Chapter 14: Q.21558-14-43P (page 563)

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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1H NMR spectroscopy

Organic structures can be determined using the 1H NMR spectroscopy. In this, the environment of protons is determined.

Splitting of signals in the 1H NMR spectroscopy

The geminal and trans protons split into doublets. The formula used to determine the peaks is n+1, where n is the number of protons.

Explanation

The compound CH₂=C(Br)CO₂CH₃ has geminal protons, H_aand H_b, that split into a doublet.

The compound BrCH=CHCO₂CH₃ has trans protons,H_a and H_b, that also split into a doublet.

Proton NMR

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

Short Answer

Step by step solution

1H NMR spectroscopy

Splitting of signals in the 1H NMR spectroscopy

Explanation

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Most popular questions from this chapter

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

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

Short Answer

Step by step solution

1H NMR spectroscopy

Splitting of signals in the 1H NMR spectroscopy

Explanation

One App. One Place for Learning.

Most popular questions from this chapter

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

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Chemical Reactions

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Study anywhere. Anytime. Across all devices.

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