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Chapter 18-3 - CHEM 262 Wei You Chapter 18 Functional...

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CHEM 262 Wei You Chapter 18. Functional Derivatives of Carboxylic Acids (3)
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Rxn with Grignard Reagents treating a formic ester with 2 moles of Grignard reagent followed by hydrolysis in aqueous acid gives a 2° alcohol treating other esters with 2 moles of Grignard reagent followed by hydrolysis in aqueous acid gives a 3° alcohol HCOCH 3 O 2 RMgX H 2 O ,  HC l HC - R R OH CH 3 OH + magnesi u m       al koxi de         sa lt + CH 3 COCH 3 O 2 RMgX H 2 O ,  HC l CH 3 C - R R OH CH 3 OH magnesi u m       a l k ox i de         sa lt + +
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Reaction with Grignard Reagents 1. addition of 1 mole of RMgX to the carbonyl carbon gives a TCAI 1. collapse of the TCAI gives a ketone (an aldehyde from a formic ester) O CH 3 -C-OCH 3 R MgX O R OCH 3 CH 3 -C [MgX] + CH 3 -C R O CH 3 - [ MgX] + 1 1 + - + A magnesium salt (a tetrahedral carbonyl addition intermediate) A ketone 2 2
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Reaction with Grignard Reagents 3. reaction of the ketone with a 2nd mole of RMgX gives a second TCAI 4. treatment with aqueous acid gives the alcohol CH 3 -C O R R MgX CH 3 -C-R R [MgX] + H 2 O, HCl CH 3 -C-R R OH Magnesium salt A ketone + A 3 °  alcohol 3 3 (4)
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Rxns with RLi
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