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Chapter 18: 18-32P (page 677)

Synthesize each compound from benzene.

Short Answer

Expert verified

Retrosynthesis is a process that involves the breakdown or formation of bonds of an available starting molecule to reach the required compound.

Step by step solution

01

Retrosynthesis

Retrosynthesis is a process that involves the breakdown or formation of bonds of an available starting molecule to reach the required compound.

02

Steps in the synthesis  

  1. Retrosynthesis for forming benzoic acid from benzene
  • Oxidation of ethylbenzene gives benzoic acid.
  • Ethyl benzene can be formed by the Friedel-Craft alkylation of benzene.

  1. Retrosynthesis for forming aniline from benzene
  • \({\rm{N}}{{\rm{H}}_{\rm{2}}}\)group cannot be directly substituted to benzene; it can be formed by the reduction of the nitro group.
  • Nitro group can be introduced by nitration using a strong acid.

  1. Retrosynthesis for forming 2-bromo benzoic acid from benzene
  • Oxidation of ethylbenzene gives an acid group.
  • Bromine is an ortho, para-directing group. It can be introduced by the bromination of toluene.
  • Acylation of benzene gives toluene.

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Most popular questions from this chapter

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° 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: Draw a stepwise, detailed mechanism for the following intramolecular reaction.

Explain why \({{\rm{C}}_{\rm{6}}}{{\rm{H}}_{\rm{5}}}{\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{Br}}\)is not formed during the radical bromination of \({{\rm{C}}_{\rm{6}}}{{\rm{H}}_{\rm{5}}}{\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{C}}{{\rm{H}}_{\rm{3}}}\).

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.

The 1 H NMR spectrum of phenol (\({C_6}{H_5}OH\)) shows three absorptions in the aromatic region: 6.70 (2 ortho H’s), 7.14 (2 meta H’s), and 6.80 (1 para H) ppm. Explain why the ortho and para absorptions occur at lower chemical shift than the meta absorption.
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