An unknown compound has a molecular formula of C8H14O. The IR spectrum of this c

Question

An unknown compound has a molecular formula of C8H14O. The IR spectrum of this compound has two important signals: one at 1715 cm–1 (strong) and one at 1675 cm–1 (medium). This compound absorbs light in the UV spectrum. The 1H NMR spectrum of this compound is shown below. 1)What is the index of hydrogen deficiency (IHD) 2)Since this compound absorbs UV light, what does this imply about its structure? 3)What kind of bond is likely responsible for the IR signal at 1715 cm–1? 4)The signal at 2.25 ppm in the 1H NMR spectrum is a singlet. What does this imply? 5) What is the likely structure of this compound?

Explanation / Answer

1) IHD or degree of unsaturation is given by the formula ,IHD= 2c+2-h-x+n

c=number of carbon atoms

h=number of hydrogen atoms

x=number of halogen atoms

n=number of nitrogen atoms

C8H14O

IHD=0.5(2*8+2-14-0+0)=2

IHD=2

2)The compound has conjugated double bond system so only it absorbs uv or visible wavelength of light

3) 1715 cm-1 for ketone -C=O group

1675 for C=C alkene stretch GROUP C=C-COR

4) (CH3CO -) with C=O ketone is present with singlet at 2.25 ppm .all ch3 hydrogens are equivalent

5) CH3CO-CH=CH2CH2C-(CH3)2

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