From each group of three molecules, choose the one whose structure is most consistent with the proton-decoupled

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From each group of three molecules, choose the one whose structure is most consistent with the proton-decoupled 13C NMR data. Explain your choices.

(a) CH3(CH2)4CH3, (CH3)3CCH2CH3, (CH3)2CHCH(CH3)2; δ = 19.5 and 33.9 ppm.

(b) 1-Chlorobutane, 1-chloropentane, 3-chloropentane; δ = 13.2, 20.0, 34.6, and 44.6 ppm.

(c) Cyclopentanone, cycloheptanone, cyclononanone; δ = 24.0, 30.0, 43.5, and 214.9 ppm.

(d) ClCH2CHClCH2Cl, CH3CCl2CH2Cl, CH2 = CHCH2Cl; δ = 45.1, 118.3, and 133.8 ppm.

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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