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Organic Chemistry I

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Organic Chemistry I 6: Organic Chemistry I 6A. Introduction to Organic Chemistry Basic definitions Hydrocarbon is a compound consisting of hydrogen and carbon only to know Saturated: Contain single carbon-carbon bonds only Unsaturated : Contains a C=C double bond Molecular formula: The formula which shows the actual number of each type of atom Empirical formula: shows the simplest whole number ratio of atoms of each element in the compound General formula: algebraic formula for a homologous series e.g. CnH2n Structural formula shows the minimal detail that shows the arrangement of atoms in a molecule, eg for butane: CH3CH2CH2CH3 or CH3(CH2)2CH3, Displayed formula: show all the covalent bonds present in a molecule Drawing Displayed formulae Remember that the shape around the carbon atom in saturated hydrocarbons is H H H H When drawing organic tetrahedral and the bond angle is 109.5o H C C C C H compounds add the hydrogen atoms so that H H H H H H C H each carbon has 4 bonds H C C H H H H Skeletal formula shows the simplified organic formula, shown by removing hydrogen atoms from alkyl chains, leaving just a carbon skeleton and associated functional Groups. OH But-2-ene Butan-1-ol 2-methylbutane cyclohexane cyclohexene N Goalby chemrevise.org 1 Homologous series are families of organic compounds with the same functional group and same general formula. •They show a gradual change in physical properties (e.g. boiling point). • Each member differs by CH2 from the last. • same chemical properties. Functional group is an atom or group of atoms which when present in different molecules causes them to have similar chemical properties prefix / suffix homologous functional example (* = usual use) series group Alkane CH CH CH CH C C -ane 3 2 2 3 Butane H H Alkenes C C suffix -ene C C H propene H C H H C OH suffix* -ol H H H Propan-1-ol Alcohols prefix hydroxy- H C C C O H OH H H H H H H Halogenoalkanes C halogen 1-chloropropane prefix chloro- H C C C Cl bromo- H H H Cl iodo- O suffix -al H O Aldehydes C H ethanal prefix formyl- H C C H O H O suffix* -one H O H O Propanone C prefix oxo- Ketones H C C C H H H O suffix -oic acid H O O Ethanoic acid carboxylic acids C OH H C C OH H OH O -yl –oate C O methylethanoate Esters H O H O H C C O C H H H O N Goalby chemrevise.org 2 no of General rules for naming carbon chains code carbons Count the longest carbon chain and name appropriately meth 1 Find any branched chains and count how many carbons they contain eth 2 Add the appropriate prefix for each branch chain prop 3 Eg -CH3 methyl or -C2H5 ethyl –C3H7 propyl 1 but 4 CH3 pent 5 2 CH2 hex 6 5 3,5-dimethylheptane hept 7 H C CH CH CH CH 3 3 2 3 4 oct 8 6 CH2 non 9 dec 10 7 CH3 Basic rules for naming functional groups •When using a suffix, add in the following way : If the suffix starts with a vowel- remove the –e from the stem alkane name e.g. Propan-1-ol, butan-1-amine, ethanoic acid, ethanoylchloride, butanamide If the suffix starts with a consonant or there are two or more of a functional group meaning di, or tri needs to be used then do not remove the the –e from the stem alkane name e.g. Propanenitrile, ethane-1,2-diol, propanedioic acid, propane-1,2,3-triol, Pentane-2,4-dione. The position of the functional group on the carbon H H H O H chain is given by a number – counting from the end of H C C C C H Butan-1-ol the molecule that gives the functional group the lowest 4 3 2 1 number. For aldehydes, carboxylic acids & nitriles, the functional group is always on carbon 1. H H H H H H H We only include numbers, H C C C H methylpropane however, if they are needed to CHCl trichloromethane H H 3 avoid ambiguity. H C H H •The functional groups take precedence over branched 3-methylbut-1-ene is correct and not 2-methylbut-3-ene chains in giving the lowest number H H H H H Where there are two or more of the same groups, di-, tri- , H C C C C C H 2,3-dibromopentane. tetra-, penta- or hexa- are used. Note the point made above H H Br H about the addition of ‘e’ to the stem Br Words are separated by numbers with dashes CH FCCl CH CH 2,2-dichloro-1-fluorobutane. numbers are separated by commas 2 2 2 3 If there is more than one functional group or side chain, the CH FCH CHBrCH CH 3-bromo-1-fluoropentane groups are listed in alphabetical order (ignoring any di, tri). 2 2 2 3 H H Br H Halogenoalkanes Class the halogen as a substituent on the C chain and use the 2-bromobutane suffix -fluoro, -chloro, -bromo, or –iodo. (Give the position H C C C C H number if necessary) H H H H N Goalby chemrevise.org 3 Alkenes 4 2 Double bond between The double bond will be between two carbons. Use the lower 1 3 C2 and C3 so But-2-ene number of the two to show the position of the double bond The name for alkenes may include E or Z at start to show Z-but-2-ene the type of stereoisomer If more than one double bond is present then suffix Penta-1,3-diene ends diene or triene. The stem ends in a CH2OHCHBrCH=CH2 2-bromobut-3-en-1-ol The suffix for alkenes can go in front of other suffixes. OH E-but-2-enoic acid O Alcohols OH These have the ending -ol and if necessary the position Butan-2-ol number for the OH group is added between the name stem CH3 CH CH2 CH3 and the –ol 1 2 3 4 O 2-hydroxypropanoic acid If the compound has an –OH group in addition to other H3C CH C functional groups that need a suffix ending then the OH can be named with the prefix hydroxy- OH OH Ethane-1,2-diol HO CH2 CH2 OH If there are two or more -OH groups then di, tri are used. H2C CH CH2 Add the ‘e’ on to the stem name though propane-1,2,3-triol OH OH OH Aldehydes H An aldehyde’s name ends in –al O Ketones H O H It always has the C=O bond on the Ketones end in -one H C C C H first carbon of the chain so it does H C C not need an extra number. It is by When ketones have 5C’s or more H H default number one on the chain in a chain then it needs a number H H to show the position of the double Propanone Ethanal bond. E.g. pentan-2-one If two ketone groups then H O H O H di is put before –one and H C C C C C H an an e is added to the stem H H H Pentane-2,4-dione Carboxylic acids These have the ending - H H oic acid but no number is O If there are carboxylic acid groups on both ends of the necessary for the acid chain then it is called a - dioic acid group as it must always be H C C C O O at the end of the chain. Ethanedioic acid C C The numbering always O H starts from the carboxylic H H HO OH Note the e in this name acid end Ethanoic acid Esters H H O H Esters have two parts to their names H C C C O C H The bit ending in –yl comes from the alcohol that has formed it and is next to the single bonded oxygen. H H H The bit ending in –anoate comes from the carboxylic acid. O (This is the chain including the C=O bond) methylpropanoate O N Goalby chemrevise.org 4 Isomers Structural isomers: same molecular formula different structures (or structural formulae) Structural isomerism can arise from EDEXCEL does not split structural •Chain isomerism isomers into the different categories. •Position isomerism They are all classed as structural isomers. •Functional group isomerism Chain isomers: Compounds with the same molecular formula but different structures of the carbon skeleton H H H H H H H H H H H C H H H H C C C C C H H C C C C H H C C C H H H H H H H H H H C H H H H C H H pentane H 2-methylbutane 2,2-dimethylpropane Position isomers: Compounds with the same molecular formula but different structures due to different positions of the same functional group on the same carbon skeleton H H H H H H H C C C H 1-bromopropane H C C C H 2-bromopropane Br H H H Br H Functional group isomers: Compounds with the same molecular formula but with atoms arranged to give different functional groups H H H H Methoxymethane: an ether H C C O H ethanol: an alcohol H C O C H H H H H H H H H C H C C H Cyclohexane- cyclo alkane CH3CH2CH2CH2CH=CH2 hexene- alkene H C C H C H H H H Note: alkene and cyclo alkanes have the same general formula.
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