Chapter 16: Q 73 E (page 524)
Question: Use your knowledge of directing effects, along with the following data, to deduce the directions of the dipole moments in aniline and bromobenzene.

Short Answer
Directions of the dipole moment as:

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Chapter 16: Q 73 E (page 524)
Question: Use your knowledge of directing effects, along with the following data, to deduce the directions of the dipole moments in aniline and bromobenzene.

Directions of the dipole moment as:

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Electrophilic substitution on 3-phenylpropanenitrile occurs at theortho and para positions, but reaction with 3-phenylpropenenitrileoccurs at the meta position. Explain, using resonance structures of theintermediates.

An electrostatic potential map of (trifluoromethyl)benzene, , is shown. Would you expect (trifluoromethyl)benzene to be more reactive orless reactive than toluene toward electrophilic substitution? Explain.

Monobromination of toluene gives a mixture of three bromotoluene products. Draw and name them.
At what position would you expect electrophilic substitution to occur in each of the following substances?
a.

b.

c.

Question: Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring has a large effect. The of unsubstituted phenol, for example, is 9.89, while that of p-nitrophenol is 7.15. Draw resonance structures of the corresponding phenoxide anions and explain the data.
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