Predict the product formed when the conjugate-base enolate ion of ethyl 2-methylpro panoate (shown in Eq. 22.81)
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Predict the product formed when the conjugate-base enolate ion of ethyl 2-methylpro panoate (shown in Eq. 22.81) is treated with bromobenzene and a catalytic amount of Pd[P(t-Bu)3]4, and explain the role of the catalyst.
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CH3 O floo. Agh Lit H3C-C- C -OEt + H ethyl 2-methyl- propanoate -78 °C THF < 15 min lithium cyclohexylisopropylamide (LICHA) H3C H3C + Lit :O: enolate OEt H a quaternary a-carbon CH3 H3C-I DMSO H3C-C- CH3 OEt ethyl 2,2-dimethylpropanoate (ethyl pivalate) (87% yield) + Li+I (22.81)
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