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Chapter 14: Q.21558-14-29P. (page 558)

Esters of chrysanthemic acid are naturally occurring insecticides. How many lines are present in the NMR spectrum of chrysanthemic acid?

Short Answer

Expert verified

The 13C NMR spectrum consists of nine lines.

Step by step solution

01

13C  NMR spectroscopy

The 13C NMR spectroscopy is used to describe the carbon environment of a compound.

The signals in the 13C 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 13C NMR spectrum of chrysanthemic acid

Non-equivalent carbon atoms in chrysathemic acid

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

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Most popular questions from this chapter

The reaction of (CH3)3 CCHO with (C6H5)3 P=C(CH3)OCH3 , followed by treatment with aqueous acid, afford R . R has strong absorption in its IR spectrum at 1717 cm-1 and three singlets in its -NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 21.

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.

For each compound give the number of NMR signals, and then determine how many peaks are present for each NMR signal.

a.

b.

c.

d.

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: How many different types of protons are present in each compound?
See all solutions

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