Fundamentals of Organic ChemistryChemistryHydrocarbons
Identify the major product [ X ] in the following reaction: CH ₃- C CH HOBr [ X ]
Correct answer
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Step-by-step solution
The reaction involves the electrophilic addition of hypobromous acid ( HOBr ) to an alkyne. In HOBr , the electrophile is Br ^+ and the nucleophile is OH ^- . The electrophile Br ^+ attacks the alkyne following Markovnikov's rule. It adds to the terminal carbon to form the more stable secondary carbocation: CH ₃- C CH + Br ^+ CH ₃- C ^+= CHBr The nucleophile OH ^- attacks the carbocation to form an enol intermediate: CH ₃- C ^+= CHBr + OH ^- CH ₃- C ( OH )= CHBr Enols are highly reactive towards electrophilic addit