Chapter 17: Q39P (page 892)
Show how you would synthesize the following compounds, using the indicated starting materials.
(a) 3-phenylbutan-1-ol from styrene

Short Answer


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Chapter 17: Q39P (page 892)
Show how you would synthesize the following compounds, using the indicated starting materials.
(a) 3-phenylbutan-1-ol from styrene



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What substituted alkene would you use in the Heck reaction to make the following products?

Predict the products formed when m-cresol (m-methylphenol) reacts with
(a) NaOH and then ethyl bromide
(b) CH3 acetyl chloride, CH3COCI
(c) bromine in CCI4 in the dark
(d) excess bromine in CCI4 in the light
(e) sodium dichromate in H2SO4
(f) two equivalents of tert-butyl chloride and AICI3
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 鈥渄ioxin.鈥 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

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

Propose products (if any) and mechanisms for the following AICI3-catalyzed reactions:
猞 chlorocyclohexane with benzene
猞 methyl chloride with anisole
猞 3-chloro-2,2-dimethylbutane with isopropylbenzene
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