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Organic Chemistry 1

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Moderate

NMR Spectra of Alcohols 2

ORGO1-F$IBUB

Choose the four carbon alcohol that is most likely to produce this $_{ }^{ 1 }{ H }$ NMR spectrum in $CDC{ l }_{ 3 }^{ }$ solvent.

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The singlet at 4.3 ppm integrates for one hydrogen. The doublet at 3.4 ppm integrates for two hydrogens. The multiplet at 1.3 ppm integrates for one hydrogen and the doublet at 0.9 ppm integrates for six hydrogens. The singlet at 4.3 ppm disappears when the sample is shaken with several drops of $D_{ 2 }^{ }O$.

A

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B

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C

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D

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