8. Draw the structure of compounds A-E in the following synthetic scheme. HBr 40 °C D+ A NaCN H B H3O+ E H₂ Pd NaOH H₂O A ů OH + En 1. CH₂N₂ 2. DIBAL -78 °C 3. H+ OH HO + En

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Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.