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Chapter 18: 4P (page 912)

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

Short Answer

Expert verified

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.

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.

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.

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.

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Most popular questions from this chapter

Propose a mechanism for each cyanohydrin synthesis just shown.

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

Give the structures of the carbonyl compound and the amine used to form the following imines.

(a)

(b)

(c)

(d)

(e)

(f)

Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions)

(a) CH3CH2COCH3

(b) CH3CH2CHO

(c) CH3CH2CH=CHCH=CHOH

(d) CH3CH2 CH2CH(OH)OCH3

(e) CH3CH2 CH2CH(OCH3)2

(f)

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

a.

b.

c.

d.

e.

f.

g.

h.
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