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33 Cards in this Set
- Front
- Back
aromatic =
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unusually stable ring system
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aromatic compounds are:
-cyclic -conjugated (alternating double/triple bonds -4n + 2(pi) electrons -planar conformations |
know
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huckel's rule with aromaticity
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4n+2pi
-if follows this rule = aromatic |
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antiaromatic =
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have e- in higher energy non-bonding/antibonding orbital
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neutral compounds, anions and cations may be ____
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aromatic
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aliphatic
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any compound that is not aromatic
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anti-aromatic
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4n pi electrons
-2, 4 double bonds |
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ring structures that have...
have 1, 3, 5, 7, double bonds are considered to be... |
aromatic
OR 2, 6, 10, 14 and 18 electrons from double bonds = aromatic |
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benzoic acid
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Ring-COOH
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toluene
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CH3-Ring
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phenol
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Ring-OH
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aniline
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Ring-NH2
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anisole
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Ring-OCH3
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methyl phenyl ketone
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Ring-(C=O)-CH3
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benzyl chloride
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Ring-CH2Cl
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ortho =
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1,2 substituted
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meta =
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1,3 substituted
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para =
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1,4 substituted
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pg 103
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look
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physical properties of aromatic compounds
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dependent upon aromaticity
-6ring structures are inert/unreactive since very stable |
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electrophilic aromatic substitutions
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no loss of aromaticity
-hydrogen replaced by something else... |
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halogenation of aromatic compound
ring + FeCl3, FeBr3, AlBr3 or AlCl3 = (lewis acids) + heat |
use of F or I are less effective
= Ring-X |
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Sulfonation and aromatic compounds
Ring + SO3/H2SO4 + heat |
= Ring-SO3H
H2SO4 = sulfuric acid |
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Nitration and aromatic compounds
Ring + H2SO4/HNO3 |
= Ring-N2O
-LEAST REACTIVE PRODUCT FORMED |
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acylation(friedal-craft)
Ring + R-(C=O)-Cl + AlCl3 --> |
Ring-(C=O)-R + HCl
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substituent effects
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affect EAS
-determine location of electrophilic attack |
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2 categories of substituents
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1. activating (enhance substitution)
2. deactivating (inhibit substitution) |
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donation of electron density =
withdrawal of electron density = |
activating
deactivating |
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activators direct incoming substituents to...
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ortho/para
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deactivators direct incoming substitutents to...
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meta
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halogens are the exception...they are deactivators YET add to ortho/para
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exception :/
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para > ortho due to less steric hindrance
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know
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catalytic reduction
ring + H2, Rh/C + heat |
hydrocarbon ring (no double bonds)
-Ruthenium or Rhodium -platinum or palladium can be used...require high Pressure though |