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Introduction to Organic Chemistry

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  1. Introduction to Organic Chemistry

  2. Curriculum Outcomes • recognise and understand the use of a variety of formula types • understand that an organic compound generally consists of a hydrocarbon component plus a functional group • recognise the common functional groups • understand and be able to use the IUPAC nomenclature • understand the formation of homologous series and understand the similarity of properties

  3. Counting Carbon Atoms 1 – meth 2 – eth 3 – prop 4 – but 5 – pent 6 – hex 7 – hept 8 – oct You must learn to count the longest carbon chain and name it by giving the prefixes shown.

  4. The Alkanes The alkanes are made by joining carbon atoms together and completing the molecule by adding hydrogen atoms.

  5. Build it! Create the molecules • Methane • Ethane • Propane • Butane

  6. Representing Organic Molecules Molecular Formula • This formula is used where the shape of the molecule is unimportant. E.g. combustion of propane. C3H8 + 5O2 3CO2 + 4H2O

  7. Representing Organic Molecules Full Structural Formula Propane

  8. Representing Organic Molecules Condensed Structural Formula CH3 – CH2 – CH3 Propane

  9. Representing Organic Molecules Skeletal Formula Propane At the end of each line it is assumed that there is a carbon and a full compliment of hydrogens, except where an other group is shown

  10. Representing Organic Molecules Representing 3 Dimensions Out of the page Into the page On the page Propane

  11. Homologous Series A homologous series is a series of compounds with • The same general formula • The same functional group The alkanes are one homologous series. Each successive compound in the series adds one CH2 group.

  12. Functional Groups • Each homologous series has a unique functional group • A functional group is a specific group of atoms or bonds that is responsible for the characteristic chemical reactions of the molecules in the homologous series.

  13. Alkenes The functional group for the alkenes is a carbon carbon double bond. C=C Build the alkenes • ethene • propene • butene (can it be done in more than one way?)

  14. Naming We name organic molecules by numbering the location of the functional groups Build: • 1-butene • 2-butene • 3-butene When we name organic molecules we ensure the the numbers are as small as possible, thus 1-butene is the correct name and 3-butene is incorrect.

  15. IUPAC International Union of Pure and Applied Chemistry We name organic molecules according to the IUPAC rules.

  16. Alkynes The functional group for the alkynes is the carbon carbon triple bond. C Ξ C Build the model ethyne. This is also called acetylene and is used in welding and cutting torches. The triple bond contains a lot of energy

  17. Alkanols (Alcohols) The functional group for the alkanols is the hydroxyl group. -OH Build one molecule of etheneand one molecule of water.

  18. Location of the –OH group Alkanols are named according to the location of the functional group. • 1-propanol is a primary alkanol • 2-propanol is a secondary alkanol • Make these two molecules.

  19. More than one –OH group? Glycerol is an organic molecule that is the byproduct from soap manufacture. How can we name this molecule according to the iupac rules? 1,2,3-propanetriol

  20. Hydration Reaction When ethene is heated to 300ºC in the presence of steam and a phosphoric acid (H3PO4) the ethene is hydrated to produce industrial ethanol. C2H4 + H2O C2H5OH Simulate this reaction with your molecules H3PO4 Catalyst 300ºC

  21. Carboxylic Acid The functional group for the carboxylic acids is Vinegar contains ethanoic acid. It also has the name acetic acid. Make this molecule.

  22. Carboxylic Acids When writing the molecular formula, the functional group is written as: -COOH

  23. Aldehydes The functional group of the aldehydes is: The double bonded oxygen is known as a carbonyl group Aldehydes have a strong odour and are found in many essential oils.

  24. Aldehydes • Formaldehyde (methaldehyde) was used for many years as a preservative and disinfectant, but is now known to cause cancer • Make an aldehyde molecule. An octopus preserved in formaldehyde

  25. Aldehydes and Alkanols When we write the condensed structural formula for an aldehyde we write the functional group as: -CHO This distinguishes it from the alcohols which are written as: -COH

  26. Ketones Ketones contain a carbonyl group like the aldehydes, however it is between two carbon atoms rather than the end of a chain. R and R’ are the generic way of representing a carbon chain of unknown length

  27. Ketones Acetone is an important industrial solvent. It is also used as nail polish remover. Make a molecule of acetone. What do you think its IUPAC name would be?

  28. Ketones Name the molecule below

  29. Amines • Amines are biologically significant molecules. • Important amines include amino acids – the building blocks to make proteins

  30. Amines The condensed structural formula for the functional group of a primary amine is: -NH2

  31. Amines • Make a molecule of methylamine. • Make a molecule of trimethylamine. • Trimethylamine is the molecule associated with the smell of rotting fish and bad breath.

  32. Haloalkanes • A single hydrogen can be substituted with a single halogen molecule to make a haloalkane. • Name each of the haloalkanes below. • Construct a model of one of them

  33. Naming Haloalkanes When writing the name of a haloalkanes • commas (,) are used to separate numbers, eg, 1,2 or 2,3 • hyphens (-) are used to separate numbers and letters, eg, 1-chloro and 1,2-dichloro • Name the longest carbon chain. • Carbon atoms bonded to halogen atoms are given the lowest possible numbers.

  34. Naming Haloalkanes • Halogens are named before alkyl groups : 
        fluorine atom is named as fluoro 
        chlorine atom is named as chloro 
        bromine atom is named as bromo 
        iodine atom is named as iodo • For more than one of the same halogen: 
        di = 2 
        tri = 3 
        tetra = 4 • For more than one type of halogen, name them alphabetically.

  35. Naming Haloalkanes Name the following haloalkanes

  36. Branched Chain Alkanes All organic compounds looked at so far have had only one straight chain of carbon atoms. In the same way that a halogen can be substituted we can also substitute another organic molecule.

  37. Alkylation When we substitute one hydrogen for a hydrocarbon chain we call this process alkylation.