Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major end products A , B , and C for the following reactions: CH ₃ CH = CH ₂ [ (ii) H ₂ O ] (i) D ^ A CH ₃ CH = CH ₂ [ (ii) D ₂ O ] (i) H ^ B CH ₃ CH = CH ₂ [ (ii) D ₂ O ] (i) D ^ C
Options
- AA = CH ₃ CH ( OH ) CH ₂ D , B = CH ₃ CH ( OD ) CH ₃ , C = CH ₃ CH ( OD ) CH ₂ D
- Bin all cases
- Cin all cases
- Din all cases
Correct answer
A. A = CH ₃ CH ( OH ) CH ₂ D , B = CH ₃ CH ( OD ) CH ₃ , C = CH ₃ CH ( OD ) CH ₂ D
Step-by-step solution
The acid-catalyzed hydration of an alkene proceeds via an electrophilic addition mechanism following Markovnikov's rule. The electrophile ( H ^ or D ^ ) attacks the double bond to form the more stable secondary carbocation. The nucleophile ( H ₂ O or D ₂ O ) attacks the carbocation, followed by deprotonation or dedeuteration to give the final alcohol. For reaction 1: CH ₃ CH = CH ₂ + D ^ CH ₃ CH ^ CH ₂ D CH ₃ CH ^ CH ₂ D + H ₂ O CH ₃ CH ( OH ) CH ₂ D (Product A) For reaction 2: CH ₃ CH = CH ₂ + H ^ CH ₃ CH ^ CH ₃ C