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Chapter 13: Q13-11P (page 402)

The integrated 1H NMR spectrum of a compound of the formulaC4H10Ois shown in Figure. Propose a structure.

Short Answer

Expert verified

The possible structure isCH3-CH2-O-CH2-CH3.

Step by step solution

01

Step-by-Step SolutionStep 1: Degree of unsaturation

The degree of unsaturation gives the total number of 蟺bonds in the system.

DOU = C+1鈭�H2+N2

=role="math" localid="1651737414957" 4+1-102

= 5-5

=0

It indicates that the given compound is saturated.

02

Spectral information

The given data show that a given organic compound has two types of protons. One set of protons shows a triplet which means an adjacent carbon atom shows two identical protons.

Also, one set shows a quartet which means it adjacent carbon atom shows four identical hydrogen atoms.

So the possible structure isCH3鈭�CH2

03

Effect of an electronegative group on chemical shift

In the above example, oxygen is electronegative so it causes deshielding because of that proton shows a chemical shift at higher ppm.

Possible structure isCH3-CH2-O-CH2-CH3.

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Most popular questions from this chapter

The amount of energy required to spin-flip a nucleus depends both on the strength of the external magnetic field and on the nucleus. At a field strengthof 4.7 T, rf energy of 200 MHz is required to bring a H1nucleus into resonance, but energy of only 187 MHz will bring a F19nucleus into resonance. Calculate the amount of energy required to spin-flip a F19nucleus. Is this amount greateror less than that required to spin-flip a H1nucleus?

The following compounds all show a single line in their 1HNMR spectra. List them in order of expected increasing chemical shift:

CH4,CH2Cl2,cyclohexane ,CH3COCH3,H2C=H2C,benzene

Propose structures for the two compounds whose1H NMR spectra are

shown.

(a) C4H9Br

(b) C4H8CI2

Question: Identify the indicated protons in the following molecules as unrelated,

homotopic, enantiotopic, or diastereotopic.

a)



b)

Propose a structure for compound E, C7H12O2 , which has the following13C NMR spectral data:

Compound E Broadband-decoupled13C NMR: 19.1, 28.0, 70.5, 129.0, 129.8, 165.8未 DEPT-90: 28.0, 129.8未 DEPT-135: positive peaks at 19.1, 28.0, 129.8未 ; negative peaks at 70.5, 129.0未
See all solutions

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