Solutions_Manual_for_Organic_Chemistry_6th_Ed 289

Solutions_Manual_for_Organic_Chemistry_6th_Ed 289 - 1 3-23...

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1 3-23 Ha = [) 2.4 (singlet, IH) Hb = [) 3.4 (doublet, 2 H) He = [) 1 .8 (multiplet, 1 H) Hd = [) 0.9 (doublet, 6H) 13-24 d CH3 H2 I H-O-C -C-H I Q c b (a) The formula C4H802 has one element of un saturation. The IH singlet at [) 1 2. 1 indicates carboxylic acid. The IH multiplet and the 6H doublet scream isopropyl group. ° CH3• II CH i CH-C-OH (b) The formula C9HlOO has five elements of unsaturation. The 5H pattern between [) 7.2-7.4 indicates monosubstituted benzene. The peak at [) 9.85 is unmistakably an aldehyde, trying to be a triplet because it is weakly coupled to an adjacent CH2. The two triplets at [) 2.7-3.0 are adjacent CH2 groups. H2 ° V c , c Jl H I H2 h- (c) The formula CSH802 has two elements of unsaturation. A 3 H singlet at [) 2.3 is probably a CH3 next to carbonyl. The 2H quartet and the 3H triplet are certain to be ethyl; with the CH2 at [) 2.7, this also appears to be next to carbonyl. ° ° I I II CH3CH2 -C-C-CH3 (d) The formula C4H80 has one element of unsaturation, and the signals from
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