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Adrian Hum

Priority order of attack of grignard reagents on functional groups

Brandon Ross  Follow

For the compound given in the question, the priority order of Grignard reagent attack follows,

$\ce{R-OH > R-CO-R' > R-COOR'}$

Reason:

  • Acid-base neutralisation are very fast.

  • Carbonyl carbon is more nucleophilic than carboxylic carbon, as the latter one is stabilized by resonance.


Therefore, first alcohol is attacked and hence P is (a), then the carbonyl part is attacked and hence Q is (b).

Finally, one more mole of RMgX gets used up on the carboxyl part, hence R is not (d).

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