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1) Occurrence of carbon :-
 i) Carbon is found in the atmosphere, inside the earth’s crust and in
     all living organisms.
 ii) Carbon is present in fuels like wood, coal, charcoal, coke, petroleum,
     natural gas, biogas, marsh gas etc.
iii) Carbon is present in compounds like carbonates,
     hydrogen carbonates etc.
iv) Carbon is found in the free state as diamond, graphite, fullerenes etc.
2) Bonding in carbon – Covalent bond :-
  The atomic number of carbon is 6, its electronic arrangement is 2,4, it
has 4 valence electrons. It can attain stability by gaining 4 electrons,
losing 4 electrons or sharing 4 electrons with other atoms.
  It does not gain 4 electrons because it is difficult for the 6 protons to
hold 10 electrons.
  It does not lose 4 electrons because it needs a large amount of
energy to lose 4 electrons.
  So it shares 4 electrons with other atoms to attain stability resulting in
the formation of covalent bonds.
  Since carbon atom needs 4 electrons to attain stability, its valency is 4
and it is tetravalent.

                     X                           I
                                           _         _
                X   C    X
                                               C
                     X
                                                 I
3) Formation of covalent bonds :-
 Covalent bond is chemical bond formed by the sharing of electrons
between atoms.
 The sharing of one pair of electrons results in the formation of single
covalent bond, sharing of two pairs of electrons results in the formation
of double covalent bond and sharing of three pairs of electrons results
in the formation of triple covalent bond.
Eg :- Formation of single covalent bond in Hydrogen
      molecule - H2
The atomic number of hydrogen is 1, its electronic arrangement is 1, it
has 1 valence electron. It needs 1 electron more to attain stability. So
two hydrogen atoms share 1 pair of electrons resulting in the formation
of a single covalent bond in hydrogen molecule H2.



     Hx +    x   H            H   XX   H          H–H            H2
Formation of double covalent bond in oxygen molecule - O2
 The atomic number of oxygen is 8, its EC is 2,6, it has 6 VE, it needs 2
electrons more to attain stability. So two oxygen atoms share two
pairs of electrons resulting in the formation of a double covalent bond
in oxygen molecule O2

  X X                 XX      XX        XX
          X       X                XX
          X       X                XX
  XX                  XX      XX        XX
  O           +       O       O         O         O=O            O2



Formation of triple covalent bond in Nitrogen molecule - N2
 The atomic number of nitrogen is 7, its EC is 2,5, it has 5 VE, it needs
3 electrons more to attain stability. So two nitrogen atoms share three
pairs of electrons resulting in the formation of a triple covalent bond in
nitrogen molecule N2
   X             X                X      X
      X               X                 XX
      X               X                 XX
      X               X X               XX
  X                                X         X



  N           +        N           N         N       NΞN              N2
4) Electron dot structures :-

  Methane molecule – CH4    Ethane molecule – C2H6




                H
                X                       H
                                        X            H
                                                     X

                                             X
        X           X           X                        X
                                             X
                X                       X            X


    H       C           H   H       C                C       H



            H                       H            H


                H                       H        H
                I                        I       I
5) Formation of a very large number of carbon compounds :-
    Carbon forms a very large number of compounds. The number of
carbon compounds is more than three million. It is more than the
number of compounds formed by all other elements. This is because :-
 i) Carbon atom can form bonds with other carbon atoms to form long
    chains, branched chains and closed rings. This property is called
    catenation.
ii) Since the valency of carbon is 4, it can form bonds with other
    carbon atoms or with atoms of other elements like hydrogen,
    oxygen, nitrogen, halogens etc.
                                           I
                                         _   _
                                           C
     I   I I     I I    I              I   I    I I           C
 _                        _        _                _
    C–C–C–C–C–C                       C–C–C–C             C      C
     I   I I     I I    I              I   I    I I       C      C
                                             _    _
                                               C              C
                                                I
        Long chain                  Branched chain       Closed ring
6) Hydrocarbons, Saturated and Unsaturated hydrocarbons :-
 i) Hydrocarbons :- are compounds containing carbon and hydrogen
    atoms.

 ii) Saturated hydrocarbons :- are hydrocarbons having all single
     covalent bonds between the carbon atoms.
     Eg : Alkanes :- have all single covalent bonds between the carbon
     atoms and their names end with – ane.

                          H
                          I
     Methane – CH4      H–C–H
                          I
                          H

                         H H
                         I I
      Ethane – C2H6    H–C–C–H
                         I I
                         H H
iii) Unsaturated hydrocarbons :- are hydrocarbons having a double or
    triple covalent bond between two carbon atoms. Eg : Alkenes and
    Alkynes.
    Alkenes :- have a double covalent bond between two carbon atoms.
    and their names end with – ene.
                          H H                             H       H
                          I I                              I       I
  Ethene - C2H4       C=C           Propene – C3H6   H–C=C– C–H

                         I I                                 I  I
                         H H                                 H H
 Alkynes :- have a triple covalent bond between two carbon atoms
 and their names end with – yne.

  Ethyne – Ethyne – C2H2   H–CΞC–H

                                H
                                I
  Propyne - C3H4   H–C ΞC–C–H
                           I
                          H
7) Isomerism :-
   Carbon compounds having the same molecular formula but different
structural formulae are called isomers. This property is called isomerism.
 Eg:- Butane – C4H10 has 2 isomers. They are Normal butane and Iso butane.
              H H H H                  H H H
              I  I I I                  I I I
            H–C–C–C–C–H              H–C–C–C–H       Iso butane
              I  I I I                  I    I
              H H H H                  H     H
                                       H– C –H
              Normal butane               I
                                          H
 Pentane – C5H12 has 3 isomers. They are Normal pentane, Iso pentane and Neo
 pentane.                                               Neo pentane
                                    Iso pentane               H
                                          H                    I
                                          I                 H– C–H

              Normal pentane           H–C–H              H     H
                                                           I      I
             H H H H H                H   H H           H–C– C– C–H
             I  I I I I               I   I  I             I     I
           H–C–C–C–C–C–H            H–C–C–C–C–H           H     H
             I I I  I I               I I I  I             H–C–H
             H H H H H                H H H H                I
                                                             H
8) Functional groups :-
   An atom or a group of atoms which decides the properties of a
carbon compound is called a functional group.
 i) Halide ( Halo group) :- - Cl, - Br, etc. ( Names end with – ane )
    Eg :- CH3Cl – Chloro methane, C2H5Br – Bromo ethane

ii) Alcohol :- - OH ( Names end with – ol )
    Eg :- CH3OH – Methanol, C2H5OH – Ethanol

                               H
iii) Aldehyde :- - CHO   -C        ( Names end with – al )
                               O
   Eg :- HCHO – Methanal, CH3CHO – Ethanal
                                    O

                                    II
iv) Carboxylic acid :- - COOH - C - OH (Names end with – oic
acid )
    Eg :- HCOOH – Methanoic acid, CH3COOH – Ethanoic acid
 v) Ketone :- - CO      - C - (Names end with – one )
                          II
                          O
9) Homologus series :-
   Homologus series is a group of carbon compounds having similar
structures, similar chemical properties and whose successive members
differ by a – CH2 group. Eg :- Alkanes, Alkenes, Alkynes etc.
   Alkanes :- have general molecular formula CnH2n+2 . Their names end
with – ane and the members are as follows :-
       Methane - CH4
       Ethane - C2H6
       Propane - C3H8
       Butane - C4H10
       Pentane - C5H12

                    H
                    I
Methane :– CH4 H – C – H
                    I
                   H

                   H H                        H H H
                   I I                        I I I
Ethane :– C2H6   H–C–C–H   Propane – C3H8   H–C–C–C–H
                   I I                        I I I
                   H H                        H H H
Alkenes :-
 Alkenes have general molecular formula CnH2n . Their names end
with – ene and the members are as follows :-
 Ethene - C2H4
 Propene - C3H6
 Butene - C4H8
 Pentene - C5H10

                     H H
                     I  I
Ethene :-   C2H4    C=C
                     I  I
                     H H

                     H H H                           H H H H
                     I I  I                          I I I I
Propene :- C3H6    H–C=C–C–H     Butene :- C4H8   H–C=C–C–C–H
                       I                              I   I
                            H                                 H   H
Alkynes :-
 Alkynes have general molecular formula CnH 2n – 2 .Their names end
with – yne and the members are as follows :-
 Ethyne    - C2H2
 Propyne   - C3H4
 Butyne    - C4H 6


 Ethyne :- C2H2      H–C   C–H
                                     H
                                     I
 Propyne :- C3H4     H–C       C–C–H
                                     I
                               H
                                    H H
                           I       I
 Butyne :- C H    H–C      C–C–C–H
Saturated and Unsaturated
Compounds

 Saturated compounds (alkanes) have
  the maximum number of hydrogen
  atoms attached to each carbon atom
 Unsaturated compounds have fewer
  hydrogen atoms attached to the
  carbon chain than alkanes
 Unsaturated compounds contain
  double or triple bonds
3 Classes of Unsaturated
Hydrocarbons
1st CLASS
Alkenes – contains one or more C-C double
bonds
               H2C=CH2
           ethene (ethylene)

2nd CLASS
Alkynes – contains one or more C-C triple
bonds
               HC≡CH
           ethyne (acetylene)
Unsaturated Hydrocarbons
3rd CLASS Arenes- aromatic hydrocarbons
      H
                 Benzene
       C
H-C        C-H
H-C        C-H
       C
       H
(not chemically reactive under any of the
conditions described)
Arenes are found in proteins, nucleic acids, and
pharmaceuticals like aspirin
Alkenes

Carbon-carbon double bonds
Names end in –en-e

 H2C=CH2         ethene (ethylene)

 H2C=CH-CH3      propene
 (propylene)
                 cyclohexene
Shapes of Alkenes
VSEPR predicts 120o for bond angles in
ethene and propene

       H2C=CH2               H2C=CH-CH3
       ∠ 121.7°                ∠ 124.7°
The actual ∠ for these molecules are close
to the predicted; however, in other alkenes
the predicted angles will have a larger
deviation from that predicted in the VESPR
model b/c there is limited rotation around a
double bond
Alkynes
Carbon-carbon triple bonds
Names end in -yne

 HC≡CH
 ethyne(acetylene)

 HC≡C-CH3       propyne
Shapes of Alkynes

VSEPR predicts 180o for bond angles in
ethyne
           H C≡C H

                ethyne
                ∠ 180°
Naming Alkenes

The double bond takes precedence over substituents in
   numbering the parent chain.
2. Use the infix “en” for all alkenes and cycloalkenes
3. Use the suffix “e” for all alkenes and cycloalkenes
Change the infix “an” to the corresponding alkane to “en”

       •   butane               butene

       •   propane              propene

       •   octane               octene
Naming Alkenes

1. For open chain alkenes, identify the
parent chain as the longest sequence of
carbons that includes the double bond.
        CH2

 CH3CH2CCH2CH2CH2CH3


There is a longer chain of 7C but it does
   not include the double bond.
Naming Alkenes
4. For an open chain alkenes, number the parent chain
for whichever end gives the lower number to the first
carbon of double bonds.

These rules give precedence to the location of the double
bond over the location of the first substituent on the
parent chain.
                  CH3

              CH3CHCH2CH=CH2
              double bond is at position 1
              4-methyl-1-pentene
Naming Alkenes

5. For cycloalkenes always give position 1 to one
of the two carbons at the double bond



          CH3


              3-methylcyclohexene
Naming Alkenes

6. Place the # that locates the 1st carbon of the double
bond as a prefix, and separate this number from the
name by a hyphen
1   2 3 4
CH2=CHCH2CH3 1-butene

CH3CH=CHCH3           2-butene


*Remember to separate # from numbers by commas,
but use hyphens to connect a number to a word
Naming Alkenes

7. When a compound has two double bonds, it is
named as a diene with 2 numbers in the name to
specify the locations of the double bonds.

                                                    6
     CH3                     5       1



 CH2=CCH=CH2                     4       2
2-methyl-1,3-butadiene                   3
                             1,4 - cyclohexadiene
This pattern can be easily extended to trienes,
tetraenes, etc.
Learning Check HA2

 Write the IUPAC name for each of the
 following unsaturated compounds:


                              CH3
         CH3


A.    CH3C=CHCH3         B.
Solutions HA2

 Write the IUPAC name for each of the
 following unsaturated compounds:


                           CH3
        CH3

A.   CH3C=CHCH3       B.
Isomers of Alkenes
3rd Geometric isomerism
•No free rotation at the double bond in a ring
•Have identical constitution including the location of the
double bond but differ in geometry
•Differ only in the direction taken by their end of chain
methyl group
•Common at the molecular level , particularly in edible
fats, oils and in related compounds that make up most of
a cell membrane
Alkenes
• Alkene Nomenclature
  – Cis isomer:
    • two groups (on adjacent carbons)
      on the same side of the C = C
      double bond

  – Trans isomer:
    • two groups (on adjacent carbons)
      on opposite sides of the C = C
      double bond
Isomers of Alkenes

Alkenes can exist as isomers in 3 ways
Constitutional isomers:
1st different carbon skeletons         CH3

CH2=CHCH2CH3                    CH2=CCH3
       1-butene                     2-methylpropene
2nd H atoms attached differently to the skeleton
                                    CH3

 CH3CH=CHCH3               CH2=CCH3
     2-butene                   2-methylpropene
Alkenes
• Alkene Nomenclature
• Different geometric isomers are
  possible for many alkenes.
  – Compounds that have the same
    molecular formula and the same groups
    bonded to each other, but different
    spatial arrangements of the groups

     • cis isomer
     • trans isomer
Geometric Isomers
•When there are two identical groups at one end
of a double bond, geometric isomers are not
possible

•Cyclic compounds can also have geometric
isomers

•This cis-trans isomerism is found in the many
cyclic structures of carbohydrates.

•Geometric differences alone make most
carbohydrates unusuable in human nutrition.
Alkene


CH3          CH3   CH3               H
      C=C                C=C
H            H      H                CH3

                    trans-2-butene
    cis-2-butene
Geometric Isomers

Double bond is fixed
Cis/trans Isomers are possible

CH3          CH3        CH3         H

     C=C                      C=C

 H           H           H           CH3

(bp 3.7°C)                    (bp 0.9°C)
Naming Alkenes
 – Name all other substituents in
   a manner similar to the
   alkanes.

 – Use a prefix to indicate the
   geometric isomer present, if
   necessary.
Learning Check

Draw the structures for the
following compounds:

cis-6-methyl-3-heptene
Alkynes
• Alkynes:
  – unsaturated hydrocarbons that contain a
    C C triple bond

• Alkyne Nomenclature:
  – Identify the longest continuous chain
    containing the triple bond

  – To find the base name, change the infix of
    the corresponding alkane from “an” to
    “yn”
Alkynes
• Alkyne Nomenclature:
  – Use a number to designate the
    position of the triple bond
    • number from the end of the chain
      closest to the triple bond
       – just like with alkenes


  – Name substituents like you do with
    alkanes and alkenes
Learning Check HA3

Write the IUPAC name for each of the
following unsaturated compounds:


  CH3CH2C≡CCH3
Solutions HA3

  Write the IUPAC name for each
  of the following unsaturated
  compounds:
• CH3CH2C≡CCH3
    2-pentyne
Alkynes
 Name the following compounds:


 CH3CH2C   CCHCH3
             CH2CH3


 CH3CH2C C
           Cl
Alkynes
Draw the following alkynes.



4-chloro-2-pentyne

3-propyl-1-hexyne
Physical Properties
• alkenes and alkynes are nonpolar compounds
• the only attractive forces between their
  molecules are London dispersion forces
• their physical properties are similar to those of
  alkanes with the same carbon skeletons
• alkenes and alkynes are insoluble in water but
  soluble in one another and in nonpolar organic
  liquids
• alkenes and alkynes that are liquid or solid at
  room temperature have densities less than 1 g/
  mL; they float on water
Reactions of Alkenes &
Alkynes
• More reactive than alkanes or
  aromatics, why?

• Generally undergo addition
  reactions
• Presence of easily accessible π
  electrons
• Unsaturated: can fit more atoms
  around the carbons
Reaction of Alkenes

Additions reactions of the double bond
The new double bond is broken and in
its place single bonds are formed to the new
atoms or groups of atoms

The double bond becomes a single bond
  H H                      H H

H– C= C–H +     X-Y     H–C–C–H


                           XY
Hydrogenation

 Adds a hydrogen atom to each carbon
  atom of a double bond
   H H                               H H
                  Ni
H–C=C–H + H2                     H–C–C–H

                                      H H
    ethene
  ethane
Reacts with H2 in the presence of transition
metal catalyst (Pd, Pt, Ru, Ni)
Products of Hydrogenation

 Adding H2 to vegetable oils produces
 compounds with higher melting
 points
 Margarines
 Soft margarines
 Shortenings (solid)
Trans Fats
In vegetable oils, the unsaturated fats
 usually contain cis double bonds.
During hydrogenation, some cis
 double bonds are converted to trans
 double bonds (more stable) causing a
 change in the fatty acid structure
If a label states “partially” or “fully
 hydrogenated”, the fats contain trans
 fatty acids.
Learning Check HA4

What is the product of adding H2
(Ni catalyst) to 1-butene?
Solution HA4

What is the product of adding H2
(Ni catalyst) to 1-butene?

                          Ni
CH2=CHCH2CH3 + H2


                CH3CH2CH2CH3
Learning Check HA5
 Write the product of the following
 addition reactions:

 CH3CH=CHCH3 + H2



        + Br2
Solution HA5

Write the product of the following addition
reactions:

CH3CH=CHCH3 + H2            CH3CH2CH2CH3



             + Br2                     Br

                                     Br
Addition of Bromine




•    Br2 (in CCl4) is added to an unknown liquid
•    The unknown is saturated b/c Br2 does not lose its red color.
•    The unknown was unsaturated. The deep red color of Br2 is
    decolorized as it reacts with the double bond.
Orientation of Addition
• Both alkene & reagent are
  symmetric: one possible product
• One is symmetric and the other
  is asymmetric: one possible
  product
• Both alkene & reagent are
  asymmetric:
  two possible products
Markovinkov’s Rule
• When an unsymmetrical reactant
  of the type X-Y adds to an
  unsymmetrical alkene, the
  carbon with the greater number
  of hydrogens gets more H
• Used to predict the product of
  many alkene addition reactions
  however it does not explain
  Why???
Markovinkov’s Rule




  Try This !!!
Addition of Hydrogen Halides

Adds a H atom and Cl to each
 carbon atom of a double bond
  H H                   H H

H–C=C–H +    HCl     H–C–C– H

                        H Cl
  ethene           chloroethane
Addition of Hydrogen
Halides
Markovnikov’s rule – when
 unsymmetrical reagent adds to
 an unsymmetrical carbon, the
 carbon with the greater # of
 hydrogens gets more H

                             Cl
CH3C=CH2 + HCl   CH3CCH3

   CH3             CH3
Learning Check
CH3CH=CH2 +HI


          +     HBr




      =CH2 + HBr
Question 3
• What is the major product of the
  following reaction?



           +    HBr
Addition of Water
(Hydration)
• Water does not react with an
  alkene in the absence of an acid
  catalyst
• Water is a weak donor of H+ b/c it
  holds it protons too strongly
Addition of H2O
• Addition of water is called hydration
    – hydration is acid catalyzed, most
      commonly by H2SO4
    – hydration follows Markovnikov’s rule;
      H adds to the less substituted carbon
      and OH adds to the more substituted
      carbon

                                       OH H
                         H 2 SO4
CH3 CH=CH 2   +   H2 O             CH3 CH-CH2
  Propene                           2-Propanol
CH3                              CH3
                          H2 SO4
  CH3 C=CH2   +    H2 O            CH3 C-CH2
                                     HO H
2-M ethylpropene               2-Methyl-2-propanol
Alkene Addition
10) Chemical properties of Carbon compounds :-
a) Combustion :-
   Carbon compounds burn in oxygen to form water, carbon dioxide,
   heat and light.
   Eg :- C + O2       CO2 + heat + light
         CH4 + 2O2        2H2O + CO2 + heat + light
         C2H5OH + 3O2         3H2O + 2CO2 heat + light

b) Oxidation :-
   Carbon compounds like alcohols are oxidised to carboxylic acids on
   heating with oxidising agents like alkaline Potassium permanganate
   – KMnO4 or acidic potassium dichromate - K2Cr2O7 .
   Eg:- Alcohols are oxidised to Carboxylic acids
                alkaline KMnO4 + heat
    C2H5OH                            CH3COOH
    Ethanol acidic K2Cr2O7 + heat Ethanoic acid
c) Addition reaction :-
   Unsaturated hydrocarbons undergo addition reaction with hydrogen in the
presence of nickel or palladium as catalyst to form saturated hydrocarbons.
  Eg:- Ethene undergoes addition reaction with hydrogen to form ethane in the
presence of nickel or palladium as catalyst.
                    Ni or Pd catalyst
      C2H4 + H2                         C2H6
       H     H                                   H H
        I    I      Ni or Pd catalyst             I   I
       C = C + H2                             H–C–C–H
        I    I                                      I   I
       H     H                                    H H
   The addition of hydrogen to unsaturated hydrocarbons to form saturated
hydrocarbons is called hydrogenation. Hydrogenation is used to convert
unsaturated oils and fats to saturated oils and fats.
d) Substitution reaction :-
    Saturated hydrocarbons undergo substitution reaction with halogens to
form substitution products.
 Eg :- Methane undergoes substitution reaction with chlorine in the presence
of sunlight to form substitution products.
  CH4 + Cl2           CH3Cl + HCl       CH3Cl + Cl2           CH2Cl2 + HCl
  CH2Cl2 + Cl2            CHCI3 + HCl CHCI3 + Cl2            CCl4 + HCl
11) Some important carbon compounds :-
 a) ETHANOL :- C2H5OH - Ethyl alcohol
     Properties :-
  i) Ethanol is a colourless liquid with a pleasant smell and burning
     taste.
 ii) It is soluble in water.
iii) Ethanol reacts with sodium to form sodium ethoxide and hydrogen.
      2C2H5OH + 2Na                   2C2H5ONa + H2
iv) Ethanol reacts with hot conc. H2SO4 to form ethene and water. Conc.
      H2SO4 is a dehydrating agent and removes water from ethanol.
               conc. H2SO4
     C2H5OH                   C2H4 + H2O
     Uses :-
  i) Ethanol is used for making alcoholic drinks.
 ii) It is used as a solvent.
iii) It is used for making medicines like tincture iodine, cough syrups,
     tonics etc.
b) ETHANOIC ACID :- CH3COOH – Acetic acid
   Properties :-
  i) Ethanoic acid is a colourless liquid with a pungent smell and sour taste.
 ii) It is soluble in water.
iii) A solution of 5% to 8% ethanoic acid in water is called Vinegar.
iv) Esterification :-
     Ethanoic acid reacts with ethanol to form the ester ethyl ethanoate in the presence
     of conc. H2SO4.
                             conc.H2SO4
     CH3COOH + C2H5OH                        CH3COOC2H5 + H2O
     The reaction between carboxylic acid and alcohol to form an ester is called
     esterification.
  v) Saponification :-
     When an ester reacts with sodium hydroxide solution, the sodium salt of the
     carboxylic acid and the parent alcohol are formed. This reaction is called
     saponification.
     Eg :-Ethyl ethanoate reacts with sodium hydroxide to form sodium acetate and ethanol.
     CH3COOC2H5 + NaOH                      CH3COONa + C2H5OH
 vi) Ethanoic acid reacts with bases to form salt and water.
     CH3COOH + NaOH                        CH3COONa + H2O
vii) Ethanoic acid reacts with carbonates and hydrogen carbonates to form salt, water
     and carbon dioxide.
     2CH3COOH + Na2CO3                       2CH3COONa + H2O + CO2
     CH3COOH + NaHCO3                         CH3COONa + H2O + CO2
12) Soaps and detergents :-
a) Soaps :-    Soaps are long chain sodium or potassium salts of carboxylic
acids.   Eg:- Sodium stearate – C17H35COONa
  Structure of soap molecule :- A soap molecule has two parts. A long
hydrocarbon part which is hydrophobic (water repelling) and soluble in oil and
grease and a short ionic part which is hydrophyllic (water attracting) and
insoluble in oil and grease.
                                                   +
                                      COO     Na


               Hydrocarbon part       Ionic part
               (Water repelling)   (Water attracting)
 Cleansing action of soap :- When soap is dissolved in water it forms
spherical structures called micelles. In each micelle the soap molecules are
arranged radially such that the HC part is towards the centre and the ionic part
is towards the outside. The HC part dissolves the dirt, oil and grease and forms
an emulsion at the centre of the micelles which can be washed away by water.
b) Detergents :-
    Detergents are long chain sodium salts of sulphonic acids.
    Soaps do not wash well with hard water because it forms insoluble
precipitates of calcium and magnesium salts in hard water.
    Detergents wash well with hard water because it does not form insoluble
precipitates of calcium and magnesium salts in hard water.


c) Differences between soaps and detergents :-

             Soaps                            Detergents

  i) Soaps are sodium salts of           Detergents are sodium salts of
     fatty acids.                        sulphonic acids.
 ii) Soaps clean well in soft water but Detergents clean well with both
     do not clean well in hard water.    hard and soft water.
iii) Soaps do not clean as well as       Detergents clean better than soaps.
     detergents.
iv) Soaps are biodegradable and         Some detergents are non biodegradable
     do not cause pollution.            and cause pollution.
alkenes and alkynes

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alkenes and alkynes

  • 1. 1) Occurrence of carbon :- i) Carbon is found in the atmosphere, inside the earth’s crust and in all living organisms. ii) Carbon is present in fuels like wood, coal, charcoal, coke, petroleum, natural gas, biogas, marsh gas etc. iii) Carbon is present in compounds like carbonates, hydrogen carbonates etc. iv) Carbon is found in the free state as diamond, graphite, fullerenes etc.
  • 2. 2) Bonding in carbon – Covalent bond :- The atomic number of carbon is 6, its electronic arrangement is 2,4, it has 4 valence electrons. It can attain stability by gaining 4 electrons, losing 4 electrons or sharing 4 electrons with other atoms. It does not gain 4 electrons because it is difficult for the 6 protons to hold 10 electrons. It does not lose 4 electrons because it needs a large amount of energy to lose 4 electrons. So it shares 4 electrons with other atoms to attain stability resulting in the formation of covalent bonds. Since carbon atom needs 4 electrons to attain stability, its valency is 4 and it is tetravalent. X I _ _ X C X C X I
  • 3. 3) Formation of covalent bonds :- Covalent bond is chemical bond formed by the sharing of electrons between atoms. The sharing of one pair of electrons results in the formation of single covalent bond, sharing of two pairs of electrons results in the formation of double covalent bond and sharing of three pairs of electrons results in the formation of triple covalent bond. Eg :- Formation of single covalent bond in Hydrogen molecule - H2 The atomic number of hydrogen is 1, its electronic arrangement is 1, it has 1 valence electron. It needs 1 electron more to attain stability. So two hydrogen atoms share 1 pair of electrons resulting in the formation of a single covalent bond in hydrogen molecule H2. Hx + x H H XX H H–H H2
  • 4. Formation of double covalent bond in oxygen molecule - O2 The atomic number of oxygen is 8, its EC is 2,6, it has 6 VE, it needs 2 electrons more to attain stability. So two oxygen atoms share two pairs of electrons resulting in the formation of a double covalent bond in oxygen molecule O2 X X XX XX XX X X XX X X XX XX XX XX XX O + O O O O=O O2 Formation of triple covalent bond in Nitrogen molecule - N2 The atomic number of nitrogen is 7, its EC is 2,5, it has 5 VE, it needs 3 electrons more to attain stability. So two nitrogen atoms share three pairs of electrons resulting in the formation of a triple covalent bond in nitrogen molecule N2 X X X X X X XX X X XX X X X XX X X X N + N N N NΞN N2
  • 5.
  • 6. 4) Electron dot structures :- Methane molecule – CH4 Ethane molecule – C2H6 H X H X H X X X X X X X X X X H C H H C C H H H H H H H I I I
  • 7. 5) Formation of a very large number of carbon compounds :- Carbon forms a very large number of compounds. The number of carbon compounds is more than three million. It is more than the number of compounds formed by all other elements. This is because :- i) Carbon atom can form bonds with other carbon atoms to form long chains, branched chains and closed rings. This property is called catenation. ii) Since the valency of carbon is 4, it can form bonds with other carbon atoms or with atoms of other elements like hydrogen, oxygen, nitrogen, halogens etc. I _ _ C I I I I I I I I I I C _ _ _ _ C–C–C–C–C–C C–C–C–C C C I I I I I I I I I I C C _ _ C C I Long chain Branched chain Closed ring
  • 8. 6) Hydrocarbons, Saturated and Unsaturated hydrocarbons :- i) Hydrocarbons :- are compounds containing carbon and hydrogen atoms. ii) Saturated hydrocarbons :- are hydrocarbons having all single covalent bonds between the carbon atoms. Eg : Alkanes :- have all single covalent bonds between the carbon atoms and their names end with – ane. H I Methane – CH4 H–C–H I H H H I I Ethane – C2H6 H–C–C–H I I H H
  • 9. iii) Unsaturated hydrocarbons :- are hydrocarbons having a double or triple covalent bond between two carbon atoms. Eg : Alkenes and Alkynes. Alkenes :- have a double covalent bond between two carbon atoms. and their names end with – ene. H H H H I I I I Ethene - C2H4 C=C Propene – C3H6 H–C=C– C–H I I I I H H H H Alkynes :- have a triple covalent bond between two carbon atoms and their names end with – yne. Ethyne – Ethyne – C2H2 H–CΞC–H H I Propyne - C3H4 H–C ΞC–C–H I H
  • 10. 7) Isomerism :- Carbon compounds having the same molecular formula but different structural formulae are called isomers. This property is called isomerism. Eg:- Butane – C4H10 has 2 isomers. They are Normal butane and Iso butane. H H H H H H H I I I I I I I H–C–C–C–C–H H–C–C–C–H Iso butane I I I I I I H H H H H H H– C –H Normal butane I H Pentane – C5H12 has 3 isomers. They are Normal pentane, Iso pentane and Neo pentane. Neo pentane Iso pentane H H I I H– C–H Normal pentane H–C–H H H I I H H H H H H H H H–C– C– C–H I I I I I I I I I I H–C–C–C–C–C–H H–C–C–C–C–H H H I I I I I I I I I H–C–H H H H H H H H H H I H
  • 11. 8) Functional groups :- An atom or a group of atoms which decides the properties of a carbon compound is called a functional group. i) Halide ( Halo group) :- - Cl, - Br, etc. ( Names end with – ane ) Eg :- CH3Cl – Chloro methane, C2H5Br – Bromo ethane ii) Alcohol :- - OH ( Names end with – ol ) Eg :- CH3OH – Methanol, C2H5OH – Ethanol H iii) Aldehyde :- - CHO -C ( Names end with – al ) O Eg :- HCHO – Methanal, CH3CHO – Ethanal O II iv) Carboxylic acid :- - COOH - C - OH (Names end with – oic acid ) Eg :- HCOOH – Methanoic acid, CH3COOH – Ethanoic acid v) Ketone :- - CO - C - (Names end with – one ) II O
  • 12. 9) Homologus series :- Homologus series is a group of carbon compounds having similar structures, similar chemical properties and whose successive members differ by a – CH2 group. Eg :- Alkanes, Alkenes, Alkynes etc. Alkanes :- have general molecular formula CnH2n+2 . Their names end with – ane and the members are as follows :- Methane - CH4 Ethane - C2H6 Propane - C3H8 Butane - C4H10 Pentane - C5H12 H I Methane :– CH4 H – C – H I H H H H H H I I I I I Ethane :– C2H6 H–C–C–H Propane – C3H8 H–C–C–C–H I I I I I H H H H H
  • 13. Alkenes :- Alkenes have general molecular formula CnH2n . Their names end with – ene and the members are as follows :- Ethene - C2H4 Propene - C3H6 Butene - C4H8 Pentene - C5H10 H H I I Ethene :- C2H4 C=C I I H H H H H H H H H I I I I I I I Propene :- C3H6 H–C=C–C–H Butene :- C4H8 H–C=C–C–C–H I I I H H H
  • 14. Alkynes :- Alkynes have general molecular formula CnH 2n – 2 .Their names end with – yne and the members are as follows :- Ethyne - C2H2 Propyne - C3H4 Butyne - C4H 6 Ethyne :- C2H2 H–C C–H H I Propyne :- C3H4 H–C C–C–H I H H H I I Butyne :- C H H–C C–C–C–H
  • 15. Saturated and Unsaturated Compounds  Saturated compounds (alkanes) have the maximum number of hydrogen atoms attached to each carbon atom  Unsaturated compounds have fewer hydrogen atoms attached to the carbon chain than alkanes  Unsaturated compounds contain double or triple bonds
  • 16. 3 Classes of Unsaturated Hydrocarbons 1st CLASS Alkenes – contains one or more C-C double bonds H2C=CH2 ethene (ethylene) 2nd CLASS Alkynes – contains one or more C-C triple bonds HC≡CH ethyne (acetylene)
  • 17. Unsaturated Hydrocarbons 3rd CLASS Arenes- aromatic hydrocarbons H Benzene C H-C C-H H-C C-H C H (not chemically reactive under any of the conditions described) Arenes are found in proteins, nucleic acids, and pharmaceuticals like aspirin
  • 18. Alkenes Carbon-carbon double bonds Names end in –en-e H2C=CH2 ethene (ethylene) H2C=CH-CH3 propene (propylene) cyclohexene
  • 19. Shapes of Alkenes VSEPR predicts 120o for bond angles in ethene and propene H2C=CH2 H2C=CH-CH3 ∠ 121.7° ∠ 124.7° The actual ∠ for these molecules are close to the predicted; however, in other alkenes the predicted angles will have a larger deviation from that predicted in the VESPR model b/c there is limited rotation around a double bond
  • 20. Alkynes Carbon-carbon triple bonds Names end in -yne HC≡CH ethyne(acetylene) HC≡C-CH3 propyne
  • 21. Shapes of Alkynes VSEPR predicts 180o for bond angles in ethyne H C≡C H ethyne ∠ 180°
  • 22. Naming Alkenes The double bond takes precedence over substituents in numbering the parent chain. 2. Use the infix “en” for all alkenes and cycloalkenes 3. Use the suffix “e” for all alkenes and cycloalkenes Change the infix “an” to the corresponding alkane to “en” • butane butene • propane propene • octane octene
  • 23. Naming Alkenes 1. For open chain alkenes, identify the parent chain as the longest sequence of carbons that includes the double bond. CH2 CH3CH2CCH2CH2CH2CH3 There is a longer chain of 7C but it does not include the double bond.
  • 24. Naming Alkenes 4. For an open chain alkenes, number the parent chain for whichever end gives the lower number to the first carbon of double bonds. These rules give precedence to the location of the double bond over the location of the first substituent on the parent chain. CH3 CH3CHCH2CH=CH2 double bond is at position 1 4-methyl-1-pentene
  • 25. Naming Alkenes 5. For cycloalkenes always give position 1 to one of the two carbons at the double bond CH3 3-methylcyclohexene
  • 26. Naming Alkenes 6. Place the # that locates the 1st carbon of the double bond as a prefix, and separate this number from the name by a hyphen 1 2 3 4 CH2=CHCH2CH3 1-butene CH3CH=CHCH3 2-butene *Remember to separate # from numbers by commas, but use hyphens to connect a number to a word
  • 27. Naming Alkenes 7. When a compound has two double bonds, it is named as a diene with 2 numbers in the name to specify the locations of the double bonds. 6 CH3 5 1 CH2=CCH=CH2 4 2 2-methyl-1,3-butadiene 3 1,4 - cyclohexadiene This pattern can be easily extended to trienes, tetraenes, etc.
  • 28. Learning Check HA2 Write the IUPAC name for each of the following unsaturated compounds: CH3 CH3 A. CH3C=CHCH3 B.
  • 29. Solutions HA2 Write the IUPAC name for each of the following unsaturated compounds: CH3 CH3 A. CH3C=CHCH3 B.
  • 30. Isomers of Alkenes 3rd Geometric isomerism •No free rotation at the double bond in a ring •Have identical constitution including the location of the double bond but differ in geometry •Differ only in the direction taken by their end of chain methyl group •Common at the molecular level , particularly in edible fats, oils and in related compounds that make up most of a cell membrane
  • 31. Alkenes • Alkene Nomenclature – Cis isomer: • two groups (on adjacent carbons) on the same side of the C = C double bond – Trans isomer: • two groups (on adjacent carbons) on opposite sides of the C = C double bond
  • 32. Isomers of Alkenes Alkenes can exist as isomers in 3 ways Constitutional isomers: 1st different carbon skeletons CH3 CH2=CHCH2CH3 CH2=CCH3 1-butene 2-methylpropene 2nd H atoms attached differently to the skeleton CH3 CH3CH=CHCH3 CH2=CCH3 2-butene 2-methylpropene
  • 33. Alkenes • Alkene Nomenclature • Different geometric isomers are possible for many alkenes. – Compounds that have the same molecular formula and the same groups bonded to each other, but different spatial arrangements of the groups • cis isomer • trans isomer
  • 34. Geometric Isomers •When there are two identical groups at one end of a double bond, geometric isomers are not possible •Cyclic compounds can also have geometric isomers •This cis-trans isomerism is found in the many cyclic structures of carbohydrates. •Geometric differences alone make most carbohydrates unusuable in human nutrition.
  • 35. Alkene CH3 CH3 CH3 H C=C C=C H H H CH3 trans-2-butene cis-2-butene
  • 36. Geometric Isomers Double bond is fixed Cis/trans Isomers are possible CH3 CH3 CH3 H C=C C=C H H H CH3 (bp 3.7°C) (bp 0.9°C)
  • 37. Naming Alkenes – Name all other substituents in a manner similar to the alkanes. – Use a prefix to indicate the geometric isomer present, if necessary.
  • 38. Learning Check Draw the structures for the following compounds: cis-6-methyl-3-heptene
  • 39. Alkynes • Alkynes: – unsaturated hydrocarbons that contain a C C triple bond • Alkyne Nomenclature: – Identify the longest continuous chain containing the triple bond – To find the base name, change the infix of the corresponding alkane from “an” to “yn”
  • 40. Alkynes • Alkyne Nomenclature: – Use a number to designate the position of the triple bond • number from the end of the chain closest to the triple bond – just like with alkenes – Name substituents like you do with alkanes and alkenes
  • 41. Learning Check HA3 Write the IUPAC name for each of the following unsaturated compounds: CH3CH2C≡CCH3
  • 42. Solutions HA3 Write the IUPAC name for each of the following unsaturated compounds: • CH3CH2C≡CCH3 2-pentyne
  • 43. Alkynes Name the following compounds: CH3CH2C CCHCH3 CH2CH3 CH3CH2C C Cl
  • 44. Alkynes Draw the following alkynes. 4-chloro-2-pentyne 3-propyl-1-hexyne
  • 45. Physical Properties • alkenes and alkynes are nonpolar compounds • the only attractive forces between their molecules are London dispersion forces • their physical properties are similar to those of alkanes with the same carbon skeletons • alkenes and alkynes are insoluble in water but soluble in one another and in nonpolar organic liquids • alkenes and alkynes that are liquid or solid at room temperature have densities less than 1 g/ mL; they float on water
  • 46. Reactions of Alkenes & Alkynes • More reactive than alkanes or aromatics, why? • Generally undergo addition reactions • Presence of easily accessible π electrons • Unsaturated: can fit more atoms around the carbons
  • 47. Reaction of Alkenes Additions reactions of the double bond The new double bond is broken and in its place single bonds are formed to the new atoms or groups of atoms The double bond becomes a single bond H H H H H– C= C–H + X-Y H–C–C–H XY
  • 48. Hydrogenation  Adds a hydrogen atom to each carbon atom of a double bond H H H H Ni H–C=C–H + H2 H–C–C–H H H ethene ethane Reacts with H2 in the presence of transition metal catalyst (Pd, Pt, Ru, Ni)
  • 49. Products of Hydrogenation Adding H2 to vegetable oils produces compounds with higher melting points  Margarines  Soft margarines  Shortenings (solid)
  • 50. Trans Fats In vegetable oils, the unsaturated fats usually contain cis double bonds. During hydrogenation, some cis double bonds are converted to trans double bonds (more stable) causing a change in the fatty acid structure If a label states “partially” or “fully hydrogenated”, the fats contain trans fatty acids.
  • 51. Learning Check HA4 What is the product of adding H2 (Ni catalyst) to 1-butene?
  • 52. Solution HA4 What is the product of adding H2 (Ni catalyst) to 1-butene? Ni CH2=CHCH2CH3 + H2 CH3CH2CH2CH3
  • 53. Learning Check HA5 Write the product of the following addition reactions: CH3CH=CHCH3 + H2 + Br2
  • 54. Solution HA5 Write the product of the following addition reactions: CH3CH=CHCH3 + H2 CH3CH2CH2CH3 + Br2 Br Br
  • 55. Addition of Bromine • Br2 (in CCl4) is added to an unknown liquid • The unknown is saturated b/c Br2 does not lose its red color. • The unknown was unsaturated. The deep red color of Br2 is decolorized as it reacts with the double bond.
  • 56. Orientation of Addition • Both alkene & reagent are symmetric: one possible product • One is symmetric and the other is asymmetric: one possible product • Both alkene & reagent are asymmetric: two possible products
  • 57. Markovinkov’s Rule • When an unsymmetrical reactant of the type X-Y adds to an unsymmetrical alkene, the carbon with the greater number of hydrogens gets more H • Used to predict the product of many alkene addition reactions however it does not explain Why???
  • 58. Markovinkov’s Rule Try This !!!
  • 59. Addition of Hydrogen Halides Adds a H atom and Cl to each carbon atom of a double bond H H H H H–C=C–H + HCl H–C–C– H H Cl ethene chloroethane
  • 60. Addition of Hydrogen Halides Markovnikov’s rule – when unsymmetrical reagent adds to an unsymmetrical carbon, the carbon with the greater # of hydrogens gets more H Cl CH3C=CH2 + HCl CH3CCH3 CH3 CH3
  • 61. Learning Check CH3CH=CH2 +HI + HBr =CH2 + HBr
  • 62. Question 3 • What is the major product of the following reaction? + HBr
  • 63. Addition of Water (Hydration) • Water does not react with an alkene in the absence of an acid catalyst • Water is a weak donor of H+ b/c it holds it protons too strongly
  • 64. Addition of H2O • Addition of water is called hydration – hydration is acid catalyzed, most commonly by H2SO4 – hydration follows Markovnikov’s rule; H adds to the less substituted carbon and OH adds to the more substituted carbon OH H H 2 SO4 CH3 CH=CH 2 + H2 O CH3 CH-CH2 Propene 2-Propanol
  • 65. CH3 CH3 H2 SO4 CH3 C=CH2 + H2 O CH3 C-CH2 HO H 2-M ethylpropene 2-Methyl-2-propanol
  • 67. 10) Chemical properties of Carbon compounds :- a) Combustion :- Carbon compounds burn in oxygen to form water, carbon dioxide, heat and light. Eg :- C + O2 CO2 + heat + light CH4 + 2O2 2H2O + CO2 + heat + light C2H5OH + 3O2 3H2O + 2CO2 heat + light b) Oxidation :- Carbon compounds like alcohols are oxidised to carboxylic acids on heating with oxidising agents like alkaline Potassium permanganate – KMnO4 or acidic potassium dichromate - K2Cr2O7 . Eg:- Alcohols are oxidised to Carboxylic acids alkaline KMnO4 + heat C2H5OH CH3COOH Ethanol acidic K2Cr2O7 + heat Ethanoic acid
  • 68. c) Addition reaction :- Unsaturated hydrocarbons undergo addition reaction with hydrogen in the presence of nickel or palladium as catalyst to form saturated hydrocarbons. Eg:- Ethene undergoes addition reaction with hydrogen to form ethane in the presence of nickel or palladium as catalyst. Ni or Pd catalyst C2H4 + H2 C2H6 H H H H I I Ni or Pd catalyst I I C = C + H2 H–C–C–H I I I I H H H H The addition of hydrogen to unsaturated hydrocarbons to form saturated hydrocarbons is called hydrogenation. Hydrogenation is used to convert unsaturated oils and fats to saturated oils and fats. d) Substitution reaction :- Saturated hydrocarbons undergo substitution reaction with halogens to form substitution products. Eg :- Methane undergoes substitution reaction with chlorine in the presence of sunlight to form substitution products. CH4 + Cl2 CH3Cl + HCl CH3Cl + Cl2 CH2Cl2 + HCl CH2Cl2 + Cl2 CHCI3 + HCl CHCI3 + Cl2 CCl4 + HCl
  • 69. 11) Some important carbon compounds :- a) ETHANOL :- C2H5OH - Ethyl alcohol Properties :- i) Ethanol is a colourless liquid with a pleasant smell and burning taste. ii) It is soluble in water. iii) Ethanol reacts with sodium to form sodium ethoxide and hydrogen. 2C2H5OH + 2Na 2C2H5ONa + H2 iv) Ethanol reacts with hot conc. H2SO4 to form ethene and water. Conc. H2SO4 is a dehydrating agent and removes water from ethanol. conc. H2SO4 C2H5OH C2H4 + H2O Uses :- i) Ethanol is used for making alcoholic drinks. ii) It is used as a solvent. iii) It is used for making medicines like tincture iodine, cough syrups, tonics etc.
  • 70. b) ETHANOIC ACID :- CH3COOH – Acetic acid Properties :- i) Ethanoic acid is a colourless liquid with a pungent smell and sour taste. ii) It is soluble in water. iii) A solution of 5% to 8% ethanoic acid in water is called Vinegar. iv) Esterification :- Ethanoic acid reacts with ethanol to form the ester ethyl ethanoate in the presence of conc. H2SO4. conc.H2SO4 CH3COOH + C2H5OH CH3COOC2H5 + H2O The reaction between carboxylic acid and alcohol to form an ester is called esterification. v) Saponification :- When an ester reacts with sodium hydroxide solution, the sodium salt of the carboxylic acid and the parent alcohol are formed. This reaction is called saponification. Eg :-Ethyl ethanoate reacts with sodium hydroxide to form sodium acetate and ethanol. CH3COOC2H5 + NaOH CH3COONa + C2H5OH vi) Ethanoic acid reacts with bases to form salt and water. CH3COOH + NaOH CH3COONa + H2O vii) Ethanoic acid reacts with carbonates and hydrogen carbonates to form salt, water and carbon dioxide. 2CH3COOH + Na2CO3 2CH3COONa + H2O + CO2 CH3COOH + NaHCO3 CH3COONa + H2O + CO2
  • 71. 12) Soaps and detergents :- a) Soaps :- Soaps are long chain sodium or potassium salts of carboxylic acids. Eg:- Sodium stearate – C17H35COONa Structure of soap molecule :- A soap molecule has two parts. A long hydrocarbon part which is hydrophobic (water repelling) and soluble in oil and grease and a short ionic part which is hydrophyllic (water attracting) and insoluble in oil and grease. + COO Na Hydrocarbon part Ionic part (Water repelling) (Water attracting) Cleansing action of soap :- When soap is dissolved in water it forms spherical structures called micelles. In each micelle the soap molecules are arranged radially such that the HC part is towards the centre and the ionic part is towards the outside. The HC part dissolves the dirt, oil and grease and forms an emulsion at the centre of the micelles which can be washed away by water.
  • 72.
  • 73. b) Detergents :- Detergents are long chain sodium salts of sulphonic acids. Soaps do not wash well with hard water because it forms insoluble precipitates of calcium and magnesium salts in hard water. Detergents wash well with hard water because it does not form insoluble precipitates of calcium and magnesium salts in hard water. c) Differences between soaps and detergents :- Soaps Detergents i) Soaps are sodium salts of Detergents are sodium salts of fatty acids. sulphonic acids. ii) Soaps clean well in soft water but Detergents clean well with both do not clean well in hard water. hard and soft water. iii) Soaps do not clean as well as Detergents clean better than soaps. detergents. iv) Soaps are biodegradable and Some detergents are non biodegradable do not cause pollution. and cause pollution.