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Chapter 18: 15 P (page 694)

Classify each substituent as electron donating or electron withdrawing.

Short Answer

Expert verified

a. Electron donating substituents.

b. Electron withdrawing substituents.

c. Electron donating substituents.

Step by step solution

01

Substituents

The substituents (placed on the ring) can have an electron attracting tendency or electron-donating tendency. The nature of the substituents depends upon the atoms present in the substituents.

02

Electron donating and electron-withdrawing groups

  • The electron-withdrawing substituents have an electronegative atom that attracts electrons towards themselves. Therefore, the positive charge delocalizes on the ring.
  • The electron-donating substituents have an electropositive atom which gives electrons to the ring. Therefore, the negative charge delocalizes on the ring.
03

Explanation

a. The CH3O group is an electron-withdrawing substituent but the oxygen has lone pair of electrons which is donated to the ring. Therefore, here CH3Ogroup is an electron-donating substituent.

b. The iodine group is an electron-withdrawing substituent because iodine is an electronegative atom.

c. The CH33C-group is an electron-donating substituent because carbon is an electropositive atom.

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Most popular questions from this chapter

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.

Question: Using resonance structures, explain why a nitroso group (-NO) is an ortho, para director that deactivates a benzene ring toward electrophilic attack.

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

Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?

Draw the products of each reaction.
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