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Organic Chemistry By: Charlie Carrick 9C Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Pg Table of Contents 1 – Cover Page 2 – Table of Contents 3 – Carbon General Information 4 – Carbon Diagram 5 – Substances Containing Carbon 6 – Impact of Carbon on the Environment 7 – Alkenes General Information 8 – Alkenes Diagram 9 – Alkanes General Information 10 – Alkanes Diagram 11 – How to name a complicated branched alkane 12 – General Information – Alkenes 13 – Alkene Diagram 14 – Substitution 15 – Bromination 16 – Hydrogenation 17 – Hydration 18 – Haloalkenes 19 – Isomers 20 – Alcohols 21 – Organic Acids - Bibliography Carbon-General Information Carbon is an element that forms many things when joined with other elements. It can form over ten million compounds that we know of. It’s chemical symbol is C, it’s atomic number is 6. We breathe in 0.003% of carbon and breathe out 4%, which is absorbed in by the plants, who depend on it to live. Carbon is , however, a major contributor of air pollution and it can be very harmful to us. Carbon is a non-metal and forms covalent bonding, making it different from other elements because it is the only element that is able to do this. There are 810 gigatonnes of carbon in the earth’s atmosphere It has a valency of 4 Carbon Diagram http://www.chemicalelements.com/bohr/b0006.gif Different Substances that Contain Carbon Coal-over 50% Diamonds-pure carbon Soot Coke Graphite Carbon is the basis of all organic chemistry Antibiotics Alcohol Fat Fossil Fuels Pencils Hydrocarbons Long chains or ring structure Burnt in excess air – Co2+H2O Simplest organic carbon Impacts that Carbon has on the Environment It reacts with other elements and contributes to acid rain which is dangerous for our skin. It is actually what plants breathe, so it is good for us when it is plants breathing it. As I already said, carbon is the basis for all organic chemistry (life). Carbon by itself is not usually the problem, it is when we burn it and when it is mixed with other elements to form some very deadly and toxic gases that pollute and kill the environment Compounds Containing Carbon Carbon dioxide, a very common gas Carbon monoxide, a gas that comes out of cars Carbon Disulfide Carbon monofluoride Carbon subnitride Carbon suboxid Carbon tetrachloride Carbon tetra iodide Carbon trioxide Carbonic acid Carbonyl sulfide You can find out how much carbon you are using by going to this website and answering the questions: http://www.carbonfootprint.com/ Alkanes-General Information An alkane is an acyclic saturated hydrocarbon, similar to an alkene, but still different Alkanes are known to bond to certain metals They are not as reactive as alkenes The simplest alkane there is, is methane Alkanes can form different isomers if they have more than two carbon atoms Another name for an alkane is “paraffin,” but this is more of a general term Alkanes Diagram http://www.webelements. com/webelements/elements /media/kossel-pics/C.jpg http://www.coolschool.ca/lor/C H11/unit7/U07L06/CHEM11_A3 _694.jpg These are the steps to name more complicated branched alkanes taken straight from a website: Identify the longest linear chain of carbon atoms. This portion is named as if it were a linear alkane (i.e. 4 linear carbon atoms would be a butane). One of the terminal ends of this chain is numbered 1. The terminus which has the fewest carbon atoms from the branch is numbered 1. the nomenclature is determined for the branching group in a similar fashion as above. the compound is then named (branching number e.g. 2)-(name of branching group, e.g. methyl)-(name of longest linear chain, e.g. butane) so as to give you the alkane's name, e.g. 2-methylbutane which is shown right. Alkenes-General Information An alkene can also be called an olefin, vinyl compound or olefin It contains at least one carbon-to-carbon bond The simplest ones form a hydrocarbons series The simplest forms are also usually gases Alkenes are relatively stable Cracking of petroleum is a common synthesis path Diagram of Alkenes http://wps.prenhall.com/wps/media/objec ts/476/488316/Instructor_Resources/Chapt er_18/FG18_02-13un.JPG http://www.chem.unsw.edu.au/re search/groups/images/cyclopentan e_complex.gif Alkynes An alkyne is a type of hydrocarbon that has a triple bond, always between carbon atoms Formula - CnH2n-2. Alkynes are very reactive and they are also unstable “RC≡CH + B → RC≡C− + HB+, where B denotes a strong base.” There are terminal and internal kinds of alkynes Terminal alkynes have joined to the triple bond (through the carbon) a hydrogen atom Internal alkynes have a different atom linked to the carbon atom in the triple bond, sometimes they can be carbon as well Alkynes are used a lot in organic chemistry Dehydrohalegenation is a way to prepare alkynes for what you want to do with them Substitution To substitute in organic chemistry is to replace an atom, functional group, or a substituent in a molecule They could be replaced by things like alkyls, hydroxyls or halogens Common substitution reactions are nucleophilic substitutions and halogenations Bromination Bromination is where you combine a substance with a bromine It is a word used to specify the type of halogen Alkene + Bromine water =Bromo-ethane Hydrogenation Hydrogenation is a chemical reaction where the result is an addition of hydrogen Usual targets are unsaturated organic compounds Unsaturated hydrogenation is known as an alkene Hydration The addition of water Double alkene-C-C Alcohol or ethanol, good for disinfecting things Methanol however is very toxic for people and animals Haloalkanes Also known as halogenoalkanes or alkyl halides A compound where halogen atoms replace hydrogen atoms in an alkane They have different classes to determine the type of haloalkane depending on where the halogen atom is The three types are primary, secondary and tertiary The primary types are where the carbon atom is only linked to one other alkyl group The secondary type carbon atoms are linked to 2 other alkyl groups, they can be the same or different, it doesn’t matter The tertiary type is where the carbon atoms are linked to 3 different/similar alkyl groups Isomers The same atoms and chemical formula but they are arranged differently (structural forms) There are two main forms; structural isomerism and stereoisomerism There are many different kinds of isomers and they are used for a wide range of things, although it can be quite pricy Alcohols Is gained by the method of fermentation A simple equation for an alcohol is CnH2n+1OH Generally refers to the word ethanol There are primary, secondary and tertiary alcohols based on how many carbons are connected together The simplest primary alcohol is methane Ethanol is the only one that is not poisonous, is colourless and strong smelling, it is a liquid, the boiling point is 78.5ْ It is a compound that has hydroxyl –OH group Flammable, burning produces carbon dioxide and water Methanol is a good disinfection Organic Acids The most common are the carboxylic acids They are usually quite weak acids They are usually soluble in solvents They are used as oil and gas simulation treatments These are less reactive Some are used in buffer solutions Acid + base =salt + water Ethanoic acid + ethanol = ethyl ethanoate(ester) = water carboxylic acids Characterized by presence of the carboxyl group The formula is -C(=O)OH, usually written -COOH They are Bronsted acids (even though the are weak acids, they react with metals to form salts) React with carbonates to form carbon dioxide React with alcohols to form esters and water React with alcohol and a strong acid to form esters and water Carboxylates are salts and anions of these acids Do not associate with ions easily Alkaloid acid R-COOH Simplest is meathanoic acid and also ethanoic The three related acids are esters, acid chloride, and acid anhydride (RC=O-O) Equations Acid + base =salt + water Ethanoic acid + ethanol = ethyl ethanoate (ester) = water 3 Fatty acid + glycerol = ethyl ethanoate ----Fats (triglyceraldehyde) Fats +alkali (NaOH) --- Soap (fats/oils) = glycerids (salt of carboxylic acid) Esters In which a hydrogen atom is replaced by an organic group The carboxylate esters are most common Unstable acids can be manipulated to form stable esters Their name is quite similar to salts A condensation reaction of an acid and an alcohol is what forms an ester This is when a small molecule is taken out of the equation after two larger molecules join Ester + water and acid = carboxylic acid + alcohol Ester + water and alkali = salt + alcohol Ester + alkali = soap + water Most things we smell we smell because of esters Esters are used in perfumes and polmers They form long chains called polyester and add them to plastic to give them flexibility Aldehydes and Ketones An aldehyde is a kind of organic acid and it contains a “terminal carbonyl acid” The aldehyde group has a few other names, such as formyl and methanoyl In an aldehyde group, there is a carbon atom bonded to another kind of atom called a hydrogen atom, it is then double-bonded to an oxygen atom Aldehydes are more acidic than alkanes It also creates an electron deficiency because of the oxygen Adding oxygen to aldehydes is easier than adding it to ketones Aldehyde – Ethynol Ketones – Propane Aromatic compounds They have a defined ring structure of chains looping Most common one is benzene, which is colourless and it is a volatile liquid It is used a lot in the industrial world Carcinogen Polymers A polymer is made up of molecules with a large MW Monomers are the sub unit of polymers They are repeated using covalent bonds There is a glucose called monosaccharide Monosaccharide + monosaccharide= disaccharide ++++=polysaccharide (polymer) Amino acids form a chain called polypeptide Plastic Synthetic polymers Bakelite – polymers They are a hard substance Polymerisation Condensation reaction (dehydration synthesis) Glucose + glucose = Add on monomer (alkenes – double bonds) Addition polymerisation Amides/amines – nitrogen Thermo setting/softening Amino acids join in peptide links Amines + carboxylic acid = polyamide (nylon – very versatile) Kevlar used to make bulletproof vests, very strong Polyester used in fabrics using carboxylic acids Polyurethane used for foam and lycra for swimsuits Bibliography http://ull.chemistry.uakron.edu/genobc/chapter_11/ http://en.wikipedia.org/wiki/Carbon http://www.chemicalelements.com/bohr/b0006.gif http://www.webelements.com/webelements/elements/media/kossel-pics/C.jpg http://www.carbonfootprint.com/ http://en.wikipedia.org/wiki/Alkene http://www.coolschool.ca/lor/CH11/unit7/U07L06/CHEM11_A3_694.jpg http://en.wikipedia.org/wiki/Alkane http://wps.prenhall.com/wps/media/objects/476/488316/Instructor_Resources/ Chapter_18/FG18_02-13un.JPG http://www.chem.unsw.edu.au/research/groups/images/cyclopentane_complex. gif http://www.chemguide.co.uk/organicprops/haloalkanes/background.html http://en.wikipedia.org/wiki/Carboxylic_acid http://en.wikipedia.org/wiki/Ester http://en.wikipedia.org/wiki/Polymer