Homologous series
have the same functional group and each successive member differs by CH2 unit
Aliphatic hydrocarbons
the carbon atoms are joined together in either unbranched or branched chains
Alicyclic hydrocarbons
the carbon atoms are joined together in a ring structure but are not aromatic
Aromatic hydrocarbons
there’s at least one benzene ring in the structure
nomenclature
naming system for compounds
Alcohol functional group
OH
Aldehyde functional group
CHO
Alkane functional group
C-C
Alkene functional group
C=C
Carboxylic acid functional group
COOH
Haloalkane functional group
halogen
Ketone functional group
C-CO-C
Saturated
only single bonds
Unsaturated
have a C=C double bond
functional group
a group of atoms that is responsible for the characteristic chemical reactions of a compound
general formula
the simplest algebraic formula for all the organic compounds in a homologous series
Alkane general formula
CnH2n+2
Alkene general formula
CnH2n
Alcohol general formula
CnH2n+1OH
displayed formula
shows the relative positions of atoms and the bonds between them
structural formula
provides the minimum detail for the arrangement of atoms in a molecule
empirical formula
the smallest whole-number ratio of atoms of the elements in a compound
molecular formula
shows the numbers and types of atoms in a compound
skeletal formula
a simplified structural formula drawn by removing hydrogen atoms from alkyl chains
hydrocarbons
compounds that contain only hydrogen and carbon atoms
isomers
have the same molecular formula but different arrangement of their atoms
Types of isomers (2)
structural isomers
stereoisomers
Structural isomers
compounds with the same molecular formula but different structural formulae
What are the three kinds of structural isomer? (3)
alkyl groups in different places
functional group bonded to a different part of the chain
different functional group
Stereoisomers
organic compounds with the same molecular formula but have different arrangements of atoms in space
Types of stereoisomerism (2)
E/Z isomerism
cis-trans isomerism
What causes E/Z isomerism?
the restricted rotation around the double bond
Cis-trans isomerism
a type of E/Z isomerism in which the two substituent groups attached to both carbon atoms of the C=C bond are the same
Reaction mechanisms
models that show the movement of electron pairs during a reaction
curly arrows
model the movement of electron pairs during a reaction
homolytic fission
happens when each bonding atom receives one electron from the bonded pair, forming two radicals
radicals
species with one or more unpaired electrons
heterolytic fission
happens when one bonding atom receives both electrons from the bonding pair
alkanes
a homologous series of saturated hydrocarbons
What is the bond shape and angle in alkanes?
tetrahedral and 109.5
What kind of bonds are C-C and C-H bonds examples of?
sigma bonds
Are alkanes polar or non-polar and why?
non-polar because the electronegativity of C and H are similar so there are no dipoles
What forces are between alkane molecules?
London forces
In alkanes, how does increasing carbon chain length affect boiling point?
increased chain length = increased boiling point
Why does increased chain length increase boiling point?
Relative molecular mass increases and there are more surface area contacts between adjacent molecules so more energy is needed to overcome the intermolecular attraction between molecules
In alkanes, how does increased branching affect boiling point?
increased branching = decreased boiling point
Why does increasing branching decrease boiling point?
More branching means fewer surface area interactions between molecules so there are fewer induced dipole-dipole attractions
Do alkanes have high or low reactivity?
low reactivity
Why do alkanes have low reactivity? (2)
covalent bonds have high bond enthalpies
C-H sigma bonds have low polarity
Reactions with alkanes (2)
combustion
radical substitution
complete combustion
oxidising a fuel in a plentiful supply of air
incomplete combustion
oxidising a fuel in a limited supply of air
What is produced in complete combustion?
carbon dioxide and water
What is produced in incomplete combustion?
carbon (soot), carbon monoxide and water
What colour flame does incomplete combustion make due to soot?
cooler, dirty yellow flame
What colour flame does complete combustion make?
clean blue flame
Stages of radical substitution (3)
initiation
propagation
termination
What do alkanes react with in radical substitution?
halogens
initiation
formation of radicals
propagation
two repeated steps that build up the desired product in a side reaction
termination
two radicals collide and make a stable product
Characteristics of radical substitution
unpredictable and difficult to control
What are the reactions in free radical substitution caused by?
a very reactive radical randomly colliding with another species
conditions required for the initiation step of radical substitution
UV
alkenes
a homologous series of unsaturated hydrocarbons
How is a sigma bond formed?
between two carbon atoms using the direct overlap of the electron clouds of two atoms
How is a pi bond formed?
by the electrons in the adjacent p-orbitals overlapping above and below the carbon atoms
What do pi bonds cause alkanes to have?
restricted rotation around the double bond
Shape and bond angle of alkenes
(trigonal) planar and 120
Why are pi bonds reactive?
high electron density
What type of isomerism do alkenes show?
stereoisomerism
stereoisomerism
compounds with the same structural formula but different arrangements of atoms in space
electrophile
electron pair acceptor
Are alkanes or alkenes more reactive?
alkenes
Why are alkenes reactive?
the double bond is an area of high electron density so attracts electrophiles
Examples of electrophiles
Br2, HBr and NO2+
Are pi or sigma bonds weaker?
pi bonds are weaker
Reactions with alkenes (5)
hydrogenation
halogenation
hydration
addition of hydrogen halides
addition polymerisation
Hydrogenation conditions (3)
150 degrees
nickel catalyst
hydrogen gas
Halogenation
an addition reaction where a halogen is added across C=C
What can halogenation be used for?
test for saturation
What is the positive test for saturation?
decolourisation
What is formed when bromine gets close to an electron-rich C=C bond?
dipole induced
hydration
addition reaction between gaseous alkene and steam
hydration conditions
high temperature and pressures and phosphoric acid catalyst
formular of phosphoric acid
H3PO4
Addition of hydrogen halides to alkenes
addition reaction in which a hydrogen halide is added across the C=C bond producing haloalkanes
Which carbocations are most stable?
tertiary
Which carbocations are least stable?
primary
What carbocation makes the major product?
the most stable carbocation intermediate (tertiary)
monomer
small molecules that are used to make polymers
polymers
macromolecules made from small repeating units
repeating unit
a specific arrangement of atoms that occurs in a structure over and over again
what bonds break in monomers during a polymerisation reaction?
pi bond
polymer of ethene
poly(ethene)
Uses of poly(ethene)
plastic bags and bottles
Uses of poly(propene)
ropes and crates
uses of poly(chloroethene) (PVC)
electrical cable insulation
uses of poly(phenylethane)
packaging
uses of poly(tetrafluoroethene)
non-stick coatings on cooking pans