REAKSI ALKILASI FRIEDEL-CRAFTS

Kimia Organik II
Jurusan Pendidikan Kimia
 Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa

Persamaan umum

The mechanism for the reaction starts with the formation

of a carbocation.
The carbocation then acts as an electrophile and attacks
the benzene ring to form an arenium ion.
The arenium ion then loses a proton.
Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa
 Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa

REAKSI ASILASI FRIEDEL CRAFTS

Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa
 Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa

BATASAN REAKSI FRIEDEL CRAFTS

1. When the carbocation formed from an alkyl halide,
alkene, or alcohol can rearrange to one or more
carbocations that are more stable, it usually does
so,and the major products obtained from the reaction
are usually those from the more stable carbocations.
 Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa

2. FriedelCrafts reactions usually give poor yields when

powerful electron-withdrawing groups(Section 15.11)
are present on the aromatic ring or when the ring bears
an NH2, NHR, or NR2group. This applies to both
alkylations and acylations.
 Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa

We shall learn in Section 15.10 that groups present on an

aromatic ring can have a large effect on the reactivity of the ring
toward electrophilic aromatic substitution. Electron-withdrawing
groups make the ring less reactive by making it electron
deficient. Any substituent more electron withdrawing (or
deactivating) than a halogen, that is, any meta-directing
group(Section 15.11C), makes an aromatic ring too electron
deficient to undergo a FriedelCrafts reaction. The amino
groups,NH2, NHR, and NR2, are changed into powerful
electron-withdrawing groups by the Lewis acids used to catalyze
FriedelCrafts reactions. For example,
 Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa

3. Aryl and vinylic halides cannot be used as the halide

component because they do not form carbocations
readily
 Irah namirah, M.Si - Universitas Sultan Ageng Tirtayasa

4. Polyalkylations often occur.Alkyl groups are electron-

releasing groups, and once one is introduced into the
benzene ring, it activates the ring toward further
substitution