please FIND the corret structure for each formula and WRITE a detailed interpret

Question

please FIND the corret structure for each formula and WRITE a detailed interpretation for each spectrum for IR- H1 NMR- C13 NMR for each formula

Problem 217 IR Spectrum 1096 (liquid film) 4000 2000 1600 1200 3000 800 Mass Spectrum M+ 66 C10H1402 40 80 120 160 200 240 280 m /e 13c NMR spectrum resolves into 00.0 MHz, 2 separate peaks at higher lield strength CDCI, solution) 30 125 ppm DEPT solves into 2 separate peaks at higher field strength solvent 125 ppm proton decoupled o (ppm) 160 120 80 40 200 Exchanges H NMR Spectrum with D20 (400 MHz, CDC solution) expansion expansion 3.7 3.6 (ppm)

Explanation / Answer

A quintet at 1.8 ppm for 2H and two triplets at 3.5 and 3.6 ppm for 2H each indicates an unsymmtrically substituted propylene residue (A-CH2CH2CH2-B). A brs at 4.1 for 1H indicates an OH group. So A = OH. A singlet at 4.5 ppm for 2H and a broad signal for 5H in aromatic region indicates that B = CH2C6H5 ie benzyl group. Presence of benzyl group is also supported by MS (m/z: 91). So, the structure of compound is C6H5CH2OCH2CH2CH2OH. 13 C NMR is also consistent with the structure.

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