Chapter 17: Q49P (page 899)
Starting from toluene, propose a synthesis of this trisubstituted benzene
Chapter 17: Q49P (page 899)
Starting from toluene, propose a synthesis of this trisubstituted benzene
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Get started for freeWhat products would you expect from the following Suzuki coupling reactions?
Phenol reacts with three equivalents of bromine in CCl4(in the dark) to give a product of formula C6H3OBr3. When this product is added to bromine water, a yellow solid of molecular formula C6H2OBr4 precipitates out of the solution. The IR spectrum of the yellow precipitate shows a strong absorption (much like that of a quinone) around 1680cm-1 . Propose structures for the two products.
In Chapter 14, 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 a reaction with sodium chloroacetate, ClCH2CO2Na.
(a) Draw the structures of these compounds, and write equations for these reactions.
(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.
(c) Show how the TCDD contamination might be eliminated, both after the first step and on completion of the synthesis
1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with
(a) buta-1,3-diene
(b) cyclopenta-1,3-diene
Predict the major products when the following compounds are irradiated by light and treated with (1) 1 equivalent of Br2 and (2) excess Br2.
(a) isopropylbenzene
(b) tetralin
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