mechanism of the reaction with DIBAL-H to prepare aldehyde?
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Answer: It's a reduction. The lone pair of the electrons of C=O:: (or one from Cl or N) attacks the DIBAL's electrophilic site on Al. Then there is an electrophylic site on the carbonyl adduct so a free -H from DIBAL attacks to the carbonyl group. Then the aryl/alcohol part of the molecule becomes the most powerful nucleophile of the bunch and attacks again at the electrophilic site of DIBAL at the Al and the whole aryl group adducts to the DIBAL part and the carbonyl group is released away. And that is the end of the reaction.
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