The IR spectrum of a dilute solution of compound 1 (in CS2) exhibits a signal at 3617

Chapter 15, Problem 15.78

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The IR spectrum of a dilute solution of compound 1 (in CS2) exhibits a signal at 3617 cm-1 , while the IR spectrum of a dilute solution of compound 2 exhibits a signal at 3594 cm-1 (J. Am. Chem. Soc. 1957, 79, 243247). H H H CH3 H CH3 CH3 R HO Cl H H H H CH3 R Cl HO 1 2 (a) Explain why the latter signal appears at a lower wavenumber of absorption. (b) Identify the signal that you expect to be broader. Explain your choice.

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