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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 πbonds in the system.

DOU = C+1−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−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

How many peaks would you expect in the 1H NMR spectrum of 1,4-dimethylbenzene(para-xylene, or p-xylene)? What ratio of peak areas would youexpect on integration of the spectrum? Refer to Table 13-3 for approximatechemical shifts, and sketch what the spectrum would look like. (Rememberfrom Section 2-4 that aromatic rings have two resonance forms.)

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

formula C4H7O2CI and has an infrared absorption peak at 1740cm-1.

Propose a structure.

Question: When measured on a spectrometer operating at 200 MHz, chloroform (CHCl3)shows a single sharp absorption at 7.3δ.

(a)How many parts per million downfield from TMS does chloroform absorb?

(b)How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz?

(c)What would be the position of the chloroform absorption inδunits when measured on a 360 MHz spectrometer?

How many kinds of electronically non-equivalent protons are present in each of the following compounds, and thus how many NMR absorptions might you expect in each?

aCH3CH2Br(b)CH3OCH2CH(CH3)2(c)CH3CH2CH2NO2(d)Methylbenzene(e)2-Methyl-1-butene(f)cis-3-Hexene

When the 1H NMR spectrum of acetone, CH3COCH3, is recorded on an instrument operating at 200MHz , a single sharp resonance at 2.1 σis seen.

(a) How many hertz downfield from TMS does the acetone resonance correspondto?

(b) If the 1H NMR spectrum of acetone were recorded at 500NHz , what wouldthe position of the absorption be in σunits?

(c) How many hertz downfield from TMS does this 500MHz resonance correspond to?
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