NOTES UNIT 3: ALKENES AND AKLYNES

III. Number the chain from the end that gives the
lower numbers to the carbons of the C=C.
OUTLINE IV. Locate the C=C by the number of its first
I Alkenes and Alkynes
A Alkenes carbon.
i Structure V. Use the ending -ene to show the presence of
ii IUPAC Names the C=C
iii Alkynes IUPAC
iv Common Names
VI. Branched-chain alkenes are named in a
B Cycloalkenes manner similar to alkanes in which
i Naming substituted groups are located and named.
C Physical Properties
D Reaction of Alkenes
i Addition of HX Examples
ii Common Mechanism Steps
iii Addition of HCL to 2-Butene
iv Addition of H2O
v Addition of CL2 and BR2
vi Polymerization

ALKENES AND ALKYNES

 Alkene: A hydrocarbon that contains one or more
carbon carbon double bonds.
o Ethylene is the simplest alkene.
ALKYNES IUPAC NAMES
 Alkyne: A hydrocarbon that contains one or more
 Follow the same rules as for alkenes, but use the
carbon carbon triple bonds.
ending -yne to show the presence of the triple bond.
o Acetylene is the simplest alkyne.

ALKENES
COMMON NAMES
STRUCTURE:  Common names are still used for some alkenes and
 The VSEPR model predicts bond angles of 120° alkynes, particularly those with low molecular weight.
about each carbon of a double bond.
 In ethylene, the actual angles are close to 120°.
 In substituted alkenes, angles about each carbon of
the double bond may be greater than 120° because of
repulsion between groups bonded to the double bond.

Cis-trans isomerism
 Because of restricted rotation about a carbon-carbon
double bond, an alkene with two different groups on
each carbon of the double bond shows cis-trans
isomerism.
CYCLOALKENES
 Alkenes that contain more than one double bond are
named as alkadienes, alkatrienes, and so forth.
 Those that contain several double bonds are referred
to more generally as polyenes (Greek: poly, many).

IUPAC NAMES

I. To name an alkene;
II. The parent name is that of the longest chain
that contains the C=C.

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TO NAME A CYCLOALKENE:
 Number the carbon atoms of the ring double bond 1
and 2 in the direction that gives the lower number to
the substituent encountered first.
 Note that it is not necessary to explicitly number the
position of the double bond in a cycloalkene as in
linear alkenes.
 Number and list substituents in alphabetical order.
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 1.0 g/mL; they
float on water.
REACTIONS OF ALKENES
 Most alkene addition reactions are exothermic.
 the products are more stable (lower in energy) than
the reactants.
CREATED BY: HYACINTH LEI R. CUYNO
 Just because they are exothermic does not mean that
alkene addition reactions occur rapidly.
 Reaction rate depends on the activation energy.
 Many alkene addition reactions require a catalyst.
ADDITION OF HX
 Addition of HX (HCl, HBr, or HI) to an alkene gives a
haloalkane.
o H adds to one carbon of the C=C and X to the
other.
 Reaction is regioselective. One direction of bond
forming (or bond breaking) occurs in preference to all
other directions.
 Markovnikov’s rule: H adds to the less substituted
carbon and X to the more substituted carbon.
 Chemists account for the addition of HX to an alkene
by a two-step reaction mechanism.
 We use curved arrows to show the repositioning of
electron pairs during a chemical reaction.
 The tail of an arrow shows the origin of the electron
pair (either on an atom or in the double bond).
 The head of the arrow shows its new position.
 Curved arrows show us which bonds break and which
new ones form.
COMMON MECHANISM STEPS
 Pattern 1: Add a proton
o An acid is a proton donor and a base is a proton
acceptor. We can use curved arrows to show how
a proton transfer occurs.
 Patterns 2: Take a proton away.
o If we run the above reaction, in reverse it
corresponds to taking a proton away.
 Pattern 3: Reaction of an electrophile and a
nucleophile to form a new covalent bond.
 An electrophile is an electron-poor species that can
accept a pair of electrons to form a new covalent
bond.
2
 A nucleophile is an electron-rich species that can  Step 1: Add a proton
donate a pair of electrons to form a new covalent
bond. Common Mechanism Steps

 Pattern 4: Reaction of a proton donor with a carbon

carbon double bond to form a new covalent bond. The
double bond provides both of the electrons that forms  Step 2: Reaction of an electrophile and a nucleophile
the new covalent bond. In the following reaction we to form a new covalent bond.
show the hydronium ion as the proton donor.


 While the above equation is the most accurate way to

show the proton transfer, we will simplify the equation
to just show the proton and formation of the new
covalent bond.

Step 3: Take a proton away.

ADDITION OF CL2 AND BR2

 Addition takes place readily at room temperature.
ADDITION OF HCL TO 2-BUTENE  Reaction is generally carried out using pure reagents,
 Step 1: Add a proton or mixing them in a nonreactive organic solvent.
o Reaction of the carbon-carbon double bond with
H+ gives a secondary (2°) carbocation
intermediate, a species containing a carbon atom
with only three bonds to it and bearing a positive
charge.

 Step 2: Reaction of an electrophile and a nucleophile

to form a new carbon-carbon bond.
o Reaction of the carbocation intermediate with
chloride ion completes the addition.
 Addition of Br2 is a useful qualitative test for the
presence of a carbon-carbon double bond.
 Br2 has a deep red color; dibromoalkanes are
colorless.

ADDITION OF H2—REDUCTION
 Virtually all alkenes add H2 in the presence of a
ADDITION OF H2O transition metal catalyst, commonly Pd, Pt, or Ni.
 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.

Figure 12.1 The addition of hydrogen to an alkene

involving a transition metal catalyst.

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 o Only minimal chain branching; chains pack well
and London dispersion forces between them are
strong.
o Has higher melting point than LDPE and is
stronger
o Can be blow molded to squeezable jugs and
bottles.

Polyethylene Figure 12.2 Fabrication of LDPE film.

POLYMERIZATION
 From the perspective of the organic chemical industry,
the single most important reaction of alkenes is
polymerization:

 polymer: Greek: poly, many, and meros, part; any

longchain molecule synthesized by bonding together
many single parts, called monomers.
 monomer: Greek: mono, single and meros, part. 25
Polymerization

 Show the structure of a polymer by placing

parentheses around the repeating monomer unit.
 Place a subscript, n, outside the parentheses to
indicate that this unit repeats n times.
 The structure of a polymer chain can be reproduced
by repeating the enclosed structure in both directions.
 The following is a section of polypropene
(polypropylene).

Polyethylene Figure 12.3 Blow molding an HDPE

container.

Ethylene Polymers

 Low-density polyethylene (LDPE):

o A highly branched polymer; polymer chains do
not pack well and London dispersion forces
between them are weak.
o Softens and melts above 115°C.
o Approximately 65% of all LDPE is used for the
production of films for packaging and for trash
bags.

 High-density polyethylene (HDPE):

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 TRANS: Unit title

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