Experiment: Synthesis of Dimedone 3. Describe and explain the possible effect on

Question

Experiment: Synthesis of Dimedone

3. Describe and explain the possible effect on your results of the following experimental errors or variations.

a) You neglected to evaporate methanol from the reaction mixture (hint: consider the role of the hydroxide ion at this point in the synthesis and that methanol and hydroxide will exist in the following equilibrium: HO- + MeOH <--> H2O + MeO-

b) The mesityl oxide bottle was contaminated with water

c) The bottle labeled "dimethyl malonate" actually contained dimethyl maleate.

Egerimfnt 46 Synthesis he and explain the yeeible bet t your resats ol the lore Dectibc rtebanol frum the reaction mixtir acually cur tainee dimeth ibc an h moityl od btie with watex. ic The bmtled -denell aa

Explanation / Answer

a) Methanol if it is not evaporated, the formed methoxide ion at equilibriium reacts to the keto groups in dimedone and forms corresponding hemiacetal forms.

b) If there is a water in mesityl oxide, water reacts directly with base of dimethyl malonate. So it leads to backward reaction and the yield of product will be lesser.

c) Dimethyl maleate can't give reaction because correspondin base can't be created by dimethyl maleate.

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