Chem 3

What is Thiol?
Thiols can be defined as a sulfur analog of

alcohols that is in simple it is an organic compound
consisting of compounds with a sulfur atom. It is also
referred as mercaptan. It consists of sulfhydryl group,
i.e., Thiol = R-SH.
Alcohols and Thiols share some similarity i.e.
sulfur emergers to be a larger element compared to that
of oxygen, the length of C–S bond is more than that of
C–O bond. The hydrogen bonding between the thiol
groups is much weaker in liquids or solids mainly
because of the cohesive force. They exhibit low dipole
moment than alcohol.
Properties of Thiol
Many thiols consist of odors that are usually strong which may be resembling scent of onions and garlic.
Thiols possessing a low molecular weight consists of repulsive and strong smell. For example, consider skunks
consisting of the lower molecular weight of thiol and it is easily detectable by humans. It is also responsible for
some sort of wine faults that have resulted due to some unintended reactions caused between sulfur and yeast.
Not all kind of thiols holds bad odor; they are many other thiols with a pleasant smell. For example
furan-2-yl methanethiol, responsible for the beautiful aroma of roasted coffee, monoterpenoid thiol responsible
for the mesmerizing scent of a grapefruit. One can find it only at low concentration levels.
Thiols are less likely soluble in water. Thioether functional groups possess similar boiling points and
solubility features, well this does not hold true for alcohols. Volatile thiols can be easily identified due to their
distinctive odors.
 Reactions of Thiol
Many reactions are exhibited by Thiols similar to that of hydroxyl compounds involving the formation
of sulfides and thioesters. Oxidation would affect the sulfur atom in thiols, whereas in alcohol it would lead to
the generation of a new product where it changes the oxidation state of a carbon atom.
 Thioxanthates
Thiolates react with carbon disulphide to produce thioxanthate.
 Metal ion complexation
Thiolates form transition metal thiolate complexes with metal ions.
 Redox
Thiols readily oxidize through a reagent iodine, in the presence of a base to produce organic sulphide.
 Acidity
Thiols are more acidic in nature. Thiolate is a conjugate base of thiol. It is obtained from thiol treatment
with alkali metal hydroxides.
Uses & Occurrence

 Thiols are added to natural gas to serve as an easily detectable warning in case of leaks.
 The most common reaction in biological systems is between thiols and disulfides.
 Thiols are often found in petroleum, pulp, and paper industries.
 Thiols occur naturally such as in onions and garlic oil.
Amide
Amide, any member of either of two classes of nitrogen-
containing compounds related to ammonia and amines.
The covalent amides are neutral or very weakly acidic substances formed
by replacement of the hydroxyl group (OH) of an acid by an amino group
(NR2, in which R may represent a hydrogen atom or an organic combining
group such as methyl, CH3). The carboxamides (R′CONR2), which are
derived from carboxylic acids (R′COOH), are the most important group.
Sulfonamides (RSO2NR2) are similarly related to the sulfonic acids
(RSO3H).
Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia,
an amine, or a covalent amide with a reactive metal such as sodium.
Covalent amides derived from ammonia are solids, except formamide, which is liquid; those containing
fewer than five carbon atoms are soluble in water. They are nonconductors of electricity and solvents for both
organic and inorganic substances. Covalent amides, even those of low molecular weight, have high boiling
points.
There are no practical natural sources of simple covalent amides, although polyamides (amides linked
together to form large molecules called polymers) occur in great abundance as the protein of living systems.
Simple amides ordinarily are prepared by reaction of acids or acid halides with ammonia or amines. They can
also be produced by the reaction of water with nitriles.
Physical properties of amides:

 Basicity:
Thegood example for weak bases is nitriles. The resonance structure of nitriles is quiet stable, because
its resonance structure resembles a vinyl cation but it is not very stable. The protonation of nitriles is important
in their acid catalyzed reactions even with their feeble basiccharacter. Nitriles are very poor hydrogen bond
acceptors due to the weak basic nature. For performing many organic reactions, Acetonitrile is mostly used as a
solvent because it is not much reactive in mild acidic and basic conditions. Due to its high polarity, it can
dissolve a variety of reactants. And since it has moderate boiling point and can be easily removed. It can be
miscible with water and a number of organic solvents.
 Solubility:
Thecyanides having low molecular mass are soluble in water. The Acetonitrile is miscible with water
whereas propionitrile has low solubility in water. Themolecules with increased molecular mass and higher
nitriles are insoluble in water, this is due to the bulk of the non-polar position (that is R-) increases and as a
result the solubility in water decreases. On the other hand, the cyanides are fairly soluble in organicsolvents.
The small amides have the ability to hydrogen bond with the water molecules and hence they are soluble in
water. Theenergy is required to break the hydrogen bonds between amide molecules and between water
molecules before they can mix - but the required energy is released again when the new hydrogen bonds are set
up to allowt his to happen.
 Melting point:
Usually the amides are solids at room temperature except Methanamide which is a liquid at room
temperature (melting point: 3°C). Forexample, Ethanamide having melting point of 82°C which forms colorless
deliquescent crystals. Deliquescent is defined as it is a substance in which picks up water from the atmosphere
and dissolves in it. So Ethanamide crystals always look wet. For the size of the molecules, the melting points of
the amides are high because they can form hydrogen bonds. In -NH2 group, the hydrogen atoms are sufficiently
positive to form a hydrogen bond with a lone pair of electrons on the oxygen atom of another molecule.
Uses of Amides
Amides may be used to form resilient structural materials (e.g., nylon, Kevlar). Dimethylformamide is an
important organic solvent. Plants produce amides for a variety of functions. Amides are found in many drugs.
Benzene
Benzene is an organic chemical compound with
the molecular formula C6H6. The benzene molecule is
composed of six carbon atoms joined in a ring with one
hydrogen atom attached to each. As it contains only carbon and
hydrogen atoms, benzene is classed as a hydrocarbon.
Benzene is a natural constituent of crude oil and is one
of the elementary petrochemicals. Due to the cyclic
continuous pi bonds between the carbon atoms, benzene is
classed as an aromatic hydrocarbon, the second [n]-
annulene ([6]-annulene). It is sometimes abbreviated PhH. Benzene is a colorless and highly flammable liquid
with a sweet smell, and is responsible for the aroma around petrol (gasoline) stations. It is used primarily as a
precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of
which billions of kilograms are produced annually. As benzene has a high octane number, aromatic derivatives
like toluene and xylene typically comprise up to 25% of gasoline (petrol). Benzene itself has been limited to
less than 1% in gasoline because it is a known human carcinogen. Most non-industrial applications have been
limited as well for the same reason.
Benzene derivatives
Many important chemical compounds are derived from benzene by replacing one or more of its
hydrogen atoms with another functional group. Examples of simple benzene derivatives are phenol, toluene,
and aniline, abbreviated PhOH, PhMe, and PhNH2, respectively. Linking benzene rings gives biphenyl, C6H5–
C6H5. Further loss of hydrogen gives "fused" aromatic hydrocarbons, such
as naphthalene, anthracene, phenanthrene, and pyrene. The limit of the fusion process is the hydrogen-free
allotrope of carbon, graphite.
In heterocycles, carbon atoms in the benzene ring are replaced with other elements. The most important
variations contain nitrogen. Replacing one CH with N gives the compound pyridine, C5H5N. Although benzene
and pyridine are structurally related, benzene cannot be converted into pyridine. Replacement of a second CH
bond with N gives, depending on the location of the second N, pyridazine, pyrimidine, or pyrazine.
Physical and chemical properties of benzene:

 Benzene belongs to the family of aromatic hydrocarbons which are nonpolar molecules and are usually
colorless liquids or solids with a characteristic aroma.
 Benzene being non-polar is immiscible with water but is readily miscible with organic solvents.
 Upon combustion of benzene sooty flame is produced.
Chemical properties of benzene:
 Electrophilic substitution reaction:
 Nitration of Benzene: Benzene reacts with nitric acid at 323-333 K in the presence of sulphuric acid to
form nitrobenzene. This reaction is known as nitration of Benzene.
 Sulfonation of Benzene: Sulfonation of benzene is a process of heating benzene with fuming sulphuric
acid (H2SO4 +SO3) to produce Benzene sulfonic acid. The reaction is reversible in nature.
 Halogenation of Benzene: Benzene reacts with halogens in the presence of Lewis acids like FeCl3,
FeBr3 to form aryl halides. This reaction is termed as halogenation of benzene.
 Friedel Craft’s alkylation reaction: When benzene is treated with an alkyl halide in the presence of a
Lewis acid such as anhydrous aluminum chloride, alkyl benzene is formed. This reaction is popularly
known as Friedel Craft’s alkylation reaction.
 Friedel Craft’s acylation reaction: When benzene is treated with an acyl halide in the presence of Lewis
acid such as anhydrous aluminum chloride, acyl benzene is formed. This reaction is popularly known as
Friedel Craft’s acylation reaction.
 Addition reactions: Addition of chlorine in the presence of ultraviolet light produces benzene
hexachloride better known as gammaxene.
 Combustion of benzene: Upon combustion of benzene, benzene burns with a sooty flame along with the
evolution of CO2 gas.
C6H6 + O2 → CO2 + H2O
Uses of benzene
Benzene is a widely used industrial chemical. Benzene is found in crude oil and is a major part of
gasoline. It's used to make plastics, resins, synthetic fibers, rubber lubricants, dyes, detergents, drugs and
pesticides. Benzene is produced naturally by volcanoes and forest fires.
In homes, benzene may be found in glues, adhesives, cleaning products, paint strippers, tobacco smoke
and gasoline. Most benzene in the environment comes from our use of petroleum products.
Benzene quickly evaporates from water or soil. If benzene leaks from buried storage tanks or landfills, it
can contaminate nearby drinking water wells. Benzene can move long distances in groundwater.

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Chem 3

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What is Thiol?

Thiols can be defined as a sulfur analog of

Uses & Occurrence

Physical properties of amides:

Physical and chemical properties of benzene:

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