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Organic Chemistry 2

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Moderate

Synthesis: Ketone to Alkene Conversion with C-C Bond Formation

ORGO2-AKTYHD

Ketones are converted to alkenes accompanied by carbon-carbon bond formation through the Wittig reaction. Alternatively, this same transformation can be accomplished through the addition of a Grignard reagent to the ketone followed by dehydration of the resulting alcohol.

Evaluate the four reactions below as to their potential for producing the alkene depicted in the box.

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Which reaction sequence produces exclusively the product in the box?

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Which reaction sequence produces NONE of the product in the box?

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Which reaction sequences produce some of the compound in the box, accompanied by one or more isomeric compounds?

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