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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

Draw the structures of the following derivatives.

(a) the 2,4-dinitrophenylhydrazone of acetone

(b) the semicarbazone of cyclopentanone

(c) cyclcobuanone oxime

(d) the ethylene acetal of hexan-2-one

(e) acetaldehyde diethyl acetal

(f) the ethyl hemiacetal of acetaldehyde

(g) the (Z) isomer of the ethyl imine of propiophenone

(h) the hemiacetal form of 6-hydroxyhexanal

For each compound,

  1. Name the functional group,
  2. Show what compounds result from complete hydrolysis.

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

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

(a)

(b)

(c)

Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.

(a) bromobenzene 鈫� propiophenone

(b) CH3CH2CN 鈫� heptan-3-one

(c) benzoic acid 鈫� phenyl cyclopentyl ketone

(d) 1-bromo-hept-2-ene 鈫� oct-3- enal
See all solutions

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