Predict the product and provide the complete

Chapter 9, Problem 9

(choose chapter or problem)

Predict the product and provide the complete electron-pushing mechanism for the following two-step synthetic processes.

Equation Transcription:

$C\equiv{}CH$

$NaN{H}_{2}$

$C{H}_{3}I$

$HC\equiv{}CCOC{H}_{2}C{H}_{3}$

$NaN{H}_{2}$

$C{H}_{3}C{H}_{2}I$

$C{H}_{3}C{H}_{2}C\equiv{}CH$

$NaN{H}_{2}$

$PhC{H}_{2}Br$

Text Transcription:

C{equiv}CH

NaNH_2

CH_3I

HC{equiv}CCOCH_2CH_3

NaNH_2

CH_3CH_2I

CH_3CH_2C{equiv}CH

NaNH_2

PhCH_2Br

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