Chapter 17: Q44P (page 896)
Predict the site(s) of electrophilic attack on these compounds.
(a)

(b)

Short Answer
(a)

(b)

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Chapter 17: Q44P (page 896)
Predict the site(s) of electrophilic attack on these compounds.
(a)

(b)

(a)

(b)

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Propose mechanisms for the Birch reductions of benzoic acid and anisole just shown. Show why the observed orientation of reduction is favored in each case.
What products would you expect from the following reactions?

The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.

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
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