Compound A has molecular formula C7H14O and reacts with sodium borohydride in methanol

Chapter 20, Problem 20.76

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Compound A has molecular formula C7H14O and reacts with sodium borohydride in methanol to form an alcohol. The 1 H NMR spectrum of compound A exhibits only two signals: a doublet (I = 12) and a septet (I = 2). Treating compound A with 1,2-ethanedithiol (HSCH2CH2SH) under acidic conditions, followed by Raney nickel gives compound B. (a) How many signals will appear in the 1 H NMR spectrum of compound B? (b) How many signals will appear in the 13C NMR spectrum of compound B? (c) Describe how you could use IR spectroscopy to verify the conversion of compound A to compound B.

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