(a) The 1H NMR spectrum of [18]annulene shows two signals, at d 5 9.28 (12 H)and 22.99

Chapter 15, Problem 64

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(a) The 1H NMR spectrum of [18]annulene shows two signals, at d 5 9.28 (12 H)and 22.99 (6 H) ppm. The negative chemical shift value refers to a resonance upfi eld (to theright) of (CH3)4Si. Explain this spectrum. (Hint: Consult Figure 15-9.) (b) The unusual molecule1,6-methano[10]annulene (shown in the margin) exhibits two sets of signals in the 1H NMRspectrum at d 5 7.10 (8 H) and 20.50 (2 H) ppm. Is this result a sign of aromatic character?

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