modern organic synthesis and selected reagents

Modern Organic Synthesis by Dr. Anand S. Burange

1. MODERN ORGANIC SYNTHESIS
Mr. Anand S Burange,
Institute Of Chemical Technology,
Matunga , Mumbai-400019
E-mail: [email protected]
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2. Sir, Robert Boyle ; First
man who independently
started working in
scientific field of
chemicals now termed as
Chemistry.
In 1828, when F. Wohler
accidently got urea in
the laboratory, from that
day Organic Chemistry
came into an existence
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3. WHAT IS A CHEMICAL REACTION?
Chemical reaction is an effective interaction between two or more molecules/atoms /ions
leading to the formation of new compound(s).
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4. Synthesis
Organic synthesis is a construction
of complex organic compounds by
a series of chemical reactions.
There are two main areas of
research in the field of organic
synthesis, namely total synthesis
and methodology.
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5. Three main keys in organic synthesis
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6. Functional group Interconversions
I.(CH
3 )
2S
+
CH
2
-
(DMSO,NaH,Me
3S
+
)
II.NaBH
4/ EtOH
III.Zn-Hg/ HCl OR N
2H
4 / KOH
IV.SeO
2
V.(a) NaBH
4/ EtOH (b) H
+
/Heat
VI.NaOH
VII.LDA, PhSeBr/H
2O
2
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7. i.NaOH (Cannizaro) OR H
-
donor
reductant
ii.K
2
Cr
2
O
7
/H
+
OR KMnO
4
/H
+

iii. CH
2N
2 OR (a) KMnO
4
/H
+
(b) 2eq.
MeLi
iv.(a) KMnO
4
/H
+
(b) SOCl
2
(c) EtMgBr
v.RhCl(Pph
3
)
3
: Wilkinson’s catalyst
vi.NaCN/EtOH
vii. Conc. HNO
3
/Conc. H
2
SO
4
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8. i.CH
2
I
2
, Zn(Cu)/ Et
2
O
ii.m-CPBA (Bartlett Mechanism)
iii. SeO
2
iv. (a) SeO
2
(b) MnO
2
v.(a) SeO
2
(b) MnO
2
(c)

-
CH
2
–SOMe
2
vi.(a) SeO
2
(b) MnO
2
(c)H
2
O
2
/OH
-
vii. (a) HBr (b) Mg /Dry ether (C) Ph-
CHO
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9. i.m-CPBA
ii.CH
2N
2
iii. (a) Cl-CH
2-COOEt/Me
3CONa
(b) H
3O
+
OR Ph
3P=CH-OMe
iv. (a)Mg-Hg/ TiCl
4 (b) H
2O
v.(a) H
2N-OH (b) H
+
vi.(a)Pyrrolidine/TsOH (b) CO (OEt)
2
vii. Ph
3P=CH
2
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10. Some Functional group Interconversions for practice
i. 9-BBN
ii. Ethanolamine
i. Cl-PO(OEt)
2/NaH
ii. NaNH
2/NH
3 (Via Benzyne)
i. Hg(OAc)
2
/H
2O
ii. NaBH
4
/ OH
-
i. B
2
H
6
/ solvent
ii. H
2
O
2
/ OH
-
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11. Asymmetric Synthesis
OsO
4 OR KMnO
4
I
2/AgOAc (dry) OR (a)m-CPBA (b)
Hydrolysis
Alkene dihydroxylation
Reduction
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Luche’s Reduction

12. Stereospecific cycloaddition reactions
[4+2] cycloaddition reactions takes place in presence of heat
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13. Epoxidation
m-CPBAi. NBS
ii. OH
-
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14. GETTING SLEEPY
NOW IT’S TIME TO MOVE YOUR HEAD UP & DOWN
!!ANTI PERIPLANAR RELATIONSHIP!!
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15. DON’T GET FRUSTRATED!!!
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