Síntese Orgânica - Introdução

qmclink 13,741 views 34 slides Aug 20, 2010
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à quando ingd
a dos produtos ind
Fe outros comtipostos aid
os os anos@Mmnilhares de novos

da Oni processo de obtençäo de co:
AN La Wapples transformagáo química e1
& acdes químicas em sequéncia.

a Criaçäo de um campo de gy

Und projeto de síntes

imento$ a respeito de métodos sintéticos,

ge análise (IV, RMN, eic.), entre outr

a foi introduzido por E. J. Col
nsével, hoje, para qualqug

NH,*NCO>

nto da Quimica ad

ativaffrustrada de preparacáo da quiking

aminho para o o y

Penicilina
intese da Reserpina
Sintese do Dodecaedrano

R. Willstate (1915)
R. Robinson (1917)
R.B. Woodward (1945)

J.C. Sheehan (19
R.B. Woodw
L. Paquete (19

+
Me OH Me ”

Palitoxina

2 mv
, partir de mater
i comercialmg

3) A de-¿málogó We
com atividad e biológ icf

+

D cogcentna .
uire Uma carga parcial

negativo adquire carga

H,C—CH,

ethane

nonpolar

rai os eléfrons do hidrogé

SS

E 0 produto das magnitudes, ee
eletrostáticas: esu) e a dist:
A unidade de medi
1x108 esu cm
Dipole moment

Formula

He
eb
HF
HCl
HBr
HI
Bl

and negative

sd Sy)

Formula

H=19D | u=39D

chloromethane hlor acetonitrile

es, are characterized
eldurrangement of ato
TROWSIO

Carbon-Carbon
bonds are gen

xy)

orogen from an 4

ALKYL GROUP.
CHy—
Methyl group
CH,CH, CH,CH,— or C3H;—
Ethane Ethyl group
>H,CH,CH

Propane

“HCH, CH SHES or CH¿CH

Propane Isopropyl group

Methyl
Ethyl others

CH,CH,CH, Propyl an be
CH,CHCH esignated by R.

or CcHs— or Ph— or d— or Ar—(if ring substituents are present)

Ways of represent enyl group

methyl hydrogg
inzyl p

—CH5— or (E )}-CH— or CC, — or Bn—

Ways of representing a henzyl grou
N

HS

|

HH
A L alkyl
chloride

CH,CH 1

+ Ethane Ethyl

= This is a differgÚ y
alcohols

General formu

cue

Acetamide

Functional
Ñ bond

These names are

Alkene Alkyne | Aromatic

Ethy

Haloalkane

Alcohol

H,OH

Dimethyl eth

Aldehyde

RNH,
R,NH
RN

ethylamine

Methyl acetate

Nitrite

nenitrile

Acetonitrile

these are nucleophiles because they
have a pair of electrons to share

Ht CH,CH) BH;

‘Br° RO:

AA

these are electrophiles because they
can accept a pair of electrons

these are electrophiles because
they are seeking an electron

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Introduçäo à Sintese Organica 20/08/2010

Electrophilic Addition of HBr to Alkene

# $

CH¿CH=CHCH;z + H—Br CH¿CH cu + Br — CH,;CH—CHCH;
H Br H

a carbocation 2-bromobutane

an alkyl halide

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um par de elétrons

>.

to de um elétron

EN

Utilizaçäo dé Sétas curvas

CH,;CH=CHCH, + H—Br —> CH;CH A + ¿Br
H

ae + Bn —> CHsCH—CHCHs
H Br H

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correct

CH; 0H — CH;

HA
[correct

[incorrect]
5)

|

CH;
CHAS H — CH,—Ö—-H + H

|
H

\
[incorea]

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Introduçäo à Sintese Orgánica

CH;CH=CHCH; + H~Br: — CHHÈH—CHCH, +

correct

CH¿CH=CHCH, + H—Br — CH,;CH—CHCH; +
|
H

H

incorrect

= Mata]

yo
¡OH

ll I
+ CH;CCH; — CH;CCH; + H™

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the highest
energy state
free energy on the reaction
of the pathway
reactants
free energy
of the
products

>
oO
=
©
£
©
y
o
te
ira

im. Nova@2002; Vol. 25,
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