Identify the lettered compounds $D$ to $G$ in the following reaction schemes.

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Solution

The acetylide ion displaces the epoxide oxygen to form alkoxy alcohol. This on hydrolysis in acidic medium forms diol.The primary $- O H$ group is tosylated and reduced with $L i A l H_{4}$ . The net effect is the replacement of primary $- O H$ group with $H$ atom. The secondary $- O H$ group is then alkylated with $N a H$ and Ethyl lithium to form an ether. The acidic hydrogen atom attached to triple bond is then removed with $N a H$ and the acetylene carbon is methylated with methyl iodide to give the final product.

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Identify A, B, C, D, and E in the following schemes and write their structures:

N a_{2} C O_{3} S O_{2} - - \to (A) N a_{2} C O_{3} - ---- \to (B) S \to (C) A g N O_{3} - --- \to (D)

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