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Question:

CH3CH=CHCN (a) DIBAL-H (b) H2O?

Solution:

The products of the reaction are as shown (i)Cyclohexanone reacts with HCN to form 1-hydroxycyclohexanecarbonitrile. A molecule of HCN is added to C=O double bond (ii) When sodium benzoate is heated with NaOH+CaO, benzene is formed. It is an example of decarboxylation (iii) DIBAL-H reduces but-2-enenitrile to but-2-enal. Cyano group is reduced to aldehyde group. C=C double bond remains intact.