668 CHAPTER 16 Reactions of Substituted Benzenes
- How could you distinguish among the following compounds, using
a. their infrared spectra?
b. their NMR spectra?- The following tertiary alkyl bromides undergo an reaction in aqueous acetone to form the corresponding tertiary alcohols. List
the alkyl bromides in order of decreasing reactivity.
64.p-Fluoronitrobenzene is more reactive than p-chloronitrobenzene toward hydroxide ion. What does this tell you about the rate-
determining step for nucleophilic aromatic substitution?
- a. Explain why the following reaction leads to the products shown:
b. What product would be obtained from the following reaction?- Describe how mescaline could be synthesized from benzene. The structure of mescaline is given on p. 622.
- Propose a mechanism for the following reaction that explains why the configuration of the asymmetric carbon in the reactant is
retained in the product: - Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole, but has no effect on the reaction of
piperidine with 1-chloro-2,4-dinitrobenzene.
N
H
piperidineO
O
O
HH
NH 2
COO−COO−C NaNO 2
−OCCH 2 CH 2 HClCCH 3NaNO 2
HClOHCNH 2CH 3CH 3 CH 3NaNO 2CH 3 CHCH 2 NH (^2) HCl CH 3 CCH 3 + CH 3 CCH 2
CH 3 CH 3
OH
CH 3
ABCDE
CH 3 CCH 3
Br
CH 3 CCH 3
Br
CH 3 CCH 3
Br
CH 3 CCH 3
CH 2 CH 2 CH 3 OCH 2 CH 3 SO 3 H OCCH 3
O
CH 3 CCH 3
Br
ClCHCH 3
Br
SN 1
CCH 3
O
COCH 3
O
CH
O
COH
O
CH 2 OH CH 2 OH CH 2 OCH 3
ABC DEFG
(^1) H