Chapter 15: Aryl Derivatives Flashcards
How can a nitro group be added to a benzene?
- HNO3
- H3O+
How is a halogen added to a benzene?
X2 and FeX3 (X = halogen)
How is an acetyl group added to a benzene?
Friedel-Crafts acylation
RCOCl, AlCl3
How to convert acetyl group to carboxylic acid?
- KMnO4, OH-, heat
- H3O+
How can bromine be added to the methyl chain of a benzene?
2 alternatives
Ex: on CH3 group of toluene
Radical bromination
NBS: ROOR, heat, or light
or
Br2: light
How can a primary alkyl halide be added to a benzene ring?
Friedel-Crafts alkylation
R-X and AlCl3
What is something important to consider with Friedel-Crafts alkylation?
It often results in rearrangement of the carbocation, disrupting the connectivity of the product
-OH is … directing
ortho, para
-OR is … directing
ortho, para
-NO2 is … directing
meta
-NH2, -NHR, -NR2 are … directing
ortho, para
-CN is … directing
meta
-COOH, -COH, COOR are … directing
meta
-CH3, -X groups are … directing
ortho, para
All activating groups are … directing
ortho, para
EAS leads to the formation of an … intermediate
arenium ion
