folhas teoricas pi 2011
TRANSCRIPT
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Instituto Superior Técnico
Departamento de Engenharia Química e Biológica
Química Orgânica
QUÍMICA ORGÂNICAhttps://fenix.ist.utl.pt/disciplinas/qo3/2010-2011/2-semestre
Texto de apoio às aulas teóricas
Parte I
Mestrado integrado em Engenharia BiomédicaMestrado integrado em Engenharia do Ambiente
Licenciatura Bolonha em Engenharia de Materiais
Docente responsável: Dulce Elisabete Bornes Teixeira Pereira Simão
2º Semestre 2010/2011
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Índice
Parte I
121Eliminação
96Substituição nuclófila alifática
94Halogenação de alcanos
65Estereoquímica
47Reacções ácido-base
40Reacções Orgânicas
34Estrutura Molecular
22Estrutura Molecular
17Estrutura Electrónica
3Nomenclatura e Grupos Funcionais
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Nomenclatura de aminasTerminação: -amina
Classificação de aminas
etilamina etilmetilamina
� Quando –NH2 não é o grupo principal é designado por amino-
etilmetilpropilamina
NH2 NH
N
● Considerar a cadeia de carbono mais comprida
● Indicar a posição do substituinte -OR (alcoxi)
Nomenclatura de éteres
Éter fenil metílicoMetoxibenzenoAnisole
Éter dimetílico Éter di-isopropílico
Éter metil etílico Éter metil neopentílico1-metoxi-2,2-dimetilpropano
O O O
OO
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Terminação: -al (aldeídos) -ona (cetonas)
metanal etanal etilmetilcetona acetofenona
Nos aldeídos mais complicados pode dar-se o sufixo carbaldeído
� Quando há outra função prioritária o grupo aldeído aparece com oprefixo -formil
3-formil-ciclo-hexanona
O
CH
Nomenclatura de aldeídos e cetonas
O
H H
O
H3C H
OO
� Quando há outra função prioritária o grupo aldeídoaparece com o prefixo -formil
O
H
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Nomenclatura de ácidos carboxílicos
Terminação: ácido…-óico
Ácido heptanóico
Ácido 2-hidroxi-4-metilpentanóico
Ácido fórmico Ácido acético
O
H OH
O
H3C OH OH
O
OH
O
OH
Nomenclatura de anidridos
Terminação: anidrido…-óico
Anidrido hexanóico
Anidrido acético Anidrido acético e propiónico
O
O
O
O
O
O
O
O
O
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Nomenclatura de ésteres
Butanoato de metiloAcetato de etilo
Terminação: ato…-ilo
O
O
O
O
Nomenclatura de halogenetos de acilo
Cloreto de acetilo
Terminação: …eto…-ilo
Brometo de hexanoílo
Cloreto de 4-metil pentanoílo
O
Cl
O
Br
O
Cl
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Nomenclatura de amidas
benzamidaacetamida
3-N,N-trimetilbutanamida
hexanamida
N-metilbenzamida
Terminação: …-amidaO
NH2
O
NH2
O
NH2
O
NH
CH3
O
N
CH3
CH3
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Estereoquímica de polímeros
Os principais polímeros vinílicos são monosubstituidos, do tipo:
Nestas polimerizações há formação de carbonos quirais (∗)
Cada átomo está ligado a 4 substituintes diferentes (se n≠m)
* CH2CH *
Xn
CH
X
H2CH2C
HC
∗
X
H2C
HC
∗
X
H2C
HC
∗
X
H2C
HC
∗
X
C∗
X
H2C
HH2C
HC*
X
HC *
Xn m
O átomo de carbono é quiral (se n≠m)
Há várias hipóteses de orientações relativas para os vários carbonos quirais:
Isotactico Sindiotactico Atactico
X H
X H
HX
X H
X H
H X
HX
H X
X H
X H
HX
H X
X X X HH H H XX H X HH X H XX X X XH H H H
≡ ≡ ≡
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Mono e polissacáridos
Hidratos de carbono são aldeídos ou cetonas poli-hidroxílicas ou substâncias que por hidrólise dão aldeídos ou cetonas poli-hidroxílicas.
Monossacárido é o hidrato de carbono mais simples e é classificado consoante o número de átomos de carbono e se contém o grupo aldeído ou cetona
Classificação de monossacáridos
Triose – 3 átomos de carbonoTetrose – 4 átomos de carbonoPentose – 5 átomos de carbonoHexose – 6 átomos de carbono
Aldose – contém grupo aldeídoCetose – contém grupo cetona
CH
O
(CHOH)
CH2OH
n
C
(CHOH)
CH2OH
n
O
CH2OH C
CHOH
O
CH2OH
CHOH
CH2OH
CH
O
CHOH
CHOH
CH2OH
Aldose Cetose Aldotetrose Cetopentose
Monossacáridos mais simples:
C
CH2OH
C
H OH
O H
C
CH2OH
C
HO H
O H
CH
O
CHOH
CH2OH
C
CH2OH
O
CH2OH
D (+)-Gliceraldeído L (-)-Gliceraldeído
R S ∗
Açucar D: Quando o monossacáridotiver o estereocentro mais alto (penúltimo carbono) com a mesma configuração que o D-(+)-gliceraldeído.
Açucar L: Quando o monossacáridotiver o estereocentro mais alto (penúltimo carbono) com a mesma configuração que o L-(+)-gliceraldeído.
Gliceraldeído(aldotriose)
Di-hidroxiacetona(cetotriose)
CH
O
CHOH
CHOH
C
CH2OH
OHH
C
CHOH
O
CH2OH
CHOH
C
CH2OH
HHO
D-aldopentose L-cetohexose
As designações D e L (tal como R e S) não estão relacionadas com as rotações específicas dos açucares. Podemos ter açucares D-(+)- ou D-(-)- e L-(+)- e L-(-)-.
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CH
O
C
C
C
C
CH2OH
OHH
HHO
OHH
OHH
D,α-Glucopiranose
D,β-Glucopiranose
As pentoses e as hexoses existem naturalmente nas formas cíclicas (hemiacetálicas)
D-(+)-Glucose
CHOH
C
C
C
C
OHH
HHO
OHH
HHOH2C
O
OH
OH
H
OH
H
OHH
OH
CH2OH
H
OH
OH
OH
H
H
OHH
OH
CH2OH
H
D-(+)-Glucose:
O
H
HO
H
HO
H
OH
OHHH
OH
O
H
HO
H
HO
H
H
OHHOH
OH
≡
≡
CH2OH
OHCH2OH
OH
OH
O
O
O
OH
OH
OH
CH2OH
H
Dissacárido
Sucrose
De D-glucose De D-frutose
Polissacáridos: São polímeros naturais constituídos por um número mais ou menos elevado de unidades de monossacáridos. Os mais importantes na natureza são o amido e a celulose.
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3.
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Resumo da características de SN1 e SN2
SN1
Unimolecular(Electrófilo)
SN2
Cinética
Tipo de nucleófilo
Efeitos estereoquímicos
Estereoquímica
Não afecta velocidade
Pouco influentes
Afecta muito a velocidade(afecta k)
Racemização Inversão
Bimolecular(Electrófilo / Nucleófilo)
Muito influentes
Processo Por passos Concertado (um só passo)
Intermediário SIM, carbocatião NÃO
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