Testbank Question 132 Suggest a stepwise synthesis of 3pheny

Testbank, Question 132

Suggest a stepwise synthesis of 3-phenylpropanal from benzyl alcohol.

Answers should be in words, not pictures.

Solution

In presence of PBr3, benzyl alcohol converted into benzyl bromide.

Ph-CH2OH + PBr3.................> Ph CH2Br

In presence of Mg / ether, benzyl bromide is converted into Grignard reagent.

Ph CH2Br + Mg / ether .............> Ph-CH2MgBr

Ph-CH2MgBr react with ethylene oxide followed by treating H3O+ to form the 3-phenylpropanol.

3-phenylpropanol is oxidized in presence of PCC to 3-phenylpropanal.