1. Show the reaction mechanism for the SN1 reaction of 2-iodo-2-methylpentane with sodium bromide. Is the product of this reaction chiral? Consider elimination reactions for each of the following reagent combinations: a) Determine whether the substrate is more likely to undergo an E1 or E2 mechanism. b) Draw the reaction mechanism you chose including all reagents, the organic product, and an necessary intermediates. 2. CH3CH2Cl in reaction with sodium hydroxide 3. tert-butylbromide in reaction with H₂O For each of the following organic compounds, indicate whether it is more likely to undergo nucleophilic substitution by the S1 mechanism, S2 mechanism, or both. 4) 2-chloro-2-methylpentane 6) CH, 5) 7) For each of the following reagent combinations, state which reaction mechanism(s) is most likely to take place (SN1, S2, E2, and/or E1) and justify your choice. If more than one will occur, state each in your explanation and indicate which (if any) is more likely. You do not need to draw the product. 8. CH,CH,C(CH)Br and H₂O Justification: Mechanism(s): 9. CHICH, and sodium ethoxide Mechanism(s): Justification: 10. CH,CH-Cl and potassium tert-butoxide Mechanism(s): Justification: