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Spectroscopic identification of organic compounds: Question 8

This page on identifying a compound from its spectra can be marked as direct student access either for assigning it as
a test or for students to work on in their own time. If you do not wish to use student access, links to downloadable
versions of the question and, separately the worked answer, can be found at Printable versions of written tasks.

Identify Compound H and explain how the data from each of (a) to (d) provides the information to support your
answer.

(a) Elemental analysis of Compound H

(b) Mass spectrum of Compound H

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(c) Infrared spectrum of Compound H

(d) Low resolution 1H NMR data for Compound H

Words: 1-500
Show model answer

(Students can only see the model answer after they have submitted the task)
(a) From the elemental analysis the empirical formula is C2H4O

(b) The M+ peak at m/z = 88 leads to the conclusion that the molar mass of Compound H is twice the empirical mass and the
molecular formula is C4H8O2. The fragment at m/z = 73 is due to the loss of a methyl group (M – CH3)+ leaving C3H5O2+. The
fragment at m/z =  59 is due to the loss of an ethyl group (M – C2H5)+ leaving C2H3O2+ and the fragment at m/z = 45 is due to
the loss of an propyl group (M – C3H7)+ leaving CHO2+.

(c) The sharp absorption at around 3000 cm-1 is due to C–H. The absorption at about 1740 cm-1 shows the presence of a
carbonyl group, C=O and the absorption at about 1190 cm-1 the presence of a carbon to oxygen single bond, C-O. 
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(d) The 1H NMR spectrum shows that the hydrogen atoms are in four different chemical environments. These equate to one –
CH3 group, two –CH2- groups and one hydrogen atom bonded singly to a carbon atom to which no other alkyl groups are
bonded. From the CHO2+ fragment in the mass spectrometer it would seem that a propyl group is attached directly to the
oxygen atom by a single bond. This is backed up by the fact that the signal due to the two hydrogen atoms of the –CH2- group
bonded to the oxygen atom is shifted upfield (4.2 ppm) away from the next –CH2-  protons at 1.5 ppm followed by the methyl
group at 0.9 ppm. The remaining single hydrogen atom is bonded directly to carbon atom of the carboxyl group.

All this information taken together confirms that Compound H is propyl methanoate, HCOOCH2CH2CH3.

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Spectroscopic identification of organic compounds: Question 10

This page on identifying a compound from its spectra can be marked as direct student access either for assigning it as
a test or for students to work on in their own time. If you do not wish to use student access, links to downloadable
versions of the question and, separately the worked answer, can be found at Printable versions of written tasks.

Identify Compound J and explain how the data from each of (a) to (d) provides the information to support your
answer.

(a) Elemental analysis of Compound J

(b) Mass spectrum of Compound J

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(c) Infrared spectrum of Compound J

Note that this infrared spectrum is in the gas phase. In the liquid phase there is also a broad absorption present,
centred just below 3000 cm-1.

(d) Low resolution 1H NMR data for Compound J

Words: 1-500
Show model answer

(Students can only see the model answer after they have submitted the task)
(a) From the elemental analysis the empirical formula is C4H4O

(b) The M+ peak at m/z = 136 is evidence that the molar mass of Compound J is 136 g mol-1 and hence its molecular formula
is twice its empirical formula, i.e. C8H8O2. The fragment at m/z = 91 is due to loss of –CO2H leaving C7H7+ and the fragment at
m/z = 77 is due to loss of –CH2CO2H leaving C6H5+.

(c) The absorptions at approximately 3000 cm-1 are due to C–H and the sharp absorption at just below 1800 cm-1 is due to the
presence of a C=O bond. The absorption at approximately 1100 cm-1 is due to the C–O single bond. The broad absorption just
below 3000 cm-1 in the liquid phase signifies a carboxylic acid with hydrogen bonding. (This broad absorption occurs in the
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liquid state as it is due to the vibrational stretching of the intermolecular hydrogen bonds that occurs between molecules, as
carboxylic acids dimerize in the liquid state. In the gaseous state this absorption is absent as the molecules will have sufficient
energy and be too far apart for this hydrogen bonding to occur.)

(d) The 1H NMR spectrum shows that the hydrogen atoms are in three different chemical environments. The position of the
single proton with a shift of 10.8 ppm is indicative of a carboxylic acid, –COOH. The five protons with a shift of 7.4 ppm
suggest a phenyl group, C6H5–  and the remaining two protons with a chemical shift of 3.7 ppm suggest a –CH2– group
bonded between the phenyl group and the carboxylic acid group.

All this information taken together confirms that Compound J is phenylethanoic acid, C6H5CH2COOH.

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Spectroscopic identification of organic compounds: Question 20

This page on identifying a compound from its spectra can be marked as direct student access either for assigning it as
a test or for students to work on in their own time. If you do not wish to use student access, links to downloadable
versions of the question and, separately the worked answer, can be found at Printable versions of written tasks.

Identify Compound T and explain how the data from each of (a) to (d) provides the information to support your
answer.

(a) Elemental analysis of Compound T

(b) Mass spectrum of Compound T

(c) Infrared spectrum of Compound T

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(d) 1H NMR data for Compound T

Words: 1-500
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(Students can only see the model answer after they have submitted the task)

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(a) From the elemental analysis the empirical formula of Compound T is CH2.

(b) The M+ peak at m/z = 70 gives a mass equal to five times that of the empirical mass so the molecular formula of
Compound T is C5H10. The peak with the m/z value of 55 suggests loss of a methyl group to give the C4H7+ fragment.  Loss
of an ethyl group (M – C2H5)+, i.e. C3H5+ is likely to have produced the peak at m/z = 41.

(c) The strong sharp absorptions at just below 3000 cm-1 show the presence of the C–H bonds. The sharp absorption at 1651
cm-1 suggests a C=C double bond so Compound T is an alkene.

(d) The 1H NMR spectrum shows that the ten hydrogen atoms are in four different chemical environments in the ratio 2:2:3:3.
The singlet at 4.6 ppm has the chemical shift due to –C=CH2– which suggest the double bond is on the first carbon atom
which is bonded to two hydrogen atoms with no H atoms on the adjacent carbon atom. The singlet at 1.6 ppm suggests a
methyl group attached to a carbon atom containing no hydrogen atoms bonded to it. The quartet and triplet at 2.0 ppm and 1.0
ppm respectively are indicative of an ethyl group attached to the other carbon atom of the double bond.

All this information taken together confirms that Compound T is 2-methylbut-1-ene, H2C=C(CH3)C2H5.

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