Using Table 6.1, write an equation for each of the following substitution reactions:
a. p-methylbenzyl chloride + sodium acetylide
b. n-propyl bromide + sodium cyanide
c. 2-iodopropane + sodium hydrosulfide
d. 1-bromopentane + sodium iodide
e. 2-chlorobutane + sodium ethoxide
f. t-butyl bromide + ethanol
g. 1,6-dibromohexane + sodium cyanide (excess)
h. allyl chloride + ammonia (2 equivalents)
i. 1-methyl-1-chlorocyclohexane + water

Table 6.1 Reactions of Common Nucleophiles with Alkyl Halides (Eqs. 6.2 and 6.3) Nu Formula Oxygen nucleophiles 1. HO,-hydroxide R-Nu ame Formula Comments alcohol ether alkyloxonium ion .RO alkoxide R OR .. R-0 These ionsROH lose a proton and the products are alcohols and ROR 3. (alcoho) 4. ROH alcohol dialkyloxonium ion ether) 0 carboxylate ester Nitrogen nucleophiles alkylammonium ion With a base, RNH NH ammonia these ions readily lose a proton to give amineS. RNH2 primary amine R-NH,R dialkylammonium ion RNH condary amine R-NHR trialkylammonium ion tertiary amine R-NR tetraalkylammonium ion Sulfur nucleophiles 10. HS: 11. RS: 12. RS: Halogen nucleophiles 13. hydrosulfide RSH mercaptide R-SR thioether thiol thioether (sulfide) trialkylsulfonium ion R-SR The usual solvent is acetone. Sodium iodide is soluble in acetone, but sodium bromide and sodium chloride are not. iodide R-I: alkyl iodide Carbon nucleophiles 14. C N: Sometimes the isonitrile R-N C:, is formed. cyanide R-C-N: alkyi cyanide (nitrile) 15. :C CR acetylide R-C-CR alkyne