13'7 How an Alkene Addition Reaction Occurs - PowerPoint PPT Presentation

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13'7 How an Alkene Addition Reaction Occurs

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In the 2nd step, this reactive carbocation immediately reacts ... d j vu: Oh no! It is orbitals and electrons again! Electrons are neither particle nor waves. ... – PowerPoint PPT presentation

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Title: 13'7 How an Alkene Addition Reaction Occurs


1
13.7 How an Alkene Addition Reaction Occurs
  • Reaction mechanism A description of the
    individual steps by which old bonds are broken
    and new bonds are formed.

2
  • In the 1st step, the alkene reacts with H from
    the acid HBr and produces a carbocation. In the
    2nd step, this reactive carbocation immediately
    reacts with Br- ion to form the product.

3
  • Cation An atom or group of atoms with a positive
    charge.
  • Carbocation A carbon atom with a positive
    charge. This is just a special name given to the
    cation formed by carbon atoms.

4
13.8 Alkene Polymers
  • Polymer A large molecule formed by the
    repetitive bonding together of many smaller
    molecules called monomers. Many simple alkenes
    undergo polymerization reaction when treated with
    the proper catalyst.

5
Ethene or Ethylene
Polyethylene
Propene or Propylene
Polypropylene
6
the process continues in this fashion forming a
long chain that we call polymer
7
In this course I will only make you responsible
for writing structures of polymers that are
derived from ethene (ethylene) with or without
substituents.
We can think of this molecule as a substituted
ethylene.
To see this, lets write the molecule in the
following way
The substituent part
The ethylene part
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10
déjà vu Oh no! It is orbitals and electrons
again!
  • Electrons are neither particle nor waves. They
    share properties of both at the same time.
  • One of the properties of electrons that make them
    similar to waves is that we cannot pinpoint at
    any time their exact position.
  • The best we can do is to define a region of space
    in which the probability of finding the electron
    has a certain value. This value is normally taken
    as 90. These regions of space where the
    probability of finding an electron has a certain
    value is what we call an orbital.

11
  • In atoms, orbitals are given the names s (a in
    the figure below), p (b in the figure below), d,
    f.
  • Notice that some of these orbitals have a
    particular direction in space.

12
  • Bonds are formed when two atoms get close and
    their orbitals overlap sharing their electrons
  • The figure above shows how two hydrogen atoms
    form a hydrogen molecule by approaching one
    another until their orbitals overlap. Notice that
    a new orbital, called a molecular orbital, is
    formed in the process.

13
  • Sometimes it is energetically favorable to
    rearrange the electrons and orbitals of a
    particular energy level when an atom forms a
    compound.
  • The reason for this is that the energy spent in
    the rearrangement is less than the energy gained
    in the new compound formed. This process is
    called hybridization.

14
When C forms compounds containing double bonds,
these 3 orbitals from energy level 2 rearrange.
The resulting orbitals are called sp2 (in green).
Notice that there is one p orbital (orange)
unchanged. Each of these orbitals contain 1
electron and is ready for bonding.
15
  • Hydrocarbons that contain double or triple bonds
    contain two different types of molecular
    orbitals. The first set of molecular orbitals
    form the backbone of the hydrocarbon
  • Here we see the backbone of the ethene (ethylene)
    molecule. These molecular orbitals and the bonds
    they form are called sigma (s).

16
  • Notice that the s bonds are formed by the carbon
    orbitals (green) that lie in the plane.
  • Notice also that another orbital (in orange) is
    not involved in forming the backbone.

17
  • The unused p orbitals (depicted above in green
    before bonding) are used in forming the second
    bond between the carbons. Notice that for clarity
    I have omitted the s bonds.

18
  • When these two orbitals overlap they form a new
    molecular orbital called p orbital and the bond
    is called a p bond. Notice that the electronic
    density is on top and below the plane of the
    molecule. This is characteristic of p bonds.

19
The chemical properties of systems containing
double or triple bonds is related to the p bonds
and electrons.
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