Exam 1 Flashcards
Styrene
benzene with a C=C attached
Toluene
benzene with methyl attached
Phenol
benzene with an alcohol attached
Aniline
benzene with NH2 attached
Anisole
benzene with OCH3 attached
Acetophenone
benzene with acetone attached
Benzaldenyde
benzene with an aldehyde attached
Benzoic acid
benzene with a carboxylic acid attached
Meta-xylene
benzene with 2 methyl groups attached with a carbon between them
Para-xylene
benzene with 2 methyl groups attached 180 degrees apart from each other
EWG
-Electron withdrawing group
-destabilizes carbocation and slows down EAS reaction
EDG
-Electron donating group
-Stabilizes carbocation and speeds up EAS reaction
-Usually has an oxygen or nitrogen with a filled electron shell
-The lower electronegativity, the more readily the atom is to give up its electrons
EDG or halogen as a substituent
ortho and para
EWG substituent
meta
Rate of Diels-Alder reactions
-Increases with increasing number of EWGs on dienophile
-In order for the reaction to proceed, the diene must be able to access the s-cis conformation
How to determine aromaticity
- molecule must be flat
- all atoms in the ring are sp2
If neither are true then the molecule is nonaromatic
If both are true then - If the number of pi electrons is 4n then the molecule is antiaromatic
If the number of pi electrons is 4n+2 then the molecule is aromatic
If a frost cycle is made and orbitals are filled then the molecule is aromatic but if there are partially filled orbitals then it’s antiaromatic
If the number of pi electrons divided by 2 is odd then it’s aromatic but if it’s even then it’s antiaromatic
Bromination electrophile
Br+
Nitration electrophile
NO2+
Friedel-Craft Alkylation electrophile
R+
Friedel-Craft Acylation electrophile
R-C+
||
O
Sulfonation electrophile
HSO3+
Bromination mechanism
draw
Nitration mechanism
draw
FC Alkylation mechanism
draw
FC Acylation mechanism
draw
Sulfonation mechanism
draw
EAS Reaction mechanism
draw
Para
substituents are 180 degrees apart
Ortho
substituents are right next to each other
Meta
substituents are attached with a space between them
Kinetic products
-require less energy
-formed faster than thermodynamic product
-will be above thermodynamic product
Thermodynamic products
-require more energy to make
-will be below kinetic product
-more stable than kinetic products
Bromination catalysts
Br2 and FeBr3
Nitration catalysts
HNO3 and H2SO4
Sulfonation catalysts
SO3 and H2SO4
FC Acylation catalysts
carbon with an attached chlorine R group, and double bonded oxygen and AlCl3
FC Alkylation catalysts
sp2 or sp3 alkyl halide and AlCl3
