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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Addition of HBr to 1-phenylpropene yields only (1-bromopropyl) benzene. Propose a mechanism for the reaction, and explain why none of the other regioisomer is produced.

The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy conformation of the molecule. Why are the two benzene rings tilted at a 63° angle to each other rather than being in the same plane so that their p orbitals overlap? Why doesn’t complete rotation around the single bond joining the two rings occur?

Starting with benzene as your only source of aromatic compounds,
how would you synthesize the following substances? Assume that you
can separate ortho and para isomers if necessary.
(a)p-Chloroacetophenone (b)m-Bromonitrobenzene
(c)o-Bromobenzenesulfonic acid (d)m-Chlorobenzenesulfonic acid
Propose a mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone. Use curved arrows to show the electron flow in each step.

How would you synthesize the following compound starting from benzene? More than one step is needed.

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