A.

THE TITLE OF EXPERIMENT

Synthetic of acetanilide.
B. THE AIM OF EXPERIMENT
After the experiment, apprentice are expected to:
1. Skilled at compiling and using tools in the work of synthesis of organic
substances.
2. Explain the multilevel distillation technique.
3. Explain the basic principles of chemical science of amine derived compounds.
C. REVIEW OF THEORY
Nitrogen-containing compounds are essential to life. Their ultimate source
is atmospheric nitrogen which, by a process known as nitrogen fixation, is
reduced to ammonia, then converted to organic nitrogen compounds. This chapter
describes the chemistry of amines, organic derivatives of ammonia. Alkylamines
have their nitrogen attached to sp3-hybridized carbon; arylamines have their
nitrogen attached to an sp2-hybridized carbon of a benzene or benzene-like ring.

Amines, like ammonia, are weak bases. They are, however, the strongest
uncharged bases found in significant quantities under physiological conditions.
Amines are usually the bases involved in biological acid–base reactions; they are
often the nucleophiles in biological nucleophilic substitutions. Our word
“vitamin” was coined in 1912 in the belief that the substances present in the diet
that prevented scurvy, pellagra, beriberi, rickets, and other diseases were “vital
amines.” In many cases, that belief was confirmed; certain vitamins did prove to
be amines. In many other cases, however, vitamins were not amines.
Nevertheless, the name vitamin entered our language and stands as a reminder
that early chemists recognized the crucial place occupied by amines in biological
processes. Acetanilide is an acceptable IUPAC synonym for the
Nphenylethanamide (Carey, 2000 : 858-879).
 Amines are widely distributed in plants and animals, and many amines
have physiological activity. For example, two of the body's natural stimulants of
the sympathetic ("fight or flight") nervous system are norepinephrine and
epinephrine (adrenaline).

Both norepinephrine and epinephrine are /i-phenylethylamines (2-

phenylethylamines). A number of other j8-phenylethylamines act upon the
sympathetic receptors. These compounds are referred to as sympathomimetic
amines because they "mimic," to an extent, the physiological action of
norepinephrine and epinephrine (Fessenden, 1982 : 706).
Amines. Amines are preferably named by adding the suffix -amine (and
any multiplying affix) to the name of the parent radical. Examples are

Locants of substituents of symmetrically substituted derivatives of symmetrical

amines are distinguished by primes or else the names of the complete substituted
radicals are enclosed in parentheses. Unsymmetrically substituted derivatives are
named similarly or as N-substituted products of a primary amine (after choosing
the most senior of the radicals to be the parent amine). For example,

Complex cyclic compounds may be named by adding of the suffix -amine or the
prefix amino- (or aminoalkyl-) to the name of the parent compound or as N-
substituted products. Complex linear polyamines are best designated by
replacement nomenclature (Gokel, 2004 : 1.29-1.30).
Amines undergo hydrogen bonding. The N-HN hydrogen bond is weaker
then the O-HO hydrogen bond because N is less electronegative than O and
therefore the NH bond is less polar. This weak hydrogen bonding between amine
molecules results in boiling points that fall between those for nonhydrogen-
bonded compounds (like alkanes or ethers) and those for strongly hydrogen-
bonded compounds (like alcohols) of comparable molecular weight.

Because they do not have an NH bond, tertiary amines in the pure liquid state
cannot undergo hydrogen bonding. The boiling points of tertiary amines are lower
than those for comparable primary or secondary amines, and are closer to the
boiling points of alkanes of similar molecular weight.

Amines of low molecular weight are soluble in water because they can of undergo
hydrogen bonding with the water. Tertiary amines, as well as primary and
secondary (Fessenden, 1982 : 711).
Amines are much more likely to act as bases. In fact, amines are the most
common organic bases. Instead of talking about the strength of a base in terms of
its value, it is easier to talk about the strength of its conjugate acid as indicated by
its value, remembering that the stronger the acid, the weaker is its conjugate base.
For example, protonated methylamine is a stronger acid than protonated
ethylamine, which means that methylamine is a weaker base than ethylamine.
Notice that the values of protonated amines are about 10 to 11.
It is important to know the approximate values of the various classes of
compounds we have discussed. An easy way to remember them is in units of five,
as shown in Table 1.8. (R is used when the particular carboxylic acid or amine is
not specified.) (Bruice, 2000 : 43)
Unlike alcohols and alkyl halides, which are classified as primary,
secondary, or tertiary according to the degree of substitution at the carbon that
bears the functional group, amines are classified according to their degree of
substitution at nitrogen. An amine with one carbon attached to nitrogen is a
primary amine, an amine with two is a secondary amine, and an amine with three
is a tertiary amine.

The groups attached to nitrogen may be any combination of alkyl or aryl groups.
Amines are named in two main ways, in the IUPAC system: either as alkylamines
or as alkanamines. When primary amines are named as alkylamines, the ending –
amine is added to the name of the alkyl group that bears the nitrogen. When
named as alkanamines, the alkyl group is named as an alkane and the -e ending
replaced by –amine.

(Carey, 2000 : 859)

Aromatic and aliphatic representative thiols were tested for their
acetylation. In both cases the reaction is complete in about 1 h at room
temperature, no progress was observed by extending the reaction time. Besides,
some aromatic amines were tested for the reaction, requiring lower reaction time
than phenol or thiophenol to obtain very good yields of the corresponding amides.
Furthermore, different both aliphatic and aromatic acid anhydrides were also used
for performing the catalytic WD-acylation of phenol and benzyl alcohol as the
selected substrates (Romanelli, 2008).
D. APPARATUS AND CHEMICALS
1. Apparatus
a. Distillation flask 250 mL 1 Piece
b. Thermometer 110oC 1 Piece
c. Erlenmeyer 250 mL 1 Piece
d. Buchner funnel 1 Piece
e. Graduated cylinder 50 mL 1 Piece
f. Graduated cylinder 100 mL 1 Piece
g. Beaker 250 mL 1 Piece
h. Beaker 800mL 1 Piece
i. Watch glass 1 Piece
j. Oven 1 Piece
k. Spraying bottle 1 Piece
l. Stirring bar 1 Piece
2. Chemicals
a. Aniline C6H5NH2
b. Acetic acid glacial CH3COOH
c. Alcohol 2% C2H5OH
d. Aquadest H2O
e. Ice H2O(s)
f. Boiling stones
g. Filtering paper
h. Aluminum foil
i. Whatman filter paper
E. WORK PROCEDURES
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 100.
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 cystal was formed.
 6. The solution was filtered. Then, the cystal 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 weighted before to use in Buchner 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 Observation Result
1. 20 mL C6H5NH2 + 25 mL of CH3COOH Hot solution and yellow
solution

2. Solution distillate until 104-105oC Solution change colour

into soft yellow

3. Solution enter into cold water, still walting and Turbid solution and
stirrer white sediment

4. Filter with 10 mL of cold water and 10 mL of Formed crystal

ethanol

5. Enter the crystal into hot water and stir The solution is cream
and there is sediment

6. Filter with 10 mL of cold water and 10 mL of Formed crystal smaller

ethanol 2% with colour is cream

7. Enter the crystal into oven Formed small crystal

8. Weight the crystal 6,80-0,70 = 6,10 gram

9. Melting point test Melting point = 60oC
Last melting = 123oC
G. DATA ANALYSIS
Known : V C6H5NH2 = 20 mL
V CH3COOH = 25 mL
Fw CH3COOH = 60 gr/mol
Fw C6H5NH2 = 93 gr/mol
Fw CH3COONHC6H5 = 135 gr/mol
ρ C6H5NH2 = 1,024 gr/mol
ρ CH3COOH = 1,051 gr/mol
Asked : Randement = … ?
Solution :
Mass C6 H5 NH2 = ρ C6 H5 NH2 × V C6 H5 NH2
= 1,024 g/mL × 20 mL
= 20,48 g
mass C6 H5 NH2
n C6 H5 NH2 =
Fw C6 H5 NH2
20,48 g
=
93 g/mol
= 0,220 mole
Mass CH3 COOH = ρ CH3 COOH × V CH3 COOH
= 1,051 g/mL × 25 mL
= 26,27 g
massa CH3 COOH
n CH3 COOH =
Mr CH3 COOH
26,27 g
=
60 g/mole
= 0,437 mole
C6H5NH2 + CH3COOH CH3COONHC6H5 + H2O
first 0,220 mol 0,437 mol - -
Reaction 0,220 mol 0,220 mol 0,220 mol 0,220 mol
Residu - 0,217 mol 0,220 mol 0,220 mol
m CH3COONHC6H5 = n CH3COONHC6H5 × Fw CH3COONHC6H5
= 0,220 mol × 135 g/mol
 = 29,70 g (mass of theory)
massa praktek
% Randament = × 100 %
Massa teori
6,10 g
= × 100 %
29,70 g
= 20,53%
H. DISCUSSION
Asetanilida merupakan senyawa turunan asetil amina aromatis yang
digolongkan sebagai amida primer, dimana satu atom hidrogen pada anilin
digantikan dengan satu gugus asetil. Proses pembuatan asetanilida pada intinya
adalah mereaksikan anilin dengan asam asetat berlebih. Dalam percobaan ini
dilakukan asetilasi aniline dengan menggunakan asam asetat glacial sebagai
pereaksi, dalam proses ini air yang dihasilkan akan dihilangkan dengan proses
destilasi. Larutan anilin dimasukkan kedalam labu bulat dengan menambhakan
larutan asam asetat glacial. Fungsi dari aniline disini yaitu sebagai penyedia gugus
amina, sedangkan asam asetat glacial berfungsi sebagai penyedia gugus asetat
yang bersifat asam (melepas ion H+/H3O+) yang juga memengaruhi reaksi agar
terbentuk garam amina. Setelah itu, campuran larutan kemudian di destilasi untuk
memisahkan larutan dengan hasil reaksi samping yang terbentuk yaitu air.
Adapun fungsi proses destilasi yaitu untuk mempercepat reaksi karena dengan
adanya proses pemanasan tersebut. Pemanasan akan meningkatkan suhu dalam
sistem sehingga terjadi tumbukan antar molekul akan lebih banyak dan lebih cepat
sehingga mempercepat reaksi. Reaksi yang terjadi :

Sebelum melakukan proses destilasi, labu bulat diisi dengan bebrapa butir
batu didih yang bertujuan untuk mencegah letupan-letupan yang terjadi pada
proses destilasi. Prinsip dasar dari destilasi itu sendiri yaitu salah satu teknik
pemisahan dengan perbedaan titik didihnya. Dan adapun prinsip kerja destilasi
yaitu pemanasan, penguapan dan pendinginan. Dalam proses destilasi suhu atau
temperature tetap harus dijaga suhunya yaitu antara suhu 104-105oC. Pada suhu
tersebut asetanilida dapat terbentuk dan bila suhu melebihi suhu yang dianjurkan
maka asetanilida akan ikut larut keluar bersama air. Setelah didestilasi larutan
yang tersisa dalam labu bundar diuji dengan air dingin dan apabila sudah keruh,
maka semua larutan tersebut dituangkan kedalam air dingin yang kemudian
terbentuk kristal. Tujuan pendinginan dalam air dingin adalah agar diperoleh
kristal asetanilida dan untuk menghidrolisis asam asetat yang masih tersisa dalam
larutan.
Hasil pengkristalan ini berupa kristal yang berwarna kuning yang masih
terdapat zat pengotor didalamnya yaitu sisa reaktan atau hasil reaksi samping.
Kemudian ditambahkan dengan air dan etanol 2%. Penambahan air dingin
berfungsi untuk mengikat alkohol karena bersifat polar dan alkohol berfungsi
mengikat sisa-sisa asam, dan ditambahkan norit, adapun fungsi norit sebagai
penyerap warna atau mengikat warna. Kemudian kristal dimasukkan kedalam air
panas kemudian di saring menggunakan corong bucnher. Proses penyaringan ini
menggunakan prinsip sedimentasi dan dibantu dengan vakum uap, adapun tujuan
dari penyaringan sewaktu panas karena bila larutan dingin maka larutan akan
mengkristal. Kristal yang didapatkan berwarna putih kekuningan kemudian
dikeringkan dalam oven, tujuannya untuk mempercepat penguapan air yang masih
terkandung dalam kristal. Secara teori kristal asetanilida berwarna putih. Warna
kristal yang diperoleh sesuai dengan teori, hal ini disebabkan karena asetanilida
sudah tidak mengandung anilin yang bereaksi dengan asam asetat. Selanjutnya
Kristal asetanilida yang diperoleh di timbang untuk mengetahui beratnya. Adapun
berat yang diperoleh yaitu 6,10 gram, dengan rendemen sebesar 20,53 %. Dari
100 gram yang dicari hanya 20,53 gram yang didapatkan dari tingkat
keberhasilan. Adapun mekanisme reaksi:
 H

- -
N H O H O
+ +
+ H3C C N C CH3
OH H OH
- -
H O H O
+ +
N C CH3 N C CH3 + H

H OH OH

- -
H O H O
+ + -
N C CH3 + H
+
N C CH3 + H + OH

OH

-
H O H O
+ + -
N C CH3 + H + OH N C CH3 + H2O

(Acetanilide) (Water)
I. CONCLUSION
1. A manner used in synthesis asetanilida that is synthesis asetanilida from aniline
and acetic acid with distillation method.
2. The basic principle distillation the separation a mixture of based on boiling
points differences.
3. Acetanilide is a compound of derivative acetyl aromatic amines who are
categorized as amides primary, where one atom of hydrogen which on aniline
used or replaced with one of an acetyl group. The crystals acetanilide obtained
by 6,10 grams and the results of data analysis of obtained rendement 20,53 %.
J. SUGGESTION
It is expected that the next apprentice should be more careful in reacting a
substance such as in the process of distillation, filtration, so that the experiments
can be as expected and expected to master working procedures to achieve the
objectives of the experiment.
 BIBLIOGRAPHY

Bruice. Paula. Y., 2000, Organic Chemistry Fourth Edition, The McGraw-Hill
Companies: America.

Carey. Francis, 2000, Organic Chemistry fourth edition, McGraw-Hill Higher

Education: North America.

Fessenden. R. J., Fessenden. J. S., 1982, Organic Chemistry Second Edition,

United State of America : PWS Publishers.

Gokel. George. W, 2004, Deans’s Handbook Of Organic Chemistry, The

McGraw-Hill Companies: America. Bruice. Paula. Y., 2000, Organic
Chemistry Fourth Edition, The McGraw-Hill Companies: America.

Romanelli. G. P.,Bennardi. D. O., Autino. J. C., Baronetti. G. T., Thomas. H. J,

2008, E-Journal of Chemistry, A SIMPLE AND MILD ACYLATION
OF ALCOHOLS, PHENOLS, AMINES, AND THIOLS WITH A
REUSABLE HETEROPOLY ACID CATALYST (H6P2W18O62 . 24
H2O), Vol. 5, No. 3, ISSN; 0973-4945.