Which one of the following compounds will be most readily dehydrated?
Option 1
Option 2
4
Option 4
Acidic dehydration of alcohols involves the protonation of the alcohol followed by the loss of a water molecule to form a carbocation intermediate. This is the rate-determining step. The ease of dehydration is directly related to the stability of the carbocation formed. The order of stability of carbocations is Tertiary () > Secondary () > Primary () due to inductive and hyperconjugation effects. Consequently, the order of reactivity of alcohols towards dehydration is Tertiary > Secondary > Primary. Therefore, the compound that is a tertiary alcohol (or forms the most stable carbocation, such as allylic or benzylic) will be most readily dehydrated. (See NCERT Class 12, Unit 11, Section on Chemical Reactions of Alcohols; NCERT Class 11, Unit 12, Section 12.7.5 on Carbocation Stability).
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