Unit 6- Introduction to organic chemistry

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  • Created by: McTighe
  • Created on: 22-04-18 10:26
Why can carbon form many compounds?
1. Ability to form chains, branched chains and rings 2.Relative inertness and unreactive nature of c-c and c-h. They have high bond enthalpies
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What is a functional group?
Group of atoms which give an organic compound its characteristic properties and reaction
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What is a homologous series?
A family of compounds which contain the same functional group, have same general formula and similar chemical and physical properties
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What is the functional group of an alkene?
C=C
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What is the functional group of an alkyne?
C=-C (TRiple bond)
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What is the functional group of an alcohol?
-OH
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What is the functional group of an ether?
R-O-R
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What is the functional group of an aldehyde?
o=c-H (Double bond to oxygen, single to hydrogen)
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What is the functional group of a ketone?
C=O
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What is the functional group of a carboxylic acid?
o=c-o-H (DOuble bond to oxygen, single to OH)
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What is the functional group of an ester?
O=C-O
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What is the functional group of an amine?
H-N-H H-N or N
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What is the functional group of an amide?
O=C-N-H
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Give an example of a molecule with two or more functional group
Latic acid in sour milk has both -OH and -COOH.
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What is the Empirical formula?
The simplest whole number ratio of atoms of each element in a compound
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What is a molecular formula?
The actual number of atoms of each element in a molecule
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What is the structural formula?
Shows which atoms/groups of atoms are attached to each other in one molecule of a compound
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What are structural formulas?
Molecules with same molecular formula but different structural formulae
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Name the three types of structural isomers
Chain Isomerism, Position Isomerism, Functional Group Isomerism
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What is chain Isomerism?
Different branching on carbon atoms
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What is Position Isomerism?
Functional group moves position
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What is Functional Isomerism?
Isomers contain different functional groups
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What is an Addition reaction?
Reaction where two molecules join to form a single product
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What type of molecule does an addition reaction always occur on?
Unsaturated molecules (Double bond opens up)
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What is it called when hydrogen is the addition molecule?
Hydrogenation
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What catalyst is required for a hydrogenation reaction to occur?
Platinum or Palladium (Room temp) or Nickel (150*)
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What is it called when water is the addition molecule?
Hydration
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What is an elimination reaction?
Reaction used to produce an unsaturated product by loss of atom
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What type of molecule does this reaction occur on?
Saturated (Forms a double bond)
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Give an example of an elimination reaction
Hydrogen halides are removed from hydrogenalkane to produce alkene
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What is it called when water is removed?
Dehydration
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What is a substitution reaction?
Replacing one or more atoms by others
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Give an example of a substitution reaction
Halogenalkanes are formed when the halogen replaces the hydrogen atom, in presence of UV light
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What is addition Polymerisation?
Linking monomers together to form polymers
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What is hydrolysis?
Compounds split apart in reaction involving water
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Give an example of a hydrolysis reaction
Halogenalkane to alchol and hydrogen halide
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What is esterfication?
Reactants join together to produce a product and water
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What is another name for esterfication?
Condensation
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What is a free radical?
A species with an unpaired electron
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Describe homolytic fission
Occurs between two of the same molecules. When bond splits, each atom gets an unpaired electron (Equal Splitting). Free radicals are intermediates. They are in gas stage or non-polar solvents. UV light speeds up reaction
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Give three examples of homolytic fission
1. Thermal cracking of hydrocarbons 2.Burning of petrol and other alkanes 3.Substitution reactions of alkanes with halogens
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Describe heterolytic bond fission
Bond splits, one atom takes both electrons to produce ionic intermediates. Polar solvents as bonds are polar. Reagants which seek s+ end are nucleophiles, reagents which seek out s- are electrophiles
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What is a nucleophile?
An electron pair donor. They are negative ions with lone pair of electrons that attack positive ions
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What is an electrophile?
An electron pair acceptor. They are positive ions with vacant orbitals that attack negative ions
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Give three examples of nucleophiles
Hydroxide ions, Cyanide ions, Water molecules, Ammonia molecules
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Name three ways reaction mechanisms can be studied
Trapping Intermediates, Labelling with Isotopes, Study reaction rates, Study the shapes of molecules
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What are the most common hydrocarbons found in crude oil?
Alkanes and Alkenes
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What is a Aliphatic hydrocarbon?
Branched/Unbranched chains of carbon chains. They can also have non-aromatic rings e.g. cyclohexane
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What is a Aromatic hydrocarbon?
Rings of carbon atoms with delocalised electrons. They have distinctive smells. E.g. Benzene and Naphthalene
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What is another name of Aromatic hydrocarbons?
Arenes
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What is the general formula for CnH2n+2
Alkanes
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What are saturated compounds?
Only have single bonds between atoms in their molecules
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Why are saturated hydrocarbons not good for the health?
They can lead to higher chloestrol levels in blood, which can block major arteries, which could lead to a heart attack.
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What type of hydrocarbon is also not good for the health?
Trans fat (Unsaturated)
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What is the formula for cycloalkanes?
CnH2n
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What is the trend in boiling point for alkanes?
As the alkane chain length increases, boiling point also increases
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Why does the boiling point increase?
The bond between carbon and hydrogen is non-polar so only dispersion forces. As molecules increase, more eletrons so higher chance of temporary-induce dipole, so higher dispersion forces
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Do branched chains have higher or lower boiling points?
Lower as the molecules are not as close, so the dispersion forces are weaker
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Why do cycloalkanes have a higher boiling point?
The molecules can lie closer together
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Are alkanes soluble or insoluble in water?
Insoluble as they are non-polar. Attraction between alkane and water is not strong enough to overcome attraction in water. In solvents, main attraction are van der waals dispersion.
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What are the three main reactions alkanes are restricted to?
Burning, reacting with halogens and cracking
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Which cycloalkane is not similar to alkanes in reactivity?
Cyclopropane
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Name three types of fuels with alkanes
Natural gas (Methane), Calor Gas (Propane) and Gaz (Butane)
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When alkanes burn in complete oxygen, what is produced?
Carbon Dioxide and Water
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Is the reaction of combustion exothermic or endothermic?
Highly Exothermic
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Why do alkanes become harder to ignite as they increase in size?
They don't vapourise as easily, as they have larger london dispersion forces, making them more difficult to break away
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What is produced in alkanes burn in not enough oxygen?
Particulates, carbon monoxide and carbon dioxide
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Are alkanes energetically stable or unstable?
Unstable
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What colour is a flame, if carbon is present?
Yellow
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What is burning of alkanes used for?
To create energy
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Why does burning alkanes sometimes produce sulfur dioxide?
They may contain sulfur impurities which produced SO2. This can lead to acid rain
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How can less SO2 be produced?
Removing waste gases by flue gas desulphurisation. Gases pass through calcium oxide to produce calcium sulfate
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Describe how alkanes react with halogens
Alkanes react with chlorine or Bromine by heating or UV light. Hydrogen atoms are replaced by halogen atoms (substitution). Reaction continues until all hydrogen atoms have been substituted.
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What are the three main stages in a chain reaction?
Initiation, Propagation, Termination
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Describe Initiation
Forms the radical, by molecules splitting by homolytic fission. Not many radicals means hitting each other is small
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Describe Propagation
The chain reaction where collision occur between molecules. A radical hits a non-radical
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Describe Termination
Two radicals combine to remove them
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Why are free radicals not useful for synthesis?
Too many species are present and the percentage of each present will be unpredictable
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What is cracking of an alkane?
Breaking large hydrocarbon molecules into smaller bits. This can be achieved with high temperature and pressure without a catalyst, or low with a catalyst
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What is catalytic cracking?
Long chain alkanes turned into small alkanes and alkenes with Zeolites as catalyst. (500*C and low pressure)
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Why are synthetic catalysts good?
They can be developed with active sites to favour shape and sizes of molecules which react to give the desired products
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What is thermal cracking?
No catalyst, but temperatures up to 750*C and 70 atmospheres. Higher proportionals of alkenes produced
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What are the four main fossil fuels?
Natural gas, Crude oil, Coal, Peat
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What is reforming?
Octane numbers increases by branching alkanes and adding cycloalkanes with platinum catalyst, 500*C and 20 atmospheres
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What three processes does crude oil undergo to satisfy demand of different products?
Fractional Distillation, Cracking and Reforming
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What is fractional distillation?
Separates crude oil into fractions by heating to different boiling points
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Name three reasons why engines pollute
-They do not burn the fuel completely -Fuel contains impurities -Run at high temperatures so nitrogen and oxygen react
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Which natural causes can pollute the air?
Volcanoes, Anaerobic Decomposition of organic matter and atmospheric reactions
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Why is carbon monoxide bad for the body?
It combines with haemoglobin so blood carries less oxygen
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Why are particulates bad for the body?
They pentrate lungs to cause coughing, heart disease and lung cancer
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Describe how sulfur is removed by mixing crude oil with hydrogen
It passes over a hot catalyst to form hydrogen sulfide and hydrocarbon. The hydrogen sulfide then oxidises to sulfur
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What are these large quantities of sulfur used for?
Sulphuric acid
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What produced carbon dioxide?
Burning of fossil fuels, Depletion of forests, respiration
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What does carbon dioxide cause?
Global warming
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What produced carbon monoxide?
Incomplete combustion, biological oxidation of marine organisms
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What does carbon monoxide affect?
Respiratory activity
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What produces sulfur dioxide?
Burning of fossil fuels, industrial boilers, electric generation plants and volcanic eruptions
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What does sulfur dioxide affect?
Respiratory problems and acid rain
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What produces nitrogen dioxide?
Car exhausts, burning of fossil fuels, smelting plants, lightning spark plugs, volcanoes
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What does nitrogen dioxide affect?
Produces photo chemical smog, affects photosynthesis and produces acid rain
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Describe how nitrogen oxides form
Nitrogen monoxide forms inside combustion engine at 2800*C. NO goes on to react with more oxygen to form nitrogen dioxide.
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How is Nitric acid formed?
Nitrogen dioxide reacts with water and oxygen
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What happens to NO2 molecules in the sun?
They break downinto nitrogen monoxide and oxygen radicals. These radicals will then jin to O2 to form Ozone
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What is the reaction of Ozone wiith hydrocarbons?
Forms a mixture of chemicals to produce a photochemical smog
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Name some of the causes of acid rain
-Lakes become acidic and fish die -Marble, stone, metal structures erode -Enter soil, affect soil pH, crops no longer grow -effects plants by damaging leaves -cause respiratory problems and skin disorders
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How can acid rain be reduced?
Lakes are neutralised with base. scrubbers are placed in chimney
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Name four affects of global warming
-Climate in different regions -Distribution of plants and animals -Disturbance of plants and animals -Melting snow caps
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What is the purpose of a catalytic convertor?
Improves air quality by removing harmful pollutants
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Why are catalytic convertors honeycomb shape?
To increase surface area to increase rate of reaction
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What catalysts are found in a catalytic convertor?
Platinum, Rhodium and Palladium
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What reactions occurs in catalytic convertor?
Carbon monoxide and hydrocarbons react with nitrogen oxides to form nitrogen, carbon dioxide and water
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What is a heterogeneous catalyst?
Reactants and catalyst in different states
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What is a homogeneous catalyst?
Reactants and catalyst in same states
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What is it called when a reactant binds to a catalyst surface (active site for enyme)
Adsorption
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How does adsoption help speed up a chemical rection?
It increases local concentration, so increases rate of reaction. Another reactant will approach catalyst where rearrangement of electrons take place (reaction)
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Why are fossil fuels non-renewable?
They are being consumed much faster than they are being replenished
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What does living a more sustainable life mean?
Using earth's resources so they are available for future generations
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What does carbon neutral?
Carbon dioxide released is balanced by actions which remove carbon dioxide
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How is bioethanol made?
Made by fermenting carbohydrates in crops. Starch is converted to glucose, then to ethanol and CO2
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How is Biodisel made?
Produced by extracting oils from crops (e.g. rapeseed).
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What is the general formula for alkenes?
CnH2n
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Does the boiling point increase or decrease as the molecule increases in size?
Increases
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Why does the boiling point increases?
More electrons in longer chains means more longon dispersion forces. It is lower than alkanes however as two less electrons
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Which alkenes are gases at room temperature?
Ethene, Propene, Butene
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Are alkenes soluble or insoluble in water?
Insoluble
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What are the two bonds called in a double bond?
Sigma and Pi
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Where is the sigma bond found?
Between two carbon nuclei
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Where is the Pi bond found?
In orbital above/below plane
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What is Stereoisomerism?
When molecules have the same atoms joined in the same order but have different spatial arrangement
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What is E/Z isomerism?
Occurs when there is a restricted rotation about a bond and different groups are attracted to carbon atoms at each end of the bond
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Is E diagonal or horizontal?
Diagonal
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Is Z diagonal or horizontal?
Horizontal
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Is trans diagonal or horizontal?
Horizontal
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Is Cis diagonal or horizontal?
Horizontal
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What are the two rules to give priority in E/Z?
1. Atoms with higher priority have higher atomic number 2.Heavier isotopes have priority
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What is produced when alkenes burn?
Water and carbon dioxide
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Why do alkenes rarely get used as fuels?
Because they are more useful in other ways
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Why is the flame more smoky when alkenes burn?
Higher percentage of carbon
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What conditions are required for hydrogenation of alkenes?
RTP with Platinum/palladium catalyst or 150*C with Nickel catalyst
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What is the process used to manufacture margarine from unsaturated oils?
Catalytic hydrogenation
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Why are vegetable oils liquid at room temperature?
They have a higher proportion of unsaturated fats
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What type of reaction is the addition of halogens to alkenes?
Electrophilic addition reaction
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What is produced when ethene reacts with fluorine?
carbon and hydrogen fluoride
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What is produced when an alkene reacts with steam?
Alcohol
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What conditions does hydration occur in?
Phosphoric acid, 570K, 60 atmospheres
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What is produced when potassium manganate reats with alkene?
A diol
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What is produced when ethene reacts with hydrogen bromide?
Bromoethane
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Why is hydrogen Iodide the fastest hydrogen halide reaction?
The hydrogen halide bond is less electronegative
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What happens when ethene reacts with cold bromine?
Double bond opens up where bromine join to it. This causes bromine solution to lose red-brown colour and become colourless
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What happens when the bromine water is shaken with ethene?
carbocation reacts with Br- and water molecules to form 1,2-Dibromoethane or 2-bromoethanol
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What is Markovnikov's rule?
When a compound HX is added an unsymmetrical alkene, the hydrogen becomes attached to the carbon with the most hydrogens attached to it.
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What does the stability of a carbocation depend on?
Number of alkyl groups attatched
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What is the inductive effect?
The way in which electrons are either pushed towards or pulled away from a carbon atoms, by atoms or groups to which it is bonded to
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How is the inductive effect produced?
Alkyl groups push electrons towards carbon atom, creating positive inductive effect. Any carbon atom with positive charge is more stable the more alkyl groups it has attached to it
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Why is a secondary carbocation more stable than primary?
It has two alkyl groups pushing electrons towards positively charged carbon atom. This extra inductive effect helps stabilise ion by reducing its positive charge so carbocation more likely to form.
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What are the two types of poly(ethene)?
Low-density polyethene or High-density polyethene
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How is LDPE formed?
Ethene placed at high pressures and temperatures with special substances caused by initiators.
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What are the conditions for LDPE?
200*C, 2000 atmospheres and small amount of oxygen as impurity
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Why is LDPE low density?
Lots of branching prevents them lying close together. Weak intermolecular so low meltiing point, weak strength.
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Give some properties of LDPE
Light, flexible, easily moulded, transparents, good insulators, resistnt to water, acids and alkalis
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What are LDPE used for?
Plastic bags, Bottles, Beakers, Insulators for cable, joint replacements
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What are the conditions formed for HDPE?
60*c, low pressure and Ziegler-Natta catalyst
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Is HDPE more or less crystalline than LDPE?
More as there are less branches, so chains are close together
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Name three things HDPE is used for?
Washing up bowls, Plastic Pipes, milk bottles
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Name three features of poly(propene)
Tough, easily moulded, easily coloured, very resistant to water/acid/alkali
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What is poly(propene) used for?
Rope fibres, carpets, creates, toys
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Name three features of poly(chloroethene)
ROugh, ridgid, flexible, very resistant to water/acid/alkalis
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What is poly(chloroethene) used for?
Guttering, window frames, insulation for cables, waterproof clothing, flooring, cling flim
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What is a halogenalkane?
A compound which consists of an alkane, and one hydrogen has been replaced by a halogen atom
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Is the bond between the halogen and carbon polar or non-polar?
Polar
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What is a primary halogenoalkane?
Carbon which carries halogen atom is only attached to one alkyl group
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Which is the most stable carbocation?
Tertiary
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Which halogenoalkanes are gases at room temperature?
Chloro-methane, Bromo-methane and Chloro-ethane
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What are all the rest of halogenalkanes at room temperature?
Colourless liquids
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Does the boiling point increase or decrease as the molecules get bigger?
Increase
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Why does the boiling point increase?
More attraction between molecules due to more electrons, so larger dispersion forces. More energy is need to overcome this attraction
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Are the boiling points larger or smaller than the parent alkanes?
Larger
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Why are the boiling points larger than the parent alkanes?
because polarity of the C-X bond leads to larger london dispersion forces. There are permanenet dipoles-permanent dipole attraction
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Are halogenoalkanes soluable in water?
No because dipole-dipole attractions are not strong enough to break hydrogen bonds
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How do you form a halogenalkane from an alkane?
React alkanes with bromine or chlorine under UV light or heat to form free-radical substitution. This forms hydrogen halide and halogeoalkane
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How do you form a halogenalkane from an alkene?
Reaction between alkene and hydrogen halide at room temperature to form halogenoalkne with one halogen atom. Can also react with diatomic molecules to form molecule with two halides
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How are halogeoalkanes formed from alcohols?
Reaction between hydrogen halides and alcohol. (Bromoalkane is formed by potassium bromide and sulfuric acid, NOT hydrogen bromide). Chloroalkane can be formed with hydrogen chloride or Phosphorus chloride
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Describe the nucleophilic substitution between water and halogenolkanes
Cold water replaces halogen with -OH to form alcohol. It is carried out with silver nitrate and ethanol (to dissolve insoluble halogenoalkane)
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Does the rate of reaction of primary alkanes increase or decrease down the group?
Increase as the C-X bond becomes electonegative, so the bond can be broken more easily
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Does the rate of reaction of a primary alkane, or of a tertiary alkane react quicker>
Tertiary structures are more stable, so a reaction is more likely to occur
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Is the reaction between primary halogenalkanes and water a Sn1 or Sn2 reaction?
Sn2 as lack of steric hindrance
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Is the reaction between a tertiary halogenalkane and water a SN1 or SN2 reaction?
Heated under reflux, hydrogen replaced by -OH. Tends to be a slow reaction as more steric hindrance, so SN1 reaction
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What conditions are needed for an elimination reaction to take place on a halogenalkane?
Refluxed with hydroxide ions, anhydrous conditions. NaOH in ethanol at 78*
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Describe the reaction between halogenalkane and cynaide ions?
Heated under reflux with a solution of potassium/sodium cyanide in ethanol. Halogen is replaced by -CN to form nitrile
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What is the reaction called between halogenalkanes and cynaide ions?
Nucleophilic substitution
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When is the reaction between cyanide ions and halogenalkanes used?
To increase length of carbon chain in a molecule
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What conditions are needed for halogenalkane and ammonia to react?
Concentrated ammonia and Ethanol
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What type of reaction is this?
Nucleophilic substution
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What is produced in this reaction?
1.salt 2.Primary amine
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What is the salt called which is produced?
Ethylammonium bromide
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What is the amine called which is produced?
Ethylamine
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Describe an elimination reaction from halogenalkane
Potassium/sodium hydroxide in ethanol (hot ethanonic acid) reacts with halogenalkane under reflux. Forms alkene
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What is the functional group of an alcohol?
-OH
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What is the general formula of alcohols?
CnH2n+1OH
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Why is the boiling always much higher than alkanes?
More hydrogen bonds, so stronger and more energy needed to break it
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Are alcohols soluble in water?
Yes as they are polar. This falls as the chain increases in length
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What is a test used to test for alcohols?
React with Phosphorus Chloride to produce white fumes
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Describe the combustion of alcohols
They burn on a clean, blue flame in plentiful supply of air
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Which two molecules can be used for substituion of -OH by halogen atom?
Hydrogen halides or Phosphorus halides
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Which chemical is used to prepare chloroalkane?
Phosphorus Chloride
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Describe the react of Phosphorus chloride and an alcohol
Room temperature. Produced hydrogen chloride gas and misty fumes
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Write the balanced equation for the reaction of Phosphorus chloride and propanol?
C3H7OH + PCl5 --> C3H7Cl + POCl3 + HCl
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Write the balanced equation for the reaction of Hydrogen Chloride and butanol?
C4H9OH + HCl --> C4H9Cl + H2O
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Which chemical is used to prepare Bromoalkane the best?
Hydrogen Bromide
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Describe the reaction with butan-1-ol and hydrogen bromide
React on heating with sulfuric acid to form 1-bromobutane
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Write the balanced equation of ethanol and hydrogen bromide
C3H7OH + HCl --> C4H9Cl + H2O
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Write the balanced equation of propanol with Phosphorus (III) bromide
(UNDER REFLUX) 3C3H7OH + PBr3 --> 3C37Br + H3PO3
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What chemical is used to prepare Iodoalkane?
Red phosphorus (From phosphoric acid) and Iodide
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Write the reaction between ethanol and Hydrogen Iodide?
C2H5OH + HI --> C2H5I + H2O
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Write the reaction between propanol and Phosphorous (III) iodide
3C3H7OH + PI3 --> 3C3H7I +H3PO3
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What is needed to oxidise alcohols?
Potassium Dichromate (VI) and dilute sulphuric acid, under reflux
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What colour change occurs if oxidation occurs?
Orange --> Green
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What does a primary alcohol oxides to?
Aldehyde --> Carboxylic acid
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What does a secondary alcohol oxides to?
Ketones
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What does a tertiary alcohol oxides to?
No reaction
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What do the names of aldehydes end in?
-al
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What is the functional group of an aldehyde?
Single bond to hydrogen, Double bond to oxygen
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What is the functional group of a carboxylic acid?
Single bond to oxygen and hydrogen, Double bond to oxygen
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What is the functional group of a ketone?
Double bond to oxygen
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What do the names of ketones end in?
-One
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What is the colour change of ketones with potassium dichromate and sulfuric acid?
Orange --> Green
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What colour do tertiary alcohols change to when added to potassium dichromate and sulfuric acid?
NO COLOUR CHANGE (Stays orange)
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Which three reagents can be used to distinguish between Aldehydes and Ketones?
Fehlings/Benedicts/Pho
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Which three reagents can be used to distinguish between Aldehydes and Ketones?
Fehlings/Benedicts/Pho
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Which three reagents can be used to distinguish between Aldehydes and Ketones?
Fehlings/Benedicts/Pho
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Which two reagents can be used to distinguish between Aldehydes and Ketones?
Fehlings/Benedicts
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What does Fehling's solution contain?
Copper (ii) sulphate in water, 2,3-dihydroxybutanedioate in strong alkali
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How does Fehling's/Benedict's help distinguish between aldehyde and ketone?
Aldehyde reduces Cu(II) ions to form orange-brown precipiate
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How can alcohols be changed into alkenes?
Dehydrated with concentrated acids (Phosphoric acid).
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