Drug Synthesis Study Guides

1. What are the main 5 or- - Addition ganic reactions? - Elimination - Substitution - Oxidation and Reduction - Rearrangement 2. What is functional group interconversion? Where one functional group is transformed to another 3. What is a conjugation Two molecules react to make a larger molecule reaction? 4. What is oxidation? Loss of electrons, gain of oxygen 5. What is reduction? Gain of electrons, loss of oxygen 6. What functional Carboxylic acid and acid chloride as they're at the groups cannot be inter- same oxidation level converted and why? 7. What is an electrophile? A molecule/atom that accepts electrons to form a new bond (electron loving). 8. What is a nucleophile? A molecule/atom that donates electrons (nucleus-loving). 9. What do the electrons The movement of electrons to depict the bond makshow in mechanisms? ing and breaking process 10. What is Le Chatelier's When a system in equilibrium is disturbed, the new principle? equilibrium changes to counteract the effect of the change and establish a new equilibrium. 11. How are amides formed? What type of reaction is this? Amine + Acid -> Amide + H2O A condensation reaction. 12. To 'mask' the corresponding acid which tends to have poor physicochemical properties. 1/4 What are esters mostly used for in the context of drug deliver? 13. Why does ester hydrol- As the process is very slow, even in boiling water so ysis require accelerat- acids, bases or enzymes need to be used. ing? 14. What happens when With acids, the equilibrium is reversible, with bases ester hydrolysis ocit is not. curs under acids compared to bases? 15. What is de-protonation? Loss of H+ ions 16. What is protonation? Gain of H+ ions 17. What is a carbonyl group? C=O 18. Can carbonyl groups be an electrophile or nucleophile? They can act as both 19. What is an enolate (or De-protonated alpha carbon; nucleophile enol)? 20. What happens when an The product is still nucleophilic, so will go on to react amine reacts with an until an ammonium ion is produced. organic halide? 21. What is reductive ami- A method to stop over-alkylation. nation? 22. What is molecule rearrangement? Where the molecule is able to reorganise itself into a substitution pattern which is more stable or lower in energy 23. 2/4 Why is less likely to react compared to alkenes alkenes? It has a delocalised electron ring so is stables and less like to react unless a good (reactive) electrophile is used. 24. What are the reactants Concentrated nitric acid (HNO3) and concentrate for nitration of bensulphuric acid (H2SO4) zene? 25. What are the reacChlorine and Iron (III) Chloride (FeCl3) tants for halogenation - can also be done with bromine of benzene? 26. What are the reactants Concentrated sulphuric acid for the sulfonylation of benzene? 27. What are the reactants CH3Cl and AlCl3 for the alkylation of benzene? 28. What are the reactants CH3COCl and AlCl3 for the acylation of benzene? 29. What is semi-synthesis? Utilisation of compounds that have been isolated from natural sources, such as bacteria, as starting materials 30. What is Coartem? An antimalarial drug derived from naturally occurring artemisinin. 31. Why (and what) is the lactone group in artemisinin replaced by? Because the lactone group is unstable, it's replaced by acetal In a two step process. 32. How is the lactone group in artemisinin re- 1. Reduction with potassium borohydride placed? 3. Methoxylation 3/4 33. What is chlorampheni- Broad spectrum antibiotic useful for the treatment of col? a number of bacterial infections 34. Why is chlorampheni- It's cheap and easy to manufacture col frequently the antibiotic of choice? 35. What do in-silico tools Predict the behaviour of a compound do? 36. Why are in-silico tool predictions not accurate? The human body is very complex so can react differently 4/4