Methylcyclopropane

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Methylcyclopropane
IUPAC name methylcyclopropane
Identifiers
CAS number 594-11-6
PubChem 11657
SMILES
Properties
Molecular formula C4H8
Molar mass 56.11 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox references

Methylcyclopropane (C4H8) is the alkyl cycloalkane compound of methane and cyclopropane.

Usage

It is used as functional group in tertiary amines.

Reactions

Methylcyclopropane provides an extreme example of the general decrease in the stability of alkyl cycloalkanes with decreasing ring size, due to the Baeyer tension. They react in a similar way to alkenes, although they don't react with the EA (cf. electrophilic addition), but with the SN2 (cf. nucleophilic substitution) reaction mechanism. These reactions are both ring opening reactions and bond cleavage reactions outside the ring. Two examples are the halogenation reactions

H3C-CycProp + HBr → H3C-CHBr-CH2-CH3 (ring opening)
H3C-CycProp + HBr → H3C-H + Br-CycProp (bond cleavage)

The latter reaction is important due to cleavage of the cyclopropyl ring in tertiary amines.


Wikipedia content modification information:

  • This page was last modified on 10 October 2008, at 20:14.

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