High School

Draw the mechanism of the Grignard Synthesis of Malachite Green. Ensure that all mechanistic arrows are correctly drawn.

Show the following:

- The generation of the Grignard reagent followed by the reaction of that reagent with the ester.
- The role of HCl in the reaction (protonation of the alkoxide ion and reaction with excess Mg/Grignard reagent).
- The subsequent dehydration of the tertiary alcohol to yield the final product (Malachite Green).

Answer :

In Grignard Synthesis of Malachite Green, an alkoxy magnesium halide, commonly known as a Grignard reagent, is generated by the reaction of magnesium metal with an alkyl halide.

This Grignard reagent is then reacted with an ester to form an intermediate alkoxide ion. This alkoxide ion is then protonated by HCl and simultaneously reacted with excess magnesium/Grignard reagent. Finally, the tertiary alcohol formed is then subjected to dehydration to yield Malachite Green.

The Grignard synthesis of Malachite Green starts with the reaction of an alkyl halide with magnesium metal to generate an alkoxy magnesium halide, also known as a Grignard reagent. This Grignard reagent is then reacted with an ester to form an intermediate alkoxide ion.

This alkoxide ion is then protonated by HCl and simultaneously reacted with excess magnesium/Grignard reagent. The reaction of the alkoxide ion with the Grignard reagent yields a tertiary alcohol, which is then subjected to dehydration to form Malachite Green.

The role of HCl in this reaction is to protonate the alkoxide ion, thus allowing it to react with the excess Grignard reagent to form the tertiary alcohol.

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