APPROVAL SHEET

Complete report of Organic Chemistry II Experiment with the title

“Synthetic of Acetanilide”, by :
Name : Nur Aulia S.
Id : 1613441002
Group : V
Class : ICP of Chemistry
has been checked by Assistant and Assistant Coordinator, so the report has
accepted.

Makassar, November 2017

Coordinator Assistant Assistant

Yudhi Priyatmo, S.Pd Iis Cahyani Basuki

Known by,
Lecturer of Responsibility

Dr. Netty Herawaty, S, Pd, M.Si

ID. 19741027 200002 2 001
A. THE TITLE OF EXPERIMENT
The title of this experiment is Synthetic of Acetanilide
B. THE AIM OF EXPERIMENT
The aim of this experiment is the apprentice can understand about:
1. Be skillful to arrange and use the apparatus to do synthetic of organic
substances.
2. Explain about fractional distillation technique.
3. Explain the basic principle of chemistry science in derivation of amine
compound.
C. REVIEW OF THEORY
The process of repeated vaporizations and condensations, called fractional
distillation, allows us to separate liquid components of a mixture by exploiting the
vapor pressure differences of the components. In a simple distillation, perhaps only
two or three vaporizations and condensations occur. The condensed liquid is called
the distillate or condensate. A simple distillation would not effectively separate a
1:3 molar solution of pentane and hexane. As the distillation proceeds, the
remaining pentane/hexane solution does become increasingly more concentrated in
hexane and the boiling point of the solution increases, but the separation of pentane
and hexane is not nearly complete (Mohrig, 2010: 147).
According to (Gilbert, 2011: 56), typical apparatus for miniscale simple
distillation at atmospheric pressure or under vacuum. Inset shows correct placement
of thermometer in still head
 In a fractional distillation many vaporizations and condensations take place
before the distillate is collected. Each vaporization and condensation cycle causes
the vapor to become enriched in the more volatile compound. If a number of
vaporization/condensation cycles are carried out in a fractionating column, the
components of a mixture can be efficiently separated based on their vapor pressure
differences. The fractionating column is inserted between the distillation flask and
the distilling head of the distillation apparatus and provides a large surface area over
which a number of separate liquid-vapor equilibria can occur. As vapor travels up
a column, it cools, condenses into a liquid, then vaporizes again after it comes into
contact with hotter vapor rising from below. The process can be repeated many
times. If the fractionating column is efficient, the vapor that finally reaches the
distilling head at the top of the column is composed entirely of the component with
the lower boiling point (Mohrig, 2010: 158).
Before assembling the apparatus, clean and dry the inner tube of the
distillation column to avoid contaminating your product. It is not necessary to dry
the water jacket, because traces of water in it will not affect the distillation. Pack
the column by adding the desired column packing, a small quantity at a time,
through the top of the column while holding it vertical. The column packing is an
inert material such as glass, ceramic, or metal pieces in a variety of shapes (helices,
saddles, woven mesh, and so on). Common packings include glass tubing sections,
glass beads, glass helices, or a stainless steel sponge. Some column packings are
sufficiently large that they will stop at the indentations. If the packing falls through
the column, put a small piece of glasswool, wire sponge, or wire screen into the
column just above the indentations by pushing it down the column with a wooden
dowel or a piece of glass tubing. The column packing should extend to the top of
the water jacket but should not be packed too tightly (Gilbert, 2011: 58).
Types of fractionating columns. Fractionating columns that can be used to
separate two liquids boiling at least 25°C. The larger the column surface area on
which liquid vapor equilibria can occur, the more efficient the column will be. The
fractionating columns have from six to eight theoretical plates. A fractionating
column with eight theoretical plates can separate liquids boiling only 25°C apart. A
more efficient column can be made by packing a simple fractionating column with
a wire spiral, glass helixes, metal sponge, or thin metal strips. These packings
provide additional surface area on which liquid-vapor equilibria can occur. Care
must be used in selecting packing materials to ensure that the packing does not
undergo chemical reactions with the hot liquids in the fractionating
column (Mohrig, 2010: 158).
According to (Brown, 2012: 947), amines are derivatives of ammonia in
which one or more hydrogens are replaced by alkyl or aryl groups. Amines are
classified as primary, secondary, or tertiary, depending on the number of carbon
atoms bonded directly to nitrogen

Amines are further divided into aliphatic and aromatic amines. In an aliphatic
amine, all carbons bonded to nitrogen are derived from alkyl groups; in an aromatic
amine, one or more of the groups bonded to nitrogen are aryl groups.
Amines are moderately polar substances; they have boiling points that are
higher than those of alkanes but generally lower than those of alcohols of
comparable molecular weight. Molecules of primary and secondary amines can
form strong hydrogen bonds to each other and to water. Molecules of tertiary
amines cannot form hydrogen bonds to each other, but they can form hydrogen
bonds to molecules of water or other hydroxylic solvents. As a result, tertiary
amines generally boil at lower temperatures than primary and secondary amines of
comparable molecular weight (Solomons & Craib, 2011: 913).
According to (Brown, 2012: 948), an amine in which the nitrogen atom is
part of a ring is classified as a heterocyclic amine. When the nitrogen is part of an
aromatic ring, the amine is classified as a heterocyclic aromatic amine. Following
are structural formulas for two heterocyclic aliphatic amines and two heterocyclic
aromatic amines

According to (Solomons & Craib, 2011: 947) acetylation of aniline produces

acetanilide (2) and protects the amino group from the reagent to be used next.

Nicotine is a suitable reference material not only for δ13C and δ15N, but also
for δ2H, because the hydrogen atoms in nicotine are exclusively bonded to carbon,
and because they have high proton acidity pKa values and therefore have limited
isotopic exchangeability in the presence of H2O. In contrast, acetanilide and urea
are not suitable as stable isotope reference materials for hydrogen because they both
contain isotopically exchangeable hydrogen atoms linked to nitrogen that
continuously re-equilibrate with H2O, including atmospheric moisture. Acetanilide
and urea contain some exchangeable hydrogen and therefore are inappropriate as
reference materials for δ 2H. Fourteen laboratories participated in a direct EA-IRMS
comparison of our acetanilides and ureas with L-glutamic acids USGS40 and
USGS41 (Schimmelmann, 2009).
D. APPARATUS AND CHEMICAL
1. Apparatus
a. Distillation flask 500 mL 1 piece
b. Thermometer 110oC 1 piece
c. Hot plate and condenser @ 1 piece
d. Beaker glass 50 mL 1 piece
e. Beaker glass 250 mL 2 pieces
f. Beaker glass 400 mL 1 piece
g. Beaker glass 1000 mL 1 piece
h. Graduated cylinder 50 mL 1 piece
i. Drop pipette 2 pieces
j. Water bath 1 piece
k. Funnel 1 piece
l. Buchner funnel 1 piece
m. Suction flask 500 mL 1 piece
n. Stir bar 1 piece
o. Spatula 1 piece
p. Watch glass 1 piece
q. Analytical balance 1 piece
r. Melting point tool 1 unit
s. Capillary tube 1 piece
t. Spray bottle 1 piece
u. Boiling stone 3 pieces
v. Matches 1 piece
w. Rough and smooth rag @ 1 piece
2. Chemical
a. Aniline (C6H5NH2)
b. Glacial acetic acid (CH3COOH)
c. Alcohol 2% (C2H5OH)
d. Activated carbon (C)
e. Aquadest (H2O(l))
f. Ice (H2O(s))
g. Filter paper
h. Whatman filter paper
E. WORK PROCEDURE
1. As much 20 mL of aniline was filled into distillation flask.
2. Then, 25 mL of glacial acetic acid was filled into distillation flask too.
3. As much 3 pieces of boiling stone was added into the mixture of solution. After
that distillation was done until distillate was gotten.
4. Next, the mixture of solution was poured into cold water.
5. The solution was let until crystal was formed.
6. The solution was filtered. Then, the crystal was washed with the mixture of
alcohol and H2O.
7. The crystal was filtered again. While the activated carbon was dissolved with
hot water and it was heated.
8. The crystal was added with activated carbon that have dissolved and heated.
While the crystal was filtered.
9. After that, the crystal was filtered again with Buchner funnel. But the whatman
filter paper was weighed before to use in Bucher funnel.
10. Next, the crystal was dried.
11. Then, the crystal was weighed.
12. The melting point of crystal was checked with melting point tool.
F. OBSERVATION RESULT
No Activity Result
1 20 mL of aniline (yellow) + 25 mL of Light yellow solution
glacial acetic acid (purple)
2 Distillation at 104-105oC Brown solution
3 Pour the solution into cold water Turbid solution and crystal
formed
4 Filtering Turbid crystal
5 The crystal washed with the mixture of Turbid crystal
ethanol and water
 6 The crystal added with activated carbon White crystal
7 Filtering with Buchner funnel White crystal
8 Drying White crystal
9 Weighed the crystal White crystal with its mass
W whatman filter paper: 1,1 gr
W whatman filter paper + crystal: 5,8 gr
W crystal: 4,7 gr
10 Melting point test Melting point of crystal is
1180C
G. DATA ANALYSIS
Known:
V aniline (C6H5NH2) = 20 mL
V glacial acetic acid (CH3COOH) = 25 mL
Fw C6H5NH2 = 93 gram/mole
Fw CH3COOH = 60 gram/mole
ρ CH3COOH = 1,024 gram / mL
ρ C6H5NH2 = 1,051 gram / mL
Mass crystal = 4,70 gram
Asked: % rendement ?
Answer:
Mass of C6H5NH2 = ρ C6H5NH 2 x V C6H5NH2
= 1,024 gram/ mL x 20 mL
= 20,48 gram
mass of C6H5NH2
Mole of C6H5NH2 = Fw C6H5NH2
20,48 gram
= 93 gram/mole

= 0,22 mole
Massa CH3COOH = ρ CH3COOH x V CH3COOH
= 1,051 gram/ mL x 25 mL
= 26,28 gram
mass of CH3COOH
Mole of CH3COOH = Fw CH3COOH
 26,28 gram
= 60 gram/mol

= 0,44 mole
The equation reaction is :
CH3COOH + C6H5NH2 C6H5NHCOOCH3 + H2O
Initial 0,22 mole 0,44 mole - -
React 0,22 mole 0,22 mole 0,22 mole 0,22 mole
Remain - 0,22 mole 0,22 mole 0,22 mole
So, mole of C6H5NHCOOCH3 is 0,22 mole.
Mass of C6H5NHCOOCH3 = mol C6H5NHCOOCH3 × Mr C6H5NHCOOCH3
= 0,22 mole × 135 gram/mole
= 29,70 gram
mass of experiment
% Rendement = x 100 %
mass of theory
4,70 gram
= x 100 %
29,70 gram

= 15,82 %
H. DISCUSSION
Percobaan ini bertujuan agar mahasiswa terampil dalam menyusun dan
menggunakan alat untuk mensintesis senyawa organic, menjelaskan teknik
destilasi, dan mampu pula dalam menjelaskan asas dasar ilmu kimia dalam
penurunan senyawa amina. Reaksi antara asam asetat glasial dan anilin merupakan
reaksi asetilasi yang membentuk amida dalam hal ini asetanilida. Asetanilida
merupakan senyawa turunan asetil amina aromatis yang digolongkan sebagai amida
primer karena satu atom hidrogen pada anilin digantikan dengan satu gugus asetil.
Sehingga dalam proses pembuatan asetanilida adalah dengan mereaksikan anilin
dengan asam asetat glasial. Pada pencampuran anilin dengan asam asetat glasial
menghasilkan larutan kuning dan panas. Larutan terasa panas menandakan bahwa
telah tejadi reaksi eksoterm yaitu perpindahan panas dari sistem ke lingkungan.
Adapun reaksi yang terjadi, adalah :
This experiment aims to enable students to be skilled to set and using tools
to synthesize organic compounds, describe distillation techniques, and also to
explain basic principles of chemistry in the reduction of amine compounds. The
reaction between glacial acetic acid and aniline is an acetylation reaction that forms
amides in this case acetyl amide. Acetyl an aromatic acetyl derivative derivative
which is classed as a primary amide because one hydrogen atom in aniline is
replaced by one acetyl group. Thus in the process of making acetylchide is by
reacting aniline with glacial acetic acid. In mixing aniline with glacial acetic acid
yields a yellow and hot solution. The hot solution indicates that an exothermic
reaction has occurred, ie heat transfer from the system to the environment. The
reactions that occur, are:
C6H5NH2(aq) + CH3COOH(aq) C6H5NHCOCH3(aq) + H2O(aq)
Penggunaan anilin berfungsi sebagai penyedia gugus amina dalam hal ini gugus
C6H5NH. Sedangkan asam asetat glasial berfungsi sebagai penyedia gugus asetat
dalam hal ini COCH3 yang bersifat asam karena melepas ion H+/H3O+ yang sangat
mempengaruhi reaksi agar terbentuk suatu garam amina.
The use of aniline serves as a provider of amine groups in this case C6H5NH group.
While glacial acetic acid functions as a provider of acetic groups in this case acidic
COCH3 because it releases H + / H3O + ions which greatly influence the reaction
to form an amine salt.

Asam asetat juga berfungsi sebagai katalis yang mempercepat terjadinya

reaksi, serta untuk menetralkan muatan oksida sehingga asetanilida yang terbentuk
tidak terhidrolisis kembali karena pengaruh air dan untuk mencegah terjadinya
reaksi samping dari senyawa turunan asetil. Kemudian campuran anilin dan asam
asetat glacial di destilasi. Prinsip dasar dari destilasi adalah pemisahan campuran
zat atau senyawa berdasarkan perbedaan titik didihnya. Adapun prinsip kerja dari
destilasi adalah pemanasan, penguapan, pendinginan, dan pengembunan.
Campuran tersebut didestilasi untuk memisahkan asetanilida dengan hasil
samping reaksi yang terbentuk yaitu air. Larutan yang akan di destilasi, terlebih
dahulu ditambahkan batu didih. Batu didih ini berfungsi untuk mencegah terjadinya
letupan-letupan akibat pemanasan. Hal ini terjadi, karena pada batu didih terdapat
pori-pori yang mampu menyerap panas. Selain itu, pemanasan berfungsi agar
terjadi pencampuran senyawa yang sempurna sehingga mempercepat reaksi melalui
penguapan. Terjadinya reaksi sempurna ketika pemanasan karena terjadi
peningkatan suhu dalam sistem yang mengakibatkan tumbukan antar molekul akan
lebih banyak dan cepat. Dengan adanya pendinginan, uap yang akan terbentuk akan
mengembun kembali sehingga mengurangi konsentrasi senyawa yang menghilang
akibat pemanasan.
Pada saat pelarut mulai menguap, maka konsentrasi larutan di dalam labu
akan meningkat. Hal ini terlihat dari warna larutan yang semakin pekat. Suhu
destilat dijaga agar tidak melebihi 104-105oC agar asetanilida yang terbentuk tidak
ikut keluar bersama air karena titik didih air pada 100oC atau asam asetat tidak
bereaksi pada suhu 117oC. Residu dalam labu destilasi setelah dilakukan destilasi
diuji dengan air dingin. Apabila larutan sudah keruh, maka semua larutan
dituangkan ke dalam air dingin dan diaduk hingga terbentuk padatan kristal yang
berupa asetanilida. Tujuan pendinginan dengan air dingin untuk memperoleh kristal
asetanilida. Hasil kristalisasi ini berupa larutan keruh dengan endapan kuning
kekeruhan, yang menandakan bahwa pada kristal terdapat zat pengotor yang berupa
sisa reaktan ataupun hasil samping reaksi seperti, sisa-sisa asam dan H2O. Untuk
itu, dilakukan penyaringan agar memisahkan kristal dengan pelarutnya. Kemudian
kristal dilarutkan dengan campuran etanol dan aquadest untuk melakukan proses
rekristalisasi.
Penambahan etanol berfungsi untuk mengikat sisa-sisa asam dan juga
sisa-sisa air pada larutan. Sedangkan penambahan norit berfungsi untuk menyerap
zat warna dan pengotor-pengotor yang berukuran besar karena karbon aktif
memiliki pori-pori yang besar. Sehingga kristal yang awalnya berwarna keruh
menjadi warna putih bersih. Dengan demikian, kristal yang diperoleh lebih murni.
Setelah pencampuran dilakukan, ditambahkan lagi dengan air panas lalu
menyaringnya dalam keadaan panas. Fungsi dari air panas adalah agar dapat
melarutkan kristal yang terbentuk sehingga kristal tidak megendap di dalam gelas
kimia. Penyaringan dilakukan sewaktu panas, karena bila larutan dingin maka
larutan sudah menjadi kristal (asetanilida) bersama dengan karbon aktif atau norit
dan penggotor lainnya.
 Hasil penyaringan yang diperoleh terdiri atas residu yang berupa endapan
hitam pada kertas saring atau norit dan zat pengotor lainnya dan diperoleh pula
filtrat berupa larutan tak berwarna dan kristal berwarna putih. Kristal yang
diperoleh kemudian disaring kembali dengan corong buchner. Hasil penyaringan
ini diperoleh residu yang tak berwarna dan kristalnya berwarna putih yang
menandakan bahwa larutan yang disaring tidak mengandung lagi zat pengotor.
Kristal yang diperoleh ini, kemudian dikeringkan yang bertujuan agar terjadi
penguapan air yang masih terkandung dalam kristal.
Kemudian dilakukan penimbangan kristal dan diperoleh sebesar 4,70 gram
kristal asetanilida. Hasil ini tidak sesuai dengan hasil analisis data bahwa jika 20
mL anilin dan 25 mL asam asetat glacial dicampurkan maka seharusnya diperoleh
kristal asetanilida sebesar 29,70 gram. Sedangkan berdasarkan analisis data
diperoleh persentase rendemen sebesar 15,82 %. Hal ini berarti hanya terdapat
15,82 % kristal asetanilida yang diperoleh. Adanya ketidaksesuaian antara teori
dengan hasil yang diperoleh disebakan karena akibat dari kurang ketelitian dan
kurang hati-hati praktikan dalam melakukan proses praktikum. Yaitu, karena
kurang hati-hati saat proses rekristalisasi dan banyaknya kristal yang tertumpah
pada saat pengeringan sehingga banyak kristal yang terbuang. Oleh karena itu,hasil
yang diperoleh kurang maksimal. Adapun kristal yang diperoleh, berwarna putih
dengan titik leleh sebesar 118oC. Hasil ini tidak sesuai teori (Wigal, 2004), bahwa
titik leleh asetanilida adalah 113-115oC. Ketidaksesuaian ini terjadi kemungkinan
disebabkan oleh kesalahan pembacaan termometer ketika pengamatan dilakukan
saat uji titik leleh selain itu kurang perhatiannya dalam memperhatikan apakah
kristal telah meleleh semua di dalam alat penentu titik leleh sehingga kristal tetap
berada dalam alat penentu titik leleh padahal kristal telah meleleh semua.
Adapun tahapan reaksi pembentukan asetanilida yang terjadi adalah :
 H H -
O O
N N
+ H3C + H3C
H OH H OH
asam asetat glasial
anilin -
H O
H - +
O N CH3
N + +
+ H3C C H OH + H
H OH

- -
H O H O
+ +
N CH3 - N CH3
+ HO + -
H OH + H H + H + HO

-
H O H O
+
N CH3 N CH3
+ -
H + H + HO + H2O

asetanilida air

I. CONCLUSION
1. Salah satu metode sintesis senyawa organik adalah untuk pembuatan
asetanilida. Pembuatan asetanilida menggunakan metode destilasi dengan
mereaksikan anilin dengan asam asetat glasial.
2. Salah satu metode pembuatan asetanilida adalah dengan teknik destilasi yaitu
pemisahan campuran senyawa berdasarkan perbedaan titik didihnya.
Sedangkan prinsip kerjanya yaitu pemanasan, penguapan, pendinginan, dan
pengembunan, sehingga terjadi penetesan destilat.
3. Asetanilida dapat dibuat malalui reaksi asetilasi, yang mana anilin diubah
dengan menggunakan asam asetat glacial dengan reaksi subtitusi asil
nukleofilik sehingga membentuk asetanilida.
J. SUGGESTION
Untuk praktikan selanjutnya harus lebih berhati-hati dalam melakukan
rekristalisasi sehingga tidak ada kristal yang terbuang. Dan praktikan harus
mengingat prosedur kerja dengan baik.
 BIBLIOGRAPHY

Brown, W.H., Christopher, S.F., Brent, L.I., Eric, V.A., Bruce, M.N. 2012. Organic
Chemistry Sixth Edition. USA: Cengage Learning.

Gilbert, J.C., & Stephen, F.M. 2011. Experimental Organic Chemistry A Miniscale
and Microscale Approach Fifth Edition. USA: Cengage Learning.

Mohrig, J.R., Christina, N.H., & Paul, F.S. 2010. Techniques in Organic Chemistry
Third Edition. USA: W. H. Freeman and Company.

Schimmelmann, A., Andrea, A., Peter, E.S., Haiping, Q., Roland, M., & Francois,
M. 2009. Nicotine, Acetanilide and Urea Multi-Level 2H-, 13C- and 15N-
Abundance Reference Materials for Continuous-Flow Isotope Ratio Mass
Spectrometry. Rapid Communications in Mass Spectrometry. Vol 23. No.10
Solomons, T.W.G., & Craig, B.F. 2011. Organic Chemistry Tenth Edition. USA:
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