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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

NMR spectra for two compounds are given here, together with the molecular formulas. Each compound is a ketone or an aldehyde. In each case, show what characteristics of the spectrum imply the presence of a ketone or an aldehyde, and propose a structure for the compound.

Question. An unknown compound gives a molecular ion of m/z 70 in the mass spectrum. It reacts with semicarbazide hydrochloride to give a crystalline derivative, but it gives a negative Tollens test. The NMR and IR spectra follow. Propose a structure for this compound, and give peak assignments to account for the absorptions in spectra. Explain why the signal atin the IR spectrum appears at an unusual frequency.

Rank the following carbonyl compounds in order of increasing equilibrium constant for hydration:

CH3COCH2Br BrCH2CHO      CH2O      CH3COCH3      CH3CHO

Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.

(a)

(b)

(c)

The family of macrolide antibiotics all have large rings (macrocycle) in which an ester is what makes the ring; a cyclic ester is termed as a lactone. One example is amphotericin B, used as an anti-fungal treatment of last resort because of its liver and heart toxicity. Professor Martin Burke of the University of Illnois has been making analogs to retain the antifungal properties but without the toxicity, including this structure published in 2015. (Nature Chemical Biology, (2015) doi: 10.1038/nchembio.1821). The carboxylate of amphotericin B has been replaced with the urea group (shown in red).

(a) Where is the lactone group that forms the ring?

(b) Two groups are circled. What type of functional group are they? Explain.
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