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26 August, 20:15

Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), ethyl bromide, potassium tert-butoxide, isobutyl chloride, hot aqueous naoh, hcl, and heat. what is the final product?

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  1. 26 August, 23:53
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    In first step the acidic proton at alpha position is abstracted by NaOEt and forms Enolate.

    The resulting enolate undergoes SN² reaction with Ethyl Bromide.

    The resulting product again on treatment with Potassium tertiary Butoxide gives corresponding Enolate.

    This second enolate on treatment with Isobutyl Chloride undergo SN² reaction.

    At last treatment with NaOH (aq) and HCl at high temperature yield 2-Ethyl-4-methylpentanoic Acid.
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