Q29E
Question
Propose a pericyclic mechanism to account for the following transformation.
Step-by-Step Solution
Verified Answer
The pericyclic mechanism for the following transformation can be proposed.
1Step 1: Sigma tropic rearrangement
The reaction is [3,3] sigma tropic rearrangement. There is an involvement of 3 electron pairs in the reaction. Thus, it is under thermal conditions through the suprafacial pathway to produce an enol. The enol was then tautomerized to produce ketone.
2Step 2: Cyclic mechanism for the transformation
The cyclic mechanism can be drawn as,
Other exercises in this chapter
Q27E
Two sequential pericyclic reactions are involved in the following furan synthesis. Identify them, and propose a mechanism for the transformation.
View solution Q28E
Predict the product of the following pericyclic reaction. Is this [5,5] shift a suprafacial or an antarafacial process?
View solution Q30E
Vinyl-substituted cyclopropanes undergo thermal rearrangement to yield cyclopentenes. Propose a mechanism for the reaction, and identify the pericyclic process
View solution Q.30-12
The 13C NMR spectrum of homotropilidene taken at room temperature shows only three peaks. Explain.
View solution