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Chapter 18: Q 64. (page 725)

Question: Synthesize each compound from toluene and any other organic or inorganic reagents.

Short Answer

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Answer

Step by step solution

01

Organic synthesis

Different organic compounds can be synthesized by treating simple organic compounds with varying reagents in a sequential manner.

02

Synthesis of compound a

Synthesis of compound a

Toluene, on reaction with bromine molecule in the presence of ferric bromide, yields p-bromotoluene.

The treatment of p-bromotoluene with butyryl chloride in the presence of substitutes the butyryl group on the meta position of p-bromotoluene (Friedel-Crafts acylation).

The methyl group can be converted into the alcohol functional group by transforming it into alkyl bromide and then treating it by a base.

03

Synthesis of compound b

Synthesis of compound b

Synthesis of compound b involves the following steps:

  • Friedel-Crafts acylation on toluene (using butyryl chloride and )
  • Nitration of p-butyryl toluene
  • Reduction of carbonyl group using (Wolff-Kishner reduction)
  • Reduction of to by hydrogenation
04

Synthesis of compound c

Synthesis of compound c

Synthesis of compound c involves the following steps:

  • Friedel-Crafts acylation on toluene (using butyryl chloride and )
  • Chlorination of p-butyryl toluene
  • Conversion of methyl group to methyl bromide
  • Conversion of alkyl bromide to alcohol
  • Oxidation of alcohol to aldehyde

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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: What is the major product of electrophilic addition of HBr to the following alkene? Explain your choice.

Which halides are unreactive in a Friedel–Crafts alkylation reaction?

a. Draw resonance structures for the carbocation formed after loss of a leaving group from phytyl diphosphate.

b. Draw the two-step mechanism for Friedel–Crafts alkylation of 1,2-dihydroxynaphthoic acid with this carbocation to form X.

For each of the following substituted benzenes: (1) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{Br}}\); (2) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{CN}}\) ; (3) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{OCOC}}{{\bf{H}}_{\bf{3}}}\):

  1. Does the substituent donate or withdraw electron density by an inductive effect?
  2. Does the substituent donate or withdraw electron density by a resonance effect?
  3. On balance, does the substituent make a benzene ring more or less electron-rich than benzene itself?
  4. Does the substituent activate or deactivate the benzene ring in electrophilic aromatic substitution?
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