Compound A has molecular formula C 7 H 14 O and reacts with sodium borohydride in methanol

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Compound A has molecular formula C7H14O and reacts with sodium borohydride in methanol to form an alcohol. The 1H 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) followed by Raney nickel gives compound B.

(a) How many signals will appear in the 1H 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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Organic Chemistry

ISBN: 978-0470917800

1st edition

Authors: David R. Klein

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