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GOVT P.G.

COLLAGE BARAN
WRITE UP OF SEMINAR PRESENTATION
2016-2017

DEPARTMENT OF CHEMISTRY
GOVERNMENT P.G.COLLEGE,BARAN
SUPERVISED BY:MISS. AARTI BANSAL

PRESENTED BY:ANIL PRAJAPAT


(M.SC FINAL)

RETROSYNTHESIS
OR
DISCONNECTION

CONTENTS
1.INTRODUCTION
2.TERMINOLOGY
3.SYNTHON & SYNTHATIC EQUIVALENT
4.GENRAL GUIDELINE /BASIC RULE
5.CLASSIFICATION OF DISCONNECTION
6. C-X DISCONNECTION
7. CHEMOSELECTIVITY

INTRODUCTION
1.An analytical approach in organic synthesis in which
the target molecule is broken into starting material
(synthon) is known as Retro synthesis or
disconnection approach
2. It is exactly the reverse of chemical synthesis there
for also called Retro synthesis
Target molecule

Starting molecule

TERMINOLOGY
DISCONNECTION:-An imaginary bond breaking process
in which bonds breaks between atoms.

TARGET MOLECULE:- A molecule which is synthesis


from probable reactant is known as target molecule.

F.G.I :- The process of Inter converting one functional


group into another functional group during retro
synthesis is known as F.G.I.

SYNTHON & SYNTHATIC EQUIVALANT

Synthon

synthetic equivalant

GENRAL GUIDELINE /BASIC RULE


Disconnection must be a bond correspond to the reverse of Real and
workable Reactant.
Disconnection of a bond should be such that stable fragment ion are
obtained e.g. two mode of disconnection A&B.

A will be preferred as carbocations are stabilized by electron donor


group. -R,-OR ,etc, While carbinions are stabilized by electron
withdrawing group. -NO2,-CN, -COOR etc.

3 Number of fragments generated through a disconnection


should be as minimum as possible.

When a compounds consisting two parts join a Heteroatom


then molecule disconnect next to the Heteroatom.
This guideline use disconnection
Amine,Acetel,Ketal &Sulphide etc.
Example : Chlorbeniside

for

Ester,Amide,Ether

Conclusion:- All over this guideline conclusion that more


reactive group (alkynes etc.) must be disconnected first and
in organic synthesis more reactive group add last.
Some time a disconnection doesnt generate sufficient
stabilised fragments but such fragment can be obtained
using FGI or introducing additional electron withdrawing &
removing them .
E.g.

The most electronegative group disconnect first E.g.

If FGI is needed do it at an appropriate stage to get the


desired
effect
on
orientation.
eg1
chloro
4(trichloromethyl
benzene)

When two opposite directing nature group attach in benzene ring Ortho
position to each other then there is no any chemical reaction in organic
chemistry is known so this disconnection is avoid by direct disconnection.

Following compound will not be disconnected.

Salicylic aldehyde

Cresol

mesitylene

Di hydroxy benzen

Biphenyl

Classification of Disconnect
C-X TWO
Other
ONE
DISCONNECTION
specific
GROUP
GROUP
DISCONNECTION
C-X
C-C
C-X DISCONNECTION
C-C
DISCONNECTION
X=

1. C-X Disconnection
The disconnection In Which we disconnect c-x bonds, is
known as c-x disconnection. These are two types
1. One-group C-X Disconnection
The disconnection In Which only one functional group is
present these known as one-group c-x disconnection
We disconnect a bond joining the heteroatom (X) to the rest
of the molecule : a C-O ,C-N,C-S disconnection .

2. Two-group C-X Disconnection:-

The disconnection in which two functional group is present but we


disconnect only one C-X these known as Two-group c-x disconnection.
These are following three types
1. 1,1 di functionalized disconnection
E.g. acetel & ketel
2. 1,2 di functionalized disconnection
E.g. two functional group with heteroatom attach on one carbon atom.
3. 1,3 di functionalized disconnection
E.g. - unsaturated carbonyl compounds (Michal accepter)

Chemo selectivity

If a molecule has two reactive group & we want to react one of them &
not the other we need chemo selectivity.

Then this problem more reactive group (alkynes etc.) must be


disconnected first and in organic synthesis more reactive group add last.

The amide is paracetamol the popular analgesic. Amine are more


Nucleophilic than phenol so reaction with acetic anhydride gives the
amide we want without any of ester the aminophenol 1 can be made by
methods.

Multiple step synthesis avoid chemo selectivity


problem
E.g. ICI- D7114 (N benzyl 1-2-(4 benxyloxy phenoxy ether amine

In this structure with two ether & an amine? functional gr. it


requires several disconnection to take it back to simple comp. The
question is which do we do first?
Here there are four reasonable disconnection one at each of the
ether gr. ( a, b) or on either side of the amine.( c, d)

Reference
E. J. Corey, X-M. Cheng (1995).The Logic of Chemical Synthesis. New York:
Wiley.ISBN0-471-11594-0.
E. J. Corey(1991).
"The Logic of Chemical Synthesis: Multistep Synthesis of Complex
Carbogenic Molecules (Nobel Lecture)"(Reprint).Angewandte Chemie
International Edition in English.30(5): 455465.
James Law et.al:"Route Designer: A Retrosynthetic Analysis Tool Utilizing
Automated Retrosynthetic Rule Generation", Journal of Chemical Information
and Modelling (ACS JCIM) Publication Date (Web): February 6, 2009;
Wilhelm
p.760

Wenner

(1963)."Phenylacetamide".Org. Synth.;Coll.

Vol.,4,

Roger Adams; A. F. Thal (1941)."Benzyl Cyanide".Org. Synth.;Coll. Vol.,1,


p.107

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