Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product formed in the following reaction.
Correct answer
3
Step-by-step solution
The given reactant is 3-methylbut-2-en-1-ol, which is an allylic alcohol. When treated with HCl, the hydroxyl group is first protonated to form a good leaving group ( -OH₂^+ ). (CH₃)₂C=CH-CH₂OH + H^+ (CH₃)₂C=CH-CH₂OH₂^+ Loss of a water molecule generates an allylic carbocation, which is stabilized by resonance: (CH₃)₂C=CH-CH₂^+ (CH₃)₂C^+-CH=CH₂ The chloride ion ( Cl^- ) can attack either of the electrophilic carbon atoms, leading to two possible products: 1. Attack at the primary carbon yields 1-chloro-3-methylbut-