Alcohol with Dichlorocarbene
Chemistry
Level
2
Which of the following would be the most probable product when three degree alcohol reacts with chloroform(CHCl3) and KOH
Alkyl chloride
Aldehyde
Ketone
Ether
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1 solution
CHCl3 + KOH is Dichlorocarbene(CCl2) which has a vacant orbital and oxygen of ROH can provide lone pair to it and form RO(+)H-C(-)Cl2. Now HCl will be removed from it and it will form ROCCl here, carbon again has a vacant orbital so oxygen will again give lone pair to carbon which will form positive on oxygen. Now since R is 3 degree therefore R+ will be formed and Cl- will be removed results in the formation of CO(carbon monoxide) and R+ and Cl- so it will form R-Cl