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Organic Chemistry

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16 Sep 2012 19:58:11 IST

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stability of carbocation

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why ethyl is more stable as compare to n-propyl carbocation

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Yateendra Singh

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20 Sep 2012 14:03:45 IST

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since the ethyl carbocation cannot undergo any rearrangement..........while the n-propyl carbocation can...........and if it is an n-propyl carbocation it will immediately undergo rearrangement and form an isopropyl carbocation.........because isopropyl carbocation is a secondary while n-propyl carbocation is a primary carbocation.................whereas in case of ethyl, its most stable carbocation is the ethyl carbocation itself.........hence is is more stable than the n-propyl carbocation........

Nidhi Gupta

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20 Sep 2012 14:08:41 IST

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i think electronic shielding of valence or bonded electrons comes into play in such indefinite atomic number comparisons

Madhusudan Chavan

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20 Sep 2012 19:34:41 IST

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The relative stability of carbocations can be easily measured through heterolytic bond dissociation energies. The lower the value of heterolytic bond dissociation energy, greater is the stability of the carbocation. For CH3CH3-Cl = 799, and for CH3CH2CH2-Cl = 744. Thus n-propyl > ethyl.

However, n-propyl isomerises to more stable iso-propyl carbocation.

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