PCH200: Pharmaceutical Organic Chemistry (A.

Y 2022- 2023)
Midterms Supplemental Notes (TLA 2 and TLA3)

1. Relative Strength of Intermolecular interactions (Strongest to Weakest)

Ionic Bonding > Hydrogen Bonding > Dipole-Dipole Interactions > London Dispersion

2. Decreasing order of boiling points (Top to Bottom)

Amide > Carboxylic Acid > Alcohol > Ketone > Aldehyde > Amine > Ester > Ether > Alkane

3. Decreasing order of acidity (Top to Bottom)

H+ > Carboxylic Acid > Phenol > Nitrile > Ammonium > Thiol > Water > Alcohol > Aldehyde > Ketone > Ester > Alkyne >
Hydrogen > Amine > Alkene > Alkane

4. Factors affecting Reaction Rates

A. Concentration – directly proportional (↑ concentration, ↑ rate)
• Ways to increase concentration
o ↑ particles, the same volume
o ↓ volume, the same particles
B. Temperature – directly proportional (↑ temperature, ↑Kinetic Energy, ↑ rate)
C. Pressure – directly proportional (↑ pressure, ↓ volume, ↑ rate)
• Only affects GASES
D. Surface Area - directly proportional (↑ surface area, ↑ rate)
• Surface area – total area occupied by the particle
E. Catalyst
• Catalyst – substance that speeds up reaction rate by lowering activation energy
o ↓ Activation energy, ↑ reaction
o Not consumed in the reaction

5. Chemical Equilibrium
• Balance equation: 𝑎𝑨 + 𝒃𝑩 ⇋ 𝒄𝑪 + 𝒅𝑫
o a, b, c and d → Coefficients / Number of Moles
o A, B, C and D → Concentration of atoms / molecules
o A and B → Reactant
o C and D → Product
[𝐶]𝑐 [𝐷]𝑑
• Equilibrium Constant, Keq: 𝐾𝑒𝑞 =
[𝐴]𝑎 [𝐵]𝑏
o Keq is always product over reactant
o Solid and liquid states are constant, therefore not included in the formula
o Only the concentration of gases is considered
o Keq values
Direction Meaning
Keq > 1 Forward [Product] > [Reactant]
Keq = 1 Equilibrium [Reactant] = [Product]
Keq < 1 Backward [Reactant] < [Product]
**Backward Reaction – Right to Left (Products to Reactants)
**Forward Reaction – Left to Right (Reactants to Products)
**[ ] - Concentration
• Le Chatelier’s Principle
o System at equilibrium under stress will shift to relieve the stress
a. Concentration
Reactant Product
Increase To the Right To the Left
Decrease To the Left To the Right
b. Pressure and Volume
Pressure Volume Shift
↑ ↓ Shift towards fewer number or gas moles
↓ ↑ Shift towards larger number or gas moles
** NOTE: Compare the total gas moles of reactant and product side

University of the Immaculate Conception | Prepared by LFVL

 c. Temperature
Endothermic / Endergonic Exothermic / Exergonic
↑ Temp in Reactant Side To the right To the left
↓ Temp in Reactant Side To the left To the right
↑ Temp in Product Side To the left To the right
↓ Temp in Product Side To the right To the left
▪ Endothermic / Endergonic – absorption of energy → formation of bonds (anabolism)
▪ Exothermic / Exergonic – release of energy → breaking of bond (catabolism)
d. Catalyst
▪ No effect in equilibrium
6. Thermodynamics
• Gibbs Free Energy (ΔG)
o Change in energy that occurs during a chemical reaction
o Formula
a. ∆𝑮 = Gproducts − Greactants
b. ∆𝑮 = ∆𝑯 − 𝑻 ∗ ∆𝑺
▪ ∆𝑯 – Enthalpy change (heat of reaction)
▪ 𝑻 – Temperature
▪ ∆𝑺 – Entropy Change (change in molecular randomness during reaction)
** NOTE: ∆𝑮 < 𝟎 means the reaction is spontaneous
∆𝑯 < 𝟎 ∆𝑯 > 𝟎
∆𝑺 > 𝟎 Spontaneous (↑ T) Spontaneous
∆𝑺 < 𝟎 (↓T) Spontaneous Non-spontaneous
c. ∆𝑮° = −𝑹𝑻 (𝒍𝒏𝑲𝒆𝒒 ) - Standard Free Energy Change
▪ R = 1.987 cal/(K · mol)
▪ T = Temperature in Kelvin
▪ 𝐥𝐧𝐊 𝐞𝐪 = Natural logarithm of Keq
o Energy is released on the favored side of an equilibrium reaction
a. Exergonic Reaction
▪ Reaction that has negative free energy change
▪ Spontaneous
▪ Energy is lost
▪ Chemical Equation: AB → A + B + ∆
b. Endergonic Reaction
▪ Reaction that has positive free energy change
▪ Non-spontaneous
▪ Energy is absorbed
▪ Chemical Equation: A + B + ∆ → AB

University of the Immaculate Conception | Prepared by LFVL