, the breaking and forming of bonds is constant and there is no formation of intermediate products. Additionally, the stereospecificity (syn addition) depends on the diene and dienophile and the favored major product is endo instead of exo stereochemistry of the compound [1]. Lastly, these reactions are applied into real-life problems thus are used in the production of fragrances and biomaterials among other applications.

Figure 1 Overall Diels-Alder Mechanism

FIG1 shows the overall Diels-Alder reaction. The reactants are anthracene (diene) and maleic anhydride (dienophile) and the desired product is 9,10-dihydroanthracene-9,10-end-alpha, beta-succinic anhydride. The addition of anthracene plus maleic anhydride produce 9,10-dihydroanthracene-9,10-end-alpha, beta-succinic anhydride.

Figure 2 Possible Side Reactions A. Anthracene reacts with hydrolyzed maleic anhydride thus forming or producing two distinct stereospecific 9,10-dihydroanthracene-9,10-end-alpha, beta-succinic anhydrides.

B. Maleic anhydride is reacted with water

FIG 2 shows the possible side reactions of the Diels-Alder reaction. Chemicals Table 1.1 Chemicals Chemical

Formula Name

Molar mass (in g/mol)

Melting Point (in Celsius)

Boiling Point (in Celsius)

Properties

IUPAC Name

Maleic

C4H2O3

98.06

52.8

202

Colorless

Furan-2,5-

anhydride

crystalline [4]

dione

Xylene

C8H10

106.16

13.2

138

Colorless liquid, sweet odor [5]

Dimethyl benzene

Calcium Chloride

CaCl2

110.98

782

1670

White, odorless solid [6]

Calcium dichloride

Deuterated Chlorofor m

CHCl3

120.38

-63

60.5

White, odorless solid [7]

Trichloro(d eutero)met hane

Anthracene C4H10

178.23

218

340

Yellow-lik e powder solid, aromatic odor [8]

Anthracene

260

484

N/A [9]

9,10-dihyd roanthrace ne-9,10-en do-alpha, beta-succin ic anhydride

9,10-dihyd C18H12O3 276.3 roanthrace ne-9,10-en do-alpha, beta-succin ic anhydride

Table 1.1 shows the chemicals used in this experiment including formula name, molar mass, melting and boiling point, properties, and IUPAC Name. Toxicity of Chemicals Table 1.2 Hazards/ Toxicity of Chemicals Chemical

Hazards

Maleic anhydride

May cause digestive tract irritation; causes skin and eye burns; prolonged exposure to the skin may lead to dermatitis; may cause allergic skin and respiratory reactions [4]

Xylene

Flammable liquid and vapor; cause skin irritation and eye irritation; may be fatal and enter airways; may cause respiratory tract irritation [5]

Calcium Chloride

Causes serious eye irritation; read label before use; may form combustible dust concentrations in air [6]

Deuterated Chloroform

Suspected of causing cancer, may cause damage to the organs through prolonged exposure or repeated exposure; may cause skin and eye irritation; harmful if swallowed [7]

Anthracene

Causes skin and eye irritation; may form combustible dust concentrations in air; wash face, hands and exposed skin thoroughly after handling [8]

9,10-dihydroanthracene-9,10-endo-alpha, beta-succinic anhydride

Causes skin irritation; causes serious eye irritation; harmful if swallowed [9]

Table 1.2 shows the hazards of all chemicals used in this experiment.

Experimental Procedure

Note: Experimental section provided by TAs in Experiment/ Data lecture video [2]. Results Table 1.3 Product Analysis/ Information Mass (in grams)

0.778 g

Melting point (in Celsius)

260 °C

Appearance of crystals

White, snow-like

Percent Yield

92%

Rate of Reaction

Very fast

Table 1.3 shows the product analysis obtained from the experiment including mass, melting point, percent yield, and appearance of product. Calculations 0.6 g anthracene x (178.23 g/mol)= 0.00337 mol 0.3 g maleic anhydride x (98.06 g/ 1mol) x (276.3 g/ 1mol)=0.845 g

0.778 g/ 0.845 g x 100%=92%

1

H-NMR

Figure 3 shows the actual 1 H NMR spectrum of the Diels-Alder product.

Figure 4 shows the theoretical 1 H NMR spectrum of the Diels-Alder product. Note: Results were provided by the TAs in experiment data document and experiment video [1]. Discussion Based on the results, the melting point of the product is recorded as 260 degrees in Celsius, which is the actual literature value of the melting point of the product. Therefore, it can be interpreted that there were no impurities present. Additionally, the percent yield of desired product was calculated to be 92% thus there was a high product yield. If the percentage yield would have been recorded to be less than 50%, then there might have been significant errors

when performing the experiment such as improper mixture transfer, side reactions with intermediate products, or the reaction wasn't completed. In Figure 3 the H NMR shows a total of 3 peaks also referred to as signals, which describe the protons that are different from each other in the compound. One of the signals has about 7 to 8 peaks whereas the other two signals have 2 peaks, therefore a total of about 3 different peaks. Lastly, within the H NMR spectrum, there were smaller, less defined peaks that could be recording the solvent used. In

conclusion, the desired

product of 9,10-dihydroanthracene-9,10-endo-alpha,

beta-succinic anhydride was obtained with a high yield, thus the overall reaction was efficient.

Conclusion The aim of this experiment to use diene and dienophiles such as anthracene and maleic anhydride in order to perform a Diels-Alder reaction, thus synthesize a Diels-Alder product such as 9,10-dihydroanthracene-9,10-endo-alpha, beta-succinic anhydride. In this experiment, the desired product was obtained with a high percentage yield, thus it can be determined that the experiment accomplished its purpose. Diels-Alders are important organic reactions that can be applied to real-life problems which are used in the production of fragrances and biomaterials among other applications.

Reference 1. Results Section provided by TAs. 2. Experimental Section provided in lecture video by TAs. 3. Solomon Weldegirma. 2021. Experimental Organic Chemistry: Laboratory Manual For CHM 2210L And CHM 2211L. University of South Florida.

4. Material Safety Data Sheet Maleic Anhydride, 99% (pellets) ACC . [accessed 2021 January 24]. h ttps://fscimage.fishersci.com/msds/77426.htm 5. SAFETY DATA SHEET (SDS) XYLENE 1. Identification 2. Hazards . [accessed 2021 January 24]. h ttps://www.pcs.com.sg/wp-content/uploads/2017/04/PCS08006.pdf 6. Calcium Chloride,Dihydrate. [accessed 2021 January 24]. https://beta-static.fishersci.com/content/dam/fishersci/en_US/documents/programs/education/reg ulatory-documents/sds/chemicals/chemicals-c/S25222A.pdf 7. Safety Data Sheet. [accessed 2021 January 24]. http://www.nwmissouri.edu/naturalsciences/sds/0-9/5-Bromo-4-chloro-3-indolyl%20phosphate %20disodium%20salt.pdf 8. Material Safety Data Sheet Anthracene, p.a. ACC# 96671 Section 1 . [accessed 2021 January 24]. h ttps://fscimage.fishersci.com/msds/96671.htm 9. 9,10-dihydroanthracene-9,10-endo-α-bromo-α,β-succinic anhydride. [accessed 2021 January 24]. h ttps://www.chemsrc.com/cas/107523-13-7_113419.html...