Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter A, Problem 1PP
Interpretation Introduction

Interpretation:

The structure of the compound with molecular formula C5H10O is to be proposed with the help of given data.

Concept introduction:

Mass spectrometry is a technique used for measuring the masses of atoms and molecules with great accuracy.

In a mass spectrometer, the vapor of organic compound is bombarded with a beam of high energy electrons that makes the neutral molecule lose an electron and converts it to a radical cation known as a molecular ion.

In 13C NMR, the carbon atom equivalent by molecular symmetry produces one signal.

In 13C NMR, each carbon atom with a different environment in a compound gives one signal.

Nuclear Magnetic Resonance (NMR) is one of the most capable analytical techniques used for determining the functional groups and how the atoms are structured and arranged in a molecule.

Few elements, such as 13C and 1H, have nuclei behaving as magnets about an axis. These elements are placed in magnetic field irradiated with electromagnetic energy of specific frequency and the nuclei tend to absorb energy via magnetic resonance. There is this graph that shows energy absorption frequencies and intensities of a sample kept in the magnetic field called nuclear magnetic resonance (NMR).

In NMR spectroscopy, the proton nuclear magnetic resonance (1HNMR) is used to find out the structure of molecules with the help of 1H atom within the molecules.

Induced magnetic field consists of electricity generated from movement in a magnetic field.

The position of a signal on x-axis in the NMR spectrum depicts the chemical shift expressed in δ or ppm.

The number of signals in H1 NMR spectrum represents the number of different chemical environments for the protons.

The area covered by the signal is proportional to the number of equivalent protons causing the signal.

The hydrogen atoms on adjacent carbon atoms split the signal into two or more peaks. One, two or three hydrogen atoms split the signal into two, three or four peaks described as doublet, triplet or quartet respectively.

A decrease in the electron density around a proton deshields the signal downfield at a larger value of chemical shift.

An increase in electron density shields the signal upfield at a lower value of chemical shift.

13C NMR is only used in the observation of isotopes of carbon atoms.

The peak at δ211.0 supports the existence of a carbonyl group in the compound.

The peak at δ37 represents the CH2 group.

The peak at δ10 shows the CH3 group.

Expert Solution & Answer
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Answer to Problem 1PP

Solution: The structure of the compound with molecular formula C5H10O is as:

Organic Chemistry, Chapter A, Problem 1PP , additional homework tip  1

Explanation of Solution

The figure given below represents the 13C spectrum of the compound with the molecular formula C5H10O.

Organic Chemistry, Chapter A, Problem 1PP , additional homework tip  2

In DEPT 13C spectra, the peaks present at different regions are as:

The peak at δ211.0 supports the existence of a carbonyl group in the compound.

The peak at δ37 represents the CH2 group.

The peak at δ10 shows the CH3 group.

The presence of two signals in the alkyl group region indicates the presence of symmetry in the compound and the two unique carbon atoms.

Therefore, the structure of the compound is as:

Organic Chemistry, Chapter A, Problem 1PP , additional homework tip  3

Conclusion

The structure of the compound with molecular formula C5H10O is as:

Organic Chemistry, Chapter A, Problem 1PP , additional homework tip  4

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