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Chapter 18: Q 89 P (page 920)

Question: p-fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step fornucleophilic aromatic substitution?

Short Answer

Expert verified

The rate-determining step in a nucleophilic aromatic substitution reaction is the slow step addition of hydroxide ion. The electronegativity difference between chlorine and fluorine is the reason behind the addition of hydroxide ion to p-Fluoronitrobenzene.

Step by step solution

01

Difference in electronegativity

Among halogen group fluorine is the most electronegative element while compared to chlorine.

02

Why p-Fluoronitrobenzene is more reactive toward hydroxide ion

Presence of fluorine in p-Fluoronitrobenzene makes it more electronegative substituent than p-chloronitrobenzene. So, three will be a more chance for nucleophilic attack on the fluorine substituted benzene than chlorine substituted benzene.

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Most popular questions from this chapter

Draw the product(s) of each of the following reactions:

  1. benzoic acid + HNO3/H2SO4
  2. isopropylbenzene + Cl2 + FeCl3
  3. p-xylene + acetyl chloride + AlCl3 followed by H2O
  4. o-methylaniline + benzenediazonium chloride
  5. cyclohexyl phenyl ether + Br2
  6. phenol + H2SO4 + 螖
  7. ethylbenzene + Br2/FeBr3
  8. m-xylene + Na2Cr2O7 + HCl + 螖

What products are obtained from the reaction of the following compounds with one equivalent of Br2, usingFeBr3as a catalyst?

a.

b.

c.

d.

Show how lidocain, one of the most widely used injectable anaesthetics, can be prepared from benzene and compounds containing no more than four carbons.

Iidocain

Question: Describe how naphthalene can be prepared from the given starting material.

Show how the following compounds can be synthesized from benzene:

a. p-nitrobenzoic acid

b. m-bromophenol

c. o-chlorophenol

d. m-methylnitrobenzene

e. p-methylbenzonitrile

f. m-chlorobenzaldehyde
See all solutions

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