Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product of the following reaction:
Correct answer
3
Step-by-step solution
The given substrate is an allylic ether with a bulky isopropyl group at the C4 position (wedged) and an -OR leaving group at the C3 position (dashed). The double bond is located between C1 and C2. When this compound reacts with a secondary amine ( N R₂ ), it undergoes nucleophilic substitution. Because it is an allylic system, the reaction can proceed via direct substitution ( S_N2 ) at C3 or allylic rearrangement ( S_N2' ) at C1. 1. Regioselectivity: The C3 position is highly sterically hindered due to the adjacen