Fractional distillation

1 7 fractions, and use

(Po Po Ni Kuai Dian Lai Ba)
Petroleum gas (Cooking), Petrol, Naphtha (Feedstock for petrochemical industry), Kerosene / Paraffin
(Fuel for aircraft), Diesel oil, Lubricating oil, Bitumen (surfacing roads)
2 Trend (viscosity, color, soot, number of carbon molecules, bp/mp, flammability, exothermicality)
Down fractionating column,
1. C decreases
2. Viscosity increases
3. Bp/mp increases
4. Flammability decreases
5. Flame brighter = More soot = More C atoms = Less exothermic
3 Why fraction will not give SO2? Why?
Sulfur high melting point, petroleum gas is gaseous state, so no S
4 Why are fractions impure?
Fractions are impure, so boil over a range of temperatures
5 Which is most profitable fraction?
Petrol / Gasoline
6 Why reduce usage of coal?
Reduce SO2
7 Why is there variation in composition of crude oil?
From differing sources
Cracking
8 Definition
Breaking down larger hydrocarbons into smaller hydrocarbons
9 Types of cracking
Thermal cracking: High pressure + 800-850 degrees
Catalytic cracking: Catalysts (Alumina, Al2O3, and silica, SiO2) + 300-350 degrees
10 Aim of cracking
1. Produce hydrogen gas (For Haber process, for production of margarine from vegetable oil, eco-
friendly fuel)
2. Converting naphtha into ethane to make polyethene for plastic bags
3. Converting larger hydrocarbons into smaller, more valuable smaller hydrocarbons to meet market
demand
Physical properties (overall: alkanes, alkenes, alcohols, carboxylic acids)
11 Melting/boiling point: low for alkanes and alkenes, alcohols and carboxylic acids are liquid or solids
12 Viscosity: Increases as C atoms increases
13 Solubility in water: No for alkanes and alkenes, but alcohols and carboxylic acids can
14 Density: lower than water
15 Flammability: decreases as C atoms increases, as more number of bonds to be broken, increases
activation energy
Naming
16 Alkyl groups is? (1H lesser than alkene formula)
ALKANES
Physical properties of alkanes
17 Gases for first 4, liquid for next 12
18 Always less dense than water
19 Color of soot: Darker with more C atoms / as % mass of C atoms increases
20 Viscosity: Increases  Increased C atoms, increased IMF, molecules harder to slide past one another
21 Reactive only with non-polar substances as organic substances (oxygen and bromine) are non-polar
(C=C/C-C/C-H bonds does not have huge difference in electronegativity), so unreactive with ions and
polar molecules
Chemical properties of alkanes
22 Substitution by halogens
 Ultraviolet radiation present in sunlight overcomes activation energy to break bonds / split chlorine
molecules into highly reactive free radicals (chlorine/bromine water)
Equation:
Highly exothermic reaction = Chain reaction
4 max substitutions for methane, 6 max substitutions for ethane
Writing of structural reaction

Number of steps to form chloroalkane

Products: (3)
1. Large amounts of chloromethane
2. Small amounts of HCl gas (not acidic!)
3. Small amounts of ethane
As collision between alkanes and chlorine molecules are random
Combustion
Complete = Excess/sufficient oxygen present, CO2 + H2O produced
Incomplete = Insufficient, production of CO and C (Soot)
Larger molecules = More bonds required to break before complete combustion = Increased Ea =
Increased tendency of incomplete combustion
23 How to obtain monochloromethane as main product?
To prevent further substitution of chlorine radicals into monochloromethane to form dichloromethane,
make methane excess, and chlorine molecules limiting
24 How to ensure fully substituted chloroalkanes?
Chlorine atoms excess, methane limiting
ALKENES
Physical properties of alkenes
25 Stated in overall
Chemical properties of alkenes
26 Addition – Hydrogenation
Alkenes  Alkanes
Nickel as catalyst
Application: Manufacturing margarine from vegetable oil
Why does margarine have a higher melting point than vegetable oil
Margarine, absence of C=C double bond, decrease distortion of molecule, packed closer together,
increased IMF
Addition – Bromination
Test for alkenes (reaction with acidified potassium manganate (VII) can also test for C=C double bond)
Addition – Hydrogen halides
Addition – Steam
Formation of alchols
Phosphoric (V) acid (H3PO4) as catalyst, 300 degrees, 60 atm, steam
Only occurs in vapour phase
Possibility to form isomers as hydroxyl and hydrogen atom can be added at any sides of the C=C group
Addition – Polymerisation
27 2000 atm, 200 degrees
28 Monomer must contain C=C bonds
29 Difference between monomer and polymer
Empirical formula of monomer is almost same as polymer, due to the terminal atoms that vary between
companies
30 Why is sequence of monomers in polymer random?
Random collisions between monomer molecules, random molecules reach activation energy and react
through addition polymerisation to form polymers
31 Polyethene  Plastic bags
Polypropene  Ropes
Polychloroethene  PVC pipes
32 Why is alkenes more reactive than alkanes
Electron rich, stronger double C=C bond found in alkenes
ALCOHOLS
33 CnH2n+1OH
Physical properties of alcohols
34 Soluble in polar (water) and non-polar substances
Hydrogen bonds formed between hydroxyl groups of adjacent ethanol molecules  Soluble in water
(High affinity with water = Require calcium oxide as drying agent to make 100% ethanol)
Solubility decreases as carbon chain increases as effect of hydrogen bonds decreases
35 Low volatility
First 4 are colorless liquids at room temperature
Hydrogen bonds formed between hydroxyl groups of adjacent ethanol molecules increases IMF
36 Viscosity
Extensive hydrogen bonding between alcohol molecules = thick and sticky
37 Amphoteric
Chemical properties of alcohols
38 Combustion
39 Dehydration
To form ethane
Concentrated sulfuric acid as dehydrating agent
40 Esterification
To produce ester and water
41 Oxidation
Oxidising agents: Acidified potassium manganate (VII)
42 Preparation of ethanol
Fermentation
Exothermic reaction
Glucose/Sugar  Ethanol + Carbon dioxide
Why is it not possible to make spirits (high concentration ethanol) through fermentation?
High concentration of alcohol will kill yeast. Require fractional distillation to produce spirits
Why need anaerobic condition?
1. Yeast will adopt aerobic respiration when oxygen is present, resulting in formation of water and
carbon dioxide instead of ethanol and carbon dioxide
2. Ethanol produced may also be oxidized by oxygen to produce ethanoic acid, making beer sour
 Is ethanol produced through fermentation carbon neutral? Why
Yes. Carbon dioxide produced during combustion of ethanol will be absorbed by plants as they grow
through the process of photosynthesis. Equation
Why keep at rtp?
Denature
Hydration of ethene
Conditions
300 degrees, concentrated acidified phosphoric (V) acid, 60 atm
Advantages and disadvantages over fermentation?
Shorter time
100% yield
Higher cost than fermentation
Non-renewable as ethene comes from petroleum, a non-renewable resource
43 Uses of ethanol
As a solvent
Alcoholic drinks
Disinfectant
Fuel for motor vehicles
CARBOXYLIC ACIDS
44 CnH2n+1COOH
45 Ethanoic acid  Vinegar / Acetic acid
46 Use of ethanoic acid
To manufacture esters, which in turn are used as solvents
Manufacture insecticides
Manufacture drugs
Preparation of ethanoic acid
47 Oxidation of ethanol
Purpose of acidifying potassium manganate? Catalyst
From methane
Methanol + CO  Ethanoic acid
Chemical properties of carboxylic acids
48 As an acid
H from COOH  COO+
Carboxylic ion is written in front
Naming: Salt methanoate
Similarity between organic and inorganic acids?
1. Dissociate in water to form H+
2. Same reactions as acid
Difference between organic and inorganic acids?
Organic  Has Carbon, inorganic  doesn’t
Organic  tend to be weak acid
Test for carboxylic acid?
Add reactive metal  Effervescence
49 Ester formation
Ethanoic acid + Alcohol  Ester (colorless liquid with sweet smell) and water
Elimination reaction: Acid + Ethanol (REVERSIBLE REACTION) (alcohol)yl ethanoate + water (loss of
small molecules (g) (H2O, HCl, HCN)
Difference and similarity between esterification and neutralistion?
Same: Formation of H2O
Different: Neutralisation is H+ and OH- ions, but esterification is breaking covalent bonds hydroxyl and
hydrogen group to form H2O
Application?
Alcohol in perfumes react with organic acids in sweat to produce fragrant esters
Reactions (overall)
50 Types of reactions in organic chemistry
1. Elimination (React with removal of small molecule, results in formation of a double bond)
 2. Substitution
3. Addition (React to form 1 single compound)
Branching
51 Purpose
Increased volatility and decreased density
Isomerism
52 Definition: Same molecular formula, differing structural formula
Types of isomers
1. Position isomerism (Changing position of hydroxyl group, bromine, chlorine with no alteration of
carbon chain)
2. Chain isomerism (Carbon chain > 3, changing will shorten chain)
3. Functional group isomerism (Changing position of functional group, altering carbon chain)
53 Applications
Smoother burning, reduced knock-back effect in engines as branched alkanes explode less rapidly than
straight-chain alkanes  Increased efficiency of engines
54 Cycloalkanes
Ring encloses saturated compound
Higher melting point than alkane: Because ring structure allows molecules to be closer together than
long strands of hexane, IMF increases
Cyclo(alkane) is isomer of (that)alkene!
Redox
55 Oxidation = Gain of oxygen atom, loss of hydrogen atom
Reduction = Loss of oxygen atom, gain of hydrogen atom
Miscellaneous
56 Define non-biodegradable
Not easily broken down into simpler substances by action of bacteria or microorganisms
57 Environmental concern of fracking
Releasing gas, chemicals, pollute water table, or gas released into atmosphere – polluting gas
58 Difference between substitution and displacement
Displacement: Formation of element
Substitution: Formation of compound
59 Difference between organic reactions and inorganic
1. Reaction speed
2. Mp/bp
Ionic reactions happen faster than organic reactions, hence organic reaction require catalyst
Organic substances = lower mp/bp than inorganic
Define homologous series
Family of organic compounds with similar structural pattern
Saturated vs unsaturated
Saturated = no C=C bonds
Molecular, Empirical, Structural formula