Topic 6A,B,C - Alkanes and Alkenes (Organic Chemistry) Flashcards
What is a Homologous series?
A series of compounds containing the same functional group so have same general formula and chemical properties
What is a Functional Group?
A single atom or group of atoms that gives a compound its chemical properties
Definition of Molecular formula
The formula which shows the actual number of each type of atom
Definition of a empirical formula
Show the simplest whole number ratio of atoms of each element in the compound
Definition of Structural formula
Shows how atoms are grouped together in a molecule
Definition of Displayed formula
Shows all the atoms and all the bonds in a molecule
Definition of Skeletal formula
Shows a simplified structural formula only show carbon -carbon bonds (as lines) and functional groups of present
What are 3 properties of a homologous series
- They show a gradual change in physical properties e.g boiling point
- Each member differs by CH2 (the same difference) from the last
- They have the same chemical properties
What are the general rules for naming carbon chains?
- Count the longest carbon chain and name appropriately, find any branched chains and figure out the carbon they are coming off and the functional group that they are e.g 3,5 - dimethylheptane meaning that the longest carbon chain is 7 and there are 2 methyl groups coming off the 3rd and 5th carbon
- You have to make sure that the numbers are the smallest possible
- When naming with multiple functional groups the order of them is alphabetical
- Words are separated by numbers with dashes and numbers are separated by commas
- When writing the structural formula of molecules that have functional groups e.g methyl coming off of them you need to put brackets around it e.g CH3CH(CH3)CH3
Definition of an Isomer/ structural isomer
Molecules with the same molecular formula but a different structural formula
What are the 2 types of isomers?
- structural isomers
- stereoisomers
What are the 3 types of structural isomers?
- Chain isomers
- position isomers
- Functional group isomers
What is the definition of a chain isomer?
Compounds with the same molecular formula but different shaped/ structured chains e.g straight chain or branched e.g pent-1-ene and 3-methylbut-1-ene
What is the definition of a position isomer?
Compounds with the same molecular formula but different structures due to different positions of the functional group on the molecules e.g pent-1-ene and pent-2-ene
What is the definition of a functional group isomer?
Compounds with the same molecular formula but with the atoms arranged to give different functional groups e.g Alkenes and Cyclo Alkanes have the same molecular formula but different functional groups
What is the definition of a stereoisomer?
Molecules with the same molecular and structural formula but with a different arrangement of atoms in space e.g cis/trans isomers and E/Z isomers
What are the 5 types of reactions?
Addition, Polymerisation, Elimination, Substitution, Hydrolysis.
When do addition reactions occur?
When molecules contain a double bond e.g In Alkenes, they are said to be unsaturated and the carbon-carbon double bond can break and gain another molecule in an addition reaction.
When do polymerisation reactions occur and give an example?
Addition polymerisation occurs when small molecules (monomers) with double bonds e.g Alkenes, add to each other and join up in long chains to form polymers. The reaction
needs a suitable catalyst and temperature. An example; n(C2H4) -> -(C2H4)-n
When do elimination reactions occur and give an example?
An elimination reaction is basically the opposite of an addition reaction, it splits off a simple molecule e.g water or hydrogen chloride, from a larger molecule leaving a double bond e.g C2H5Cl -> C2H4 + HCl (in the presence of NaOH, ethanol and heat)
When do substitution reactions occur and give an example?
Substitution reactions occur when an atom or group of atoms is replaced by another atom or group of atoms e.g alkanes + halogens (in the presence of UV light) -> halogenoalkanes + Hydrogen halides
When do hydrolysis reactions occur and give an example?
Hydrolysis is used to describe any reaction in which water is used to split apart a molecule (don’t need to know the process in detail). To recognise this reaction you would see water as a reactant and the reaction is often catalysed by an alkali or acid. Hydrolysis reactions are often substitution reactions in which the chemical attack is by nucleophiles such as water molecules or hydroxide ions.
What are nucleophiles?
Nucleophiles are molecules or ions that have a lone pair of electrons that is able to form a new covalent bond. For example; Oxygen in hydrogen oxide, Carbon in carbon nitride, Oxygen in water, Nitrogen in Ammonia
- They are electron pair donors
- They attack ions/molecules with a partially positive charge
What are electrophiles?
An electrophile is a species which can accept a pair of electrons from an electron rich sire in another molecule to form a new covalent bond. Electrophiles are often positively charged e.g H+
- They are ‘electron loving’ reagents
- Electrophiles form a new bond by accepting a pair of electrons from the molecule or ion attached in the reaction
What is a polymer?
Polymers are large chains formed from huge numbers of small molecules (repeat units) called monomers
What type of addition do alkenes undergo?
Electrophilic addition - The electrophiles (the positive ions with a vacant orbital) attack the negatively charged region of the C=C bond
What is the definition of addition polymerisation?
The joining together of small molecules that contain a carbon-carbon double bond to form a long chain
What are two safety hazards when cracking and what is the solution to them?
- One hazard is that the gas you are producing and paraffin is flammable so therefore you have to make sure the gas is being collected over water
- One hazard is that the glassware can get very hot as it is being heated so before you move touch it ensure it has cooled down
What is the shape of a saturated hydrocarbon?
Tetrahedral with a bond angle of 109.5°
What is homolytic fission?
This is when each atom of a molecule gets one electron from the covalent bond, the electrons are shared equally.
What are cycloalkanes?
These molecules contain a ring of carbon atoms and have the general formula CnH2n (same as alkenes)
How would you draw 2,2 -dimethylheptane
7carbon atoms making up the main chain and then on the second carbon atom their would be two methyl groups coming off it.
What type of bonds do alkanes contain?
Single covalent bonds known as sigma bonds
What is the bond axis?
The bond axis is the invisible line between the nuclei of the atoms being bonded together
When will sigma bonds form?
When their is head on overlap of orbitals along the bond axis
What are the 3 ways sigma bonds can form?
- The overlap of 2 sigma bonds
- The overlap of a sigma bond and a head on pi bond
- The head on overlap of 2 pi bonds
Are alkanes reactive? Why?
No, as the C-C and C-H bonds have high bond energy values which require a lot of energy to overcome
Are alkanes likely to be polar molecules? Why?
No, as there are no polar bonds between the carbon and hydrogen as the difference in electronegativities is negligible
What are 2 qualities about the carbon-carbon bond in alkanes?
- It is symmetrical
- There is free rotation about the single bond
Alkane + Halogen →…
NO REACTION
What is the reaction of a Halogen with an organic compound used to test for?
Whether the compound is an alkene or alkane
What is the colour change of Bromine Water if an alkene functional group is present?
Orange→ colourless
What are the conditions need in order for the substitution reaction of; Alkane + Halogen → Halogenoalkane + Hydrogen Halide
- UV radiation (sunlight) or above 300°C
What is the definition of a substitution reaction?
Where an atom or group of atoms is replaced with a different atom or group of atoms, 2 reactants → 2 products
What is Halogenation?
Where an alkane and a halogen (chlorine or bromine) react in the presence of UV radiation (sunlight)
What type of reaction is halogenation?
Free radical substitution (also a photochemical reaction)
What are the 3 stages of a Halogenation reaction?
Initiation
Propagation
Termination
What does a half arrow indicate when drawing a mechanism?
Movement of a single electron
What does a full arrow indicate when drawing a mechanism?
Movement of a pair of electrons
What happens in the Initiation step of Halogenation?
The UV light breaks down a chlorine/bromine molecule into uncharged halogen atoms, each with an unpaired electron show as a * (*=dot)
What is heterolytic fission?
This means that the electrons are split unequally between the atoms in the molecule and one atom gains a lone pair of electrons.
What are Free radicals?
Atoms that are uncharged and have 1 unpaired electron
Write the mechanism for the initiation step of the reaction; CH4 + Cl2 → CH3Cl + HCl
(You don’t need to know the mechanism)
Cl-Cl → Cl+Cl
Half arrows would be drawn from the bond to each Chlorine atom to show the movement of electrons
How many parts are there to the Propagation step of Halogenation?
2
For a reaction to occur what must happen?
Particles must collide with each other
Write the equation for the first part of the Propagation step of the reaction; CH4 + Cl2 → CH3Cl + HCl
CH4 + Cl* → C*H3 + HCl
From the C-H bond, 1 electron goes to the Carbon atom and 1 to the Hydrogen atom. The electron from the Chlorine free radical joins with the Hydrogen free radical.
Remember to draw the radical on the carbon atom
Write the equation for the second part of the Propagation step of the reaction; CH4 + Cl2 → CH3Cl + HCl
CH3 + Cl2 → CH3Cl + Cl
A different Cl2 molecule that has already been split in the first step donates one of its electrons to form a covalent bond with the carbon atom and its electron
What does the Propagation step continually do in the reaction; CH4 + Cl2 → CH3Cl + HCl?
Produce methyl and chlorine free radicals in a chain reaction
When does the chain reaction of a Halogenation reaction stop?
When all the free radicals eventually collide with each other
What are all the possible reactions for the final Termination step of the reaction; CH4 + Cl2 → CH3Cl + HCl?
Cl* + Cl* → Cl2
CH3 + Cl → CH3Cl
CH3 + CH3 → CH3CH3
Why does the reaction; CH4 + Cl2 → CH3Cl + HCl, have a low yield of product?
This is because the Cl* is so reactive and so therefore their are further free radical reactions of the radical with the desired product, which produces unwanted products.
Explain how crude oil is split into fractions via fractional distillation?
The crude oil is vaporised into a gas and enters the fractionating column which has a temperature gradient, hottest at the bottom and cooling as you go up. The long chain hydrocarbons with the highest boiling points will condense first, ant the bottom, and exit the column. The shorter chain hydrocarbons with the lowest boiling points will condense at the top.
What are the crude oil fractions from shortest chain length to longest?
Refinery Gas
Gasoline/Petrol
Naphtha
Kerosine
Diesel Oil
Lubricating oil
Fuel oil
Bitumen
Why do different alkanes have different boiling points?
Longer chain alkanes contain more electrons, therefore stronger London Forces which require more energy to overcome.
What are the two ways fractions are processed into more useful alkanes and alkenes?
Cracking
Reforming
What is the definition of reforming?
Turning straight chained alkanes into branched or cyclic alkanes, which are more efficient fuels as they combust easier
Why are cyclic or branched alkanes more useful?
They combust more easily so are more efficient fuels
What is the definition of cracking?
The breaking down of saturated hydrocarbon molecules into smaller hydrocarbon molecules by heat
Why is cracking an important process?
The process breaks down longer chain alkanes into shorter chain alkanes and alkenes that are in higher demand and are much more useful for the production of polymers for plastics
What are the two different conditions that are needed for cracking?
High temperatures
An aluminium oxide catalyst with low temperatures (catalytic cracking)
Describe the set up for catalytic cracking
On the right;
- a water bath
- downturned test tube that collects the gaseous product
- a Bunsen valve around the neck of the small tube that connects the test tube in the water bath and the test tube where the reaction is taking place
On the left;
- a sideways test tube
- aluminium oxide granules in the centre of the test tube
- a bung on the test tube
- Heat applied to the aluminium oxide
- ceramic fibre soaked in paraffin at the bottom of the test tube
What do fuels do when burnt?
Release heat energy
When does complete combustion occur?
In an excess/ plentiful supply of oxygen