Question

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.

Short answer

DMP is a reagent used to convert hydroxyl group to ketones or aldehydes. In the above conversion DMP is used to get desired product.

Step-by-step solution

what is DMP

DMP is a reagent used to convert hydroxyl group to ketones or aldehydes. In the above conversion DMP is used to get desired product.

Acetal formation

In presence of-dihydroxyl compound and TsOH acetal is formed. Here it is A.

KMnO4 oxidation

KMnO₄is a strong oxidising agent. It can oxidisedacetsls to ketones or aldehydes.

  NaCr2O7 oxidation

It is also a strong oxidising agent. It will oxidise the ketone as the other carbonyl group from the aldehyde is protected by forming acetal.

Use of PhNHNH2

It is a part of stork inamine reaction. It can convert ketones to double bonded NNHPh compound.

Use of Grignard reagent

Grignard reagent is used to convert ketos to alcohol in presence of acidic condition. Here the G product is obtained after using Grignard reagent in acid.

 Zn Hg HCl using

Zn Hg HCl is used to reduced the keto to to methyl. The F product is obtained using this.

Last step: using another Grignard reagent

In the last step the Grignard reagent is used to get the desired product. And this Grignard reagent as marked as J using in acidic medium to get the result.