compound with the molecular formula C7H9N exhibits IR bands at 3450 cm-1 (medium, doublet), and 855 cm-1 (strong) and shows the following major mass spectral signals (m/z): 106 (base); 107 (M+, about 70% of base), 91 (40% of base), and 77 (about 20% of base). Deduce a reasonable structure from this data.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.20P
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compound with the molecular formula C7H9N exhibits IR bands at 3450 cm-1 (medium, doublet), and 855 cm-1 (strong) and shows the following major mass spectral signals (m/z): 106 (base); 107 (M+, about 70% of base), 91 (40% of base), and 77 (about 20% of base). Deduce a reasonable structure from this data.
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