14: Substituent Effects
14: Substituent Effects
14: Substituent Effects
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(9/94)(11,12/96)(11,12/04,01/05) Neuman Chapter <strong>14</strong><br />
<strong>14</strong>.4 Electrophilic Aromatic Substitution Reactions <strong>14</strong>-19<br />
Reactions on Substituted Benzenes (<strong>14</strong>.4A) <strong>14</strong>-19<br />
Rates and Products Depend on S<br />
meta versus ortho/para Directors<br />
Directive <strong>Effects</strong> of <strong>Substituent</strong>s (<strong>14</strong>.4B) <strong>14</strong>-22<br />
Resonance Structures for o, m, and p Reactions<br />
+R Groups<br />
-R Groups<br />
Reactivity of Substituted Benzenes (<strong>14</strong>.4C) <strong>14</strong>-25<br />
-R <strong>Substituent</strong>s<br />
+R <strong>Substituent</strong>s<br />
I and R <strong>Effects</strong> Can Compete<br />
Halogens have Contradictory Rate and Product <strong>Effects</strong><br />
Reactions at the ortho Positions (<strong>14</strong>.4D) <strong>14</strong>-30<br />
Statistical <strong>Effects</strong><br />
Steric Hindrance<br />
Additional Considerations<br />
Multiple <strong>Substituent</strong>s (<strong>14</strong>.4E) <strong>14</strong>-32<br />
1,4-Dimethylbenzene<br />
1,3-Dinitrobenzene<br />
1,3-Dimethylbenzene<br />
1,2-Benzenedicarboxylic Acid<br />
p-Chlorotoluene<br />
m-Chlorotoluene<br />
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