Transcript Alkene/Alkyne Addition Reactions

Alkene/Alkyne Addition Reactions
 The double and triple bonds present in
alkenes and alkynes, respectively, make
them much more reactive than alkanes.
 Alkenes and alkynes undergo addition
reactions
a reaction in which parts of a reactant are
added to the two atoms that make up a
double or triple bond
Alkene/Alkyne Addition Reactions
 Two simple addition reactions:
H
H
C=C
H
H H
+ Br2
H
H-C-C-H
Br Br
Cl Cl
H-C
C - H + 2 Cl2
H-C-C-H
Cl Cl
Alkene/Alkyne Addition Reactions
 Some of the common reactants that can add
to alkenes and alkynes include:
Br2
I2
Cl2
H2 (requires a transition metal catalyst)
H2O (requires a strong acid catalyst)
HBr
HCl
HI
Alkene/Alkyne Addition Reactions
Example: Write the structure of the product
that forms when 1-butene reacts with the
following reagents (individually):
Br2
H2 + Ni catalyst
HBr
Alkene/Alkyne Addition Reactions
 Markovnikov’s Rule: The major product
obtained from the addition of an
unsymmetrical reagent such as H-Br, H-Cl, or
H-OH to an alkene or alkyne is the one
obtained when the H atom of the reagent is
added to the C atom of the multiple bond
that already has the greater number of H
atoms.
“The rich get richer”
Alkene/Alkyne Addition Reactions
Example: Write the structure of the product
that forms when 1-propyne reacts with the
following reagents (individually):
Br2 (excess)
H2 (excess) with Ni catalyst
HBr (excess)
Alcohols
 Alcohols:
hydrocarbon derivatives in which one or
more of the H atoms has been replaced by
a hydroxyl group (alcohol functional
group)
C-O-H
OR
C - OH
Hydroxyl groups
Alcohols
 Alcohols are named in the exact same
manner as alkanes, alkenes, and alkynes
except:
To find the base name, drop the “e” from
the name of the corresponding alkane and
add “ol”
Use the carbon number to identify the
position of the alcohol.
CH3CH2CHCH3
CH3CH2CH2OH
1-propanol
OH
2-butanol
Alcohols
Examples: Draw the structures for the
following alcohols.
Methanol
Ethanol
2-Propanol
2-methyl-2-propanol
Alcohols
 The position of the alcohol in the chain has a
significant impact on the reactivity of the
alcohol.
 A primary alcohol (1o) is an alcohol in which
the OH group is attached to a carbon which
is bonded to only 1 other C atom.
CH3CH2OH
Alcohols
 A secondary alcohol (2o) is an alcohol in
which the OH group is attached to a carbon
which is bonded to two other carbon atoms.
CH3CHCH3
OH
CH3CH2CHCH2CH3
OH
Alcohols
 A tertiary alcohol (3o) is an alcohol in which
the OH group is attached to a C which is
bonded to three other carbon atoms.
CH3
CH3CCH3
OH
CH2CH3
CH3CH2CCH3
OH
Alcohols
Example: Identify the following alcohols as 1o,
2o, or 3o. Name each alcohol.
CH3
CH3CHCH2OH
CH3
CH3CH2CCH3
OH
CH3CHCH2OH
OH
Reactions of Carboxylic Acids
 Carboxylic acids contain a carboxyl group:
O
CH3C-O-H
OR
CH3CO2H
Carboxyl group
Reactions of Carboxylic Acids
 Carboxylic acids can participate in a variety
of reactions:
acid-base reactions
similar to those of inorganic (without CC bonds) acids
condensation reactions
esterification
amidation
Reactions of Carboxylic Acids
 Esterification:
a condensation reaction in which a
carboxylic acid reacts with an alcohol to
form an ester and water.
O
CH3C - OH + HO-CH2CH3
O
CH3C-O-CH2CH3 + H2O
Reactions of Carboxylic Acids
Example: Predict the products formed during
the following reactions.
O
CH3C - OH + CH3 CH2CH2OH
O
C - OH + CH3OH
Reactions of Carboxylic Acids
 Amidation:
a condensation reaction in which a
carboxylic acid reacts with an amine that
contains a hydrogen bonded to nitrogen to
form an amide and water
O
O
CH3C - OH + H2N-CH2CH3
CH3C-NH-CH2CH3 +
H2O
Reactions of Carboxylic Acids
Example: Predict the products formed during
the following reactions.
O
CH3 CH2C - OH + CH3CH2NH2
O
C - OH + CH3NH2