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Chapter 14: Q.21558-14-23P. (page 553)

How many peaks are observed in the 1HNMR signal for each proton shown in red in palau'amine, the complex chapter-opening molecule?

Short Answer

Expert verified

Ha : doublet

Hb : doublet

Hc : singlet

Hd : doublet

Step by step solution

01

The (n+1) rule

The (n +1) rule is used to predict the multiplicity of1HNMR peaks.

n represents the number of hydrogen atoms present on the carbon atoms adjacent to the carbon to which the desired hydrogen is connected.

02

Peaks observed in the 1HNMR spectrum of palau'amine

The number of peaks observed for the indicated hydrogen atoms is as follows:

Ha: 1 + 1 = 2(doublet).

Hb: 1 + 1 = 2 (doublet)

Hc: singlet (as it is connected to a nitrogen atom).

Hd : 1 + 1 = 2 (doublet)

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Most popular questions from this chapter

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

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Identify the carbon atoms that give rise to the signals in the \)^{{\bf{13}}}{\bf{C}}\) NMR spectrum of each compound.

a. \){\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{OH}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 14, 19, 35, and 62 ppm

b. \){\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)_{\bf{2}}}{\bf{CHCHO}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 16, 41, and 205 ppm

c. \){\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCH}}\left( {{\bf{OH}}} \right){\bf{C}}{{\bf{H}}_{\bf{3}}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 23, 69, 113, and 143 ppm

Question: How can you use 1H NMR spectroscopy to distinguish between CH2=C(Br)CO2CH3 and methyl (E)-3-bromopropenoate, BrCH=CHCO2CH3?

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Question: What effect does increasing the operating frequency of a1HNMR spectrum have on each value: (a) the chemical shift inδ ;(b) the frequency of an absorption in Hz; (c) the magnitude of a coupling constant J in Hz?
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