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(D) In option $A$,the reaction of $sec$-butanol with $SOCl_2$ in the presence of pyridine proceeds via an $S_N2$ mechanism,resulting in the inversion

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(D) In option $A$,the reaction of $sec$-butanol with $SOCl_2$ in the presence of pyridine proceeds via an $S_N2$ mechanism,resulting in the inversion of configuration. The product shown is consistent with this.In option $B$,the reaction of $sec$-butanol with $PBr_3$ proceeds via an $S_N2$ mechanism,resulting in the inversion of configuration. The product shown is consistent with this.In option $C$,$NaH$ deprotonates the alcohol to form an alkoxide ion,which then performs an intramolecular $S_N2$ attack on the carbon bearing the bromine atom,forming a six-membered cyclic ether (tetrahydro-2H-pyran). This is correct.In option $D$,the reaction of benzene with $I-Cl$ in the presence of a Lewis acid like $AlCl_3$ is an electrophilic aromatic substitution. Since $I$ is less electronegative than $Cl$,$I^+$ acts as the electrophile. Therefore,the major product is iodobenzene,not chlorobenzene. Thus,this reaction does not represent the correct major product.

Select the reaction that does $NOT$ represent the correct major product.

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