Each of four bottles, A, B, C, and D, is labeled only C 6 H 12

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Each of four bottles, A, B, C, and D, is labeled only “C6H12” and contains a colorless liquid. You have been called in as an expert to identify these compounds from their spectra:

Compound A:

NMR: one line only at δ 1.66 (s); IR: no absorption in the range 1620–1700 cm–1; reacts with Br2 in CCl4

Compound B:

IR: 3080, 1646, 888 cm–1; NMR spectrum in Fig. P13.45a

Compound C:

IR: 3090, 1642, 911, 999 cm–1; NMR spectrum in Fig. P13.45b

Compound D:

NMR: one line only at δ 1.40 (s); does not react with Br2 in CCl42400 absorption 8 (a) 2100 1800 compound B (C6H12) 7 6 1500 M 5 chemical shift, Hz 1200 900 2H J = 6.9 Hz 4 3

2400 absorption 8 (b) 2100 10.5 Hz compound C (C6H12) 10.5 Hz 7 1800 6 1H 1500 2H 5 chemical shift, Hz 1200

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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