How Do Esters React with Grignard Reagents

Notice that all carboxylic acid derivatives can be converted to carboxylic acids, which in turn can be converted to acid chlorides. Thus, any acid derivative can be used to synthesize another, either directly or via a carboxylic acid. 

STEP 1 Reaction of a nucleophile and an electrophile to form a new covalent bond. Reaction begins with the addition of 1 mole of Grignard reagent to the carbonyl carbon to form a tetrahedral carbonyl addition intermediate  

STEP 2 Collapse of the tetrahedral carbonyl addition intermediate to eject a leaving group and regenerate the carbonyl group. This intermediate then collapses to give a new carbonyl-containing compound and a magnesium alkoxide salt  

STEP 3 Reaction of a nucleophile and an electrophile to form a new covalent bond.The new 

STEP 4 Add a proton. Workup in aqueous acid gives a 3° alcohol (or a 2° alcohol if the starting ester was a formate)  

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How Do Esters React with Grignard Reagents of Plant Origin... 

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