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Thiol

SH (R–SH)

Ketone

C=O in middle of chain (R–C(=O)–R)

Aldehyde

C=O at end with H (R–CHO)

Carboxylic acid

C(=O)OH (R–COOH)

Ester

C(=O)OR (R–COOR)

Amide

C(=O)NR₂ (R–CONR₂)

Ether

R–O–R

Amine

R–NH₂ / R₂NH / R₃N

Alkyl halide

R–X (F

Sulfonic acid

R–SO₃H

Protonated alcohol

R–OH₂⁺

Acetic acid

pKa 4.8

Benzoic acid

pKa 4.2

Trifluoroacetic acid

pKa 0.25

Hydronium

pKa -1.7

Ammonium

pKa 9.25

Ethanol

pKa 16

Ethyne (terminal alkyne)

pKa 25

Hydrogen (H₂)

pKa 35

Ammonia

pKa 38

Ethene (sp² C-H)

pKa 44

Methane (sp³ C-H)

pKa 50

Acid strength

lower pKa = stronger acid

Base strength

higher pKa of conjugate acid = stronger base

Strong Lewis acid

electron pair acceptor

Strong Lewis base

electron pair donor

Water solubility increases

more OH/N/O groups

Benzene solubility increases

more nonpolar hydrocarbon character

Hybridization: sp

2 electron groups

Hybridization: sp²

3 electron groups

Hybridization: sp³

4 electron groups

Triple bond carbon

sp

Double bond carbon

sp²

Single-bond carbon

sp³

Benzene ring carbon

sp²

Bond strength

sp > sp² > sp³

Bond length

single > double > triple.