Provide the structure of the molecule that would give rise to these spectra. Include degree of unsaturation, functional groups present, assignment of 1H and 13C NMR peaks by labeling each peak with specific atoms in the structure (a,b,c,d) and show which atoms give rise at which peaks IR Spectrum(liquid film)400010080604020% of base peak3000401013C NMR Spectrum(500 MHz, CDCI, solution)7320080proton decoupled¹H NMR Spectrum(200 MHz, CDCI, solution)45L9-exchangeswith D₂ODEPT CH₂ CH₂ CH1401817202000115138V (cm1¹)120140m/e160160expansions160020A7m1200M+ 194/196 (<1%)120L6Mass Spectrum240200C6H₁10₂Br280M8001.0 ppm5solvent1.1804No significant UVabsorption above 220 nm4013208 (ppm)1TMS08 (ppm)

Broad band in IR shows OH, NH2, COOH Presence of M and M+2 peaks with 1:1 ratio in Ms shows 1Br atom…

IR Spectrum (liquid film) 4000 100 80 8 8 8 8 % of base peak 60 40 20 3000 40 10 13C NMR Spectrum (500 MHz, CDCI, solution) 73 200 80 proton decoupled ¹H NMR Spectrum (200 MHz, CDCI, solution) 45 9 exchanges with D₂0 DEPT CH₂ CH, CHI J M 1720 40 2000 8 138 116 V (cm¹) 140 120 160 m/e 1600 L 160 expansions ì 20 L 7 1200 M+ 194/198 (<1%) 120 Mass Spectrum 240 200 ill 6 C6H₁10₂Br 280 800 1.0 ppm 5 solvent 1 1 80 1 4 No significant UV absorption above 220 nm 40 L 3 1 2 08 (ppm) 1 TMS 0 8 (ppm)

IR Spectrum (liquid film) 4000 100 80 8 8 8 8 % of base peak 60 40 20 3000 40 10 13C NMR Spectrum (500 MHz, CDCI, solution) 73 200 80 proton decoupled ¹H NMR Spectrum (200 MHz, CDCI, solution) 45 9 exchanges with D₂0 DEPT CH₂ CH, CHI J M 1720 40 2000 8 138 116 V (cm¹) 140 120 160 m/e 1600 L 160 expansions ì 20 L 7 1200 M+ 194/198 (<1%) 120 Mass Spectrum 240 200 ill 6 C6H₁10₂Br 280 800 1.0 ppm 5 solvent 1 1 80 1 4 No significant UV absorption above 220 nm 40 L 3 1 2 08 (ppm) 1 TMS 0 8 (ppm)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter14: Mass Spectrometry

Section: Chapter Questions

Problem 14.37P

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