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When CH3MgBr interacts with a molecule that has a C=N bond, what is the resulting mechanism and product?
- CH3MgBr reacts to yield CH3C=N.
- CH3MgBr reacts to yield CH3C=NH.
- CH3MgBr reacts to form CH3C=N.
- CH3MgBr reacts to form CH3C=NH.
Correct answer: CH3MgBr reacts to yield CH3C=NH.
Solution
CH3MgBr (Grignard reagent) reacts with a compound containing a C=N bond (imine) to form an intermediate, which upon hydrolysis gives a secondary amine. The correct mechanism involves nucleophilic addition of CH3MgBr to the C=N bond, followed by hydrolysis.
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