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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

Show a complete mechanism for this equilibrium established in diethyl ether with HCl gas as catalyst.

Predict the products formed when cyclopentanecarbaldehyde reacts with the following reagents.

(a) PhMgBr, then H3O+

(b) Tollens reagent

(c) semicarbazide and weak acid

(d) excess ethanol and acid

(e) propane-1-3-diol, H+

(f) zinc amalgam and dilute hydrochloric acid

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses alkene and triphenylphospine oxide.

  1. Show each step in the reaction of trans-2,3-epoxybutane with triphenylphospine to give but-2-ene. What is the stereochemistry of the double bond in the product?
  2. Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.

Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown.

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)

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