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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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01

1H NMR spectroscopy

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

02

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.

03

Explanation

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

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

Proton NMR

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Most popular questions from this chapter

Propose a structure consistent with each set of data.

a. C9H10O2: IR absorption at 1718cm-1

b. C9H12 : IR absorption at 2850–3150cm-1

Question: Identify the structures of isomers A and B (molecular formula C9H10O ).

Compound A: IR peak at 1742 cm-1 ; 1 H NMR data (ppm) at 2.15 (singlet, 3 H), 3.70 (singlet, 2 H), and 7.20 cm-1(broad singlet, 5 H). Compound B: IR peak at 1688 ; 1 H NMR data (ppm) at 1.22 (triplet, 3 H), 2.98 (quartet, 2 H), and 7.28–7.95 (multiplet, 5 H).

How can you use \(^{\bf{1}}{\bf{H}}\) NMR spectroscopy to distinguish between \({\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = C}}\left( {{\bf{Br}}} \right){\bf{C}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\)and methyl (E)-3-bromopropenoate, \({\bf{BrCH = CHC}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\)?

For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.

a.

b.

c.

Describe the 1HNMR spectrum of each compound. State how many NMR signals are present, the splitting pattern for each signal, and the approximate chemical shift.

a.

b.

c.

d.
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