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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

Two structures for the sugar glucose are shown on page 950. Interconversion of the open-chain and cyclic hemiacetal forms is catalyzed by either acid or base.

(a) Propose a mechanism for the cyclization, assuming a trace of acid is present.

(b) The cyclic hemiacetal is more stable than the open-chain form, so very little of the open-chain form is present at equilibrium. Will an aqueous solution of glucose reduce Tollens reagent and give a positive Tollens test? Explain.

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.

A compound of formula C6H10O2 shows only two absorptions in proton NMR: a singlet at 2.67 ppm and singlet at 2.15 ppm. These absorptions have areas in the ratio 2:3. The IR spectrum shows strong absorption at 1708 cm-1. Propose structure of compound.

The Wittig reaction is useful for placing double bonds in less stable positions. For example, the following transformation is easily accomplished using a Wittig reaction
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