Question
Using Mass Spec, IR, H-NMR, and C-NMR what would the structure look like?

Relative Intensity 10 20 30 40 50 60 70 80 90
TERNSMETTANCEI D 4000 NAVENUMBERI
H NMR PPM
13C NMR 90 80 70 60 50 40 30 20 10 0 PPM PPM DEPT-90 positive DEPT-135 positive Negative Negative Negative Negative Positive
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Answer #1

According to the given data:

The compound contains 10 hydrogens and 6 carbons.

i.e. The molecular formula of the compound = C6H10

The degree of unsaturation in C6H10 = {(2*6 + 2) - 10}/2 = 2

According to the IR spectrum, the absorption at 3300 cm-1 and 2100 cm-1 indicates \equivC-H stretch and C\equivC stretch respectively.

Based on all the above data, the structure of the required compound can be drawn as follows.

CH3-CH2-CH2-CH2-C\equivCH

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