Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product of the following reaction:
Options
- ACH ₃ CHO
- BCH ₂= CH - CH ₂- CH ₂ CHO
- CCH ₂= CH - CH ₂ OH
- DCH ₃- CH = CH - CH ₂ CHO
Correct answer
B. CH ₂= CH - CH ₂- CH ₂ CHO
Step-by-step solution
The given reactant is allyl vinyl ether, CH₂=CH-O-CH₂-CH=CH₂ . When heated to around 200^ C , allyl vinyl ethers undergo a [3,3]-sigmatropic rearrangement known as the Claisen rearrangement. The reaction proceeds via a six-membered cyclic transition state. The steps involved are: 1. The C-O bond of the allyl group breaks. 2. A new C-C bond forms between the terminal carbon of the vinyl group and the terminal carbon of the allyl group. 3. The double bonds shift, resulting in the formation of a carbonyl group ( C=O )