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Asked: 2022-04-11T19:38:17+00:00 In:

Draw the major organic product from the following reaction sequence.

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Draw the major organic product from the following reaction sequence.

Draw the major organic product from the following reaction sequence.
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Grignard reagents in ether synthesis

The reaction of an ester using an excess of an Grignard Reagent, followed by acidic workup produces an Tertiary Alcohol. The reaction of the tertiary alcohol with a baseyields an alkoxide anion. The reaction of the alkoxide anion with an alkylhalide gives an ether.

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    The principal result of this reaction can be seen in the following:

    The steps required to produce the product are as follows:

    First step: nucleophilic attack Grignard reagents on the ester to create the Tetrahedral Intermediate.

    Step 2: The collapse of the tetrahedral intermediary will result in the loss of ethoxide anion, leaving group to make the ketones.

    Step 3: Nucleophilic attack the Grignard agent on the ketone, forming the Tetrahedral intermediate.

    Step 4: Protonation the tetrahedral intermediary to create the Tertiary Alcohol.

    Step 5: Deprotonation the tertiary alcohol, forming alkoxide anion.

    Step 6: The alkoxide anion reacts with bromopropane through SN2 to create the ether product.

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