ASSIGNMENT

CHM557 [ORGANIC CHEMISTRY]

20234 (OCT 2023 - MAR 2024) – SPECTROSCOPY

NAME SHAZANA AQILA BINTI

NOORHISYAM
STUDENT ID 2022471232

GROUP AS2223M2

LECTURER’S NAME DR NUR VICKY

DATE OF 4 December 2023

SUBMISSION
Question 1
A group of students subjected propanol through oxidation reaction using pyridinium
chlorochromate (PCC) to produce propanal. The propanal was then subjected through another
oxidation reaction using potassium permanganate (KMn04) to obtain propanoic acid. Explain
how the students apply infrared spectroscopy to confirm the formation of propanal and
propanoic acid.

− Students can create propanal samples and analyze their IR spectra. The presence of a
distinct peak within the specified range confirms the existence of the carbonyl group in
propanal.
− In propanal, the distinctive carbonyl group (C=O) presents a specific signal in the IR
spectrum, typically between 1700-1750 cm^-1. This signifies the stretching vibration
of the aldehyde group. Additionally, characteristic peaks at 2850 cm^-1 and 2750 cm^-
1 are observed, indicating stretching vibrations of the C-H bonds.
− On the other hand, propanoic acid contains the C=O group, C-O bond, and O-H group.
The IR spectrum of propanoic acid displays a peak between 1730 cm^-1 and 1700 cm^-
1, indicating the stretch of the C=O group. Another distinct peak appears between 1320
cm^-1 and 1210 cm^-1, signifying the stretch of the C-O bond. Lastly, there's a
prominent peak between 3400 cm^-1 and 2400 cm^-1, indicating the stretch vibration
of the O-H group.
− Additionally, comparing these obtained spectra with established reference spectra or
known absorption bands specific to propanal and propanoic acid allows students to
validate the transformation of propanol into these compounds through the oxidation
reactions.
(4 marks)
Question 2
A researcher performed oxidation reaction on cyclopentanal to produce cyclopentanoic acid.
Upon completion, the product obtained was tested using IR spectroscopy to confirm the product
formation. Based on the provided IR spectra, evaluate whether the researcher successfully
produced cyclopentanoic acid through the oxidation of cyclopentanal. Use the IR spectroscopy
data to justify your conclusion.

Different peaks in the IR spectra correspond to different group stretchings inside the
molecule. Below 1500 cm-1, the compound's C-H bond stretch vibration manifests as a
spectrum of peaks. The stretch vibration in the compound's C=O, which is located at a
distance of roughly 1710 cm-1, is the next peak that we will examine. Finally, the presence of
the O-H group in the molecule is shown by the large peak between 2500 and 3300 cm-1. We
may now conclude that the chemical has all of the characteristics of cyclopentanoic acid
because it is made up of the C=O group, the O-H group, and an attached C-H group.
(3 marks)
Question 3
Given the NMR spectra presented below and the molecular formula C4H802, illustrate the
structure of compound B and match the chemical shift values with the corresponding protons
in the drawn structure.

Question 4
Identify integration and splitting pattern for each peak that will appear on the NMR spectra for
the following compounds.
a b
C1 = integration: 3H
Splitting pattern: triplet
C2= integration: 2H
Splitting pattern: quintet
C3= integration: 1H
Splitting pattern: sextet
C4¬= integration: 3H
Splitting pattern: doublet
C5= integration: 3H
Splitting pattern: singlet
C1= integration: 2H
Splitting pattern: doublet
C2= integration: 1H
Splitting pattern: sextet
C3= integration: 3H
Splitting pattern: doublet
C4= integration: 3H
Splitting pattern: singlet
(2 marks)
c
C1 = integration: 3H
Splitting pattern: triplet
C2= integration: 2H
Splitting pattern: quintet
C3= integration: 1H
Splitting pattern: sextet
C4¬= integration: 3H
Splitting pattern: doublet
C5= integration: 3H
Splitting pattern: doublet
C6= integration: 1H
Splitting pattern: sextet
C7=integration: 2H
Splitting pattern: quintet
C8¬= integration: 3H
Splitting pattern: triplet
 (9 marks)
Question 5
A compound having molecular formula C4H80 had been analysed using NMR. Identify the
Structure from the Shorthand NMR.
1.05, triplet, 3H
2.13, singlet, 3H
2.47, quartet, 2H

(2 marks)
Question 6
The following compound C is a monosubstituted aromatic compound with the formula C9H12.
Propose the structure of the compound C based on the NMR spectra provided.
 (2 marks)

Question 7
Following are the NMR spectra of three isomeric esters with the formula C7H1402, all derived
from propanoic acid. Provide the structure of compound for each NMR spectra.

Assignment δ (ppm) No. of Multiplicity

hydrogen
1.97 3.8 2 Doublet
(neighbour: CH group)
1.92 2.2 2 Quartet
(neighbour: CH3 group)
1.04 1.8 1 Nonet
(neighbour: CH3, CH3, CH2 group)

2.89 1.2 3 Triplet

(neighbour: CH2 group)
5.85 0.9 6 Doublet
(neighbour: CH group)
NMR signals have a distinct peak count. This is known as multiplicity or signal splitting.

Assignment δ (ppm) No of Multiplicity

hydrogen
1.98 2.3 2 Quartet
(Neighbour: CH group)
8.60 1.4 9 Singlet
(neighbour: no neighboring group)

2.97 1.1 3 Triplet

(neighbour: CH2 group)
 NMR spectroscopy mostly consists on signal splitting. It is brought on by the hydrogen atom
that is close by.

Assignment δ (ppm) No of hydrogen Multiplicity

1.33 4.2 2 Triplet
(neighbour: CH2 group)
1.30 2.2 2 Quartet
(Neighbour: CH2 group)
1.31 1.8 2 Quintet
(neighbour: two CH2 group)
1.35 1.4 2 Sextet
(neighbour: CH2, CH3 group )
1.87 1.2 3 Triplet
(neighbour: CH2 group)
1.94 0.9 3 Triplet
 (neighbour: CH2 group)

A singlet signal is generated if there is no hydrogen present in the vicinity of the carbon. It
creates a doublet if it has one hydrogen in it.
(6marks)

Question 8

The following spectra for A and B correspond to two structural isomers with a molecular
formula of C4H11N. Propose structures for these isomers and explain how it is consistent with
the observed absorptions.
wavelength Gem)
 A B
CH3-CH2-CH2-CH2-NH2
A 1H sextet indicates a methine group; a 3H
triplet indicates a methyl group; and a 2H
quintet, positioned between a methyl and a
methine group, suggests a methylene group.
Spectrum A is a chain of CH2-CH-CH2,
producing butanamine, with sextets
signifying continuous chains, quintets
signifying CH2 groups, doublets signifying
methyl groups, and singlets signifying CH2
groups.
(CH3)2CH-CH2-NH2
A single proton on a nitrogen is represented
by a 1H singlet, two methyl groups next to a
methylene group by a 6H triplet, and two
methylene groups next to a methine group by
a 4H quartet.
The singlet in spectrum B most likely results
from the hydrogen atom in nitrogen,
indicating an isobutylamine structure where
nitrogen is connected to a secondary carbon.
The triplet and quartet in spectrum B show
two methyl and methylene groups.
(4 marks)
Question 9

The NMR spectra are shown for two isomeric compounds with formula CICH120. Their
infrared spectra displayed a strong absorption near 1715 cm 1. Make no attempt to interpret the
aromatic proton area between 7.1 and 7.4 ppm except to determine the number of protons
attached to the aromatic ring. Propose the structure of the compounds.

The structure could be a phenyl ketone with two methyl groups adjacent to the carbonyl
group on the same side, or a para-substituted acetophenone derivative. This is consistent with
the pattern we find for the 1.99 ppm and 2.12 ppm peaks. Deshielded protons near the oxygen
would show up downfield (at a greater ppm).
Given the triplet at 4.06 ppm, which suggests an ethyl group next to the carbonyl, this
molecule may be an ethyl phenyl ketone. Subsequently, the triplet representing the CH2
group at 2.94 ppm would be one step away from the oxygen.

(4 marks)
Question 10

Deduce the structure of the compound G that gives the following I H 13 C, and IR spectra.
Assign all aspects of the I H, and 13C spectra to the structure you propose. The mass spectrum
of compound G shows the molecular weight of 96 g/mol.

10
2987
2000 1 soo 1000
Wavenumber (cm-d )

CH2 CH2

220 200 180 160 140 120 100 60 20

BC (ppm)
a) Use the number of protons in the I H NMR spectrum, number carbons in the 13C

spectrum, and the molecular weight to determine the exact molecular formula.
- C6H8O

(2 marks)

b) Propose the structure of compound G. (Hint: Compound G consist of a cyclic structure

and two double bonds)

(2 marks)

TOTAL MARKS: 40