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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

Question: a. How many signals does dimethyl fumarate ( CH3O2CCH=CHC02CH3 with a trans C=C) exhibit in its 13C NMR spectrum? b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its 13C NMR spectrum: [1] three; [2] four; [5] five

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

a.

b.

c.

How many signals are present in the 1HNMR spectrum for each molecule? What splitting is observed in each signal?

a.

b.

c.

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.

The 1H NMR spectrum 1,2-dimethoxyethane (CH3OCH2CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?
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