Question

TUJ Iwo spectra are given below along with their molecular formulas. Propose a structure that com each spectrum CHCI 2.00 CgH
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Answer #1

Molecular formula = C3H7Cl

Sites of unsaturation = 0

1H NMR data:

3.5 (t, 2H) presence of aromatic ring

1.7 (sextet, 2H) CH2 attached to CH2 and CH3

1.1 (t, 3H) CH3 attached to CH2

Above data indicates following structure

CI 1-chloropropane

Molecular formula = C9H10O2

Sites of unsaturation = 5

1H NMR data:

7.9 (d, 2H) aromatic protons (benzene ring attached to electron withdrawing group)

6.9 (d, 2H) aromatic protons (benzene ring attached to electron donating group)

3.7 (s, 3H) CH3 attached to oxygen

2.6 (s, 3H) CH3 attached to carbonyl

Above data indicates following structure

0 1-(4-methoxyphenyl)ethan-1-one

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