Industrial Applications of Organic Chemistry

Unit 28: Industrial Applications of Organic Chemistry Unit code: H/502/5573 QCF Level 3: BTEC National Credit value: 10 Guided learning hours: 60 Aim and purpose The aim of this unit is to familiarise learners with the structure, naming and properties of a range of organic compounds and to investigate the industrial uses of these compounds. Unit introduction The majority of the substances we use every day are, or contain, organic compounds. Pharmaceuticals such as aspirin and paracetamol, synthetic fibres for our clothes such as nylon and polyesters, fuels for our transport vehicles, soaps and detergents, dyes, flavourings, perfumes and liquid crystal display materials are just a few of the many organic substances that are manufactured on an industrial scale for us all to use. In this unit, learners will develop knowledge of the key classes of organic compounds that are industrially important and their chemistry which makes them useful to us. The number of known organic compounds is enormous and growing. This is because carbon, the basis of organic compounds, can form molecules consisting of chains and rings of atoms that enable it to bond with itself and other elements. The classes of organic compounds, their naming and their ability to form different arrangements of the same atoms (isomerism) are recurring themes. Learners should find answers to the following questions: What types of organic compounds are there? What functional groups are there? How are they named? What are their properties? What are the mechanisms for their reactions? How can one class of organic compound be prepared from another? What are the industrial uses of organic compounds? Why is isomerism important? Is it easy and safe to carry out reactions of organic compounds in the laboratory? The simplest of all organic compounds are the hydrocarbons. Learners will study these and their industrially useful reactions. Learners will then look at a range of functional group compounds and collect information about them. This study will include their properties, reactions and how they can be converted into one another. This latter aspect allows the synthesis of organic compounds with particular structures, fitting them for specific commercial uses. ● ● ● ● ● ● ● ● Edexcel BTEC Level 3 Nationals specification in Applied Science – Issue 1 – January 2010 © Edexcel Limited 2009 2 This unit enables learners to consider what it is like to work in the science industry. It is suitable for all learners who are interested in a career in science. Learning outcomes On completion of this unit a learner should: 1 Know the properties of hydrocarbons 2 Know the properties of simple functional group compounds 3 Understand the importance of isomerism 4 Be able to carry out reactions involving organic compounds. 3 Edexcel BTEC Level 3 Nationals specification in Applied Science – Issue 1 – January 2010 © Edexcel Limited 2009 Unit content 1 Know the properties of hydrocarbons Hydrocarbons: straight chain and branched alkanes and alkenes, benzene Structures: structure representations, full (displayed) structural formulae showing all the bonds, shortened structural formulae, 3D representations using wedge/dashed line diagrams, skeletal formulae, sigma and pi-bonding in alkanes and alkenes, delocalised pi-bonding in benzene; bond lengths and strengths in alkanes, alkenes, benzene Nomenclature: IUPAC nomenclature, naming structural isomers, E-Z Physical properties: eg increase in boiling point with chain length, separation by fractional distillation, hydrophobicity Chemical reactions: free radical substitution in alkanes, electrophilic addition of water, halogens, hydrogen halides and sulfuric acid in alkenes, stability of carbocations, symmetric and asymmetric alkenes, electrophilic addition in benzene, nitration of benzene, mechanisms, reactions of commercial importance, eg free radical polymerisation of alkenes, hydration of ethene 2 Know the properties of simple functional group compounds Simple functional group compounds, non-carbonyl: halogenoalkanes, alcohols, amines Simple carbonyl compounds: aldehydes, ketones, carboxylic acids, esters, acyl chlorides, amides Properties of non-carbonyl compounds: nomenclature; halogenoalkanes – nucleophilic substitution of halogenoalkanes (OH– , NH3 , primary amines), SN1 and SN2 mechanisms of nucleophilic substitution, elimination reactions; alcohols – primary, secondary and tertiary alcohols, solubility of alcohols, reactions of alcohols, eg with sodium, oxidation with hot copper (II) oxide, oxidation with acidified dichromate (VI), oxidation of primary, secondary and tertiary alcohols; primary, secondary and tertiary amines, amines as bases, amines as nucleophiles, reaction of amines with halogenoalkanes; synthesis of commercially important organic compounds, eg PVC, CFCs and HCFCs Properties of carbonyl compounds: nomenclature; aldehydes and ketones – oxidation of aldehydes with Tollens’ reagent, Benedict’s or Fehling’s reagents, acidified dichromate (VI), reduction of aldehydes and ketones (NaBH4 , LiAlH4 ), nucleophilic addition of HCN to aldehydes and ketones, addition-elimination reactions of aldehydes and ketones, eg reaction with 2,4-dinitrophenylhydrazine, hydrazine, oxime; carboxylic acids – carboxylic acids as acids, weak acidity of carboxylic acids, reaction with alcohols to form esters; esters as solvents, flavours and fragrances; acyl chlorides – reaction of acyl chlorides, eg with water, alcohols, phenol, ammonia and amines; mechanisms; preparation of amides, eg from carboxylic acids, acyl chlorides and acid anhydrides; hydrolysis of amides; synthesis of commercially important polyamides, eg nylon and Kevlar; other commercially important organic compounds, eg polyester 3 Understand the importance of isomerism Isomerism: structural, chain, positional, functional group; stereoisomerism, geometric, optical Importance: three-dimensional structures and representations, recognition of isomers, different properties of isomers, eg different boiling points of chain and positional isomers, different reactions of functional group isomers, lower melting points of Z (cis) isomers, cis and trans (E and Z) fats, natural occurrence of particular optical isomers, optical isomers of sugars, optical isomers of amino acids, different therapeutic effects of optical isomers of drugs, difference between starch and cellulos