(i) Explain why In the isomerization experiment, dimethyl maleate (DM) is a liqu
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(i) Explain why In the isomerization experiment, dimethyl maleate (DM) is a liquid whereas its isomeric product, dimethyl fumarate (DF) is a solid, even though DM and DF have the same molecular formula. (ii) From TLC analysis of the isomerization of dimethyl maleate which one is more polar compound, dimethyl maleate (Rf 0.34) or dimethyl fumarate (Rf 0.57)? How many spot(s) did you see for your final product (pure crystal and why? (iii) If the TLC solvent was changed from 4:1 to 1:1 Hexane/Ethyl Acetate mixture, how this will affect the Rf values of your compound, ? Why? (iv) If 3.9g of dimethyl fumarate is recrystallized and 1.23g of pure dimethyl fumarate was obtained. What was the percentage recovery?Explanation / Answer
4) (i) Owing to the cisoidal geometry of dimethyl maleate, the self aggregation (packing ) of the molecule gets restricted relative to that of of the dimethyl fumarate, where, the transoid geometry facilitate their self packing and hence, dimethyl fumarate is a solid and dimethyl maleate is liquid.
Moreover, it is only the geometry that makes difference in their polarity and dimethyl maleate is less polar than dimethyl fumarate.
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