Cl -OCH₂CO₂H Show how 2,4-Dichlorohenoxyacetic acid or 2, 4-D can be 2,4-dichlorophenoxyacetic acid (2,4-D) prepared by a reaction that is similar to the reaction mechanism on the following figure that shows how to synthesize phenoxyacetic acid.

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C1-
Cl
-OCH₂CO₂H
Show how 2,4-Dichlorohenoxyacetic acid or 2, 4-D
can be
2,4-dichlorophenoxyacetic acid
(2, 4-D)
prepared by a reaction that is similar to the reaction mechanism on the following figure that
shows how to synthesize phenoxyacetic acid.
Transcribed Image Text:C1- Cl -OCH₂CO₂H Show how 2,4-Dichlorohenoxyacetic acid or 2, 4-D can be 2,4-dichlorophenoxyacetic acid (2, 4-D) prepared by a reaction that is similar to the reaction mechanism on the following figure that shows how to synthesize phenoxyacetic acid.
SYNTHESIS OF PHENOXYACETIC ACID
1) Phenol is treated with NaOH to form sodium phenoxide
+
OH + NaOH
-O¯Na + H₂O
Phenol
Sodium phenoxide
2) Chloroacetic acid is added to the basic solution of sodium phenoxide and immediately neutralized by excess NaOH.
+
CICH₂CO₂H + NaOH
CICH₂CO₂ Na + H₂O
3) Nucleophilic substitution through SN2 mechanism.
e
+
+
o Na CI-CH₂CH₂CO₂ Na
OCH₂CO₂ Na+ NaCl
H
H
-8---C---ci
CO₂Na
4) Neutralization of sodium salt of phenoxyacetic acid with HCl (6 N) yields free phenoxyacetic acid.
+
0
OCH₂CO₂ Na + HCl
o
+
OCH₂CO₂H + NaClH
phenoxyacetic acid
SN2 transition
state
Transcribed Image Text:SYNTHESIS OF PHENOXYACETIC ACID 1) Phenol is treated with NaOH to form sodium phenoxide + OH + NaOH -O¯Na + H₂O Phenol Sodium phenoxide 2) Chloroacetic acid is added to the basic solution of sodium phenoxide and immediately neutralized by excess NaOH. + CICH₂CO₂H + NaOH CICH₂CO₂ Na + H₂O 3) Nucleophilic substitution through SN2 mechanism. e + + o Na CI-CH₂CH₂CO₂ Na OCH₂CO₂ Na+ NaCl H H -8---C---ci CO₂Na 4) Neutralization of sodium salt of phenoxyacetic acid with HCl (6 N) yields free phenoxyacetic acid. + 0 OCH₂CO₂ Na + HCl o + OCH₂CO₂H + NaClH phenoxyacetic acid SN2 transition state
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