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1. (25 marks) Provide the names for the following compounds, making sure to correctly identify the chirality R or S at stereogenic centres: CH; a H b) Ķ CH; H, H Br Br H3C H Br. H3C CH; H:C CH; Br Br d H CH3 Br www Ή Η V H:C H Br Br C1 2. (20 marks) Make a clear 3D drawing for each of the following compounds: a) (R)-3-chloro-1-butene. b) (2R,3S)-3-bromo-2-butanol. c) (R) 2-aminopropanoic acid. d) (R,R) trans-1,3-dichlorocyclohexane in its chair conformation. 2. (25 marks) Identify each of the following reactions as SN1, SN2, E1, or E2, provide the products formed in each case and indicate the stereochemistry of the product if appropriate (mechanisms are not required). If no reaction would occur, indicate this with N.R. for “no reaction” and give the reason for which you don't expect a product. H CI OH7H20 50°C !!! CH3 H a) CHZ CI • CH₃ H2O 25°C H b)

H Br CN /DMSO !! CHZ H 25°C c) CH2CH3 Br CH,OH CH3 50°C I d) H OH CN /DMSO 25°C CHZ H e) 4. (30 marks) Provide complete mechanisms for the following reactions: a) Write the complete mechanism for the hydrolysis of 1-bromo-1-methylcyclohexane. (Note: does this occur by an SN1 or SN2 mechanism?) b) Write the complete mechanism for the reaction of methanol with HBr. (Note: does this occur by an SN1 or SN2 mechanism?) c) Write a complete E2 mechanism for the reaction of (R)-2-bromobutane with CH30, showing the stereochemistry of the attack, intermediate and most stable product.