Grignard

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123321

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Does grignard always add to the less substituted C, when there's a situation in which there is more than 1 C to choose from?

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On DAT, usually you only have one carbon to attack, especially when carbonyl molecules are involved.
When dealing with epoxides, it is depends on whether the condition is acidic or basic. The nuc attacks more substituted carbon under acidic condition and the oxygen gets protonated in the process. In basic conditions, the less substituted carbon is preferred.
 
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