STRUCTURES ELUCIDATION OF ORGANIC COMPOUNDS

Lecturing 3-4
“IR Spectroscopy”
Ihsan Ikhtiarudin, M.Si

Department of Pharmacy
Sekolah Tinggi Ilmu Farmasi Riau
Pekanbaru
2018
 Types of Spectroscopy
• UV  Observe electronic transition and provides
information on the electronic bonding in the sample
• IR  Observe the vibrations of bonds and provides
evidence of the functional groups present
• MS  bombards molecules with electrons and breaks
them apart. Analysis of the masses of the fragments
gives the molecular weight, possibly the molecular
formula, and clues to the structure and functional
groups.
• NMR  observed the chemicals environments of the
hydrogen atom (or the carbon atom) and provides
evidence for structure of the alkyl groups and clues to
the functional groups
 IR Spectroscopy
• Infrared (IR) spectroscopy measures the bond
vibration frequencies in a molecule and is
used to determine the functional group.
• Different functional groups have different
bond vibration frequencies
• So, we can determine the functional group.

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Molecular Vibrations
Hukum Hooke
 Jenis Vibrasi Ikatan
Regang Tekuk
(Streaching) (Bending)

Simetris Asimetris
Kibasan Guntingan Goyangan Pelintiran
(Waging) (Scissoring) (Rocking) (Twisting)
(Fingerprint Area)

(Specific Area)
Spektrum n-Octane
Absorption of Alcohol and Amines
Hydrogen Bonding Effect
Spike
Absorption of Simple Ketones,
Aldehyde and Acid
 Absorption of
Esters and Cycloalkanone
Contoh Soal
 Solusi dan Pembahasan
First, look at peaks outside the fingerprint region. Don’t look like
alkane peaks:

A weak peak around 3400 cm-1  O-H ?

A strong peak about 1720 cm-1  C=O
Peak around 2720 cm-1  C-H aldehyde
Peak around 2800 – 2950 cm-1  C-H alifatik

The weak peak around 3400 cm-1 might be mistaken for an

alcohol O-H. From experience, we know alcohols give much
stonger O-H absorptions. This small peak might be from an
impurity of water or from a small amount of the hydrate of the
aldehyde. Many IR show small, unexplained absorbtions in the
O-H region.
Latihan
Resonance Lowering of Carbonyl Frequencies
Absorption of C-N Bond
Latihan
Summary
Strengths and Limitation
Summaries
 Learn at Home – Compound 1

Write your interpretation here:

Around 2900 cm-1  aliphatic C-H

1714 cm-1  C=O of ketone
 Learn at Home - Compound 2

Write your interpretation here:

 Learn at Home - Compound 3

Write your interpretation here:

 Learn at Home - Compound 4

Write your interpretation here:

 Learn at Home - Compound 5

Write your interpretation here:

 Learn at Home - Compound 6

Write your interpretation here:

 Learn at Home - Compound 7

Write your interpretation here:

 See the structures below
to help you learn at Home
 Tugas Individu 2
1. Isilah kotak pada putih pada spektrum IR di bawah ini dengan
jenis vibrasi yang sesuai dengan struktur senyawa yang telah
diberikan!

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2. Gambar di bawah ini merupakan spektrum IR hasil reaksi
esterifikasi antara asam benzoat dengan metanol. Isilah kotak
putih pada spektrum IR tersebut dengan jenis vibrasi yang
sesuai dan prediksikan struktur produk reaksi esterifikasi
tersebut

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3. Perhatikan spektrum IR di bawah ini dan pilih salah satu
struktur yang paling sesuai untuk masing-masing spektrum
tersebut di antara strutkur-struktur yang tersedia dilengkapi
dengan penjelasan mengapa Anda memilih struktur tersebut!
 Tugas Kelompok 2
1. Perhatikan dua spektrum IR di bawah ini dan pilih struktur
yang paling sesuai untuk masing-masing spektrum tersebut di
antara strutkur-struktur yang tersedia dilengkapi dengan
penjelasan mengapa Anda memilih struktur tersebut!

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2. Masing-masing kelompok (1-5) mencari
jurnal dan membahas satu contoh struktur
dan spektrum IR senyawa:
a. Triterpenoid (Kelompok 1)
b. Steroid (Kelompok 2)
c. Fenilpropanoid (Kelompok 3)
d. Alkaloid (Kelompok 4)
e. Senyawa obat Sintetik (Kelompok 5)
The IR Spectra of Natural Products
IR spectra of menthol
IR spectra of menthone
IR spectra of carvone
Jurnal tentang gymnemagenol
IR spectra of gymnemagenol
 Journal Discussion
• The compound showed
strong absorption band
peak at 223, 237 and
274. FTIR spectrum was
observed at 3.445, 2.924,
1.635, and 1.457 cm-1.
Jurnal tentang β-sitosterol
 IR spectra of β-sitosterol

1653 883 800

3421 1458 1062

2866
2935
 Journal Discussion
• The IR spectrum in KBr of
compound 3 showed a
characteristic absorption band
at 3421cm-1 due to vibration
of O-H bond of hydroxyl
group. Absorption bands were
noticed at 2935 and 2866cm-
1 due to aliphatic C-H
stretching of (-CH2 & -CH)
respectively. The C=C
stretching appeared as a weak
band at 1653cm-1. The
absorption band at 1062cm-
1 was noticed due to C-O
stretching. 67
Jurnal tentang -sitosterol
dan asam linoleat
Jurnal tentang flavanone
Journal Discussion
IR spectra of quercetin
IR spectra of piperine
IR spectra of quinine
 Journal about quinine
• The IR spectra (KBr) (ν/cm) show the
peaks at
• 3206  O-H (berikatan hidrogen),
• 3010-2901  C-H (aromatik alkena dan
alifatik)
• 1620-1432  C=C (aromatik, alkene),
• 1473-1432  CH2 bend (alkane,
cycloalkane),
• 1299-1358  C-N (cyclic amine),
• 1243-1080  C-O (ether),
• 1080-1009  C-O (alcohol),
• 980-575  =C-H bend (out of plane),
• 780-718  CH2 bend-rocking type
(alkana).
IR spectra of sucrose
THANK YOU

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