How does washing with 10% sodium bicarbonate help to isolate ethyl cinnamate in each synthesis reaction? As part of your answer show the reaction of aqueous sodium bicarbonate with cinnamic acid and with cinnamoyl chloride (remembering that cinnamoyl chloride hydrolyzes to cinnamic acid in water). About the experiment:Ethyl cinnamate (a component of the essential oil of cinnamon) can be synthesized from a Fischeresterification, the reaction of an alcohol with a carboxylic acid.H++HO.ethanolethyl cinnamatecinnamic acidThe Fischer esterification requires a mineral acid catalyst (conc. H2SO4) to proceed at a reasonablerate. This reaction is an equilibrium; as such, an excess of one reactant is usually used to drive theequilibrium. Water is the byproduct of this reaction and in some cases removing water as it isformed is also used to drive the equilibrium. The reaction generally occurs under reflux for a fairlylong period of time.Esters may also be prepared from the reaction of an alkanoyl chloride with an alcohol - this reaction israpid and does not require a catalyst. The reaction is generally done at room temperature or gentlewarming.Cinnamoyl chloride will be the alkanoyl chloride necessary for this synthesis of ethylcinnamate.CI+.ethanolcinnamoyl chlorideethyl cinnamate

How does washing with 10% sodium bicarbonate help to isolate ethyl cinnamate in each synthesis reaction? As part of your answer show the reaction of aqueous sodium bicarbonate with cinnamic acid and with cinnamoyl chloride (remembering that cinnamoyl chloride hydrolyzes to cinnamic acid in water).

How does washing with 10% sodium bicarbonate help to isolate ethyl cinnamate in each synthesis reaction? As part of your answer show the reaction of aqueous sodium bicarbonate with cinnamic acid and with cinnamoyl chloride (remembering that cinnamoyl chloride hydrolyzes to cinnamic acid in water).

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section23.6: Reactions With Acids

Problem 23.9P

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Question

About the experiment:
Ethyl cinnamate (a component of the essential oil of cinnamon) can be synthesized from a Fischer
esterification, the reaction of an alcohol with a carboxylic acid.
H+
+
HO.
ethanol
ethyl cinnamate
cinnamic acid
The Fischer esterification requires a mineral acid catalyst (conc. H2SO4) to proceed at a reasonable
rate. This reaction is an equilibrium; as such, an excess of one reactant is usually used to drive the
equilibrium. Water is the byproduct of this reaction and in some cases removing water as it is
formed is also used to drive the equilibrium. The reaction generally occurs under reflux for a fairly
long period of time.
Esters may also be prepared from the reaction of an alkanoyl chloride with an alcohol - this reaction is
rapid and does not require a catalyst. The reaction is generally done at room temperature or gentle
warming.Cinnamoyl chloride will be the alkanoyl chloride necessary for this synthesis of ethyl
cinnamate.
CI
+.
ethanol
cinnamoyl chloride
ethyl cinnamate

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