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Solutions for Nuclear Magnetic Resonance Spectroscopy 012345678910 δ (ppm) C CH3 CH3 CH2CH3 CH3 H H H H CH3 Br Cl CH3CHCH3CH3CH2CH2Cl CH3 H H H H H C O CH2 C O CH3OC CH3 H3C CH3 3H 2H 9H TMS H H HH CH3O OCH3 CH3 C CH3 OH C C H five types of H three types of H two types of H three types of H c c b b bb a a a a a e d c b a (f) (c)(b)(a) 3 4 (a) c b a d c b four types of H (b) The three types of aromatic hydrogens appear in a relatively small space around δ 7.2. The signal is complex because all the peaks from the three types of hydrogens overlap. 5 c a b c a b Note: NMR spectra drawn in this Solutions Manual will represent peaks as single lines. These lines may not look like "real" peaks, but this avoids the problem of variation among spectrometers and printers. Individual spectra may look different from the ones presented here, but all of the important information will be contained in these representational spectra. c 6 The three spectra are iden tified with their structures. Data are given as chemical shift values, with the integration ratios of each peak given in parentheses. Spectrum (a) bb a a aa a = δ 6.8 (2) (4H) b = δ 3.7 (3) (6H) a b c a = δ 2.4 (1) (1H) b = δ 2.6 (1) (1H) c = δ 1.5 (6) (6H) Spectrum (b) c c two types of H b a (d) HC CH CH3 CH3H3C H3C a a a b Br CH3 H HH H(e) a a b b c three types of H 290