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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

Propose structures for compounds that fit the following 1H NMR data:

a.

2.18(3H, singlet)

4.16(2H, doublet j=7Hz)

5.71(1H, triplet j=7Hz)

b.

1.30(9H, singlet)

7.30(5H, singlet)

c.

2.11(3H, singlet)

3.52(2H, triplet j=6Hz)

5.71(2H, triplet j=6Hz)

d.

2.15(2H, quintent j=7Hz)

2.75(2H, triplet j=7Hz)

3.38(2H, triplet j=7Hz)

7.22(5H, singlet)

The compound whose 1H NMR spectrum is shown has the molecular

formula C3H6Br2. Propose a structure.

Compound A, a hydrocarbon with M+= 96 in its mass spectrum, has theC13 spectral data given below. On reaction withBH3 , followed by treatment with basic H2O2, A is converted into B, whoseC13 spectral data are also given below. Propose structures for A and B.

Compound A Broadband-decoupledC13 NMR: 26.8, 28.7, 35.7, 106.9, 149.7 d DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 d

Compound B Broadband-decoupledC13 NMR: 26.1, 26.9, 29.9, 40.5, 68.2 d DEPT-90: 40.5 d DEPT-135: positive peak at 40.5 d; negative peaks at 26.1, 26.9, 29.9, 68.2 d

How could you use and1H 13C NMR to help distinguish the following

isomeric compounds of the formula C4H8?

Question: Propose structures for the three compounds whose NMR spectra are shown.

a.C5H10O

b.C7H7Br

c.C8H9Br
See all solutions

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