(i) Identify the alpha protons in ethyl acetoacetate (shown below) and draw the structures of the two different enolates which would form under basic conditions. Explain why one enolate is more stable than the other. OEt Ethyl acetoacetate

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 56AP
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(i)
(ii)
Identify the alpha protons in ethyl acetoacetate (shown below) and draw the structures of the
two different enolates which would form under basic conditions. Explain why one enolate is
more stable than the other.
L
ملو
Ethyl acetoacetate
Draw the structure of the product N formed in the crossed aldol reaction between ketone L and
aldehyde M (no mechanism required).
H
OEt
M
NO₂
NaOH
H₂O/EtOH
N
C15H14NO4
Transcribed Image Text:(i) (ii) Identify the alpha protons in ethyl acetoacetate (shown below) and draw the structures of the two different enolates which would form under basic conditions. Explain why one enolate is more stable than the other. L ملو Ethyl acetoacetate Draw the structure of the product N formed in the crossed aldol reaction between ketone L and aldehyde M (no mechanism required). H OEt M NO₂ NaOH H₂O/EtOH N C15H14NO4
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