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Chapter 18: Q4P (page 923)

Use equations to show the fragmentation leading to each numbered peak in the mass spectrum of cotane-2-one.

Short Answer

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Fragmentation equations of octane-2-one

Step by step solution

01

Molecular ion

When high-energy electron hits an organic compound, it removes one of the electrons from the molecule and hence produces positively charged ions known as the molecular ions.

Formation of molecular ion

The molecular ion is not only acting as a cation but also as a free radical because of the presence of an odd number of electrons. Hence, it can be called as enol radical cation.

02

McLafferty rearrangement

The characteristic fragmentation of the molecular ion of a carbonyl compound ( ketones and aldehydes) having at least one gamma hydrogen is known as the McLafferty rearrangement.

03

Equations for fragmentation of octane-2-one

Fragmentation equations of

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Most popular questions from this chapter

Propose a mechanism for each cyanohydrin synthesis just shown.

Trimethylphosphine is a stronger nucleophile than triphenylphosphine, but it is rarely used to make ylides. Why is trimethylphosphine unsuitable for making most phosphorus ylides?

Show what alcohols and carbonyl compounds give the following derivatives.

(a)

(b)

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Propose a mechanism for both parts of the Wolff-Kishner reduction of cyclohexanone: the formation of the hydrazone, and then the base catalyzed reduction with evolution of nitrogen gas.

(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

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(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.
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