With step by step instruction, what is the answer to this unknown compound? Info

Question

With step by step instruction, what is the answer to this unknown compound?

Information: Each spectra below was obtained from a pure compound. Mass Spectrum parent peaks (M) are listed for a examples. IR peaks listed are strong (s) unless otherwise indicated for signals above 1500 cm^-1^1H NMR Spectra, the integral is given in number of hydrogens (#H) or as a relative ratio. Important coupling constants (J-values) are listed next to the peaks for some examples. For some spectra, an inset (grey box) is also given showing a "zoom-in" on an important part of the spectrum. Mass Spectrometry (not shown): [M] = 134 m/z Infrared Spectroscopy (not shown): 3028, 2963 cm^-1^1H Nuclear Magnetic Resonance.^13C Nuclear Magnetic Resonance.

Explanation / Answer

Interpretation of spectrum

IR

3028 cm-1 for sp2 =C-H stretch

2963 cm-1 for sp3 -C-H stretch

1H NMR

0.8 ppm (triplet, 3H) for CH3 next to CH2

1.2 ppm (doublet, 3H) for CH3 next to CH

1.5 ppm (quintet, 2H) for CH2 between CH3 and CH

2.5 ppm (multiplet, 1H) for CH between CH2, CH3 and Phenyl ring

7.3 ppm (multiplet, 5H) for phenyl protons

13C NMR

11 ppm for CH3 carbon

21 ppm for CH3 carbon

30 ppm for CH2 carbon

42 ppm for CH carbon

125-149 ppm four signals for phenyl carbons

Mass

M+ = 134

Probable structure of compound,

CH3-CH2-CH(CH3)-C6H5

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