Solvents

Let's Talk Solvents

Solvents are essential in chemistry, influencing reaction outcomes by dissolving reactants and affecting their interactions. Polarity, a key property, dictates how well substances mix ("like dissolves like"). We classify solvents as polar or nonpolar, and further categorize polar solvents as protic or aprotic.

Polarity

Polar solvents possess distinct positive and negative regions, while nonpolar solvents lack this charge separation. The dielectric constant (ε) quantifies polarity, but structural features often provide clues. Water (high ε) exemplifies polarity due to O-H bonds, whereas alkanes (low ε) are nonpolar.

Polar Protic and Aprotic Solvents

Polar protic solvents (e.g., water, alcohols) contain O-H or N-H bonds, enabling hydrogen bonding. Aprotic polar solvents (e.g., DMSO, DMF, acetone, acetonitrile) lack these bonds but remain polar due to other structural features.

Solvents and Reactions

Solvent choice is critical. SN1 reactions often favor polar protic solvents, which stabilize carbocation intermediates. SN2 reactions commonly utilize polar aprotic solvents, as these do not strongly solvate the nucleophile, allowing it to attack more readily.  We will look at this in more detail next.

Solvent Chart

Solvent Polarity (ε) Protic/Aprotic Common Use
Water 78 Protic SN1, polar compounds
Methanol 33 Protic SN1, polar compounds
Ethanol 25 Protic SN1, polar compounds
Acetic Acid 6 Protic Acidic conditions
Acetone 21 Aprotic SN2, nonpolar compounds
Acetonitrile 36 Aprotic SN2, polar compounds
DMF 37 Aprotic SN2, polar compounds
DMSO 47 Aprotic SN2, polar compounds
Hexane ~2 Nonpolar Nonpolar compounds
Key Takeaways
  • Solvent Polarity: "Like dissolves like." Polar solvents dissolve polar compounds; nonpolar solvents dissolve nonpolar compounds.
  • Protic/Aprotic: Protic solvents have O-H or N-H bonds (can hydrogen bond); aprotic solvents do not (but are still polar).
  • Reaction Solvents: SN1 reactions often use polar protic solvents; SN2 reactions often use polar aprotic solvents.
  • Solvent Chart: Use the chart to find solvent properties (polarity, protic/aprotic) and typical applications.