Wed July 27, 2011 By: Abhiraj Darshankar
what will neopentyl chloride + alcoholic KOH give....?
What mechanism will it follow (e1/e2) as it doesnt have beta hydrogen? could you give a step by step description?

neopentyl chloride + alcoholic Koh..??

Expert Reply
Wed July 27, 2011
CH3-CH2-C(CH3)2Cl  +   OH-? CH3-CH2-C(CH3)2OH   +  Cl-
mecanism :  CH3-CH2-C(CH3)2Cl CH3-CH2-(CH3)2-C+   +     Cl-      slow
                              CH3-CH2-(CH3)2-C+     +    OH-   ?  CH3-CH2-C(CH3)2OH     fast step
the reaction occurs by SN1 mecanism .It occurs in two steps as shown above .In step one C-halogen bond undergoes slow cleavage.It is a reversible step
The carbocation formed in first step is very reactive  it readily reacts with a nucleophile , OH-  
obtained from alcoholic KOH and hence forms the alcohol.
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