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Carbon and its Compounds

Nature of Bond in Organic Compounds
Types of Hydrocarbons
Nomenclature of Hydrocarbons
Functional Groups
Important Organic Compounds & Their eactions!
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Carbon)s Capacity to *hare +lectrons,
Carbon has four electrons in its outermost shell and needs to gain or lose four elec-
trons to attain noble gas configuration. If it were to gain or lose electrons
(i) It could gain four electrons forming C4 anion. But it would be difficult for the
nucleus with six protons to hold on to ten electrons, that is, four extra electrons.
(ii) It could lose four electrons forming C4 cation. But it would re!uire a large
amount of energ" to remo#e four electrons lea#ing behind a carbon cation with six
protons in its nucleus holding on to $ust two electrons.
Carbon o#ercomes this problem b" sharing its #alence electrons with other atoms of
carbon or with atoms of other elements. %ot $ust carbon, but man" other elements
form molecules b" sharing electrons in this manner. &he shared electrons 'belong( to
the outer shells of both the atoms and lead to both atoms attaining the noble gas
configuration.
&his t"pe of bond formed b" sharing of electrons is called co#alent bond. Co#alentl"
bonded molecules are seen to ha#e strong bonds within the molecule, but inter-
molecular forces are small. &his gi#es rise to the low melting and boiling points of
these compounds. )ince the electrons are shared between atoms and no charged
particles are formed, such co#alent compounds are generall" poor conductors of
electricit".
*et us now ta+e a loo+ at methane, which is a compound of carbon. ,ethane is
widel" used as a fuel and is a ma$or component of bio-gas and Compressed %atural
-as (C%-). It is also one of the simplest compounds formed b" carbon. ,ethane has
a formula C.4. ."drogen, as "ou +now, has a #alenc" of /. Carbon is tetra#alent be-
cause it has four #alence electrons. In order to achie#e noble gas configuration, car-
bon shares these electrons with four atoms of h"drogen as shown below0
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C
H
H
H
H
x
x
x
x
.
.
.
.
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-llotropes of carbon
&he element carbon occurs in different forms in nature with widel" #ar"ing ph"sical
properties. Both diamond and graphite are formed b" carbon atoms, the difference
lies in the manner in which the carbon atoms are bonded to one another. In dia-
mond, each carbon atom is bonded to four other carbon atoms forming a rigid three-
dimensional structure. In graphite, each carbon atom is bonded to three other car-
bon atoms in the same plane gi#ing a hexagonal arra". 1ne of these bonds is a
double-bond, and thus the #alenc" of carbon is satisfied. -raphite structure is
formed b" the hexagonal arra"s being placed in la"ers one abo#e the other.
.+*-TIL+ N-T/+ OF C-BON
&he numbers of carbon compounds whose formulae are +nown to chemists was re-
centl" estimated to be about three million2 &his outnumbers b" a large margin the
compounds formed b" all the other elements put together. &he nature of the co#alent
bond enables carbon to form a large number of compounds. &wo factors noticed in
the case of carbon are
(i) Carbon has the uni!ue abilit" to form bonds with other atoms of carbon, gi#ing
rise to large molecules. &his propert" is called catenation. &hese compounds ma"
ha#e long chains of carbon, branched chains of carbon or e#en carbon atoms ar-
ranged in rings. In addition, carbon atoms ma" be lin+ed b" single, double or triple
bonds. Compounds of carbon, which are lin+ed b" onl" single bonds between the
carbon atoms are called saturated compounds. Compounds of carbon ha#ing double
or triple bonds between their carbon atoms are called unsaturated compounds. %o
other element exhibits the propert" of catenation to the extent seen in carbon com-
pounds. )ilicon forms compounds with h"drogen which ha#e chains of upto se#en or
eight atoms, but these compounds are #er" reacti#e. &he carbon-carbon bond is #er"
strong and hence stable. &his gi#es us the large number of compounds with man"
carbon atoms lin+ed to each other.
(ii) )ince carbon has a #alenc" of four, it is capable of bonding with four other atoms
of carbon or atoms of some other mono-#alent element. Compounds of carbon are
formed with ox"gen, h"drogen, nitrogen, sulphur, chlorine and man" other elements
gi#ing rise to compounds with specific properties which depend on the elements oth-
er than carbon present in the molecule.
3gain the bonds that carbon forms with most other elements are #er" strong ma+ing
these compounds exceptionall" stable. 1ne reason for the formation of strong bonds
b" carbon is its small si4e. &his enables the nucleus to hold on to the shared pairs of
electrons strongl". &he bonds formed b" elements ha#ing larger atoms are much
wea+er.
Organic compounds
&he two characteristic features seen in carbon, that is, tetra#alenc" and catenation,
put together gi#e rise to a large number of compounds. ,an" ha#e the same non-
carbon atom or group of atoms attached to different carbon chains. &hese com-
pounds were initiall" extracted from natural substances and it was thought that
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these carbon compounds or organic compounds could onl" be formed within a li#ing
s"stem. &hat is, it was postulated that a '#ital force( was necessar" for their s"nthes-
is. 5riedrich 67hler dispro#ed this in /898 b" preparing urea from ammonium c"-
anate. But carbon compounds, except for oxides of carbon, carbonate and h"drogen-
carbonate salts continue to be studied under organic chemistr".
*aturated and /nsaturated Carbon Compounds
In order to arri#e at the structure of simple carbon compounds, the first step is to
lin+ the carbon atoms together with a single bond and then use the h"drogen atoms
to satisf" the remaining #alencies of carbon. 5or example, the structure of ethane is
arri#ed in the following steps
C9.: ;thane
C
2
H
4
Ethene
In the first example of ethane all #alenc" of carbon atoms is satisfied, hence
this is called as saturated carbon compound or saturated organic compound.
In the second example of ethane #alenc" of carbon atom is not full" satisfied,
hence this is called as unsaturated organic compound.
Compounds formed b" carbon and h"drogen onl" are called h"drocarbons.
&hose h"drocarbons which ha#e single bonds in molecular structure are called
al+anes. -eneric formula for al+anes is Cn.(9n9)
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."drocarbons with double bonds are called al+enes. -eneric formula for al-
+enes is Cn.9n
."drocarbons with triple bonds are called al+"nes. -eneric formula for al-
+"nes is Cn.n
Carbon seems to be a #er" friendl" element. )o far we ha#e been loo+ing at com-
pounds of carbon and h"drogen. But carbon also forms bonds with other elements
such as halogens, ox"gen, nitrogen and sulphur. In a h"drocarbon chain, one or
more h"drogens can be replaced b" these elements, such that the #alenc" of carbon
remains satisfied. In such compounds, the element replacing h"drogen is referred to
as a heteroatom. &hese heteroatoms confer specific properties to the compound, re-
gardless of the length and nature of the carbon chain and hence are called functional
groups. &he functional group is attached to the carbon chain through this #alenc" b"
replacing one h"drogen atom or atoms.
Functional Groups,
Homologous *eries
&he presence of a functional group such as alcohol dictates the properties of the car-
bon compound, regardless of the length of the carbon chain. 5or example, the chem-
ical properties of C.<1., C9.=1., C<.>1. and C4.?1. are all #er" similar. .ence,
such a series of compounds in which the same functional group substitutes for h"-
drogen in a carbon chain is called a homologous series.
3s the molecular mass increases in an" homologous series, a gradation in ph"sical
properties is seen. &his is because the melting points and boiling points increase with
increasing molecular mass. 1ther ph"sical properties such as solubilit" in a particular
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sol#ent also show a similar gradation. But the chemical properties, which are de-
termined solel" b" the functional group, remain similar in a homologous series.
Nomenclature of Carbon Compounds
&he names of compounds in a homologous series are based on the name of the basic
carbon chain modified b" a @prefixA @phrase beforeA or @suffixA @phrase afterA indicat-
ing the nature of the functional group.
%aming a carbon compound can be done b" the following method
(i) Identif" the number of carbon atoms in the compound. 3 compound ha#ing three
carbon atoms would ha#e the name propane.
(ii) In case a functional group is present, it is indicated in the name of the compound
with either a prefix or a suffix.
(iii) If the name of the functional group is to be gi#en as a suffix, the name of the
carbon chain is modified b" deleting the final 'e( and adding the appropriate suffix.
5or example, a three-carbon chain with a +etone group would be named in the fol-
lowing manner Bropane 'e( C propan 'one( C propanone.
(i#) If the carbon chain is unsaturated, then the final 'ane( in the name of the carbon
chain is substituted b" 'ene( or '"ne(. 5or example, a three-carbon chain with a
double bond would be called propene and if it has a triple bond, it would be called
prop"ne.
Functional 0refi(1*uffi( +(ample group
Functional Group 0refi(1
*uffi(
+(ample
Halogen 0refi( 2 chloro Chloropropane3
Bromopropane
-lcohol *uffi( 2 ol 0ropanol
-ldehyde *uffi( 2 al 0ropanal
4etone *uffi( 2 one 0ropanone
Carbo(yllic acid *uffi( 2 oic acid 0ropanoic acid
5ouble bond 6al7enes8 *uffie( 2 ene 0ropene
Triple bond 6al7ynes8 *uffi( 2 yne 0ropyne
CH+9IC-L 0O0+TI+* OF C-BON CO90O/N5*
Combustion, Carbon, in all its allotropic forms, burns in ox"gen to gi#e carbon diox-
ide along with the release of heat and light. ,ost carbon compounds also release a
large amount of heat and light on burning.
)aturated h"drocarbons will generall" gi#e a clean flame while unsaturated carbon
compounds will gi#e a "ellow flame with lots of blac+ smo+e. .owe#er, limiting the
suppl" of air results in incomplete combustion of e#en saturated h"drocarbons, gi#-
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ing a soot" flame. &he gasD+erosene sto#e used at home has inlets for air so that a
sufficientl" ox"gen-rich mixture is burnt to gi#e a clean blue flame. If "ou obser#e
the bottoms of coo+ing #essels getting blac+ened, it means that the air holes are
bloc+ed and fuel is getting wasted. 5uels such as coal and petroleum ha#e some
amount of nitrogen and sulphur in them. &heir combustion results in the formation of
oxides of sulphur and nitrogen which are ma$or pollutants in the en#ironment.
O(idation, Carbon compounds can be easil" oxidised on combustion. In addition to
this complete oxidation, we ha#e reactions in which alcohols are con#erted to
carbox"lic acids
-ddition eaction, Ensaturated h"drocarbons add h"drogen in the presence of
catal"sts such as palladium or nic+el to gi#e saturated h"drocarbons. Catal"sts are
substances that cause a reaction to occur or proceed at a different rate without the
reaction itself being affected. &his reaction is commonl" used in the h"drogenation of
#egetable oils using a nic+el catal"st.
*ubstitution eaction, )aturated h"drocarbons are fairl" unreacti#e and are inert
in the presence of most reagents. .owe#er, in the presence of sunlight, chlorine is
added to h"drocarbons in a #er" fast reaction. Chlorine can replace the h"drogen
atoms one b" one. It is called a substitution reaction because one t"pe of atom or a
group of atoms ta+es the place of another. 3 number of products are usuall" formed
with the higher homologues of al+anes.
*O9+ I90OT-NT C-BON CO90O/N5* 2 +TH-NOL -N5 +TH-NOIC -CI5
0roperties of +thanol, ;thanol is a li!uid at room temperature. ;thanol is com-
monl" called alcohol and is the acti#e ingredient of all alcoholic drin+s. In addition,
because it is a good sol#ent, it is also used in medicines such as tincture iodine,
cough s"rups, and man" tonics. ;thanol is also soluble in water in all proportions.
Consumption of small !uantities of dilute ethanol causes drun+enness. ;#en though
this practice is condemned, it is a sociall" widespread practice. .owe#er, inta+e of
e#en a small !uantit" of pure ethanol (called absolute alcohol) can be lethal. 3lso,
long-term consumption of alcohol leads to man" health problems.
eactions of +thanol
6i8 eaction :ith sodium 3lcohols react with sodium leading to the e#olution of
h"drogen. 6ith ethanol, the other product is sodium ethoxide.
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6ii8 eaction to gi;e unsaturated hydrocarbon, .eating ethanol at 44< F with
excess concentrated sulphuric acid results in the deh"dration of ethanol to gi#e
ethene &he concentrated sulphuric acid can be regarded as a deh"drating agent
which remo#es water from ethanol.
+ffects of -lcohol, 6hen large !uantities of ethanol are consumed, it tends to slow
metabolic processes and to depress the central ner#ous s"stem. &his results in lac+
of coordination, mental confusion, drowsiness, lowering of the normal inhibitions,
and finall" stupour. &he indi#idual ma" feel relaxed but does not realise that his
sense of $udgement, sense of timing, and muscular coordination ha#e been seriousl"
impaired. Enli+e ethanol, inta+e of methanol in #er" small !uantities can cause
death. ,ethanol is oxidised to methanal in the li#er. ,ethanal reacts rapidl" with the
components of cells. It causes the protoplasm to get coagulated, in much the same
wa" an egg is coagulated b" coo+ing. ,ethanol also affects the optic ner#e, causing
blindness. ;thanol is an important industrial sol#ent. &o pre#ent the misuse of ethan-
ol produced for industrial use, it is made unfit for drin+ing b" adding poisonous sub-
stances li+e methanol to it. G"es are also added to colour the alcohol blue so that it
can be identified easil". &his is called denatured alcohol.
0roperties of +thanoic -cid,
;thanoic acid is commonl" called acetic acid and belongs to a group of acids called
carbox"lic acids. =-8H solution of acetic acid in water is called #inegar and is used
widel" as a preser#ati#e in pic+les. &he melting point of pure ethanoic acid is 9?I F
and hence it often free4es during winter in cold climates. &his ga#e rise to its name
glacial acetic acid. &he group of organic compounds called
carbox"lic acids are ob#iousl" characterised b" a special acidit". .owe#er, unli+e min-
eral acids li+e .Cl, which are completel" ionised, carbox"lic acids are wea+ acids.
eactions of ethanoic acid,
6i8 +sterification reaction, ;sters are most commonl" formed b" reaction of an
acid and an alcohol. ;thanoic acid reacts with absolute ethanol in the presence of an
acid catal"st to gi#e an ester
;sters are sweet-smelling substances. &hese are used in ma+ing perfumes and as
fla#ouring agents. ;sters react in the presence of an acid or a base to gi#e bac+ the
alcohol and carbox"lic acid. &his reaction is +nown as saponification because it is
used in the preparation of soap.
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-lcohol as a fuel, )ugarcane plants are one of the most efficient con#ertors of sun-
light into chemical energ". )ugarcane $uice can be used to prepare molasses which is
fermented to gi#e alcohol (ethanol). )ome countries now use alcohol as an additi#e
in petrol since it is a cleaner fuel which gi#es rise to onl" carbon dioxide and water
on burning in sufficient air (ox"gen).
6ii8 eaction :ith a base, *i+e mineral acids, ethanoic acid reacts with a base such
as sodium h"droxide to gi#e a salt (sodium ethanoate or commonl" called sodium
acetate) and water0
6iii8 eaction :ith carbonates and hydrogencarbonates, ;thanoic acid reacts
with carbonates and h"drogencarbonates to gi#e rise to a salt, carbon dioxide and
water. &he salt produced is commonl" called sodium acetate.
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