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CH3 -- CH==CH--CH==O ------RLi--, Hydrolysis --------> CH3--CH==CH--CH(R)(OH) + CH3--CH(R)--CH2--CHO
Minor(KCP) Major(TCP)
CH3 -- CH==CH--CH==O ----RMgX, Hydrolysis----------->CH3--CH==CH--CH(R)(OH) + CH3--CH(R)--CH2--CHO
MAJOR( KCP) MINOR(TCP)
WHY IS THERE A DIFF IN THE ABOVE REACTIONS??
Comments (3)
RLi is being talked about, not LiAlH4 ...........
RMgX BEING A HARD(STRONG) Nucleophile WILL ATTACK ONLY HARD ELECTROPHILE C=O......NOT C=C.......
BUT AS RLi IS A SOFT NUCLEOPHILE.....SO IT ATTACKS THE SOFT ELECTROPHILE - DOUBLE BOND ADJACENT TO WITHDRAWING C=O .......i.e. IN RLi RXN,
1ST - DOUBLE BOND SHIFTS TO FORM
CH3-CH(R)-CH=CH-O- WHICH AFTER HYDROLYSIS, GIVES......CH3-CH(R)-CH2-CHO
WHILE RMgX SIMPY ATTACKS THE ALDEHYDE GROUP
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