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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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Answer

Step by step solution

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

Question: Reaction of C6H5CH2CH2OH with CH3COCl affords compound W, which has molecular formula C10H12O2. W shows prominent IR absorptions at 3088–2897, 1740, and 1606cm-1 . W exhibits the following signals in its 1 H NMR spectrum: 2.02 (singlet), 2.91 (triplet), 4.25 (triplet), and 7.20–7.35 (multiplet) ppm. What is the structure of W? We will learn about this reaction in Chapter 22.

How many \(^{{\bf{13}}}{\bf{C}}\) NMR signals do each compound exhibit?

a.

b.

c.

d.

e.

f.

g.

h.

Question: How could you use chemical shift and integration data in 1H NMR spectroscopy to distinguish between CH3OCH2CH2OCH3and CH3OCH2OCH3? The 1H NMR spectrum of each compound contains only singlets.

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).

Draw all constitutional isomers of molecular formula C3H6Cl2.

a. How many signals does each isomer exhibit in its 1HNMR spectrum?

b.How many lines does each isomer exhibit in its 13CNMR spectrum?

c. When only the number of signals in both 1Hand 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?
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