Chapter 16: Q16-1P (page 482)
Monobromination of toluene gives a mixture of three bromotoluene products. Draw and name them.
Short Answer

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Chapter 16: Q16-1P (page 482)
Monobromination of toluene gives a mixture of three bromotoluene products. Draw and name them.

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Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of . Propose a mechanism for the reaction.

Rank the compounds in each of the following groups in order of their reactivity
to electrophilic substitution:
(a) Nitrobenzene, phenol, toluene, benzene
(b) Phenol, benzene, chlorobenzene, benzoic acid
(c) Benzene, bromobenzene, benzaldehyde, aniline
Use Figure 16-11 to explain why Friedel–Crafts alkylations often give polysubstitution but Friedel–Crafts acylations do not.

Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.

Starting with either benzene or toluene, how would you synthesize the
following substances? Assume that ortho and para isomers can be
separated.
(a) 2-Bromo-4-nitrotoluene (b) 1,3,5-Trinitrobenzene
(c)2,4,6-Tribromoaniline (d)m-Fluorobenzoic acid
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