Organic Hydrocarbons
Organic Hydrocarbons
Organic Hydrocarbons
Aromatic Compounds
Hydrocarbons and Phenols
Perihan Hussein El-Shafei
114932
This Paper discusses the Hydrocarbons types, their properties, and highlights of
their important reactions. The Experiment conducted was to identify and
differentiate between two Aromatic unknowns. Benzene and Anthracene, using
the class identification Tests Sulfonation and Nitration, and the specific test for
Anthracene the Picrate Test to determine which is which.
Table of Contents
Introduction: Aromatic Compounds.......................................................................3
Structures of Aromatic Compunds........................................................................3
Reactions of Aromatic Compounds..........................................................................4
Nitration............................................................................................................... 4
Sulfonation........................................................................................................... 5
Picrate.................................................................................................................. 5
Phenols....................................................................................................................... 5
Properties of Phenols.......................................................................................... 6
Acidity of Phenols................................................................................................ 6
Electrophilic reactions............................................................................................. 6
Azodye Formation.................................................................................................... 7
Methods and experimental set-up:.............................................................................8
Results........................................................................................................................ 9
Results of hydrocarbons.......................................................................................... 9
Unknown 1:............................................................................................................. 9
Unknown 2............................................................................................................ 12
Bibliography............................................................................................................. 19
Introduction:
Aromatic Compounds
An aromatic compound is a organic molecule containing a benzene ring.
(About.com)
Aromatic compound, are unsaturated chemical compounds characterised by
one or more planar rings of atoms attached together by covalent bonds. The
exceptional stability of these compounds is alluded by aromaticity. Despite
the fact that the name aromatic formerly concerned odour, nowadays its
utilization in chemistry is constrained to compounds that have certain
electronic, structural, or chemical properties. Aromaticity results from a
distinct bonding arrangement that induces certain (pi) electrons within a
molecule to be firmly held. Aromaticity is typically reflected in a scaled-down
heats of combustion and hydrogenation than the expected, and is associated
with low reactivity. (Britannica, aromatic compound)
Structures of Aromatic Compunds
Bellow you will find three different ways to draw the structure of the most
famous aromatic compound Benzene, and some examples of Aromatic
compounds and their structure:
In this reaction the bromine atom substituted a hydrogen. For this reason the
term aromatic substitution was given to this type of reaction. This occurs
because the benzene ring is quite electron-rich, it almost always behaves as
the nucleophile in a reaction - which means that the substitution on benzene
occurs by the addition of an electrophile -> electrophilic aromatic
substitution. (Chem) The Electrophilic substitution reaction will be discussed
later on in this paper.
Nitration
making a highly electrophilic form of NO2
Nitration could be done for two main reasons. The first reason is, nitration in
order to manufacture explosives highly nitrated organic molecules are
frequently used as explosives for example (trinitrotoluene(TNT),
nitroglycerine, etc.). The second reason is, nitration inorder to produce
amines. This occurs because of the fact of nitro-groups being generally easy
to reduce to amines. As well as the fact of making amine electrophilic is
nearly impossible. (inorder to add it to an aromatic ring under electrophilic
aromatic substitution conditions), aromatic nitro compounds are about the
only precursors to aromatic amines:
Sulfonation
But you should be aware that this reaction is reversible if you add it to hot
Aqueous acid the SO3 group will fall off. However, the aromatic sulfonic acids
were formerly used as antibiotics. They also could be used to make
detergents.
Picrate
We could use both the sulfonation reaction and the nitration reaction to
determine whether a sample is aromatic or not in the laboratory. The tests
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H 2 SO 4
Aromatic compounds we have single rings and fused rings. A Single ring is
like the Benzene Ring, the fused Ring is like Anthracene.
In order to differentiate between single rings and fused rings we apply the
Picrate test. This test is applied by adding picric acid to Anthracene solvent
in a test tube where the sample was already been added, then keeping it on
water bath, after that it is added in a watch glass, if crystals are formed then
the sample is fused rings. If it doesnt for crystals then the sample is a single
ring compound.
Phenols
phenols, are known to be any organic compound that contains the hydroxyl
(OH) functional group attached to a carbon atom that is part of an aromatic
ring. Phenols are similar to alcohols but form stronger hydrogen bonds. Thus,
they are more soluble in water than alcohols are, and have higher boiling
points. Phenols are either colourless liquids or white solids at room
temperature, and may be highly toxic and caustic. (Britannica, Phenols)
Structure of Phenols.
Properties of Phenols
Pure phenol is a white crystalline solid, smelling of disinfectant. It has to be
handled with great care because it causes immediate white blistering to the
skin. The crystals are often rather wet and discoloured. The reasons behind
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the melting and boiling point being what it is is due to permanent dipoledipole attractions due to the electronegativity of the oxygen - but is mainly
due to hydrogen bonding. Hydrogen bonds can form between a lone pair on
an oxygen on one molecule and the hydrogen on the -OH group of one of its
neighbors. (ChemGuide, Introducing Phenols)
Acidity of Phenols
Phenols are more acidic than aliphatic alcohols. As illustrated in the below
figure.
There are two main factors affecting the acidity of Phenols. First, is the
inductive effect.
A benzene ring is generally considered electron withdrawing and stabilizes
the negative charge through inductive effects. The second reason is the
resonance effect. The benzene ring stabilizes the the phenoxide ion by
resonance delocalization of the negative charge. (Vanderbilt)
Electrophilic reactions
Because the benzene rings electrons were acting as the nucleophile in the
previously mentioned reactions, rings substituted with strong electrondonating groups (particularly -electron
donating) are considered activated - they will often even react without a
catalyst! Some
examples of activating groups are: OH, OR, NH2, NR2, Alkyl. The oxygen and
nitrogen-based activating groups increase reactivity by a resonance effect:
As you can see, the very nature of the activation requires ortho-para
direction!
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Alkyl groups work somewhat differently. They are not as strong at activating
the ring,
and their main function is stabilizing the positive charge formed after the
attack on the
electrophile.
Azodye Formation
Azo dye compounds contain
. Due to the N double N in the compound the
R- is much more stable than it wouldve been in the form of alkyl, this occurs
because - N = N becomes part of an extended delocalised system. The Azo
compounds are highly colored and are used as Dyes. (ChemGuide, REACTIONS OF
DIAZONIUM SALTS) Below is the reaction of Azos with Phenols.
(4college.com)
C. Cool, then
Results
Results of hydrocarbons
Benzene
Anthracene
Nitration
Forms a
coloured ppt
Forms an oily
ppt
Sulphonation
Forms a
coloured ppt
Forms an oily
ppt
Picrate test
No result
Red crystals
are formed
Unknown 1:
Physical Characteristics:
Chemical reactions:
Test
Observation
Result
Nitration Test
Yellow oil
Nitrobenzene is
formed.
Sulfonation test
Clear Solution
Benzene Sulphonic
acid is formed.
Pictrate test
-ve
Not Anthracene.
Nitration Test:
10
Mechanism:
(1)
Sufonation Test:
OR
Mechanism :
11
Stage one:
Stage Two:
(2)
12
Last test indicate that the unknown is benzene, because it would only react
with Anthracene, therefor since it gave a negative result with this unknown it
means that this is not Anthracene, So it is Benzene.
Unknown 1:
Physical Characteristics:
Chemical reactions:
Test
Observation
Result
Nitration Test
Yellow oil
Nitrobenzene is
formed.
(Aromatic compound.)
Sulfonation test
Clear Solution
Benzene Sulphonic
acid is formed.
(Aromatic compound.)
Pictrate test
-ve
Not Anthracene.
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Nitration and sulfonation tests were used to identify whether the unknown is
aromatic or not, since it gave a +ve result then the unknown is aromatic.
Next the Picrate test was done to determine whether the unknown is
Anthracene or not, since it gave a ve result then the compound is Benzene.
Unknown 2
Physical Characteristics:
Chemical reactions:
Test
Observation
Result
Nitration Test
Aromatic compound.
Sulfonation test
Aromatic compound.
Pictrate test
Red picrate
Anthracene is formed.
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Nitration and sulfonation tests were used to identify whether the unknown is
aromatic or not, since it gave a +ve result then the unknown is aromatic.
Next the Picrate test was done to determine whether the unknown is
Anthracene or not, since it gave +ve result then it shows that the product is
anthracene.
Results of Phenols
Phenol
Resorcinol
FeCl3
Violet
violet
NaOH
Azo-dye
Phthalei
ne
Green-blue
Red-dye
Pink
Brown
Red ppt
Fluorescent
green
OH
OH
Alphanaphthol
Green to
violet
No reaction
Brown red
Green
OH
OH
OH
Reagent
H2 O
NaOH
15
-naphthol
violet
greenish
turns to
violet
green or
blue
deep
green
FeCl3
Liebermann
H2 S O4
No reaction
Scarlet red
Faint green
OH
OH
OH
phenol
soln. +
Betanaphthol
Green
OH
quinol
naphthol
catechol resorcinol
green
color
slowly
green
violet color red, green
turns red discharged then
by NaOH by sodium yellow
acetate
brownish
black
deep
green
brown
red
green or blue
red
Azo-Dye
red ppt.
brownish
red color
scarlet red
Phthalin
red
green
faint green
deep blue
red
brownish
red ppt.
blue
green
fluoresence
purple
Unknown 1
Physical Characteristics:
Chemical reactions
Test
Observation
Result
Green
Phenol
FeCl3 Test
Violet color
Phenol
Phthalein Test
Pink color
Phenol
Azodye Test
-ve
Phenol
Red
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Unknown 2
Physical Characteristics:
Appearance: needles
Color : colorless
Solubility in water: soluble
Chemical reactions
Test
Observation
Result
Brown color
Resorcinol
FeCl3 Test
Violet color
Resorcinol
Phthalein Test
Fluorescent green
Resorcinol
Azodye Test
Red
Resorcinol
17
write the
Unknown 3
Physical Characteristics:
Appearance: solid
Color : white
Solubility in Water: soluble in water
Chemical reactions
Test
Observation
-ve result
FeCl3 Test
green
-naphthol
Phthalein Test
Green color
-naphthol
Azodye Test
-naphthol
Result
The(-ve) result with NaOH indicates that the unknown is a phenol, and then
three tests are carried out, and accordingly to their observation it was
deduced that the unknown is -naphthol.
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Unknown 4
Physical Characteristics:
Appearance: crystalline solid
Color : colorless
Solubility in Water: slightly soluble in water
Chemical reactions
Test
Observation
-ve result
FeCl3 Test
-naphthol
Phthalein Test
-naphthol
Azodye Test
-naphthol
Result
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Bibliography
1. (n.d.). THE SULPHONATION OF BENZENE. Retrieved from ChemGuide:
http://www.chemguide.co.uk/mechanisms/elsub/nitrationtt.html
2. (n.d.). EXPLAINING THE NITRATION OF BENZENE. Retrieved from CHEMGUIDE:
http://www.chemguide.co.uk/mechanisms/elsub/nitrationtt.html
4college.com. (n.d.). Azo Compounds. Retrieved from 4college:
http://www.4college.co.uk/a/Cd/azo.php
About.com. (n.d.). Aromatic Compound Definition. Retrieved November 11, 2013,
from About.com Chemistry:
http://chemistry.about.com/od/chemistryglossary/a/aromaticcmpndef.htm
Britannica, E. (n.d.). aromatic compound. Retrieved November 11, 2013, from
Encyclopedia Britannica:
http://www.britannica.com/EBchecked/topic/35891/aromatic-compound
Britannica, E. (n.d.). Phenols. Retrieved November 11, 2013, from Encyclopedia
Britannica : http://www.britannica.com/EBchecked/topic/455507/phenol
Chem. (n.d.). Reactions of Aromatic Compounds . Retrieved November 11, 2013,
from ChemUKY: http://www.chem.uky.edu/courses/che232/JEA/ln/3.%20Aromatic
%20Chemistry.pdf
ChemGuide. (n.d.). Introducing Phenols. Retrieved november 11, 2013, from
ChemGuide: http://www.chemguide.co.uk/organicprops/phenol/background.html
ChemGuide. (n.d.). REACTIONS OF DIAZONIUM SALTS. Retrieved from ChemGuide:
http://www.chemguide.co.uk/organicprops/aniline/propsdiazo.html
Vanderbilt. (n.d.). Phenols. Retrieved November 11, 2013, from
http://www.vanderbilt.edu/AnS/Chemistry/Rizzo/Chem220b/Ch24.pdf
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