Question

Homework 5 Organic Chemistry maerea STOTEA AIere erEA AP 5. The CSI lab found traces of an unknown substance at the scene of a crime. t was found to be soluble in CH.Ch. but insoluble in either aqueous acid or aqueous base. Elemental analysis of the substance was found to contain 5433% C,9.15%- H, and 36.329% O by mass, Infrared and mass spectra were also acquired. Unfortunately, the compound did not match any substances in their library so they had to call in real chemists (you!) to deduce the structure. 100 MASS SPECTRUM INFRARED SPECTRUM 80 60 40 06 20 04 0.0 15 30 45 60 75 90 3000 m/z 2000 1000 Wavenumber (om-1) First, determine the molecular formula from the elemental analysis and MS data. Show all work. RhasarPare units a. 0.5459 6-5 IS b. Second, determine the index of hydrogen deficiency (the number of double bonds and/or rings) from the molecular formula. Third, list the functional groups indicated by the IR spectrum and then draw your proposed structure below. c. d. Based on your structure above, draw two cation (or radical cation) fragments that could account for the m/z signals at 43 and 45, w aou a usuaus

Please answer all parts, don’t know how to do any of it.

Answer 1

Given data C S4.S2 36. 3 2 cwd ah mabb Deternintion emperical mla Elemunt at. mass Ae Nos Relatiua No 34.53 S453 G4 9.15 4 227 16 36 32 2.7 2. 27 2.27 Emperical formuda is 88 give melay mass Emperical domua teula ruda p mmass mass omuda Empasical muha). Meleeutay Cupondy Moleatoh ornula untroo Cpond Mdeatar ula