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Chapter 18: Q48P (page 969)

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

Expert verified

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

01

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.

02

Acetal formation

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

03

KMnO4 oxidation

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

04

  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.

05

Use of PhNHNH2

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

06

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.

07

 Zn Hg HCl using

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

08

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.

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Most popular questions from this chapter

Sodium triacetoxyborohydride, NaBHOAc3, is a mild reducing agent that reduces aldehydes more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.

Propose a mechanism for the acid-catalyzed reaction of benzaldehyde with methanol to give benzaldehyde dimethyl acetal.

Question: Show a complete mechanism for this equilibrium established in diethyl ether with HCI gas as catalyst.

Question. One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts and show why this mechanism does not work for the other one.

Question. The mass spectrum of unknown compound A shows a molecular ion at m/z 116 and prominent peaks at m/z 87 and m/z 101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane , and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm-1in the IR spectrum and a weak maximum at 274nm(E =16) in the UV spectrum. The mass spectrum of B shows a molecular ion of m/z 72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z 87 and 101.
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