The compound below can be prepared with an alkyl iodide and a suitable nucleophile. Identify the alkyl iodide and the nucleophile that you would use. For an anionic nucleophile, you do not need to draw the counterion. CN :C=N: :C=N: :C=N: :C=N:

15. Which of the following correctly describes the relative nucleophilicities of methoxide and tert- butoxide? A) These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects. C) tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density. D) tert-Butoxide is more nucleophilic because it is more basic. E) none of the above 16. Rank the species below in order of increasing nucleophilicity in protic solvents: CH3CO2-, CH3S-, HO-, H2O. Answer: A. H2O