Stability Overview 1 of 6

Bonds
Consider the bonds at play. The stronger the bond,
the more stable/ less volatile a molecule is.

1. Covalent Bonds: involves the sharing of

electron pairs between two or more atoms that
form a molecule. It is the strongest of the bonds/
interactions we deal with.

How to remember this? Think of the electrons as

children of the atoms. They have kids together!
Thats a pretty difficult bond to break.

2. Ionic Bonds: An interaction between two

oppositely charged ions. This is slightly weaker
than Covalent bonds, but still pretty strong.

3.Ion Dipole the interaction between a charged ion and a molecule that has a dipole
( difference in charge from one end of the atom to the other)

4.Hydrogen Bonds a type of dipole-dipole interaction that occurs between Hydrogen and
one of the following electronegative atoms: Florine, Oxygen or Nitrogen

(Mnemonic “getting HI(drogen) can be FON”)

4. Dipole-Dipole: When two or more atoms have dipoles ( an unequal charge throughout
the atom) and interact. Denoted +δ and -δ for the positive and negative ends respectively.

5. Van der Waals Interaction: technically not a bond, and very much the weakest of the
intermolecular interactions. This refers to the very weak “gravitational” pulls between
particles / molecules due to mass.

If you recall from Newtonian Physics: Fgrav= (mass A) + (mass B)/ (r^2),

When considering the size of the particles, the gravitational force between them is
astronomically small.

Degrees of Unsaturation

A degree of unsaturation refers to the number of branches, rings, double or triple bonds
a molecule has.

Saturation Number: How many Hydrogens a hydrocarbon chain could have if it were fully
saturated. ( fully saturated chains have higher boiling points than unsaturated ones)

[Saturation number = 2C +2/2]

C=number of carbons

Unsaturation Number: How many things are impeding a molecule from being fully
saturated.

[Unsaturation Number = (2C+2)-H-x+N/2]

C= number of carbons

H= number of Hydrogens

X = number of halogens

N= number of N

+ trivalent atoms ( Galium, Indium etc)

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Vaporization Points Consider the structure of the alkane presented.

1. Increasing the length of the hydrocarbon chain will raise the boiling point (↑stability)

2. Increasing branching will lower the boiling point (↓ stability)

* while lengthening a hydrocarbon chain will increase stability, remember that there are weak
van der waals interactions between alkane molecules, therefore the boiling point is still low.

Polarity: Polar compounds readily disassociate in water because they’re really soluble.

Functional Group Polarity: ( from most to least)

Mnemonic: “ Ancient Alchemists Are Kick-Ass And Exude Extreme Arrogance”

1. Amides: (CONH2) A derivative of the Carboxl (COOH), it can accept hydrogen bonds on
both or either N or O, making it very polar/soluble

2. Acids: two oxygen atoms can readily accept hydrogen bonds, making them very
hydrophilic

3. Alcohols: contain an Oxygen atom that can hydrogen bond, but also a methyl, which is
rather nonpolar.

4. Ketones and Aldehydes: both lack Hydroxyls ( OH) and so they cant make intermolecular
hydrogen bonds, but they both have Oxygens that can accept these bonds. One should
also note the considerably higher boiling point than the alkanes, indicating weak
intermolecular dipole-dipole forces.

5. Amines: Nitrogen is much less electronegative than Oxygen but it can still accept
Hydrogen bonds. As a result, it will create a weaker dipole, and therefore less polar
interaction

6. Esters: note the similar structure to the ketones and the aldehydes, however, it has a lower
boiling point, indicating its atoms are not engaged in a strong polar dipole-dipole
relationship.

7. Ethers: although an oxygen is present, it is engaged in a C-O bond, making hydrogen

bonding impossible.

8. Alkanes: good old fashioned hydrocarbons. There are very weak intermolecular forces at
play with these babies. None of these are capable of hydrogen bonding.

Acidity/Basidity:

Strong acids and bases disassociate fully in water. Acid strength can be measured in a
number of ways. Consider the following:

Acids Bases

Lewis Donates protons Lewis Receives protons

Brønsted Lowry Accepts electron pairs Brønsted Lowry Donates Electron pairs

Arrhenius Disassociates to make Arrhenius Disassociates to make

H+ ions in solution OH- ions in solution

Ka ( Acid Disassociation Constant) measures the strength of an acid ( or base) at

equilibrium. That is, how willing a substance is to donate its protons/ disassociate. A small
Ka denotes a strong acid.

Ka = [conjugate base][H+]/[acid]

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pH: the scale ranging 0-14 that shows the concentration of protons in a solution. A small
pH indicates an acidic solution. A larger pH indicates a basic solution. 7 is neutral ( equal
H+ to OH- concentration)

pH = -log[H+]

Pka: the percentage at which 50% of the substance has disassociated.

pKa = - log [Ka]

Henderson Hasselbalch Equation:

pH= pKa + log ([conjugate base]/[acid])

Rules of thumb:

• Strong acids disassociate 100% in solution, and are much less stable than weak acids

• Strong acids make weak conjugate bases.

• A low pka refers to a strong Acid

• A high Ka refers to a strong Acid

• Ph doesn’t overtly reference the strength of an acid, but rather the concentration of
protons it has released into solution.

Acid Strength:

Mnemonic “ Sally Stupidly Consumed Pure Aresnic, Was Agonizingly Killed. 1 2 3”

Strong acids > Sulfonic acids> Carboxylic acids> Phenols >Alcohols/water> Aldehydes/
Ketones>sp1 C-H bonds > sp2 C-H bonds >sp3 C-H bonds.

Strong Acids:

1. Perchloric Acid( HClO4)

2. Sulfurous Acid ( H2SO4)

3. Nitrous Acid ( HNO3)

4. Hydrochloric Acid ( HCl)

5. Hydrobromic Acid ( HBr)

6. Hydroiodic Acid (HI)

Substitution “where’s the double bond?”/ “where’s the positive charge?”

Most Stable Least Stable

Tertiary Carbon Secondary Carbon Primary Carbon Methyl ( CH3)

3 carbons attached 2 carbons attatched 1 carbon attached 0 carbons attached

Stability Overview 4 of 6

* For (-) charges, it goes goes the opposite way. ( Methyls are the most stable, and tertiary
carbons are the least)

Resonance Structures
Generally speaking, the more resonance structures a molecule has, the more stable it is. This
is helpful to consider when presented with the lewis structures of various molecules and
nothing else.

When can you make a resonance structure?

When you have excess electrons adjacent to a pi bond ( double bond), but not on it.

The most stable molecules:

1. Have the octets of all their atoms filled. ( this is the most important rule of all)

2. Have the fewest number of formal charges.

3. Have any negative charges on the most electronegative atom, or the positive charge on the
least electronegative atom.

Recall: the closer you get to Florine, the more electronegative an atom is.

Calculating formal charge:

FC = V - (L +B)

FC = formal charge

V = valence electrons

L= unpaired electrons

B= bond

Leftmost Oxygen:

Fc = 6 - (4+2) = 0

Rightmost Oxygens

Fc= 6 - (6 +1) = -1

Nitrogen

FC = 5 -( 0 + 4) = +1

Nitrate has 2 formal charges !

Drawing resonance structures:

1. Draw the molecule complete with lone pair electrons. Take the octet into account.

2. Calculate the formal charges of each of the atoms.

3. If there is a formal charge, does it lie adjacent to a double bond ?

4. If yes, you can make resonance structures!

5. Move the negative charge to the most electronegative atom. (usually Oxygen). If there is
more than one oxygen, then each oxygen can be a structure.

6. If there are both positive and negative formal charges that cancel out, let them.

7. Remember, as you move around electrons, the valence shells of different molecules may fill
and empty resulting in double bonds in new and interesting places. Make sure the number
of bonds in your new resonances match the same number of bonds in the original
molecule.

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Let’s consider a carboxylate ion. (conjugate base of carboxylic acid)

FC: topmost Oxygen

6 -(4+2) = 0

FC rightmost Oxygen:

= 6- (6+1) = -1

There is a formal charge of (-1) on the rightmost Oxygen. We can

move that charge to the topmost oxygen, but that will mean the pi
bond moves to the rightmost oxygen so that all the octets are
fulfilled.

Therefore: Carboxylic acid has two resonance structures:

Inductive Effects

The closer an acidic proton(/negative charge) is to the electronegative group, the greater the
stabilizing effect

Conformational Isomerism
Conformational Isomers: compounds with the same molecular formula and same atomic
connectivity BUT the rotation is different around a carbon single bond.

Consider Butane:

Recall: CH3 = Methane (“ME”)

<—Imagine you’re looking “down the barrel” of the rightmost carbon.

The center bond between the two innermost Carbons will be the axis
around which our molecule will rotate as seen below.
Stability Overview 6 of 6

Eclipsed conformations provide the most “steric hindrance”. That is, substituents prefer
having as much room as they can to spread out. When there are too many too close together,
the molecule experiences “steric hindrance” or “strain” In addition, covalent bonds like the
ones above are composed of excess electrons, they will electronically repel one another.

For this reason from least to most stable:

Eclipsed< Guache < Staggered (anti)

Conformations of Ring Structures:

Any time you’ve got a molecule with “cyclo”, it means you’re dealing with a ring.

Let’s have a look at cyclohexane ( here it is as a lewis diagram)

There are lots of different representations we

could use:

For our purposes, let’s focus on the chair.

The Hydrogens in red that run up and

down are Axial Hydrogens.

The Hydrogens hanging off the side at

various angles in blue are Equatorial
hydrogens.

When we get into cyclohexanes that have

substituents OTHER THAN HYDROGEN
steric strain starts becoming an issue.

Generally: you want to put large substituents in the equatorial position to minimize strain and
promote stability.