Download - Sintesis Organik
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SINTESIS ORGANIKNAMA-NAMA REAKSI KIMIA
ORGANIK
AINI FITROTUN HANIFA
120332421463
OFF I
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REAKSI ORGANIK1. Reaksi Riemer-Tiemann2. Penataan ulang Ciamcian-Dennsted3. Penataan ulang Dienon-Phenol
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1. REAKSI RIEMER-TIEMANNTujuan reaksi Riemer-Tiemann : mensintesis o-
formilfenol dari fenol dan kloroform
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SEJARAH REAKSI RIEMER-TIEMANNReaksi Reimer - Tiemann adalah reaksi kimia yang digunakan untuk orto - Formilasi fenol. Reaksi ini ditemukan oleh Karl Ludwig Reimer dan Ferdinand Tiemann.
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Reaksi khusus
Substrat produk
OH
CHCl3 KOH
OH
CHO
3 KCl 2H2O
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Mekanisme reaksi
Tahap 1: pembentukan karbena dari penyerangan gugus hidroksil kepada ion hidrogen
Cl3C H
OH
H2O CCl2
Cl
-Cl-, lambat CCl2
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Tahap 2:adisi dikloro karbon dan hidrolisis
OH
H2O
O
CCl2
O
CCl2
H
O
CHCl
ClO
H
Cl OHO Cl
H
OH
O O
H
HOH
CHO
KOH
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Jenis reaksi Riemer-Tiemann adalah substitusi gugus aldehid tehadap hidrogen posisi alfa reaksi ini termasuk oksidasi
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2. PENATAAN ULANG CIAMCIAN-DENNSTED Tujuan penataan ulang Ciamcian-Dennsted
adalah
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Reaksi khusus
Substrat produk
N
H
CHCL3
NaOH
N
Cl
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Mekanisme reaksiTahap 1: pembentukan karbena dari penyerangan gugus hidroksil kepada ion hidrogen
Cl3C H
OH
H2O CCl2
Cl
-Cl-, lambat CCl2
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Tahap 2: penyerangan karbena kedalam pirol
N
H
CCl2
N
Cl
Cl
H
OH
N
Cl
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Jenis reaksi Ciamcian-Dennsted adalah penataan ulang, reaksi didalamnya bukan termasuk oksidasi ataupun reduksi
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PENATAAN ULANG DIENON-PHENOLTujuan: penataan ulang 4,4-R siklohesadienon
menjadi 3,4-R fenol
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Reaksi umum:
Substrat produk
RR
O OH
RR
H+
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Mekanisme reaksiTahap 1: penyerangan elektrofil
RR
O
H+
RR
O
H
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Tahap 2:
RR
O
H
H
OH
R
H
R
OH
R
R
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Jenis reaksi penataan ulang Dienon-Phenol adalah penataan ulang reaksi ini termasuk reaksi reduksi
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DAFTAR PUSTAKALi,Jie Jack. 2006. Name Reactions: A Collection of Reaction Mechanism. Jerman.
Springer
.http://en.wikipedia.org/wiki/Reimer%E2%80%93Tiemann_reaction. Diakses tanggal 25-022015