A compound with molecular mass 114 and in IR spectrum, absorption bands are formed at 1770 cm¹ (s), 1650 cm-¹ (m) and 1200 cm¹ (w). In 'H NMR six signals are observed, 8 1.0 (t, 3H), 1.7 (m 2H), 2.4 (t, 2H), 4.6 (d, 1H), 4.9 (d, 1H), 7.4 (d, 1H). Predict the molecular structure of the unknown compound and justify your answer.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Section13.SE: Something Extra
Problem 64GP: Compound F, a hydrocarbon with M+=96 in its mass spectrum, undergoes reaction with HBr to yield...
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A compound with molecular mass 114 and in IR spectrum, absorption bands are formed
at 1770 cm¹ (s), 1650 cm-¹ (m) and 1200 cm¹ (w). In ¹H NMR six signals are
observed, 8 1.0 (t, 3H), 1.7 (m 2H), 2.4 (t, 2H), 4.6 (d, 1H), 4.9 (d, 1H), 7.4 (d, 1H).
Predict the molecular structure of the unknown compound and justify your answer.
Transcribed Image Text:A compound with molecular mass 114 and in IR spectrum, absorption bands are formed at 1770 cm¹ (s), 1650 cm-¹ (m) and 1200 cm¹ (w). In ¹H NMR six signals are observed, 8 1.0 (t, 3H), 1.7 (m 2H), 2.4 (t, 2H), 4.6 (d, 1H), 4.9 (d, 1H), 7.4 (d, 1H). Predict the molecular structure of the unknown compound and justify your answer.
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