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topic 4: intro to organic chem

and alkanes
INTRODUCTION
hydrocarbons
4 families of hydrocarbons

hydrocarbon chains

aliphatic: straight chain

acyclic: ring of carbon atoms

types of formulas
empirical formula

simplest whole number ratio of atoms

molecular formula

actual number of atoms in the molecule

skeletal formula

shows all the bonds between the carbon atoms

topic 4: intro to organic chem and alkanes 1

 structural formula

shows how molecules are joined together

displayed formula

shows every atom and every bond in the molecule

functional groups and homologous series

what is a functional group?

an atom or group of atoms in a molecule that give a compound its distinct

properties

e.g. -OH, -COOH, C=C

what is a homologous series?

a family of compounds with:

same functional group

same physical and chemical properties

same general formula

they differ by CH2 from the next member

nomenclature
number of carbon atoms

e.g. meth-, eth-, prop-

prefixes, multiplying prefixes and suffixes

both prefixes and suffixes indicate presence of other atoms

prefixes:

topic 4: intro to organic chem and alkanes 2

 bromo = an atom of bromine

suffixes:

ol = hydroxyl group (OH)

multiplying prefixes indicate presence of 2 or more identical groups

di- = 2

tri- = 3

locants

indicate position of side chains in a molecule using numbers and hyphens

numbers indicate which carbon atom in the longest chain that the
sidechain is attached to

e.g.: 2- = side chain is attached to 2nd carbon in the chain

more nomenclature rules

a letter and number beside each other are separated with a hyphen

two numbers beside each other are separated with a comma

REACTION MECHANISMS
what is a mechanism?

mechanisms show the movement of electrons in a reaction(with curly

arrows)

types of reactions
addition

two reactants → one product

substitution

one functional group replaced by a different one

oxidation

loses one or more electrons

topic 4: intro to organic chem and alkanes 3

 reduction

gains one or more electron

polymerization

many monomers join to form a long, repeating polymer

free radical substitution

what is a free radical?

any species with an unpaired (lone) electron

how does the reactivity of alkanes compare with free radicals?

alkanes are generally unreactive due to their non-polarity and strong

bonds

however they can react easily with free radicals

what is initiation?

homolytic fission takes place:

UV light is shined on the halogen molecules e.g. Br2

this causes the covalent bond(s) to break

this leaves each atom with a lone electron, turning them into free
radicals.

what is propagation step 1?

an alkane molecule (e.g. methane) reacts with the halogen free radical
(e.g. Br• )

topic 4: intro to organic chem and alkanes 4

 Br• takes a hydrogen and an electron from methyl

thus forming H : Br (hydrogen bromide) and a methyl free radical.

what is propagation step 2?

the methyl FR now reacts with a bromine molecule in the air (Br2)

this forms bromomethane and a bromine FR (since Br is diatomic)

what is termination?

when two FRs react to form a stable molecule (no unpaired electrons)

termination can take 3 paths:

two bromine FRs can form a bromine molecule

two methyl FRs can form an ethane molecule

methyl FR + bromine FR can form bromomethane

topic 4: intro to organic chem and alkanes 5

 bond breaking
what is homolytic fission?

UV light breaks covalent bond

electrons are divided evenly between two atoms

each atom forms a free radical

what is heterolytic fission?

one atom receives both electrons from the covalent bond breaking

forming positive and negative ions

ALKANES
isomerism
what is an isomer?

same molecular formula, different displayed formula

what is a structural isomer?

same molecular, different structural formula

can be straight or branched

topic 4: intro to organic chem and alkanes 6

 what is a position isomer?

functional group in a different position on the carbon chain

fractional distillation and cracking

what is fractional distillation?

crude oil is broken down into fractions via heating in a fractionating

column

the column is heated and fractions evaporate and condense

fractions become darker, more viscous, and higher BP as you go down the
column

what is cracking and its products?

fractions can be further cracked into shorter chain hydrocarbons

cracking can produce alkenes and short-chain alkanes

cracking can produce alkenes and some hydrogen

properties of thermal cracking

covalent bond between two Cs splits to form free radicals

very high temperatures and pressure

alkane + alkene forms, with high % of alkene

properties of catalytic cracking

uses zeolite catalyst

high temp, low pressure

long chain alkane —> branched/cycloalkanes

topic 4: intro to organic chem and alkanes 7

 useful for petrol since they combust easily

combustion of alkanes
why are alkanes good as fuels?

they are highly flammable and release a lot of energy

problems of incomplete combustion

CO is toxic

nitrogen and sulfur oxides form acid rain

carbon particulates (soot) can form which cause respiratory problems

what is a catalytic converter for?

to remove unburnt HCs from a system

it uses a rhodium catalysts to convert bad products into good ones

alkanes as fuels
what is carbon neutrality?

something that has 0 net effect on the CO2 concentration of the

atmosphere

i.e. CO2 taken in to make the fuel ≈ CO2 given out when burnt

examples of alternative fuels

biofuels

bioethanol: made by fermentation

biogas: made when organic waste breaks down

biodiesel: made from refined renewable fats and oils

hydrogen

good bc it only forms water when burnt

bad bc obtaining hydrogen from water requires energy from FF

and also cant be stored

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 pros and cons of biofuels

pros:

carbon neutral

provide money for LICs since they have the space to grow the crops

cons:

expensive to convert machinery to run on biofuel instead of FFs

many HICs dont have the space to grow crops

properties of alkanes
what type of bond is in alkanes?

sigma bonds

properties of sigma bonds

fully rotational

very strong

contain a pair of electrons

one from each atom from either side of the bond

why are alkanes insoluble?

they’re non-polar

can’t form H. bonds as they have no permanent dipoles

this is because the O and the H have similar electronegativities

reactivities of alkanes

they are generally unreactive

topic 4: intro to organic chem and alkanes 9