Ethyl (E)-3-phenylprop-2-enoate (ethyl cinnamate) is subjected to the sequence: (i) H2 (1 mol), Pd-C, room temperature; (ii) DIBAL-H (1 equivalent), -78 degC, then water; (iii) NaBH4 in methanol. The final product is

(E)-3-phenylprop-2-en-1-ol (cinnamyl alcohol)

JEE Advanced levelSingle correct optionDifficulty 3 of 3ro014

Ethyl (E)-3-phenylprop-2-enoate (ethyl cinnamate) is subjected to the sequence: (i) $H X_{2}$ (1 mol), Pd-C, room temperature; (ii) DIBAL-H (1 equivalent), $- 78^{\circ} C$ , then water; (iii) $NaBH X_{4}$ in methanol. The final product is

(i) saturates the C=C: ethyl 3-phenylpropanoate. (ii) DIBAL-H at low temperature stops at the aldehyde: 3-phenylpropanal. (iii)

NaBH X_{4}

reduces the aldehyde to

C X_{6} H X_{5} CH X_{2} CH X_{2} CH X_{2} OH