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