Reaksi Substitusi
Transcript of Reaksi Substitusi
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Kelompok 10
M.Ekaditya Albar 0806331683
Maryane Anugerah 0806331714
Mia Diniati 0806331720
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Reaksi Substitusi
Reaksi substitusi atau disebut reaksi pertukaran gugusfungsi terjadi saat atom atau gugus atom dari suatusenyawa karbon digantikan oleh atom atau gugus atomlain dari senyawa yang lain.
CH3O- + CH3CH2CH2 – Cl CH3CH2CH2 – OCH3 + Cl-
4-Apr-11 2Tugas Kimia Organik 4
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Reaksi Substitusi
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Nukleofil adalah sebuah spesies (ion atau
molekul) yang tertarik kuat ke sebuah
daerah yang bermuatan positif pada sesuatu
yang lain.
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Reaksi Substitusi C karbonil
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SYARAT !!!
Harus Ada Gugus Pergi
Leave = L
Gugus Pergi
-OH : as Karboksilat
-OR : ester
-NH2 : amida
- X : halida
- RCOO¯ : anhidrida
R L
O
Gugus
Pergiδ+
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O sebagai Nukleofil
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Air H - OH
Alkohol H - OR
NUKLEOFIL
Nu : -
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Reaksi Substitusi C karbonil
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R OH
O
R O
O
R
R NH2
O
R X
O
R O
O
O
R
NUKLEOFIL
Nu : -
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C nukleofil dari Pereaksi Organologam
[ RMet ; RMgX ]
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R – C+ – L + R - Met
O:.. ..
R – C – L
:O:
R
L: –
H+
R – C+ – R
:O: H
R
δ- δ+
R – C – R
:O:
R
..
:O
R – C+ – R
..
1
2
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Contoh Soal
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+ C2H5 – MgBr– +
CH3 – C – OH
O
CH3 – C – OH
O
C2H5
gugus pergi
CH3 – C
O
C2H5
C2H5 – MgBr
CH3 – C – C2H5
O
C2H5
– +
δ+
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CH3 – C – C2H5
O
C2H5
: :. .–
CH3 – C – C2H5
OH
C2H5
H+
3-metil-3-pentanol
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Reaksi Substitusi C jenuh
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C L
Gugus Pergi (Leave)
Basa Lemah
Basa Konjugasi dari Asam Kuat
(Cl, Br, I)
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Mekanisme Reaksi Substitusi C jenuh
Mekanisme Substitusi :
1. Substitusi Nukleofil 1 (SN 1)
2. Substitusi Nukleofil 2 (SN 2)
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Substitusi Nukleofil 1
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– C – L – C+ + L :
– C – Nu
Nu:2
disosiasi
heterolitik
1 carbocation
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Substitusi Nukleofil 2
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Nu: + – C – L → Nu – C – + L:
Harus mempunyai kenukleofilan yang tinggi
Mendorong keluar L
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Faktor yang memengaruhi Reaksi Substitusi
C jenuh
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1. GUGUS PERGI
Gugus pergi berangkat dgn e ikatannya
Gugus pergi yang baik : basa konyugasi dr asam kuat.
nilai pKa < 5
2. NUKLEOFIL
Nu:- : • kenukleofilan rendah : SN1
● kenukleofilan tinggi : SN2
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Faktor yang memengaruhi Reaksi Substitusi
C jenuh
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H2O ROH Cl- Br- OH- OR- I- CN-
Kenukleofilanmeningkat
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Faktor yang memengaruhi Reaksi Substitusi
C jenuh
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H3C – C+ >
CH3
CH3
H3C – CH2– C+ >
H
CH3
H3C–CH2-CH2- C+
H
H
SN1 SN2
3. Tempat substitusi
• C primer : SN2
• C tersier : SN1
TERSIER SEKUNDER PRIMER
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Faktor yang memengaruhi Reaksi Substitusi
C jenuh
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4. Pengaruh pelarut
Pelarut pOlar : sn1
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Contoh Soal
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CH3 – CH – Cl
CH3
+ CH3 – CH2 – OH
CH3 – CH – Cl
CH3
gugus pergi
CH3 – CH
CH3
++ C2H5O – H
+–
CH3 – CH – O – C2H5
CH3
+ H+
2-etoksi propana
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Contoh Soal
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CH3 – CH2 – CH– CH3+
Cl
CH3 – O – CH3
gugus pergi
CH3 – CH2 – CH– CH3
Cl
O – CH3
2-metoksi butana
CH3 – CH2 – CH– CH3
O – CH3
+–
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Substitusi Halida Alilik dan Benzilik (SN 1)
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Alilik (Menyerupai Alil)
Alil = Propenil
- CH = CH – CH3
CH2
Benzilik
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Contoh Soal
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CH3 – CH = CH – C – CH3
Cl
CH3
+ H2O
CH3 – CH = CH – C – CH3
CH3
+
alilik
+ H – OH+ – CH3 – CH = CH – C – CH3
OH
CH3
gugus pergi
2-metil-3-penten-2-ol
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Contoh Soal
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CH2 – CH – CH3
Br
+ H2O
gugus pergi
CH2 – CH – CH3
+
+ H – OH–+
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CH2 – CH – CH3
+ H+OH
1-fenil-2-propanol
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Referensi
www.freewebs.com/kimiadb2/MateriBab7Sem20708.doc
http://pustaka.ut.ac.id/puslata/online.php?menu=bmpshort_detail2&ID=459
http://kimia.upi.edu/utama/bahanajar/kuliah_web/2007/YAN%20FATHUROHMANSYAH_045488/WEB/reaksi_substitusi.htm
http://repository.ui.ac.id/contents/koleksi/11/d1e18c65f0a9e182bf23d80b50afdd1843f69b51.pdf
http://students.chem.itb.ac.id/organic/Kimia%20Karbon.pdf
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