Organic Chemistry

Introduction to localized & delocalized bonding

 localized and de localized bonding
•Localized bonds:
• Electron density concentrated between nuclei of combining atoms.
• CH3-CH3, CH2=CH2
Delocalized bonds:
Electron density not concentrated between two atoms but spread over
more than two nuclei.
CH2=CH-CH=CH2 , benzene
Localized Delocalized
Localized
Delocalized
1. electron density fixed between bonded atoms
1. electron density not fixed between bonded atoms
2. only one Lewis structure can be written
2. morebonded
1. electron density fixed between than one structures 1.
atoms canelectron
be written
density not fixed between bonded atoms
3. bond length, bond energies, stability of
2. only one Lewis structure can molecule predictable 2. more than one structures can be written
be written
C-C =154 pm
C=C = 134 pm
3. bond length, bond energies, stability
3. not of
predictable 3. not predictable
molecule predictable in case of benzene in case of benzene
C-C =154 pm All C-C bond lengths are equal = 139pm
All C-C bond lengths are equal = 139pm
C=C = 134 pm
4.  No alternation of bonds
4. Alternation of single and double/triple bonds
4.  No alternation of bonds 5. CH3-CH3, CH2=CH2 4. Alternation of single and double/triple bonds
5. CH3-CH3, CH2=CH2 5. CH2=CH-CH=CH2 , benzene 5. CH2=CH-CH=CH2 , benzene
Conditions for delocalized bonding

1. Double bond in conjugation with double / triple bond

H2C=CH-CH=CH2 H2C=CH-C≡N

2. Double/ triple bond in conjugation with p-orbital

H2C=CH-CH2+ ↔ +CH2-CH=CH2
3. C-C with C=C or p-orbital
Hyperconjugation [will be discussed a bit later]