Question: Draw the products formed when ${\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}\mathbf{OTs}$is treated with each reagent.

$$\begin{gathered} \mathbf{a}\mathbf{.}\mathbf{}{\mathbf{CH}}_{\mathbf{3}}\mathbf{SH} \\ \mathbf{b}\mathbf{.}\mathbf{}{\mathbf{NaOCH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{3}} \\ \mathbf{c}\mathbf{.}\mathbf{}\mathbf{NaOH} \\ \mathbf{d}\mathbf{.}\mathbf{}\mathbf{KOC}{\left({\mathrm{CH}}_3\right)}_{\mathbf{3}} \end{gathered}$$

There are several leaving groups, and tosylate is one among those leaving groups. p-toulenesulfonyl chloride (TsCl) and pyridine can be utilized to convert alcohols to alkyl tosylates.

Alkyl tosylates undergo several reactions like substitution reactions and elimination reactions.

They can combine with strong bases to get subjected to reaction if it is a substitution reaction${\mathbf{S}}_{\mathbf{N}}\mathbf{2}$and E2 reaction if it is an elimination reaction.

a. This reaction is a substitution reaction and proceeds via the ${\mathrm{S}}_{\mathrm{N}}2$mechanism. The reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_{2}O\mathrm{Ts}$with ${\mathrm{CH}}_3\mathrm{SH}$ is given as:

Reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_{2}O\mathrm{Ts}$with${\mathrm{CH}}_3\mathrm{SH}$

b. The reaction given below is a substitution reaction and moves through the${\mathrm{S}}_{\mathrm{N}}2$mechanism. The reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_{2}O\mathrm{Ts}$with${\mathrm{NaOCH}}_2{\mathrm{CH}}_3$can be given as:

Reaction of with ${\mathrm{NaOCH}}_2{\mathrm{CH}}_3$

c. The given reaction is a substitution reaction and goes via the localid="1648639191260" ${\mathrm{S}}_{\mathrm{N}}2$mechanism. The reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_{2}O\mathrm{Ts}$with NaOH can be given as:

Reaction of${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_{2}O\mathrm{Ts}$with NaOH

d. The reaction specified below is an elimination reaction and proceeds via the E2 mechanism. The reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_{2}O\mathrm{Ts}$with $\mathrm{KOC}{\left({\mathrm{CH}}_3\right)}_3$ is given as:

Reaction of ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_{2}O\mathrm{Ts}$with $\mathrm{KOC}{\left({\mathrm{CH}}_3\right)}_3$