Compound D has the composition 77.8% carbon, 7.41% hydrogen and 14.8% oxygen. It mass and 1H NMR

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Compound D has the composition 77.8% carbon, 7.41% hydrogen and 14.8% oxygen. It mass and 1H NMR spectra are shown below.

a.

b.

a. Calculate the empirical formula of D.

b. From the mass spectrum, find the molecular mass of D (ignoring the 13C peak) and hence it molecular formula.

c. i. Draw displayed formulae for five possible isomers of D that contain a benzene ring.

ii. Use the 1H NMR spectrum of D to decide which isomer is D.

iii. Explain your reasoning.

d. Explain the main features of the NMR spectrum of D.

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