Chapter 16
Problem
16-1
o-, m-, and p-Bromotoluene
Problem
16-3
o-xylene: 2; p-xylene: 1; m-xylene: 3
Problem
16-4
D+ does electrophilic substitutions on the ring.
Problem
16-5
No rearrangement: (a), (b), (e)
Problem
16-6
tert-Butylbenzene
Problem
16-10
Alkylbenzenes are more reactive than benzene itself, but acylbenzenes are less reactive.
Problem
16-11
Toluene is more reactive; the trifluoromethyl group is electron-withdrawing.
Problem
16-12
The nitrogen electrons are donated to the nearby carbonyl group by resonance and are less available to the ring.
Problem
16-13
The meta intermediate is most favored.
Problem
16-16
The phenol is deprotonated by KOH to give an anion that carries out a nucleophilic acyl substitution reaction on the fluoronitrobenzene.
Problem
16-17
Only one benzyne intermediate can form from p-bromotoluene; two different benzyne intermediates can form from m-bromotoluene.
Problem
16-19
A benzyl radical is more stable than a primary alkyl radical by 52 kJ/mol and is similar in stability to an allyl radical.
Problem
16-20
1. CH3CH2Cl, AlCl3; 2. NBS; 3. KOH, ethanol
Problem
16-21
1. PhCOCl, AlCl3; 2. H2/Pd