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Chapter 18: 18-17P (page 677)
Label each compound as more or less reactive than benzene in electrophilic aromatic substitution.
a. More reactive
b. More reactive
c. Less reactive
d. Less reactive
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Benzyl bromide\({\bf{(}}{{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{Br)}}\) reacts rapidly with \({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{OH}}\)to afford benzyl methyl ether\({\bf{(}}{{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{OC}}{{\bf{H}}_{\bf{3}}}{\bf{)}}\). Draw a stepwise mechanism for the reaction, and explain why this 1掳 alkyl halide reacts rapidly with a weak nucleophile under conditions that favor an\({{\bf{S}}_{\bf{N}}}{\bf{1}}\) mechanism. Would you expect the para-substituted benzylic halides \({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{O}}{{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{4}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{Br}}\) and \({{\bf{O}}_{\bf{2}}}{\bf{N}}{{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{4}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{Br}}\) to each be more or less reactive than benzyl bromide in this reaction?Explain your reasoning.
Question: Synthesize each compound from toluene and any other organic or inorganic reagents.
Which halides are unreactive in a Friedel鈥揅rafts alkylation reaction?
Question: Draw a stepwise mechanism for the following reaction, which results in the synthesis of bisphenol F (R = H), an additive used in a variety of packaging materials. Bisphenol F is related to BPA (bisphenol A, R = ), a reagent used to harden some plastics, now removed from certain baby products because of its estrogen-like activity that can disrupt endocrine pathways.
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