- HCl
–C–C– –C=C–
H Cl
CH3
CH3OH
CH3 H
CH3C – X X- + C+ – C – H
CH3 CH3 H
CH3
+
C = C–H + CH3 O – H
CH3 H H
B:
H
B-X
–C – C – – C=C–
β α X: -
X
Terjadi hanya satu tahap.
Semua ikatan akan terputus dan
terbentuk tanpa pembentukan
suatu intermediet
4-Apr-11 Tugas Kimia Organik 5 4
Reaksi dua Tahap
E1
E2
C=C + H Y + X-
H
–C–C– + Y-
X
H
–C–C– + X-
E1
SN1 CH3OH
CH3
H2C = C + H+ + Br -
(CH3)3COCH3 + H+ + Br -
CH3
2-metilpropena 2-metoksi-2-metilpropana
20 % 80 %
4-Apr-11 Tugas Kimia Organik 5 8
Eliminasi vs Substitusi
Persaingan Antara Reaksi E2 dan SN2
SN2 E2
H H
CH3O-Na+, CH3OH
CH3CH2CH2Br CH3CH2CH2OCH3 + C=C
H3C H
92% 8%
1-metoksipropana Propena
Sifat Pelarut
Temperatur
Sekunder : R2CHX
B: - kuat
E2
alkena
Nu: - lemah
SN1 + E1
R3CNu + alkena
Tersier : R2CHX
B: - kuat
E2
alkena
Na+ CN-
CH3 – CH2 – CH2 – CH2 – Br CH3 – CH2 – CH2 – CH2 – CN
THF - HMPA
(CH3)3CO- K+
CH3 – CH2 – CH2 – CH2 – Br CH3 – CH2 – CH = CH2
H – OH
CH3
CH3
CH3 CH3
CH3CH2O- Na+
CH3 – C – O – CH2 – CH3 + CH3 – C = CH2
CH3
CH3 3% 97%
CH3 – C – Br
CH3 CH3
CH3 CH3CH2OH
CH3 – C – O – CH2 – CH3 + CH3 – C = CH2
heat
CH3
80% 20%
Kenukleofilan Meningkat
Kebasaan Meningkat
I- Br- Cl- ROH H 2O CN- OH- OR-
Basa Pelarut
NaOH Air
KOH Air, MeOH, EtOH
NaOR ROH (grup R yang sama)
NaNH2 NH3 (liquid) -33o C