Write equations showing the reaction of octadecyl p-toluenesulfonate with each of the foll...

Write equations showing the reaction of octadecyl p-toluenesulfonate with each of the following reagents:

(a)

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(b) Potassium iodide (KI)

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(c) Potassium cyanide (KCN)

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(d) Potassium hydrogen sulfide (KSH)

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(e) Sodium butanethiolate (NaSCH₂CH₂CH₂CH₃)

Sample Solution All these reactions of octadecyl p-toluenesulfonate have been reported in the chemical literature, and all proceed in synthetically useful yield. You should begin by identifying the nucleophile in each of the parts to this problem. The nucleophile replaces the p-toluenesulfonate leaving group in an S_N2 reaction. In part (a) the nucleophile is acetate ion, and the product of nucleophilic substitution is octadecyl acetate.