Question

Propose a stepwise mechanism for the following reaction of a B-keto ester. Suggest a reason why this rearrangement reaction occurs. [1] NaOET EtOH [2] H2O* Step [1]: 00: OET OS OCH CH O OH OCHCH CO2CH.CH v DE :0: LOE :: CO.CHCH OCH CH HOCH.CH Step (2]: OE CO_CHCH SH OEt :O: OCH CH3 :: OE: 70: : Et CO2CH2CH3 OCH₂CH₂

Answer 1

Rearrangement occurs because:

Rearrangement genarates a highly resonanace-stabilised enolate between two carbonyl groups.

in oft Ort INDO EŁOW 1 1c0 mechanism EbEt din OEE ག04 }， མ ། ། ་ས་ཐད་ ལུགས་ H-9- 4, 12/ ༄༅oo-E+ （༢ : ༤ ༡ ©%E དང coE OEt 2. HAc0 Highly stabilised enolate in