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Organic Chemistry Organic Chemistry: Study of the compounds of Carbon 7 million examples Inorganic Chemistry: Study of molecules without Carbon ( 1.5 million examples)
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Hydrocarbons Organic molecules consisting only of carbon and hydrogen with covalent bonds. Major components of fossil fuels such as coal, oil or gas. They consists of partially decomposed remains of organisms that lived millions of years ago. Methane is a fossil fuel, it is easily made in anaerobic conditions with manure and bacteria (also in swamps or dumps)
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Hydrocarbons CH4 Methane
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Methane Production Methane can be produced in: Coalmines Slurry pits
Waste dumps Digestive tracts of animals
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Hazards of Methane Production
Fires and explosions Death by suffocation Contributes to the greenhouse effect
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Empirical Formula = formula represents the lowest ratios of the element in a compound
Molecular Formula = a molecular formula describes the numbers of different kinds of atoms in a molecule Structural Formula = a structural formula represents a two-dimensional model of how the atoms are bonded to each other. Each dash represents a bonding pair of electrons. Condensed Structural Formula = structural formula written not drawn
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**Ignore that it’s Spanish (I think)
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Draw a carbon atom How many monovalent atoms can bond to carbon?
What shape and bond angle will carbon molecule have? 109.5 What type of bond? Covalent or ionic
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Definition Saturated = chemical compound that has a chain of carbon atoms linked together by single bonds and has atoms filling all of the other bonding orbitals of the carbon atoms. (SINGLE BONDS ONLY- BONDING ORBITALS FULL) Unsaturated compound is a chemical compound that contains carbon-carbon double bonds or triple bonds, such as those found in alkenes or alkynes, respectively. (CONTAINS DOUBLE/ TRIPLE BOND)
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Tetrahedral compounds are saturated
Alkanes Chloroalkanes [Haloalkanes] Alcohols Where-ever there is a double or triple bond they become planar
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Carbon skeletons can vary in length.
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Organic compounds An aromatic compound is a compound that contain a benzene ring. Aliphatic compound is an organic compound that consists of open chains of carbon atoms and closed chains compounds (ring) that resemble them in chemical properties eg. Cyclohexane
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Cycloalkanes are alkanes (only carbon to carbon single bonds) which form a ring structure.eg cyclohexane The "straight" chain has carbon atoms that are able to rotate freely around their single bonds, sometimes linking up in a closed ring. Ring compounds of the first four cycloalkanes =
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Aromatic Hydrocarbons
Contain benzene rings Delocalised electrons Benzene: C6H6 unreactive (less than expected), alternating double and single bonds with bond length between single and double bond length Stable insoluble in water Toxic Carcinogenic good organic solvent planar
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Range and scope of aromatic chemistry
Methyl benzene is used as a industrial solvent Pharmaceutical compounds, e.g. Morphine Herbicides, e.g. Diuron Detergents, e.g. Sodium dodecylbenzenesulfonate Dyes, e.g. Martius Yellow The acid-base indicators phenolphthalein and methyl orange are also aromatic compounds:Phenolphthalein, Methyl orange Benzene is carcinogenic
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Homologous series Alkanes occur in what is called a homologous series.
A series of compound of uniform chemical type Showing gradations in physical properties Having a general formula for its members Each member having a similar method of preparation Each successive compound differs from the one before it only by a CH2
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Homologous series
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Alkanes Only have single bonds between carbons (saturated)
Have maximum amount of Hydrogens End with –ane CnH2n+2 Fairly unreactive but do burn in oxygen, used as fuel due to high heat of combustion, cheap and clean products Tetrahedral shape (not planar) 109.5o angles Non-polar so immiscible in water Ethane Butane C1-C4 (gas) C5-C12 (liquids) C13-C31 (waxy solids) C32+ (solids).
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C1to C4 Gases C5 to C16 Liquids C17 + Waxy Solids
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Natural gas is pure methane
Bottles gas is propane and butane
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General formula CnH2n+2 Identify the number of H’s in each alkane
C5Hx C10Hx C16Hx C55Hx C3Hx C28Hx C21Hx C4Hx C15Hx What state?
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Need to know how to draw structural formula
Must know how to draw from nameor vice versa CH3CH2CH(CH3)CH3
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(commonly called isobutane)
Branching Skeletons may be branched or unbranched. Butane C4H10 2-methylpropane (commonly called isobutane)
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Structural Isomers Are compounds with same molecular formula but different structural formulas The number of isomers increases tremendously as carbon skeletons increase in size. Only need to know to C5 2 Structural Isomers of Butane
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Naming alkanes (IUPAC)
Identify the longest continuous chain of carbons. = parent name/compound The locations or other groups of atoms attached to the longest chain are identified and numbered by counting from the end of the molecule which keeps the numbering system as low as possible. Hydrocarbon groups that are attached to the longest continuous chain and named using the parent name and changing the –ane suffix to –yl. For groups attached, priority is given based on alphabetical order i.e. ethly before methyl
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Functional groups Is an atom or group of atoms which is responsible for the characteristic properties of a series of organic compounds Eg. methyl, ethyl, propyl Eg. halogens Electronegative functional groups increase the molecules reactivity with polar molecules and solubility in polar molecule eg. water
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Chloroalkanes Physical state: Liquid, except for chloromethane and chloro-ethane, which are gases at room temperature Boiling points higher than the corresponding alkanes(most liquids except C1 &C2), due to polar C-Cl bond(s) (but only weak) Not soluble in water Soluble in non-polar solvents such as cyclohexane Because of their weak polarity, they are useful organic solvents, e.g. for removing grease and oil from machinery removing oil etc. from clothes - dry cleaning Fully halogenated alkanes are flame retardant so used in fire extinguishers
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Naming chloroalkanes Last part of name comes from base alkane on which the molecule is built, e.g. chloroethane [2 carbons] Number of chlorine atoms indicated by prefix mono, di, tri, tetra etc. in front of chloromethane, e.g. trichloromethane Position of each chlorine atom given by a number before the name, e.g. 1,2,2-trichloropropane
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Alkenes Alkenes are different to alkanes; they contain DOUBLE COVALENT bonds. CnH2n Unsaturated Ethene is the 1st member C2 to C4 are gases, boiling pt increases with increasing carbon chain More reactive than alkane Undergoes addition rxns Ethene Butene Test for alkenes = 1. they turn bromine water colourless 2. acidified KMnO4 colourless. planar
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Ethene is used to make ethanol for industrial use
make polyethene By polymerisation rxn (addition rxn with H2 as a by product) Ethene is the gas that ripens fruit, and a ripe fruit emits the gas, which will act on unripe fruit. Thus, a ripe tomato placed in a sealed bag with green tomatoes will help ripen them. Ethene is used to make ethanol for industrial use
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Naming Alkenes Naming is similar to naming alkanes except:
The longest continuous chain must contain the double bond. The base name now ends in –ene. The carbons are numbered so as to keep the number for the double bond as low as possible. Number the double bond on parent (in word or before) i.e. pro-1-ene, 1 propene The number which identifies the location of the double bond takes priority to functional groups
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Alkynes An alkyne is a hydrocarbon with at least one carbon to carbon triple bond. Naming an alkyne is similar to the alkenes, except the base name ends in –yne. Even more reactive due to triple bond Planar Highly unsaturated CnHn-2
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Alcohols In the alcohols it is the OH [hydroxyl] group
General Formula CnH2n+1OH Members of this Homologous Series are Methanol CH3OH Ethanol C2H5OH Propanol C3H7OH Butanol C4H9OH etc.
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Classification
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Primary Alcohols H H H | | | H - C - C - C - OH Propan-1-ol H H H
| | | H - C - C - C - OH H H H Propan-1-ol The C to which the OH is attached has only got one C attached directly to it.
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Secondary Alcohols H H H | | | H - C - C - C - H H OH H Propan-2-ol
| | | H - C - C - C - H H OH H Propan-2-ol The C to which the OH is attached has got two C’s attached directly to it.
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Tertiary Alcohol [Not needed now]
| H - C - H H | H | | | H - C - C - C - H | | | H OH H 2, Methyl Propan-2-ol The C to which the OH is attached has got three C’s attached directly to it.
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Intermolecular Force between molecules dictate it’s B. Pt. and M. Pt
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Boiling Points of alcohols
Higher than expected for their RMMs due to polar OH group Polarity due to a difference in electronegativity between O and H O = : H = difference 1.4 leads to Hydrogen Bonding Compare Methanol and Methane [RMM approx 30]
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Solubility is controlled by the molecules attraction to water
As a general rule ‘Like dissolves like’ i.e. polar substance will dissolve other polar substances. The lines get a bit blurry when you have slightly polar substances as the can have slight solubility or poor solubility i.e. they dissolve little bit
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Solubility Methanol in
(i) cyclohexane – not soluble methanol is polar cyclohexane is not (ii) water - completely soluble or miscible [infinitely soluble] because it is polar. Like dissolves like Polar dissolves polar As alcohol gets bigger the polar part becomes less significant so it becomes less soluble in water and more soluble in cyclohexane
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Ethanol and water can’t be totally separated by distillation.
Constant Boiling Mixture of 95% alcohol To dry ethanol totally the last of water must be removed by drying agent e.g. CaO Pure alcohol is called absolute alcohol
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Butan-1-ol in (i) cyclohexane is soluble (ii) water pretty insoluble The polar OH group is becoming less significant as the molecule gets bigger
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Comparison with water Both have polar OH [hydroxyl] groups
Alcohols have a non-polar part Water has a higher boiling point than alcohol because it has more polarity It has 2 polar OH groups therefore H bonding is even more pronounced
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Found in almond kernels
Aldehydes -CHO end in anal Planar Boiling points higher than the corresponding alkanes, due to polar +C = O- group, but lower than the corresponding alcohols Short chain aldehydes are soluble in water due to the polar carbonyl group As the number of carbon atoms in a molecule of the aldehyde increases, solubility in water decreases, while solubility in cyclohexane increases Aromatic aldehyde Found in almond kernels
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Ketone End in -one Physical state: Butanone and propanone are liquids at room temperature Boiling points higher than the corresponding alkanes, due to polar +C = O- group, but lower than the corresponding alcohols Short chain ketones such as propanone are soluble in water due to the polar carbonyl group Ketones are soluble in non-polar solvents such as cyclohexane Propanone is used as a solvent (e.g. In nail varnish remover)
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Carboxylic acid End in –oic acid
Physical state: Methanoic acid and ethanoic acid are liquids, while propanoic acid and butanoic acid are solids due to H bonding Short chain carboxylic acids are soluble in water due to the polar -COOH group Carboxylic acids are soluble in non-polar solvents such as cyclohexane Boiling points higher than the corresponding alcohols This is because carboxylic acids form dimers, where two carboxylic acid molecules are held together by two hydrogen bonds This is possible due to polarity in both the C=O and O-H bonds in each carboxylic acid molecule Examples Methanoic acid is found in the sting of ants and nettles Ethanoic acid is the principal acid in vinegar Ethanoic acid is used in the manufacture of cellulose acetate Propanoic acid, benzoic acid and their salts (e.g. sodium benzoate) are used as food preservatives Long chain carboxylics acids are fatty acids (sub unit of lipids)
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COOH
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Boiling or Melting Points
Ethanol = 78’ Ethanoic Acid = 118’
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Alcohol vs. Corresponding Carboxylic Acid B. Pt.
Alcohols: Have 1 Hydrogen bond between molecules Carboxylic Acids: have 2 H bonds between its molecules
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Dimer: a molecule or molecular complex consisting of two identical molecules linked together.
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Solubility Of Carboxylic Acids
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Esters Esters are formed by the reaction of a carboxylic acid with an alcohol e.g. CH3COOH CH3OH = CH3COOCH H2O Ethanoic acid Methanol Methyl ethanoate The first part of the ester name comes from the parent alcohol with the - anol changed to – yl and the second part of the name comes from the parent acid with the - oic acid changed to – oate.
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Boiling Point and Solubility
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Physical state: Liquid
Boiling points higher than the corresponding alkanes, but lower than the corresponding alcohols Soluble in water and non-polar solvents such as cyclohexane As the number of carbon atoms in a molecule of the ester increases, solubility in water decreases, while solubility in cyclohexane increases Occur naturally in fruits and flowers– are responsible for their pleasant smells and flavours Fats and oils are naturally occurring esters of long chain carboxylic acids Ethyl ethanoate is used as a solvent for printing inks and paints
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