Question
Download Solution PDFThe correct sequence of mechanistic steps involved in the formation of product in the following reaction is
Answer (Detailed Solution Below)
Detailed Solution
Download Solution PDFConcept:
- Prins reaction is nucleophillic addition of alkene to aldehyde or ketone assisted by an acid
- intramolecular Prins reaction leads to cyclization and thus called Prins cyclization.
- Pinacole arrangement involves conversion of 1,2 diol system to carbonyl system in the presence of an acid (lewis acid or proton ).
Explanation:
- Firstly, SnCl4 (lewis acid) coordinates with oxygen whose lone pairs are most available for donation.
- The positive charge on O coordinated to lewis acid will undergo neutralization by bond breaking and oxonium ion forms.
- In the next step, alkene adds to carbonyl carbon to form a 6-membered ring with a tertiary carbocation. This is called prins cyclization.
- Further, the formed carbocation undergoes pincaole rearrangement to give 5-membered ring
Conclusion:
The sequence of steps involved in the given chemical reaction are:
(1) formation of oxonium ion, (2) Prins cyclization and finally (3) Pinacole rearrangement.
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