Chem 116
Fall 1998

Lecture Notes
September 16, 1998

Topics

Polarity

Acids and Bases


Polarity

Polarity is an indication of the charge distribution in the molecule. Nonpolar molecules have a completely symmetrical charge distribution; there is no excess charge anywhere in the molecule. Polar molecules have a partial charge separation. This different from ionic compounds like NaCl in which there is a full separation of charge to create ions (in the case of NaCl, the ions are Na+ and Cl-). HCl is an example of a polar molecule. Here the hydrogen and chlorine attract electrons differently; the Cl has a stronger attraction for electrons than H. This means that Cl will have a partial negative charge whereas H will have a partial positive charge. Again, this is not a full separation of charge; the atoms are still covalently bound. It's just that the electron density is more concentrated around Cl. We represent partial positive and negative charges with d+ and d-, respectively. The HCl molecule may be written as

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The image below shows the space-filling structure (relative atomic sizes are shown) of HCl.

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You can identify nonpolar molecules by their symmetry - they are completely symmetrical. Polar molecules are less symmetrical. This is because different types of atoms will attract electrons differently, leading to uneven distribution of electrons. (We will learn how to assess polarity in more detail later in the semester.) Hydrocarbons tend to have low polarity.

For purposes of solubility, we will note that nonpolar molecules dissolve in nonpolar solvents and polar molecules dissolve in polar solvents ("like dissolves like"). Consequently, a nonpolar solvent can extract a nonpolar compound from a polar solvent. The in-class demonstration illustrated this; we extracted I2 (nonpolar) from water (polar) with CCl4 (nonpolar).

A quantitative measure of a molecule's polarity is its dipole moment. The dipole moment is strictly defined as the product of the partial charge and the separation of charge

Dipole Moment = partial charge x distance

Molecules that are completely nonpolar have a dipole moment of zero. A more polar molecule has a larger dipole moment. The table below lists the dipole moments of a few common molecules. (The units of dipole moment are Debye.)

Name Dipole Moment (Debye)
carbon tetrachloride (CCl4) 0.0
benzene (C6H6) 0.0
chloroform (CHCl3) 1.01
hydrogen chloride (gas), HCl 1.08
ethanol (C2H5OH) 1.69
methanol (CH3OH) 1.70
water (H2O) 1.85
acetone (C3H6O) 2.88

Acid/Base Reactivity

We can extract an acid from a solvent by reacting it with a basic solvent and we can extract a base by reacting it with an acid. For the purposes of this discussion, we will use the Bronsted-Lowry definition of acid/base behavior.

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Here HA is the acid; it donates a proton to H2O. The resulting cation, H3O+, is called the hydronium ion.

Strong acids dissociate completely in water. Weak acids do not. When HCl is dissolved in water, it becomes a strong acid (called hydrochloric acid). The relevant reaction is

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Acetic acid, CH3COOH, is an example of a weak acid; not all of the CH3COOH molecules donate protons. The relevant reaction is

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The wpeA.jpg (931 bytes)means that the reaction is reversible; it goes in both directions (I guess it can't make up its mind). Hence the acetic acid does not dissociate completely and the solution contains a mixture of CH3COOH molecules and CH3COO- (acetate) anions. Acetic acid is an example of an organic acid called a carboxylic acid. All carboxylic acids, which are characterized by the -COOH group, are weak.

The table below lists common acids.

Name Formula Strong/Weak
Hydrochloric Acid HCl Strong
Sulfuric Acid H2SO4 Strong
Nitric Acid HNO3 Strong
Perchloric Acid HClO4 Strong
Formic Acid HCOOH Weak
Acetic Acid CH3COOH Weak
Hydrofluoric Acid HF Weak
Phosphoric Acid H3PO4 Weak
Carbonic Acid H2CO3 Weak
Nitrous Acid HNO2 Weak
Ammonium NH4+ Weak

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Note that NH3 accepts a proton from H2O. The table below lists common bases.

Name Formula Strong/Weak
Sodium Hydroxide NaOH Strong
Potassium Hydroxide KOH Strong
Calcium Hydroxide Ca(OH)2 Strong
Magnesium Hydroxide Mg(OH)2 Strong
Ammonia NH3 Weak
Methanamine CH3NH2 Weak

Organic bases tend to contain nitrogen; nitrogen is a good proton acceptor. In the table above, methanamine is an example of an organic base.


Questions? Send email to pholt@bellarmine.edu