Chemistry · Ch 14 — Haloalkanes and Haloarenes
Nature of C-X Bond in Haloalkane
14.3.2
Nature of C-X Bond in Haloalkane
The C-X bond is polar because halogens are more electronegative than carbon: carbon carries a partial positive charge (delta+) and the halogen a partial negative charge (delta-). The bond forms by overlap of carbon's sp3 orbital with the halogen's half-filled p-orbital. Down the halogen group (F to I) atomic size increases, so C-X bond length increases and bond strength (enthalpy) decreases from C-F to C-I; the table below (measured for CH3X) shows bond length rising and bond enthalpy falling steadily from fluoro- to iodomethane, while dipole moment (bond polarity) actually peaks at CH3Cl rather than CH3F, since polar …
Table 14.2Bond length, bond enthalpy and polarity of the C-X bond in CH3X
| Bond | Bond length (pm) | Bond enthalpy (kJ mol-1) | Polarity (dipole moment, Debye) |
|---|---|---|---|
| CH3-F | 139 | 452 | 1.847 |
| CH3-Cl | 178 | 351 | 1.860 |