CHE101 (B.Tech.

Chemistry Course)

Lecture - 26

Carbocation &Carbanion:Stability
Prepared By

Dr. Harmider Singh

Department of Chemistry Lovely Professional University, Phagwara, Punjab, India.

E-mail: harminder.singh@lpu.in

Carbocation stability Carbocations are classified as primary (1o), secondary (2o), or tertiary (3o), based on the number of R groups bonded to the charged carbon atom. As the number of R groups increases, carbocation stability increases.

Carbocation stability

Carbocation Stability

The

inductive effect

the electron-deficient carbon bearing the

positive charge polarizes electrons of the adjacent sigma bonds toward it

the positive charge on the cation is not

localized on the trivalent carbon, but delocalized over nearby atoms

the larger the volume over which the positive

charge is delocalized, the greater the stability of the cation

Carbocation stability

Carbocation stability

Carbocation Stability
The order of carbocation stability is also a consequence of

hyperconjugation.

Hyperconjugation partial overlap of the bonding orbital of an adjacent C-H bond with the vacant 2p orbital of the cationic carbon delocalizes the positive charge and also the electrons of the adjacent bond replacing a C-H bond with a C-C bond increases the possibility for hyperconjugation

Example: CH3+ cannot be stabilized by hyperconjugation, but

(CH3)2CH+ can.

Carbocation stability

Carbanion stability

Carbanions have 8 valence electrons and a

negative charge

Carbanion stability

Carbanion stability

Carbanion stability

Carbanion stability

Carbanion stability

Carbanion stability

Carbanion stability