The following road-map problem centers on the structure and properties of A, a key intermediate in these reactions. Give structures for compounds A through J.
Solution 48SP
Aldehydes undergo oxidation in presence of PCC to form carbonyl compounds.
Primary alcohols react with PCC to form aldehydes and the secondary alcohols react with PCC to form ketones.
The reaction is as follows:
Aldehydes form acetals more readily than ketones. So, selectively protect the aldehyde as a acetal by reacting with 1,2-diol.
2-oxo cyclohexanecarbaldehyde reacts with ethane 1,2-diol to form the product A.
The reaction is as follows:
Ketones react with phenylhydrazine to form phenylhydrazone and followed by acidic hydrolysis of acetal in presence of to give the deprotected aldehyde.
The reaction is as follows:
Only aldehydes react with Tollen’s reagent to form silver mirror. Ketones cannot react with tollen’s reagent.
The reaction is as follows:
Here, aldehyde is protected as an acetal and ketone cannot react with tollen’s reagent, so, No reaction occur.
Acetal reacts with dilute chromic acid to form 2-oxo cyclohexanecarbaldehyde.
The 2-oxo cyclohexanecarbaldehyde undergoes clemmensen reduction in presence of to form the product F (methylcyclohexane).
The reaction is as follows:
Ketone reacts with methylmagnesium iodide (Grignard reagent) and followed by hydrolysis to form the product G.
The reaction is as follows:
Aldehydes undergo reduction in presence of Na to form alcohols.
The reaction is as follows:
The reactant G undergoes dehydration in presence of an acid to form the product I.
The reaction is as follows:
Aldehydes react with Grignard reagent (cyclopentyl magnesium bromide) and followed by hydrolysis () to form alcohols.
The reaction is as follows:
