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Chapter 14: Q,21558-14-75P (page 569)

Question: Explain why the 13C NMR spectrum of 3-methylbutan-2-ol shows five signals.

Short Answer

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Answer

Since the replacement of each by X atoms forms two diastereomers, the CH3 groups are not equivalent to those attached to the third carbon.. Thus, every C in this compound is different, and there are five 13-C signals.

Step by step solution

01

13C-NMR

The 13C-NMR splitting pattern reflects how many protons are directly attached to the carbon atom.The 13C-NMR helps to distinguish between CH1 ,CH2 ,CH3groups.

02

3-methylbutan-2-ol

3-methylbutan-2-ol

Since the replacement of each by X atoms forms two diastereomers, the CH3 groups are not equivalent to those attached to the third carbon.. Thus, every C in this compound is different, and there are five 13-C signals.

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Most popular questions from this chapter

Label the signals due to \({{\bf{H}}_{\bf{a}}}\), \({{\bf{H}}_{\bf{b}}}\), and \({{\bf{H}}_{\bf{c}}}\) in the 1 H NMR spectrum of acrylonitrile \(\left( {{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCN}}} \right)\). Draw a splitting diagram for the absorption due to the \({{\bf{H}}_{\bf{c}}}\) proton.

For each compound, which of the protons on the highlighted carbons absorbs farther downfield?

a.

b.

c.

Compound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?

Question: How many \(^{\bf{1}}{\bf{H}}\) NMR signals does each dimethylcyclopropane show?

a.

b.

c.

Question: Into how many peaks will the signal for each of the labeled protons be split?
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