What's in a Medicine?

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  • What's in a Medicine?
    • Equilibria
      • acids are proton donors
        • Bronsted-Lowry Theory
      • basas are proton acceptors
        • Bronsted-Lowry Theory
    • Bonding and Structure
      • Ionic
        • electrostatic attraction holds oppositely charged ions together in a lattice
        • conducts electricity when molten or in solution
        • soluble in water
      • Covalent
        • nuclei are attracted electrostatically to shared electrons
        • Molecule
          • never conducts electricity
            • Giant Structure
              • high mpt.
                • Ionic
                  • electrostatic attraction holds oppositely charged ions together in a lattice
                  • conducts electricity when molten or in solution
                  • soluble in water
                • Metallic
                  • conducts electricity
                  • positive metal ions are attracted to delocalised electrons to form a lattice
              • not soluble in water
                • Metallic
                  • conducts electricity
                  • positive metal ions are attracted to delocalised electrons to form a lattice
          • low mpt. (break id-id or H bonds only)
          • sometimes soluble in water(depending on polarity)
        • Giant Structure
          • high mpt.
            • not soluble in water
            • Dative Covalent
              • both electrons come from one atom
          • Dative Covalent
            • both electrons come from one atom
          • Electron Pair Repulsion Theory
            • electron pairs will repel each other as far as possible
            • lone pairs repel the most so have the biggest bond angles
        • Organic Functional Groups
          • phenols
            • C6H6-R
            • mix at room temp = ester
              • acyl chlorides
                • R-COCl
              • ester
                • R-COO-R
            • purple with iron(III) chloride
            • weak acid - electrons delocalise
          • carboxylic acids
            • R-COOH
            • form carboxylate ion so reacts with alkalis and carbonatesto form salts
            • heat with acid catalyst = ester
              • alcohols
                • reflux, acidified potassium dichromate
                  • primary alcohols
                    • carboxylic acids
                      • R-COOH
                      • form carboxylate ion so reacts with alkalis and carbonatesto form salts
                      • heat with acid catalyst = ester
                        • alcohols
                          • reflux, acidified potassium dichromate
                            • primary alcohols
                              • distill
                                • aldehydes
                                  • R-CHO
                            • secondary alcohols
                              • ketones
                                • R-CO-R
                        • ester
                          • R-COO-R
                    • distill
                      • aldehydes
                        • R-CHO
                  • secondary alcohols
                    • ketones
                      • R-CO-R
          • acyl chlorides
            • R-COCl
          • amines
            • reflux with excess NH3 in ethanol
              • halogenoalkanes
                • R-C-X
                • HCl, room temp /////////////// reflux with HaOH (aq)
            • halogenoalkanes
              • R-C-X
              • HCl, room temp /////////////// reflux with HaOH (aq)
              • alkanes
                • C-C
                • nickel catalyst, 150 temp, high pressure
                  • alkenes
                    • HBr or Br2, 20 temp
                      • R-C=C-R
                      • water, conc sulfuric acid //////////  reflux with sulfuric acid
                  • alkenes
                    • HBr or Br2, 20 temp
                      • R-C=C-R
                      • water, conc sulfuric acid //////////  reflux with sulfuric acid
                      • Reaction Mechanisms
                        • hydrogen cyanide
                          • cyanohydrin
                            • Nucelophilic Addition
                        • carbonyl compund
                          • cyanohydrin
                            • Nucelophilic Addition
                      • ethers
                        • R-O-R
                      • arenes
                        • C6H6
                      • acid anhydrides
                        • R-OC-O-CO-R
                      • cycloalkanes
                        • CnH2n
                    • Applications of Organic Chemistry
                      • Medicines
                        • more effective medicines can be obtained by modifying existing the structure of existing medicines
                        • Clinical Trials
                          • Step II - Does it work?
                          • Step I - Is it safe?
                          • Step III - Is it better than the standard treatment?
                      • Atom Economy
                        • % atom economy = (Mr of product / Mr of all products) x 100
                        • high atom economy reactions are better for the environment - less waste products
                        • rearrangement
                          • 100% atom economy
                            • addition
                        • addition
                        • elimination
                          • << 100% atom economy
                        • substitution
                          • < 100% atom economy
                    • Modern Analytical Techniques
                      • Thin Layer Chromatography
                        • to separate mixtures of molecules
                        • mobile phase
                          • small volume of solvent, below baseline
                        • stationary phase
                          • layer on silica on metal/glassplate
                          • pencil baseline to place mixture on
                            • small volume of solvent, below baseline
                        • solvent carries substances up plate at different speeds
                          • coloured dots for coloured substances
                            • Rf = distance travelled by spot / distance travelled by solvent
                              • UV light
                              • iodine vapour (sealed jar)
                          • colourless substances
                            • UV light
                            • iodine vapour (sealed jar)
                      • Mass Spectrometry
                        • M+ peak
                          • second highest peak
                          • Mr of compound
                        • all peaks are positive ions lost
                          • CH3 =  m/z 15
                          • C6H5 = m/z = 77
                      • Infrared Spectroscopy
                        • IR radiation absorbed by bonds, so their vibrational energy increases
                        • Peaks/troughs so the wavenumber, which corresponds to a bond in a molecule
                  • solvent carries substances up plate at different speeds
                    • coloured dots for coloured substances
                      • Rf = distance travelled by spot / distance travelled by solvent
                      • colourless substances

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