A mass spectrum has an M+ peak at 204 m/z; and additional peaks starting at 127, 77, along with some other smaller peaks. Which of the following reactions could have produced this compound?     CH3CH2Cl & AlCl3 plus toluene     KI plus a benzene diazonium ion     Fuming sulfuric acid plus toluene, followed by dilute acid     2 CuCl plus a diazonium ion     Benzonitrile plus LiAlH4 followed by fuming sulfuric acid

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Section13.SE: Something Extra
Problem 59GP: The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this...
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  1. A mass spectrum has an M+ peak at 204 m/z; and additional peaks starting at 127, 77, along with some other smaller peaks. Which of the following reactions could have produced this compound?

       

    CH3CH2Cl & AlCl3 plus toluene

       

    KI plus a benzene diazonium ion

       

    Fuming sulfuric acid plus toluene, followed by dilute acid

       

    2 CuCl plus a diazonium ion

       

    Benzonitrile plus LiAlH4 followed by fuming sulfuric acid

    Thank you!

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