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Chapter 18: Q 65. (page 725)

Question: Devise a synthesis of each compound from phenol and any other organic or inorganic reagents.

Short Answer

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Answer

Step by step solution

01

Organic synthesis

The preparation of organic compounds using easily available starting materials and reagents is referred to as organic synthesis.

Most of the complex organic compounds are prepared by treating simple compounds with a series of reagents.

02

Synthesis of a

Compound a can be synthesized as shown below.

Synthesis of a

03

Synthesis of b

Compound b can be synthesized as shown below

Synthesis of b

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Most popular questions from this chapter


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

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: Explain the following observation. Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5=CHCO2CH2CH3) reacts with electrophiles to afford meta-disubstituted arenes.

Question: Rank the aryl halides in each group in order of increasing reactivity in nucleophilic aromatic substitution by an addition–elimination mechanism.

  1. chlorobenzene, p-fluoronitrobenzene, m-fluoronitrobenzene
  2. 1-fluoro-2,4-dinitrobenzene, 1-fluoro-3,5-dinitrobenzene, 1-fluoro-3,4-dinitrobenzene
  3. 1-fluoro-2,4-dinitrobenzene, 4-chloro-3-nitrotoluene, 4-fluoro-3-nitrotoluene

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.
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