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Chapter 14: Q.21558-14-12P. (page 542)

Which compounds give a 1H NMR spectrum with two signals in a ratio of 2:3?

a.

b.

c.

d.

Short Answer

Expert verified

a. Gives a 1H NMR spectrum with two signals in a ratio of 2:3.

b. Does not give a 1H NMR spectrum with two signals in a ratio of 2:3.

c. Gives a 1H NMR spectrum with two signals in a ratio of 2:3.

d. Gives a 1H NMR spectrum with two signals in a ratio of 2:3.

Step by step solution

01

NMR Spectroscopy

Nuclear magnetic resonance spectroscopy uses the magnetic properties of certain nuclei, particularly the proton 1H and 13C .

Recording the differences in the magnetic properties of such nuclei present in a molecular species under different environments gives information about the number of each type of such nuclei present, their position within the molecules, etc.

02

Integration ratio

An integration ratio of 2:3 indicates that two types of hydrogens are present in the compound, and the ratio of one type to another is 2:3.

03

To find which compounds give an 1H NMR spectrum with two signals in a ratio of 2:3

CH3CH2Cl

2 types of hydrogen atoms are present, and the ratio is 3:2. So it gives a NMR spectrum with two signals in a ratio of 2:3.

CH3CH2CH3

2 types of hydrogen atoms are present, and the ratio is 6:2 or 3:1. So it does not give a NMR spectrum with two signals in a ratio of 2:3.

CH3CH2OCH2CH3

2 types of hydrogen atoms are present, and the ratio is 6:4 or 3:2. So it gives a NMR spectrum with two signals in a ratio of 2:3.

CH3OCH2CH2OCH3

2 types of hydrogen atoms are present, and the ratio is 6:4 or 3:2. So it gives a NMR spectrum with two signals in a ratio of 2:3.

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Most popular questions from this chapter

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 7.28โ€“7.95 (multiplet, 5 H).

Question: Draw the structure of a compound of molecular formula C4H8O that has a signal in its 13C NMR spectrum at > 160 ppm. Then draw the structure of an isomer of molecular formula C4H80 that has all of its 13C NMR signals at < 160 ppm.

Identify products A and B from the given 1HNMR data.

a. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1HNMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2H) ppm. What is the structure of A?

b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1HNMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?

Question. Reaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C11H15NO2). F absorbs at 1730 cm-1in its IR spectrum. F also shows eight lines in its 13C-NMR spectrum, and gives the following -NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 18.

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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