12. Rank the species below in order of increasing nucleophilicity in a protic solvent: CH3CO2,CH3S,HO,H2O. 13. A student attempted to prepare 1-chlorobutane by treating 1-butanol with a solution of NaCl. Did the student get the desired product? Explain. 14. What is the nucleophile in the following reaction I. III. H3O VV. IHO II. H2O 15. How does doubling the concentration of the alkyl halide in the following SN1 reaction affect the rate of the reaction? Show the step by step mechanism. (CH3)3CBr+I(CH3)3CI+Br 16. Which of the following statements is true about SN 1 reactions of alkyl halides? A) Complete inversion of configuration occurs. B) These reactions are favored by nonpolar solvents. C) These reactions are favored by polar solvents. D) Reaction rates depend only on the concentration of the nucleophile. E) The mechanism is a one-step back-side attack