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 CCl₄

Transcribed Image Text:

2400 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 chemical shift, ppm (8) 600 1H 2 3H 300 6H J = 6.9 Hz 0