This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Organic Chemistry II University of Lincoln presentation

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Contain double or triple bonds, but do not show the same reactivity as other unsaturated hydrocarbons Benzene: C 6 H 6 Used mainly as solvents Substitution rather than Addition is favoured Aromatic Hydrocarbons

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Delocalisation, Resonance: Stabilise molecules, so make them less reactive Three sp2 hybrid orbitals arrange themselves as far apart as possible -which is at 120° on a plane. The remaining p orbital is at right angles to them. Each carbon atom uses the sp2 hybrids to form σ -bonds with two other carbons and one hydrogen atom. Delocalised or Conjugated System: π-bonding electrons can move within the molecule Resonance Structure: Rearrange the bonding electrons 6 p-orbitals Delocalised orbital clouds

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License FlurobenzeneTolueneEthylbenzene 2,4,6-Trinitrotoluene (TNT) Aniline 1,2-DichlorobenzenePhenol1,3-Dichlorobenzene 1,4-Dichlorobenzeneo-Xylenem-Bromostyrene Benzoic acid -ortho -para -meta Naming Aromatic Hydrocarbons

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Substitution Aromatic Substitution reaction – Aromatic compound loses a hydrogen atom and another atom or group takes its place. It is possible for substitution to occur in more than one place on the ring. otha-Dinitrobenzenepara-Dinitrobenzenemeta-Dinitrobenzene Reactions of Aromatic Hydrocarbons

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License –OH group (hydroxyl group) Replace -e with -ol CH 3 OH, methanol, simplest alcohols are classified as primary (1°), secondary (2°), or tertiary (3°) depending on the number of carbon atoms bonded to the carbon bearing the - OH group Primary Alcohol (1 o ) Secondary Alcohol (2 o ) Tertiary Alcohol (3 o ) Alcohols

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Polyhydroxy alcohols are alcohols that possess more than one hydroxyl group methanolethanolpropanol 2-propanol or propan-2-ol or isopropyl alcohol 2-ethyl-1-butanol or 2-ethyl-butan- 1-ol 1,2-Ethanediol (ethylene glycol) 1,2-propanediol (propylene glycol) 1,2,3-propanetriol (glycerol) Naming Alcohols

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License ■ Reaction with acids to produce Esters ■ Redox reaction (Reduction and oxidation) Ethanol Acetic Acid (ethanoic acid) Ethyl acetate Acetaldehyde Alcohol Dehydrogenase Acetic Acid Reactions of Alcohols

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License –O- group (ether group) CH 3 OCH 3, dimethyl ether simplest Soluble in water- H-bonding to water - Polar Flammable – Ether can cause flash fires Low Reactivity – Make Good Reaction Solvents Naming: alkyl groups in alphabetical order followed by ether Ethers

Naming Aldehydes Change -e ending to –al ethane ethanal (acetaldehyde) Ketones Change -e ending to –one propanepropanone (acetone) This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Both contain a carbonyl group (C=O) Aldehyde Ketone Aldehydes and Ketones

Reactions of Aldehydes and ketones This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Synthesis: produced by oxidation of alcohol Reduction of carbonyl group to produce alcohols Primary Alcohol Oxidation Reduction Secondary Alcohol Oxidation Reduction Tertiary Alcohol Cannot be oxidised

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Oxidation Strong Oxidation Reduction Carboxylic acid Oxidation of carbonyl group

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Contains C=O and –OH group on same carbon Change -e to -oic acid Acetic acid: acid in vinegar Simplest: methanoic acid (formic acid) Methanoic acidEthanoic acidPropanoic acid Carboxilic acids

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License ■ Esterification reactions ■ Reduction to aldehydes Acetic Acid (ethanoic acid) Ethyl acetate Reactions of Carboxilic acids

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Derived from carboxylic acids and alcohols Tend to be fragrant –Methyl butyrateapple –Ethyl butyratepineapple An ester name has two parts - the part that comes from the acid (propanoate) and the part that shows the alkyl group (methyl). Example: Methyl propanoate Ester

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Substitution Reduction of esters Hydrolisis of esters (basic) Ester Acid Amide R 2 OH R+R+ H2OH2O R 2 NH base Carboxylate ester Sodium hydroxide Sodium Carboxylate Alcohol Reactions of Esters

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Derived from ammonia by substituting H for alkyl groups. It is an alkali We have primary, secondary or tertiary amines depending on the number of H substituted Amines Ammonia Primary amine (1 o ) Secondary amine (2 o ) Tertiary amine (3 o )

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License 1,4-butanediamine Putrescine (found in decaying meat) (1 o ) Amphetamine (dangerous stimulant) (1 o ) Piperidine Triethylamine (3 o ) Isopropylamine (1 o ) 1,5-pentanediamine Cadaverine (found in the putrefaction of cadavers Amines

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Alkylation Oxidation reduction Phenylamine Reactions of Amines

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License Acknowledgements JISC HEA Centre for Educational Research and Development School of natural and applied sciences School of Journalism SirenFM