b. the one that would be the least reactive in an electrophilic aromatic substitution reaction
c. the one that would yield the highest percentage of meta product
- Arrange the following groups of compounds in order of decreasing reactivity toward electrophilic aromatic substitution:
a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole
b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 2,4-dinitrotoluene
c. toluene,p-cresol, benzene,p-xylene
d. benzene, benzoic acid, phenol, propylbenzene
e. p-nitrotoluene, 2-chloro-4-nitrotoluene, 2,4-dinitrotoluene,p-chlorotoluene
f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene
- Give the products of the following reactions:
a. c. e.
b. d. f.
- For each of the statements in Column I, choose a substituent from Column II that fits the description for the compound at the right:
Column I Column II
a. Z donates electrons inductively, but does not donate OH
or withdraw electrons by resonance. Br
b. Z withdraws electrons inductively and withdraws
electrons by resonance.
c. Z deactivates the ring and directs ortho–para.
d. Z withdraws electrons inductively, donates electrons
by resonance, and activates the ring.
e. Z withdraws electrons inductively, but does not
donate or withdraw electrons by resonance.
- For each of the following compounds, indicate the ring carbon that would be nitrated if the compound were treated with
a. b. c. d.
OH
COOH
OCH 3
Cl
NHCCH 3
O
NO 2
COOH
HNO 3 >H 2 SO 4 :
NO 2
CH 2 CH 3
+NH 3
FeCl 3
CF 3
+ Cl 2
N
+ Br 2
- Mg/Et 2 O
- D 2 O
CH 3
Br
- NBS/∆ /peroxide
- Mg/Et 2 O
- ethylene oxide
- H+
OCH 3 CH 3
+ O
- AlCl 3
- H 2 O
O
O
+ HNO 3
H 2 SO 4
OCCH 3
O
OCH 2 CH 3 CH 2 OCH 3 COCH 3
O
N(CH 3 ) 3
+
CH 2 N(CH 3 ) 3
+
CH 2 CH 2 N(CH 3 ) 3
+
CH 3 CHF 2 CF 3
Problems 665
Z
