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15.5.14: Chapter 13

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    Problem 13-1 7.5 × 10−5 kJ/mol for 19F; 8.0 × 10−5 kJ/mol for 1H
    Problem 13-2 1.2 × 10−4 kJ/mol
    Problem 13-3

    The vinylic C − H protons are nonequivalent.

    A chemical structure of 2-chloro-1-propene. Hydrogens are labeled a (on methyl), b (cis to methyl group) and c (cis to chlorine).
    Problem 13-4
    (a) 7.27 δ
    (b) 3.05 δ
    (c) 3.46 δ
    (d) 5.30 δ
    Problem 13-5
    (a) 420 Hz
    (b) 2.1 δ
    (c) 1050 Hz
    Problem 13-6
    (a) 1.43 δ
    (b) 2.17 δ
    (c) 7.37 δ
    (d) 5.30 δ
    (e) 9.70 δ
    (f) 2.12 δ
    Problem 13-7

    There are seven kinds of protons labeled. The types and expected range of absorption of each follow. a: ether, 3.5–4.5 δ; b: aryl, 6.5–8.0 δ; c: aryl, 6.5–8.0; d: vinylic, 4.5–6.5 δ; e: vinylic, 4.5–6.5 δ; f: alkyl (secondary), 1.2–1.6 δ; g: alkyl (primary), 0.7–1.3 δ.

    Structure of 1-[(E)-but-1-enyl]-4-methoxybenzene. Hydrogens labeled a (methoxy), b and c (ortho and meta to methoxy), d (benzylic), e (trans to d), f (methylene), and g (methyl) .
    Problem 13-8 Two peaks; 3 : 2 ratio
    Problem 13-9
    (a)  −CHBr2, quartet;  −CH3, doublet
    (b) CH3O−, singlet;  −OCH2 −, triplet;  −CH2Br, triplet
    (c) ClCH2− , triplet;  −CH2−, quintet
    (d) CH3− , triplet;  −CH2− , quartet;   −CH− , septet; (CH3)2, doublet
    (e) CH3−, triplet;  −CH2−, quartet;   −CH−, septet; (CH3)2, doublet
    (f) = CH, triplet,  −CH2−, doublet, aromatic C−H, two multiplets
    Problem 13-10
    (a) CH3OCH3
    (b) CH3CH(Cl)CH3
    (c) ClCH2CH2OCH2CH2Cl
    (d) CH3CH2CO2CH3 or CH3CO2CH2CH3
    Problem 13-11 CH3CH2OCH2CH3
    Problem 13-12
    (a) Enantiotopic
    (b) Diastereotopic
    (c) Diastereotopic
    (d) Diastereotopic
    (e) Diastereotopic
    (f) Homotopic
    Problem 13-13
    (a) 2
    (b) 4
    (c) 3
    (d) 4
    (e) 5
    (f) 3
    Problem 13-15

    J1–2 = 16 Hz; J2–3 = 8 Hz

    The structure of 3-Bromo-1-phenyl-1-propene and its proton splitting tree diagram that shows J 1-2 and J 2-3 values equals 16 and 8 Hertz, respectively.
    Problem 13-16 1-Chloro-1-methylcyclohexane has a singlet methyl absorption.
    Problem 13-17
    (a) 4
    (b) 7
    (c) 4
    (d) 5
    (e) 5
    (f) 7
    Problem 13-18
    (a) 1,3-Dimethylcyclopentene
    (b) 2-Methylpentane
    (c) 1-Chloro-2-methylpropane
    Problem 13-19 −CH3, 9.3 δ;  −CH2− , 27.6 δ; C=O, 174.6 δ;− OCH3, 51.4 δ
    Problem 13-23 A DEPT-90 spectrum would show two absorptions for the non-Markovnikov product (RCH = CHBr) but no absorptions for the Markovnikov product (RBrC = CH2).

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