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Miniscale Diel-Alder Reaction

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A miniscale diels-alder reaction was performed between the conjugated diene 2,3dimethyl-1,3 butadiene and a substituted alkene such as maleic anhydride in order to produce a substituted cyclohexane. The substituted cyclohexane produced was 4,5-dimethyl-4-cyclohexene-cis-1,2-dicarboxylic acid anhydride. A diels- alder reaction does not have an intermediate state, meaning that bond breaking and bond making occurs at the same time. Heat needs to be applied in order for the reaction to occur and it is very important that 2,3 dimethyl-1,3 butadiene to be cis otherwise there will not be an reaction. During the experiment the melting point of the final product was recorded to be 88°C which is higher than the theoretical melting point of 78-79°C. A low melting point indicates impurities in the purified product where as a higher melting point could be a result of heating the sample too fast. Another error could have occurred from placing too much sample in the capillary tube while performing the recording of the melting point. …show more content…
The crude weight of the product was 0.8753g and the purified mass of the product was 0.7598g C10H12O3. The % yield was found to be 46.98 %, which is relatively low, compared to the theoretical yield. A low % yield is an indication of loss of product, which could have occurred during vacuum filtration or even during recrystallization. The crude yield was 54.13 %, which is higher than the % yield. A higher crude yield is to be expected due to the fact that the crude product contains impurities thus the crude yield is always higher than the %

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