Elemental analysis determined unknown Compound G to contain 40.0 % carbon, 6.7 % hydrogen.  Compound G had an M+ = 60 m/z on its MS.  Its IR displayed three absorbances: strong at 1710, strong below 3000, and broad from 2500 to 3500.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 55AP: A compound of unknown structure gave the following spectroscopic data: Mass spectrum: M+=88.1 IR:...
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  1. Elemental analysis determined unknown Compound G to contain 40.0 % carbon, 6.7 % hydrogen.  Compound G had an M+ = 60 m/z on its MS. 

    Its IR displayed three absorbances: strong at 1710, strong below 3000, and broad from 2500 to 3500. 

    The proton NMR showed an absorbance at 1.7 ppm (lowest whole number ratio of H =3), and an absorbance at 11.5 ppm (lowest whole number ratio of H = 1). 

    Compound G was able to turn blue litmus paper red, and neutralize a base.  What is Compound G?

       

    CH3CO2H

       

    Formaldehyde

       

    HO           

         \         

         C = CH

         /

    HO

       

    CH2(OH)CHO

       

    CH(OH)=CH(OH)

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