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Chapter 14: Q29P (page 527)

Esters of chrysanthemic acid are naturally occurring insecticides. How many lines are present in the \({}^{{\bf{13}}}{\bf{C}}\) NMR spectrum of chrysanthemic acid?

Short Answer

Expert verified

The \({}^{13}C\)NMR spectrum consists of nine lines.

Step by step solution

01

Step 1: \({}^{{\bf{13}}}{\bf{C}}\) NMR spectroscopy

The\({}^{{\bf{13}}}{\bf{C}}\)NMR spectroscopy is used to describe the carbon environment of a compound.

The signals in the \({}^{13}C\) NMR spectrum give the number of equivalent and non-equivalent carbon atoms which is used to interpret the structure of an unknown compound.

02

Equivalent and non-equivalent carbon atoms

The carbon atoms that have the same chemical environment and that resonate at the same frequency are termed chemically equivalent.

The carbon atoms that have a different chemical environment and that resonate at different frequencies are termed non-equivalent carbon atoms.

03

Number of lines in the \({}^{{\bf{13}}}{\bf{C}}\) NMR spectrum of chrysanthemic acid

There are nine non-identical carbon atoms in chrysanthemic acid and hence its \({}^{13}C\)NMR spectrum consists of nine signals/lines.

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Most popular questions from this chapter

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?

Question: Identify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound.

a. CH3CH2CH2CH2OH ; 13CNMR: 14, 19, 35, and 62 ppm

b. (CH3)2CHCHO ; 13C NMR: 16, 41, and 205 ppm

c. CH2=CHCHOHCH3 ; 13C NMR: 23, 69, 113, and 143 ppm

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

a.

b.

c.

d.

e.

f.

g.

h.

Draw all constitutional isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{6}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\).

a. How many signals does each isomer exhibit in its \({}^{\bf{1}}{\bf{H}}\) NMR spectrum?

b. How many lines does each isomer exhibit in its \({}^{{\bf{13}}}{\bf{C}}\) NMR spectrum?

c. When only the number of signals in both \({}^{\bf{1}}{\bf{H}}\) and \({}^{{\bf{13}}}{\bf{C}}\) NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?

Propose a structure consistent with each set of data.

a. Compound J: molecular ion at 72; IR peak at 1710cm-1 ; 1H -NMR data (ppm) at 1.0 (triplet, 3 H), 2.1 (singlet, 3 H), and 2.4 (quartet, 2 H)

b. Compound K: molecular ion at 88; IR peak at 3600鈥�3200 ;1H-NMR data (ppm) at 0.9 (triplet, 3 H), 1.2 (singlet, 6 H), 1.5 (quartet, 2 H), and 1.6 (singlet, 1 H)
See all solutions

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