Upload
darcy-fisher
View
225
Download
3
Embed Size (px)
Citation preview
Reactions of AlkenesAddition Reactions
• Alkenes are Alkenes are unsaturatedunsaturated — more single bonds can form — more single bonds can form
to the C atomsto the C atoms
• Molecules such as BrMolecules such as Br22, H, H22, HCl, , HCl,
HBr, and HHBr, and H22O O addadd to the to the
double bonddouble bond
An Addition Reaction
The fat in bacon is partially The fat in bacon is partially unsaturated. The fat adds Brunsaturated. The fat adds Br22
to the C=C bonds.to the C=C bonds.
An Addition Reaction• Fats can be “hydrogenated” with HFats can be “hydrogenated” with H22..
Peanut butter has partially hydrogenated vegetable oil.
Peanut butter has partially hydrogenated vegetable oil.
Saturated Fats
Reactions of AromaticsReactions of Aromatics•SubstitutionsSubstitutions — not additions
— are typical.
AlClAlCl33 is a catalyst. Catalysts typically is a catalyst. Catalysts typically
used in aromatic substitutions.used in aromatic substitutions.
+ CH3Cl
CH3
+ HClAlCl3
Alcohol ReactionsAlcohol ReactionsScreen 11.6Screen 11.6
SubstitutionSubstitution Elimination—the Elimination—the reverse of reverse of additionaddition
TYPES OF ALCOHOLSTYPES OF ALCOHOLS
R C OH
H
H
R C OH
R
H
R C OH
R
R
CH3CH2OH, ethanol
rubbing alcohol H3C C OH
CH3
H
Primary
Secondary
Tertiary
More Alcohol ReactionsMore Alcohol Reactions
C
C
C
H H
H OH
HH
()
C
H O
H OH
H
()
Ethanol
+ Oxidizing agent
Acetic acid
+ Oxidizing agentC C
H O
H H
H
()
Acetaldehyde
Ethanol is a Ethanol is a PRIMARY PRIMARY ALCOHOLALCOHOL. It is . It is oxidized to an oxidized to an ALDEHYDE and then ALDEHYDE and then to an ACID.to an ACID.
More Alcohol ReactionsMore Alcohol Reactions
SECONDARY ALCOHOLS SECONDARY ALCOHOLS are are oxidized to KETONES — and oxidized to KETONES — and reaction stops there. reaction stops there.
R—C—R'
oxidizing agent
R—C—R'
O
Secondary alcohol KetoneH
(–R and –R' are organic groups. They may be the same or different.)
OH
Reduction of theCarbonyl GroupO
C
HR
H2cat CR OH
H
H
O
C
R'R
CR R'
H
OH
LiAlH4
aldehyde primary alcohol
ketone secondary alcohol
Acids + Alcohols ESTERS
Esters have generally pleasant odorsEsters have generally pleasant odors
R C
OH
O
R C
O
O
+ HOHR'HOH+
R'
Condensation Reaction
Acids + Alcohols ESTERS
H+
O O
CH3COH + CH3CH2OH CH3COCH2CH3 + H2O
Acetic acid Ethanol Ethyl acetate
C
OC
O O
H
O
CH3Aspirin, Aspirin, acetylsalicylic acid,acetylsalicylic acid,
Acid and EsterAcid and Ester
Acids + Amines AMIDES
AcetoaminophenTylenol, Datril, Momentum, ...
AcetoaminophenTylenol, Datril, Momentum, ...
C
C
C
C
C
C
H
H
N
H
O
HCC
O
H
HH
H
H
Amide link
H2N CH C
CH3
OH
O
H2N CH C
CH2
OH
O
OH
N CH C
CH2
OH
O
OH
H2N CH C
CH3
O H
-H2O
+
Amino Acid + Amino Acid Peptide
Alanine Serine
Peptide Bond
PolymerPolymerssPolymerPolymerss
• Giant molecules made by joining many Giant molecules made by joining many small molecules called small molecules called monomersmonomers
• Average production is 150 kg per person Average production is 150 kg per person annually in the U.S.annually in the U.S.
Polymer ClassificationsPolymer Classifications
• ThermoplasticsThermoplastics (polyethylene) soften (polyethylene) soften and flow when heatedand flow when heated
• ThermosettingThermosetting plastics — soft initially plastics — soft initially but set to solid when heated. Cannot but set to solid when heated. Cannot be resoftened.be resoftened.
• Other classification: Other classification: plastics, fibers, plastics, fibers, elastomers, coatings, adhesiveselastomers, coatings, adhesives
Polymer PreparationPolymer Preparation
•AdditionAddition polymers — directly polymers — directly adding monomer units togetheradding monomer units together
•CondensationCondensation polymers — polymers — combining monomer units and combining monomer units and splitting out a small water (water)splitting out a small water (water)
Polyethylene: Addition Polyethylene: Addition PolymerPolymer
H2C CH2 C C
H
H
H
H
n
n
EthyleneEthylene PolyethylenePolyethylene
A polymer with a molar mass A polymer with a molar mass of 1 x 10of 1 x 1066 has about 360,000 has about 360,000 units.units.
Types of PolyethyleneTypes of Polyethylene
Linear, high Linear, high density PE (HDPE)density PE (HDPE)
Branched, low Branched, low density PE, density PE, LDPELDPE
Cross-linked PE, Cross-linked PE, CLPECLPE
Types of PolyethyleneTypes of Polyethylene
CH2CH
OH
CH2CH
OCCH3
CH2CH
n n n
polyvinyl alcohol polyvinyl acetate polystyrene
Polymers based on Substituted Ethylenes, CH2=CHX
O
Table 11.12: others are PVC, Table 11.12: others are PVC, acrylonitrile, polypropylene, acrylonitrile, polypropylene,
polymethyl methacrylatepolymethyl methacrylate
C C
H
H
H
Cl
C C
H
H
C
H
Cl
C
H
H
C
Cl
H
C
H
H
C
H
Cl
C
H
H
C
Cl
H
C
H
H H
Cl
C C
H
H
C
H
Cl
C
H
Cl
C
H
H
C
H
H
C
Cl
H
C
H
Cl
C
H
H
C
H
H Cl
H
PolystyrenePolystyrene
• Polystyrene is nonpolar material and Polystyrene is nonpolar material and dissolves in organic solvents.dissolves in organic solvents.
• PS foam is mostly air, and when it dissolves PS foam is mostly air, and when it dissolves it collapses to a much smaller volume.it collapses to a much smaller volume.
Slime!Slime!
Slime is Slime is polyvinylalcohol polyvinylalcohol cross-linked cross-linked with boric acidwith boric acid
Bubble Bubble Gum!Gum!
A A copolymercopolymer
Bubble Bubble Gum!Gum!
A A copolymercopolymer
Styrene + butadieneStyrene + butadiene
Condensation PolymersCondensation Polymers
HOC
O
COH
O
CO
COCH2CH2OO
+ n HOCH2CH2OH
terephthalic acid ethylene glycol
+ H2O
Polyethylene terephthalate (PET), a polyester
n
n
Polyesters, PETPolyesters, PET
Jackets made from recycled PET soda
bottles
Soda Soda bottles, bottles,
mylar film.mylar film.
Polymer Recycling Polymer Recycling SymbolsSymbols
LDPE = LDPE = Low density PE = 0.910-0.925 g/cmLow density PE = 0.910-0.925 g/cm33
HDPE = HDPE = High density PE = 0.941-0.965High density PE = 0.941-0.965PP = PP = Polypropylene = 0.90Polypropylene = 0.90V = V = PVC (Vinyl chloride) = 1.30-1.58PVC (Vinyl chloride) = 1.30-1.58
Polyamides: NylonPolyamides: Nylon
•Each monomer has 6 C atoms in its chain.Each monomer has 6 C atoms in its chain.•A polyamide link forms on elmination of HClA polyamide link forms on elmination of HCl•Result = nylon 66Result = nylon 66