The acid 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) is a herbicide that is part of the "orange agent" which by heating a tetrachlorinated benzene with methanolic NaOH, followed by treatment with was used as a defoliante in the Vietnam War. The 2,4,5-T is synthesized CI-CH2COO Na and acidification. El Write the equations for these reactions. A byproduct of this synthesis is 2,3,7,8-tetrachloro-dibenzodioxin (2,3,7,8-TCDD or dioxin) which is highly toxic and not easily biodegradable. Suggest a mechanism for the formation of 2,3,7,8-TCDD. CI HO, CI 2,4,5-T 2,3,7,8-TCDD

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
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Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...
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7. The acid 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) is a herbicide that is part of the "orange
agent" which
by heating a tetrachlorinated benzene with methanolic NaOH, followed by treatment with
was used as a defoliante
in the Vietnam War. The 2,4,5-T is synthesized
CI-CH2COO Na* and acidification. El Write the equations for these reactions.
A byproduct of this synthesis is 2,3,7,8-tetrachloro-dibenzodioxin (2,3,7,8-TCDD or dioxin)
which is highly toxic and not easily
of 2,3,7,8-TCDD.
biodegradable. Suggest a mechanism for the formation
CI
20000
HO,
2,4,5-T
2,3,7,8-TCDD
Transcribed Image Text:7. The acid 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) is a herbicide that is part of the "orange agent" which by heating a tetrachlorinated benzene with methanolic NaOH, followed by treatment with was used as a defoliante in the Vietnam War. The 2,4,5-T is synthesized CI-CH2COO Na* and acidification. El Write the equations for these reactions. A byproduct of this synthesis is 2,3,7,8-tetrachloro-dibenzodioxin (2,3,7,8-TCDD or dioxin) which is highly toxic and not easily of 2,3,7,8-TCDD. biodegradable. Suggest a mechanism for the formation CI 20000 HO, 2,4,5-T 2,3,7,8-TCDD
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