Hybridization and Bond Data

Functional Group SMILES

• Ethanol (hydroxyl): CCO
• Ethanal (aldehyde): CC=O
• Propan-2-one / acetone (ketone): CC(=O)C
• Ethanoic acid (carboxyl): CC(=O)O
• Ethylamine (amino): CCN
• Nitromethane (nitro): C[N+](=O)[O-]
• Chloromethane (halide): CCl

Key Reactions with Conditions

Free radical halogenation (substitution): C + $Cl_{2}$ --[hν or $\Delta$]--> CCl + HCl

Dehydration of ethanol (elimination): CCO --[conc. $H_{2}SO_{4}$, 170°C]--> C=C + $H_{2}O$

Dehydrohalogenation (elimination): CCBr + KOH --[alc., $\Delta$]--> C=C + KBr + $H_{2}O$

Markovnikov addition of HBr to propene (addition): CC=C + HBr --[no peroxide]--> CC(Br)C (2-bromopropane, major product)

Anti-Markovnikov addition of HBr (addition, peroxide effect): CC=C + HBr --[ROOR, hν]--> CCCBr (1-bromopropane, free radical mechanism)

Intermediate Stability Data

$\text{Carbocation stability: } 3° > 2° > 1° > \text{CH}_3^+$

$\text{Carbanion stability: } \text{CH}_3^- > 1° > 2° > 3°$

$\text{Hyperconjugative structures} = \text{number of alpha C-H bonds}$

Example: For ($CH_{3}$)_{3}$C^{+}$ (tert-butyl cation): 9 alpha C-H bonds → 9 hyperconjugative structures → highest stability among simple alkyl carbocations.