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Chapter 18: 18 P (page 697)

Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

Short Answer

Expert verified

The aromatic rings are rich in electrons because of their delocalization in the ring. Therefore, they are more reactive toward electrophilic aromatic substitution reactions.

Step by step solution

01

Electrophilic aromatic substitution reaction

The aromatic rings are rich in electrons because of their delocalization in the ring. Therefore, they are more reactive toward electrophilic aromatic substitution reactions.

02

Reactivity towards electrophilic aromatic substitution reaction

The electron density on the aromatic ring is decreased by the electron-withdrawing group whereas the electron-donating group increases the electron density.

03

Explanation

The increasing order of reactivity for the electrophilic aromatic substitution reaction is shown below.

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Most popular questions from this chapter

Question: Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed

Question: Use the reactions in this chapter along with those learned in Chapters 11 and 12 to synthesize each compound. You may use benzene, acetylene, two-carbon alcohols, ethylene oxide and any organic reagents.

d.

Draw the products of each reaction.

Draw a detailed mechanism for the chlorination of benzene using Cl2andFeCl3 .

Write out the two-step sequence that converts benzene to each compound.
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