Chapter 17, Problem 17.70SP

In Chapter14, we saw that Agent Orange contains (2.4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by reaction with sodium chloroacetate, ClCH₂CO₂Na.

1. a. Draw the structures of these compounds, and write equations for these reactions
2. b. One of the impurities in the Agent Orange used in Vietnam was 2,3,7,8-tetrachlorodibenzodioxin (2,3,7,8-TCDD), often incorrectly called “dioxin.” Propose a mechanism to show how 2,3,7,8-TCDD is formed in the synthesis of 2,4,5-T.
3. c. Show how the TCDD contamination might be eliminated, both after the first step and on completion of the synthesis.