AS Organic Chemistry Revision. Part 1

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1 AS Organic Chemistry Revision. Part Nomenclature and isomerism in organic compounds understand the terms empirical, molecular and structural formulae, homologous series and functional groups; apply IUPAC rules to naming organic compounds with up to six carbon atoms and containing up to two of the functional groups relevant to this specification; describe and explain structural isomerism for aliphatic compounds containing up to six carbon atoms; understand that stereoisomers (geometrical) isomers exist (alkenes) in cis and trans (E Z) forms due to the energy barrier to rotation in these compounds; 2.3 Hydrocarbons alkanes write the general formulae for alkanes, CnH2n+2; understand that alkanes are saturated hydrocarbons; recall the molecular and structural formulae for alkanes containing up to six carbon atoms; use IUPAC rules to name alkanes, including branched structures; explain, in terms of van der Waals forces, the variation in boiling points; recall that crude petroleum is the source of alkanes and that they are obtained by fractional distillation (no details of plant required) and understand thermal cracking; describe the combustion of alkanes in a limited and plentiful supply of air; describe the substitution reactions of alkanes by chlorine and by bromine; explain how homolytic fission leads to the mechanism for the photochemical reaction between methane and chlorine viewed as free radical substitution; discuss the environmental problems associated with spillage and the combustion of hydrocarbons; a simple account of the role of catalytic converters in reducing the environmental damage due to vehicle emissions by facilitating the conversion of carbon monoxide to carbon dioxide, of unburnt hydrocarbons to carbon dioxide and water and of NOx to nitrogen; catalyst poisoning by lead (technical details of the construction of catalytic converters are not required); 2.4 Hydrocarbons alkenes write the general formula for alkenes, CnH2n; understand that alkenes are unsaturated hydrocarbons and that they decolourise bromine water; recall the molecular and structural formulae for alkenes containing up to six carbon atoms; use IUPAC rules to name alkenes containing up to two bonds; C=C use sigma and pi bonds to explain the relative bond strength and relative bond length of the bond; C=C know that the is a centre of high electron density and use this to explain the difference in reactivity of alkanes and alkenes; C=C describe the catalytic hydrogenation of alkenes using finely divided nickel and its application to the hardening of oils (the detailed structure of the oil molecule is not required); describe the reaction of Cl2, Br2, HCl and HBr with simple alkenes. (Markovnikoff s rule not required); AS Organic Chemistry Revision. Part 1-1

2 2.4.9 explain the mechanism of the reaction between HBr and ethene viewed as electrophilic addition. Understand the term heterolytic fission; and describe the addition polymerisation of alkenes eg ethene and propene. 2.5 Halogeno-alkanes write the general formula for halogenoalkanes CnH2n+1X, where X is a halogen atom; recall the molecular and structural formulae of halogenoalkanes with up to two halogen atoms and up to six carbon atoms (refer to primary, secondary and tertiary structures); use IUPAC rules to name halogenoalkanes containing up to two halogen atoms and up to six carbon atoms; comment on the variation in boiling points of the halogenoalkane; describe the laboratory preparation of a halogenoalkane from the corresponding alcohol, with specific reference to refluxing, using a separating funnel, removal of acidic impurities, drying, simple distillation; describe the substitution reactions of halogenoalkanes with aqueous alkali, ammonia and cyanide ions; explain the mechanism for the reaction of primary and tertiary bromoalkanes with hydroxide ions viewed as nucleophilic substitution; compare the ease of hydrolysis of primary halogenoalkanes related to bond enthalpy and bond polarity; describe the elimination of hydrogen bromide from bromoethane using ethanolic potassium hydroxide; 2.6 Alcohols write the general formulae for alcohols, CnH2n+1OH; recall the molecular and structural formulae of alcohols with up to six carbon atoms (refer to primary, secondary and tertiary structures); use IUPAC rules to name alcohols containing up to two hydroxyl groups and up to six carbon atoms; refer to the effect of hydrogen bonding on boiling point and miscibility with water; recall the preparation of alcohols from halogenoalkanes; recall the industrial production of ethanol from (i) the fermentation of sugars and from (ii) the reaction of steam with ethene in the presence of H3PO4; describe the combustion of alcohols and their use as an alternative fuel; describe the reaction of primary alcohols with sodium, hydrogen bromide, phosphorus pentachloride and thionyl chloride; comment on the oxidation of alcohols using acidified potassium dichromate with reference to (a) the formation of aldehydes and carboxylic acids from primary alcohols and the isolation of each depending on reaction conditions (b) the formation of ketones from secondary alcohols (c) the resistance to oxidation of tertiary alcohols; describe the esterification reactions of alcohols with carboxylic acids and with ethanoyl chloride; prepare iodoform and know its use to distinguish between alcohols containing CH3CH(OH) and other alcohols with specific reference to recrystalisation and melting points; AS Organic Chemistry Revision. Part 1-2

3 CH3CH(OH) and other alcohols with specific reference to recrystalisation and melting points; discuss the use of ethanol in alcoholic drinks and its use as a recreational drug which can have beneficial and harmful effects. A AS Organic Chemistry Revision. Part 1-3

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