Which of the following paths is/are feasible for the preparation of ether (A)?

Path I:

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Path II:

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Path III:

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Path IV:

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Solution

The correct option is D Path IV:
Path IV is feasible for the preparation of ether (A).
2-chloroethanol is heated with conc. sulphuric acid to form an ether $C l - C H_{2} C H_{2} - O - C H_{2} C H_{2} - C l$ .
In the next step, the strong base soda amide removes two molecules of $H C l$ (dehydrohalogenation) to form two $C = C$ double bonds.
In the Pathways I, II and III, since $C = C$ double bond is present in the beginning, it will result in side reactions.

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