Module 2 – weeks 6 to 9

Nomenclature and naming binary compounds

How is H an exception?

Ionic compounds:
- cation (+) is named before the anion (-)
- Is important to balance the charges
o (Remember that when you write the name of the compounds you don’t use
prefixes like “mono, penta…” bc since the charges are balanced there is no
need)

Be able to recognize what is an ionic compound and what is a covalent compound

- Look at the differences in electronegativity

Polyatomic ions (remember list of the ones we need to know)

Covalent compounds
- Look at the periodic table, the elements more towards the left are named first, and if the
elements are in the same group the ones that are more down come first
- I think “covalent compounds need prefixes like “mono, di…” but for organic compounds
the prefixes are different!
- When they are organic compounds: C first, then H and then other elements in
alphabetical order

Organic chemistry
Different representations
- Molecular formula (C6H12O)
- Line structures (H are not shown)
- Structural formulas (CH3CH2CH2)

Naming of organic compounds

- Prefixes: meth, eth, prop, but
- Recognize the number of C atoms to name it correctly
- Remember! Naming is based on the longest C-chain
o Recognize branch points and longest C-chain

Functional groups
(You should: “be able to recognize them in a given structure, draw them, explain sm about
their physical and chemical properties (types of bonding, electronegativity, intra and
intermolecular forces – can explain melting and boiling points, ex. If it’s a strong ionic bond,
then you know that boiling point will be higher)”)

- Alkanes
o C and H joined with single bonds
 - Alkenes
o C=C double bonds
- Alkynes
o Triple bonds

Functional General Functional group Physical properties Names

groups formula
Alcohol R-OH -OH (hydroxyl -OH group is polar and can Alkyl group
groups). Ex: ethanol hydrogen bond – leading to
higher boiling points Alkane prefi

Ether R-O-R’ Not water soluble. Have low Name both a
boiling points due to inability to methyl ether
form H-bonds w/ each other
Alkyl group
Aldehyde R-CHO
Common pr
(Carbonyl
group -C=O at the Alkane prefi
end of the
compound)
Ketone R-CO-R’ Name alkyl
ketone
(Carbonyl
group inside the n of C prefix
compound) butanone; o
2-pentanone
Carboxylic acid R-COOH or Common na
R-CO2H  ex:
Alkane prefi

Ester R-CO-OR'
Alcohol alky
acetate
(Carboxylic
acid + alcohol  Alcohol alky
esterification) “oate”:

Amine RNH2 Derivates of ammonia, act as

R2NH weak bases. Name alkyl
R3 N Amine can H-bond, which
makes them have elevated “amino” + al
boiling points and be soluble in
(There are
water
3 types of amines:
 primary (1 C),
secondary (2C),
tertiary (3C)
Amide R-CONH2
Common ac
(Derivative
of Alkane prefi
carboxylic
acid where (here OH is replaced
-OH is by NH2)
replaced
by: NH2;
NHR; NR2

Esterification – formation of an ester

- carboxylic acid + alcohol  ester + water molecule
- happens during acidic conditions (H+ catalyst)

Isomerism
- Important in isomers; recognize chiral compounds (C atoms with 4 different things
attached)

- Structural
o Have the same atoms (same molecular formula) but different connectivity (in
different positions)
o Will have different physical properties (ex. Boiling point)

o and (both have C4H10)

- Stereoisomers – have the same connectivity but different 3-D structures
o Cis/trans isomers – involve double bonds
 Trans – substituents are on opposite sides of the double bond
 Cis – substituents are on the same side of the double bond

 (ignore the H atoms)

 o Enantiomers (optical isomers)
 non‐superimposable mirror images (don’t complete each other - right and
left hands on top of each other). Are a reflection of each other but non-
superimposable

Stoichiometry
Always balance the equation (check if it’s balanced)

Limiting reagents – use stoichiometric calculations to identify limiting reagents

- We can only make as much product as the limiting reagent can make (remember
hamburger example)
- Work in number of moles! When you get a question about limiting reagents the first
thing you should do is convert things to number of moles (n) because then you can
compare them.
o n=m/M
o pV=nRT
o C=n/V
- How to do a limiting reagent’ question (in this case “what is the max amount that could
be made?”):
o 1. What ratio are the reactants and product in the balanced equation?
o 2. How many moles of each reactant? (Calculate the n of each reactant)
o 3. Which is the limiting reagent? (NEVER assume that the reactant with smaller
stoichiometric number is the limiting reagent)
 To work this out assume the first reactant is the limiting reagent and work
out how many moles of product you could make. Then, do this for the
second reactant as well. Compare which one would lead to the smaller
value of moles of the product.


 In this example with nitric acid being the limiting reagent the number of
moles of the product were smaller (1.88 mol); therefore, nitric acid is the
limiting reagent.
o 4. What amount of product (in this ex. CuSO4) can be made? (Use the n of moles
from the result of the limiting reagent!)
  You should work out the mass so n=m/M always tends to work! In this
case n(CuSO4) = 1.88
 Remember to PAY ATTENTION to what the question is asking, maybe
they don’t ask for the amount. For ex. If it was a gaseous reactant, you
might get pressure, volume and temperature instead and then use the
Ideal Gas Law to find n, the number of moles.

% Yield
actual
- % yield = x 100% (remember! They have to be of the same thing and on the
theoretical
same units)
o What unit does it have to be? It doesn’t matter, as long as they are the same! It
could be moles, grams, kg, litres, etc.
- In CHEM1090 we assume that the theoretical yield: the amount of product if 100% of
the limiting reagent reacted
- Ex: 255 g of ethanoic acid is reacted with an excess of 3‐ methylbutanol in the
presence of sulfuric acid catalyst, to give 485 g of 3‐methylbutyl ethanoate.

What is the theoretical yield, in g, of the reaction?

o 1st find out the n of moles of ethanoic acid (the limiting reagent)
 M = 60.06g/mol; m=255g; n=m/M  n = 4.25 moles

o 2nd compare the ratios (limiting reagent and product)

 1 mol ethanoic acid produces 1 mole of 3‐methylbutyl ethanoate: therefore,
3‐methylbutyl ethanoate = 4.25 moles

o 3rd based on the ratio, now you have the theoretical yield in moles, of the product.
In the case of this exercise, we want the yield in grams, so use the formula:
n=m/M
 M of s 3-methylbutyl ethanoate = 130.21g/mol; n = 4.25
 m=M x n  m = 130.21 x 4.25  m = 553.4

What is the percentage yield of this reaction?

actual
o % yield = x 100%  actual is the one given in the question, theoretical
theoretical
is the one we worked out based on the n of moles of the limiting reagent and
comparing the ratios.
485 g
 % yield = x 100%  87.6%
553.4 g

- Given a percentage yield, work out what amount of starting material is needed.

Step 1 – recognize the amount (mass or moles) of the compound X the question is asking for
Step 2 – calculate the molar mass (M) of compound X
m
Step 3 – calculate n of moles of compound X (n = )
M
o This will give you the n of moles that we want to make
 Step 4 – Calculate the n of moles of the reactant, as if it was all going to react to give the
product (compound X). (the theoretical n)
o To do that compare the ratios (you have already calculated the n of moles of the
product (compound X) so just do stoichiometric calcs, ex. If the n of X=3.2 and
the ratio is 1:1, then do (3.2)x1, and find out the n of the reactant (this would give
the n of reactant if it was all going to react to give the product)
o But for ex. if the ratio is 1:1 but the question says that 1mole of reactant actually
produces 70% of compound X; then the ratio would be 1mol:0.7 mol
Step 5 - %yield tells is how much more reactant we actually need
o For ex. if the question says that only 70% of the reactant will react to form
compound X we know that the %yield is 70%
o So for ex. if the ratio is 1:1 (looking at the equation), now with the theoretical yield
we know that 1mole of reactant actually produces only 70% of compound X , so
the actual ratio will be 1 : 0.7
Step 6 – calculate the n of moles of the reactant that is actually needed
o With the actual ratio (ex. 1:0.7) you can calculate the actual n by comparing the
ratios
Step 7 – calculate the molar mass (M) of the reactant
m
Step 8 – calculate the mass of the reactant needed (n = )
M
o By doing that you find the amount of starting material needed

Simplified table explaining these steps:

Step 1 Step 2 Step 3 Step 4 Step 5 Step 6 Step

m of product M of product n of product Theoretical n % Yield Actual n of M of
of reactant reactant reac
How By comparing actual By comparing new
to do m ratio shown in theoretical ratio given by the
n=
it M the equation % yield

Energies of reaction
ΔH  enthalpy of reaction (remember, change in heat energy)

Endothermic (+ ΔH, heat is absorbed) and exothermic (- ΔH, heat is released) reactions
- Reaction pathway diagrams

o
 - Example of exothermic reactions: combustion reactions
o C3H8 + 5O2 3CO2 + 4H2O H = ‐2220 kJ mol–1 of C3H8
o 1 mole of propane releases 2200 kJ of heat energy
- Where does energy come from?
o During chemical reactions it takes energy to break a chemical bond. Energy is
released when a chemical bond is made
- Thermochemical equation stoichiometry
o “ex. How much heat is released when 10 g of H2 gas reacts with an excess of
oxygen gas?”

Rate of reaction – how much energy a reaction uses/needs, and how fast it goes

Δconc – change in concentration (of a reactant or product)

Δtime – amount of time

Collision theory
- To react, the reactants need to collide in the right orientation and with the correct
amount of energy to react
- Can explain why certain action increase the rate of reaction (increase temperature,
stirring, increase concentration, add a catalyst, increase surface area)
o Catalysts – increase rate but are not consumed by the reaction. Does not affect
equilibrium. They work by decreasing the EA barrier. Lower EA = more molecules
able to react
 o

EA - Again, with the Reaction pathway diagrams, we learned about EA (activation energy –
energy barrier that has to be overcome)

Equilibrium
Remember for concentrations! Always check if the volume is 1L, otherwise you’ll have
to convert your moles into concentration c=n/V  maybe use n=m/M as well for c
Dynamic process represented by: A ⇌ B
- Reaction is going backwards and forward all the time (doesn’t go to completion)

Equilibrium constant (Kc) for a system at equilibrium  ex: aA + bB ⇌ cC + dD

[C]C [D] d
- Kc =  Concentration of Products /reactants, all raised to their stoichiometric
Aa Bb
coefficients

o Kc < 1  reactants > products

 Position of equilibrium lies strongly towards the reactant
o Kc = 1  reactants = products
 Position of equilibrium in the middle
o Kc > 1  reactants < products
 Position of equilibrium lies strongly towards the products
- Don’t include pure liquids (l) or pure solids (s) – pay attention on heterogeneous
equilibrium
- Kc is dependent on temperature
- The equilibrium constant has the same value regardless of the concentrations of
reactants and products that are used to begin with! (Kc is different than just
concentration)
o The concentrations will be different, but the equilibrium constant will be the
same, as the temperature hasn’t changed.

What happens if there is a change in the equilibrium system? (2 ways of thinking, Le

Chatelier and Q):
- Le Chatelier principle – reaction will act to minimize the change
- Reaction quotient, Q
 o same expression as Kc but remember Q is for a system not at
equilibrium
o We can relate Q to Kc, and based on tell in which direction a reaction will go
 If Q < Kc the reaction will move in the forward (right) direction to increase
the amount of products
 If Q > Kc the reaction will move in the reverse (left) direction to increase
the amount of reactants
 If Q=K system is at equilibrium

Effects of Le Chatelier principle Reaction quotient, Q

Explained by
If we add products  If we add products, Q > Kc, so
Change in equilibrium will want to equilibrium will go in reverse (to the left)
concentration decrease the amount of
(Reactant or Product) product so it shifts towards If we add reactants Q < Kc,
reactants (left) so equilibrium will shift forward (right)

If we add reactants 
equilibrium wants to reduce
that change by making more
product, so it shifts towards
products (right)
1. add or removal of gaseous reactant or product
Changes the concentration, since C = n / V, so treat as before.
Change in pressure
2. Add an inert gas (eg. Helium)
No change in concentrations, so equilibrium position is unaffected

3. Change in volume by compression

Look below more detailed:
Compression: Increasing pressure Compression: Increasing pressure

Change in volume system responds to change by shifting Initially, Q = K but when there is compression Q > K
(Reducing volume) balance to the side with fewer moles of
gases. System adjusts by decreasing [side with more moles]
Ex: and increasing [side with fewer moles] until Q = K
N2O4 ⇌ 2NO2 (ratio is 1:2; left side has
fewer moles)
- Equilibrium shifts to the left in this
case

Treat heat energy like a product When we…

(exothermic reaction (-∆rHѲ) or as a
reactant (endothermic reaction (+∆rHѲ). Heat the reaction – equilibrium will go to the left (reactants)
Change in temperature When the reaction is exothermic – heat is Cool the reaction – equilibrium will go to the right (products)
like product, and if we add product 
equilibrium will shift to the left

When the reaction is endothermic – heat

is like a reactant, and if we add reactant 
equilibrium will shift to the right
Equilibrium calculations
- ICE tables (Initial, Change, Equilibrium) (pay attention to units)
o The side that has the “zero” will be positive and the other side will be negative
o Used to answer question like “Consider the following chemical system: 2 IBr ⇌
Br2 + I2; 6.5 moles of IBr are placed in a closed 1L container. At equilibrium the
concentration of Br2 is 0.50mol/L. What are the concentrations of I2 and IBr at
equilibrium? What is the value of Kc for this reaction?
2 IBr ⇌ Br2 + I2
Initial concentration 6.5 mol/L 0 mol/L 0 mol/L
Change in concentration -2x +x +x
Equilibrium concentration 6.5 – 2x 0.5 mol/L x

What are the concentrations of I2 and IBr at equilibrium? C of I2 = x and in here x = 0.5 mol/L
C of IBr = 6.5 – 2x  6.5 x 2(0.5)  C of IBr = 5.5 mol/L

[ Br 2 ] [I 2 ] (0.5)(0.5)
What is the value of Kc? Kc =  2  Kc = 8.26 x 10-3
IBr 2 (5.5)