Dichloromethane (CH,Cl,) can be treated with butyllithium, CH3CH,CH,CH,-Li (Bu-Li), to make a carbene in situ, analogous to the way a carbene is generated from trichloromethane (CHCI3) using HO¯. (a) Show the mechanism for the generation of a carbene from CH2CI2. (b) Why is butyllithium used instead of HO-? (c) The reaction shown here leads to a mixture of four products. Draw all four products. CH,Cl, ? Bu-Li Draw the mechanism for this reaction
Dichloromethane (CH,Cl,) can be treated with butyllithium, CH3CH,CH,CH,-Li (Bu-Li), to make a carbene in situ, analogous to the way a carbene is generated from trichloromethane (CHCI3) using HO¯. (a) Show the mechanism for the generation of a carbene from CH2CI2. (b) Why is butyllithium used instead of HO-? (c) The reaction shown here leads to a mixture of four products. Draw all four products. CH,Cl, ? Bu-Li Draw the mechanism for this reaction
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 33MP
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