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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

Question:Answer the following questions about each of the hydroxy ketones: 1-hydroxybutan-2-one (A) and 4-hydroxybutan-2-one (B).

a. What is the molecular ion in the mass spectrum?

b. What IR absorptions are present in the functional group region?

c. How many lines are observed in the 13C NMR spectrum?

d. How many signals are observed in the 1H NMR spectrum?

e. Give the splitting observed for each type of proton as well as its approximate chemical shift.

The 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upfield or downfield from the OH proton?

Question:Propose a structure consistent with each set of spectral data:

a. C4H8Br2: IR peak at 3000–2850cm-1 ;

NMR (ppm):

1.87 (singlet, 6 H)

3.86 (singlet, 2 H)

b. C3H6Br2: IR peak at 3000–2850cm-1 ;

NMR (ppm):

2.4 (quintet)

3.5 (triplet)

c. C5H10O2: IR peak at 1740cm-1 ;

NMR (ppm):

1.15 (triplet, 3 H) 2.30 (quartet, 2 H)

1.25 (triplet, 3 H) 4.72 (quartet, 2 H)

d . C6H14O: IR peak at 3600-3200 cm-1 ;

NMR (ppm):

0.8 (triplet, 6 H) 1.5 (quartet, 4 H)

1.0 (singlet, 3 H) 1.6 (singlet, 1 H)

e. C6H14O: IR peak at 3000-2850cm-1 ;

NMR (ppm):

1.10 (doublet, relative area = 6)

3.60 (septet, relative area = 1)

f . C3H6O: IR peak at 1730cm-1 ;

NMR (ppm):

1.11 (triplet)

2.46 (multiplet)

9.79 (triplet)

Question: A compound of molecular formula C4H802 shows no IR peaks at 3600–3200 or 1700 cm-1 . It exhibits one singlet in its 1H NMR spectrum at 3.69 ppm, and one line in its 13C NMR spectrum at 67 ppm. What is the structure of this unknown?

Which of the highlighted carbon atoms in each molecule absorbs farther downfield?

a.

b.

c.

d.
See all solutions

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