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Introduction

Organic synthesis involves building organic molecules from simpler precursors through chemical reactions. It is used to discover drug molecules and test reaction mechanisms. Retrosynthetic analysis works backward from a target molecule to identify precursor molecules that could react to form the target through common organic reactions. This process is repeated until reaching readily available starting materials. Identifying complementary charges on atoms in target and precursor molecules helps determine feasible reaction routes.

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31 views

Introduction

Organic synthesis involves building organic molecules from simpler precursors through chemical reactions. It is used to discover drug molecules and test reaction mechanisms. Retrosynthetic analysis works backward from a target molecule to identify precursor molecules that could react to form the target through common organic reactions. This process is repeated until reaching readily available starting materials. Identifying complementary charges on atoms in target and precursor molecules helps determine feasible reaction routes.

Uploaded by

kurniatriwijaya.2410
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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INTRODUCTION

TO ORGANIC SYNTHESIS

• Organic synthesis is the processs of building organic


molecules from simpler precursors.

• Why do organic synthesis?


1. To discover molecules with structural
attributes that enhance certain medicinal effects
or reduce undesired side effects.
2. To test a hypothesis about a reaction
mechanism or about how a certain organism
metabolizes a compound.
• Crixivian was designed by small-scale
synthesis in a research laboratory and then
quickly moved to large-scale synthesis after its
approval as a drug.
C6H5
N H OH H HO
N NH H
N
H
O
HN O
C(CH3)3

Crixian (an HIV protease inhibitor)


• a very simple organic synthesis may involve only
one chemical reaction. Others may require from
several to 20 or more steps.

Synthesis of vitamin B12 ,


announced in 1972 by
R. B. Woodward and
A. Eschenmoser, took
11 years, required more
than 90 steps, involved
the work nearly 100
people.
Synthesis of Alkanes and Cycloalkanes
a. Hydrogenation of Alkenes and Alkynes

C H Pt,Pd,or Ni C H
+
C H C H
solv.pressure

alkene alkane

C Pt H C H
+ 2 H2
C solv.pressure H C H

alkyne alkane
b. Reduction of Alkyl Halides
R-X + Zn + HX R-H + ZnX2
Zn, H-X
or R-X R-H
(- ZnX2)

c. Alkylation of Terminal Alkynes


NaNH2 R'X
R C C H R C C Na+ R C C R'
(-NH3) (-NaX)

an alkyne sodium an alkynide R' must be


amide anion methyl or 1o
and unbranched
at the second carbon
Exercises:

1. Show the reaction involved for hydrogenation of


all the alkenes and alkynes that would yield 2-
methylbutane.
2. Your goal is the synthesis of 2,3-dimethylbutane
by treating an alkyl halide with zinc and
aqueous acid. Show two methods (beginning
with different alkyl halides) for doing this.
Retrosynthetic Analysis

• An organic synthesis typically involves two


types of transformation:
1. Convert functional groups from one to
another
2. Create new carbon-carbon bond
• Often the sequence of transformations that
would lead to the desired compound is too
complex for us to “see” a path from the
beginning to the end.
Retrosynthetic Analysis
• We begin by identifying immediate precursor that
could be caused to react to form them, and so on.
This process is repeated until we have worked
backward to compounds that are sufficiently simple
that they are readily available in a typical
laboratory:

Target molecule 1st prec. 2nd prec. starting


compound
Retrosynthetic Analysis
• Retrosynthetic analysis often discloses several routes
from the target molecule back to varied precursor:

2nd precursors a
1st precursors A
2nd precursors b

2nd precursors c
Target molecule 1st precursors B
2nd precursors d

2nd precursors e
1st precursors C
2nd precursors f
Identifying Precursors
• To convert functional groups we need to have
a toolbox of reaction from which to choose
those we know can convert one given
functional group into another.
• To making carbon-carbon bonds in synthesis,
you will develop a repertoire of reaction for
that purpose and consider basic principles of
structure and reactivity.
Identifying Precursors
• Many organic reaction depend on the
interaction of molecules that have
complementary full or partial charges.

• One very important aspect is being able to


identify those atoms in a target molecule that
could have had complementary (opposite)
charges in synthetic precursor.
Example:

Retrosynthetic Analysis


_
C C CH2CH3 C C: C C H + Br CH2CH3

Synthesis

NaNH2 Br-CH2CH3
_ +
C C H C C: Na C C CH2CH3
(-NH3) (- NaBr)
Exercise:
1. Referring to the retrosynthetic analysis for 2-methylhexane
in that slide, write reactions for those synthesis routes that
are feasible.
2. Specify the missing compounds and/or reagents in each of
the following syntheses (more than one step may be
necessary in some cases):
a. trans-5-methyl-2-hexene + ?  2-methylhexane
b. 4-bromo-3,4-diethylheptane + Zn,HBr  ?
c. ? + Zn,HX  2,2-dimethylpropane
d.
CH3CH2CH2Br + ?
CH2CH2CH2CH3
e. + ?

f. + ?
• The alkyl halide used with the alkynide anion
must be methyl or primary and also
unbranched at its second carbon., if not we
can get other products.

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