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What happens during dehydrohalogenation of gem dihalide containing one chlorine and one fluorine atom?
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What happens during dehydrohalogenation of gem dihalide containing one...
The dehydrohalogenation of an alkyl halide is a good laboratory method for the synthesis of alkenes because alkyl halides are readily available from reactions of several other starting materials. Considered by itself, this reaction has a very unfavorable equilibrium constant. However, if we use a strong base such as alkoxide anion to extract a proton on the carbon adjacent to the bromine, the reaction becomes highly favorable.




The dehydrohalogenation of alkyl halides is usually carried out with sodium methoxide in methanol, sodium ethoxide in ethanol, or potassium tert-butoxide in either tert-butyl alcohol or dimethyl sulfoxide, (CH3)2SO.



For these two reactions shown above, only a single alkene can result from the dehydrohalogenation of the alkyl halide. In alkyl halides having two or three adjacent carbon atoms with hydrogen atoms that could lead to different elimination products, a regioselectivity is observed. We will discuss this feature of dehydrohalogenation reactions
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What happens during dehydrohalogenation of gem dihalide containing one chlorine and one fluorine atom?
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