REAKSI ALKIL HALIDA :

SUBSTITUSI NUKLEOFILIK
DAN ELIMINASI
Oleh : Alvan Febrian Shalas, S.
Farm., Apt

TUJUAN PEMBELAJARAN
Mahasiswa dapat memahami Mekanisme dan
Karakteristik reaksi :
1. SN1
2. SN2
3. E1
4. E2
Alkyl halides do one of two things when they
react with a nucleophile/base, such as hydroxide
ion: either they undergo substitution of the X
group by the nucleophile, or they undergo
elimination of HX to yield an alkene
REAKSI SN2
SUBSTITUSI
NUKLEOFILIK
BIMOLEKULAR
INVERSI KONFIGURASI
REAKSI ORDE KEDUA
SINGLE STEP
REAKSI SN2
REAKSI SN2
REAKSI ORDE KEDUA
The rate of reaction is linearly dependent on the
concentrations of two species
Alkil halida
Nukleofil
REAKSI SN2
SUBSTRAT
NUKLEOFIL
LEAVING GROUP
SOLVENT
REAKSI SN2
SUBSTRAT
STERIC HINDRANCE
REACTION RATE
REAKSI SN2
REAKSI SN2
NUKLEOFIL
NUKLEOFILISITAS
REACTION RATE
REAKSI SN2
REAKSI SN2
Nucleophilicity roughly parallels basicity when
comparing nucleophiles that have the same reacting atom.
Thus, OH
-
is both more basic and more nucleophilic than
acetate ion, CH3CO2
-
, which in turn is more basic and more
nucleophilic than H2O
Nucleophilicity usually increases going down a column
of the periodic table. Thus, HS
-
is more nucleophilic than
HO
-
, and the halide reactivity order is I
-
> Br
-
> Cl

Negatively charged nucleophiles are usually more
reactive than neutral ones

REAKSI SN2
LEAVING GROUP
STABILISASI MUATAN (-)
pd TRANSITION
STATE
REACTION RATE
REAKSI SN2
SOLVENT
GROUND STATE
ENERGY OF NU
POLAR PROTIC SOLVENT
(CONTAIN OH; NH)
REACTION RATE
POLAR APROTIC SOLVENT
REAKSI SN2
SOLVENT
DMSO : Dimetilsulfoksida
DMF : Dimetilformamida
HMPA : Heksametilfosforamida
REAKSI SN2
SN1
SUBSTITUSI
NUKLEOFILIK
UNIMOLEKULAR
REAKSI ORDE PERTAMA
PRODUK CAMPURAN RASEMAT
TWO STEPS
SN1
TWO STEPS
SN1
SN1
the SN1 reaction has a rate that depends only on the
alkyl halide concentration and is independent of the
nucleophil concentration. In other words, the
reaction is a first-order process; the concentration of
the nucleophile does not appear in the rate
equation.
REAKSI ORDE PERTAMA
SN1
SUBSTRAT
NUKLEOFIL
LEAVING GROUP
SOLVENT
SN1
SUBSTRAT
STABILITAS
KARBOKATION
REACTION RATE
SN1
LEAVING GROUP
Good leaving groups increase the reaction
rate by lowering the energy level of the
transition state for carbocation formation.
SN1
NUKLEOFIL
the nucleophile does not affect an SN1
reaction
SN1
SOLVENT
Solvent molecules orient around the carbocation so that the
electron rich ends of the solvent dipoles face the positive charge,
thereby lowering the energy of the ion and favoring its formation
SN vs E
Designed by TheTemplateMart.com