Metilciclopropano Uso | Reações | Referências Menu de navegação594-11-611657CRC Handbook of Chemistry and Physicsexpandindo-o

Alcanos


CHalquil cicloalcanometanociclopropanoaminas terciáriastensão de Baeyeralquenosadição eletrofílicasubstituição eletrofílicaruptura de anelclivagem de ligaçãohalogenaçãoaminas terciárias






























Metilciclopropano
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Methylcyclopropanesimp.png
Methylcyclopropane (molecular diagram).png

Nome IUPAC
methylcyclopropane
Identificadores

Número CAS

594-11-6

PubChem

11657

SMILES


Propriedades

Fórmula molecular
C4H8

Massa molar
56.11 g/mol
Aparência
colourless gas[1]

Densidade
0.6912[1]

Ponto de fusão

−117.2 °C[1]



Ponto de ebulição

4–5 °C[1]


Compostos relacionados

Cicloalcanos relacionados

Ciclopropano
1,1-Dimetilciclopropano
1,2-Dimetilciclopropano
Ciclobutano
Metilciclobutano
Metilciclopentano
Espiropentano (dois ciclopropanos com um C em comum)
Compostos relacionados

1-Metilciclopropeno
2-Metilaziridina e N-metilaziridina (``N`` no anel triangular)

Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão
Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

Metilciclopropano (C4H8) é alquil cicloalcano composto de metano e ciclopropano.



Uso |


É usado como grupo funcional em aminas terciárias.



Reações |


O metilciclopropano provê um exemplo extremo de como decresce a estabilidade de alquil cicloalcanos com o decréscimo do tamanho do anel, devido a tensão de Baeyer. Eles reagem de maneira similar aos alquenos, embora eles não reajam por meio de EA (cf. adição eletrofílica), mas com o mecanismo de reação SN2 (cf. substituição eletrofílica). Estas reações são tanto reações de ruptura de anel e clivagem de ligação externas ao anel. Dois exemplos são as reações de halogenação:


H3C-CicProp + HBr → H3C-CHBr-CH2-CH3 (rompimento de anel)
H3C-CicProp + HBr → H3C-H + Br-CicProp (clivagem de ligação)

A última reação é importante devido a clivagem do anel ciclopropil em aminas terciárias.



Referências



  1. ↑ abcd Lide, David. R, ed. (2009). CRC Handbook of Chemistry and Physics 89th ed. [S.l.]: CRC Press. ISBN 9781420066791 




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