An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.
An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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Transcribed Image Text:An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted
derivative:
Base
CH;CH2O
OCH,CH3
CH;CH,0
OCH2CH3
H2
Diethyl malonate
Base
CH;CH,0
°C
`OCH,CH3
CH;CH,O
OCH,CH3
R
Alkyl substituted diethyl malonate
NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted
derivative. Explain why.
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