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8/13/2019 Lecture 9 Organic Chemistry and Polymerization
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Organic Chemistry I:Formulas, Names,
and Properties
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Chapter Goals
Saturated Hydrocarbons1. Alkanes and Cycloalkanes2. Naming Saturated Hydrocarbons
Unsaturated Hydrocarbons 3. Alkenes4. Alkynes
Aromatic Hydrocarbons5. Benzene6. Other Aromatic Hydrocarbons7. H drocarbons: A Summar
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Chapter Goals
Functional Groups8. Organic Halides9. Alcohols and Phenols10.Ethers11.Aldehydes and Ketones12.Amines13.Carboxylic Acids14.Some Derivatives of Carboxylic Acids15.Summary of Functional Groups
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Chapter Goals
Fundamental Classes ofOrganic Reactions
16.Substitution Reactions17.Addition Reactions18.Elimination Reactions19.Polymerization Reactions
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Saturated Hydrocarbons Hydrocarbons are chemical compounds
that contain only C and H atoms. Saturated hydrocarbons contain only
single or sigma ( ) bonds. There are no double or triple bonds in these
compounds.
The primary source of hydrocarbons ispetroleum and natural gas.
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Alkanes and Cycloalkanes The simplest saturated hydrocarbons are
called alkanes. Methane, CH 4, is the simplest alkane. The alkanes form a homologous series.
Each member of the series differs by aspecific number and kind of atoms.
C
H
HH
H or CH 4
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Alkanes and Cycloalkanes
The alkanes differ from each other by a CH 2 ormethylene group.
All alkanes have this general formula.CnH2n+2
For example ethane, C 2H6 , and propane, C 3H8 , are the next two family members.
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Alkanes and Cycloalkanes
Isomers are chemical compounds thathave the same molecular formulas but
different structures. Two alkanes have the molecular formulaC4H10.
They are a specific type of isomer calledstructural isomers .
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Alkanes and Cycloalkanes
Three alkanes have the formula C 5H12. There are three structural isomers of pentane.
CH3CH2
CH2
CH2
CH 3
n-pentane
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Alkanes and Cycloalkanes
Three alkanes have the formula C 5H12. There are three structural isomers of pentane.
CH3CH2
CH2
CH2
CH 3 CH3CH C
H2
CH 3
CH 3
n-pentane 2-methylbutane
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Alkanes and Cycloalkanes
Three alkanes have the formula C 5H12. There are three structural isomers of pentane.
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Alkanes and Cycloalkanes
There are five isomeric hexanes, C 6H14.You draw them!
CH3 C
H2
CH2
C
H2
CH2
CH 3
n-hexane
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Alkanes and Cycloalkanes
There are five isomeric hexanes, C 6H14.
CH3CH2
C
H2
CH2
C
H2
CH 3CH3
CH C
H2
CH2
CH 3
CH 3
n-hexane 2-methylpentane
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Alkanes and Cycloalkanes
There are five isomeric hexanes, C 6H14.
CH3CH2
C
H2
CH2
C
H2
CH 3CH
3
CH C
H2
CH2
CH3
CH 3
CH3CH2
CH C
H2
CH 3CH 3
n-hexane 2-methylpentane 3-methylpentane
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Alkanes and Cycloalkanes
There are five isomeric hexanes, C 6H14.
CH3CH2
CH2
CH2
CH2
CH 3CH3
CH C
H2
CH2
CH 3
CH 3
CH3CH2
CH C
H2
CH 3
CH 3
CH3
CCH2 CH 3
CH 3
CH 3
n-hexane 2-methylpentane 3-methylpentane
2,2-dimethylbutane
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Alkanes and Cycloalkanes
There are five isomeric hexanes, C 6H14.
CH3CH2
C
H2
CH2
C
H2
CH 3CH
3
CH C
H2
CH2
CH3
CH 3
CH3CH2
CH C
H2
CH 3CH 3
CH3C
C
H2 CH 3
CH 3
CH 3CH
3
CH C
H CH 3
CH 3
CH 3
n-hexane 2-methylpentane 3-methylpentane
2,2-dimethylbutane 2,3-dimethylbutane
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Alkanes and Cycloalkanes
The number of structural isomers increasesrapidly with increasing numbers of carbonatoms.
The boiling points of the alkanes increase withmolecular weight.
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Alkanes and Cycloalkanes
Cyclic saturated hydrocarbons are calledcycloalkanes . They have the general formula C nH2n.
Some examples are:
CH2
CH2
CH 2CH2
CH2
cyclopentane
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Alkanes and Cycloalkanes
Cyclic saturated hydrocarbons are calledcycloalkanes . They have the general formula C nH2n.
Some examples are:
CH2
CH2
CH 2CH2
CH2CH2
CH2 CH2
CH 2
CH 2CH2
cyclopentane cyclohexane
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Alkanes and Cycloalkanes
Cyclic saturated hydrocarbons are calledcycloalkanes . They have the general formula C nH2n.
Some examples are:
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Naming Saturated Hydrocarbons
The International Union of Pure and Applied Chemistry(IUPAC) names for the first 12 "straight-chain" or "normal"alkanes are given in this table.
Number of carbonatoms in chain Name
1 Methane
2 Ethane
3 Propane4 Butane
5 Pentane
6 Hexane
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Number of carbonatoms in chain Name
7 Heptane8 Octane9 Nonane
10 Decane11 Unidecane12 Dodecane
Naming Saturated Hydrocarbons
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Naming Saturated Hydrocarbons
Other organic compounds are named asderivatives of the alkanes.
Branched-chain alkanes are named by thefollowing rules.
1. Choose the longest continuous chain ofcarbon atoms which gives the basic name orstem.
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Naming Saturated Hydrocarbons
2 Number each carbon atom in the basic chain, starting atthe end that gives the lowest number to the first group
attached to the main chain (substituent).3 For each substituent on the chain, we indicate the
position in the chain (by an Arabic numeric prefix)and the kind of substituent (by its name).
The position of a substituent on the chain is indicated by thelowest number possible.
The number precedes the name of the
substituent.
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Naming Saturated Hydrocarbons
4 When there are two or more substituents of a given kind,use prefixes to indicate the number of substituents.
di = 2, tri = 3, tetra = 4, penta = 5, hexa = 6, hepta = 7, octa =8, and so on.
5 The combined substituent numbers and names serve as a prefix for the basic hydrocarbon name.
6 Separate numbers from numbers by commas andnumbers from words by hyphens.
Words are "run together".
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Naming Saturated Hydrocarbons
Alkyl groups (represented by the symbol R) arecommon substituents. Alkyl groups are fragments of alkanes in which one
H atom has been removed for the connection to themain chain.
Alkyl groups have the general formula C nH2n+1 . In alkyl groups the -ane suffix in the name of the parent
alkane is replaced by -yl. A one carbon group is named methyl . A two carbon group is named ethyl .
A three carbon group is named propyl .
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Unsaturated Hydrocarbons
The three classes of unsaturatedhydrocarbons are:
1. alkenes and cycloalkenes, C nH2n 2. alkynes and cycloalkynes, C nH2n-2 3. aromatic hydrocarbons
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Alkenes
The simplest alkenes contain one C=C bond permolecule. The general formula for simple alkenes is C
nH
2n.
The first two alkenes are: ethene, C 2H4
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Alkenes
The simplest alkenes contain one C=C bond permolecule. The general formula for simple alkenes is C nH2n.
The first two alkenes are: and propene, C 3H6
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Alkenes
Each doubly bonded C atom is sp 2 hybridized. The sp 2 hybrid consists of:
two bonds (single bonds) and one and one p bond (double bond)
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Alkenes
The systematic naming system for alkenes uses thesame stems as alkanes.
In the IUPAC system, the -ane suffix for alkanes is
changed to -ene. Common names for the alkenes have the same stem but use
the suffix -ylene is used.
In chains of four or more C atoms, a numerical prefixshows the position of the lowest-numbered doubly
bonded C atom. Always choose the longest chain that contains the C=C
bond.
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Alkenes
Polyenes contain two or more double bonds permolecule.
Indicate the number of double bonds with suffixes:
-adiene for two double bonds. -atriene for three double bonds, etc.
The positions of the substituents are indicated as foralkanes.
The position of the C=C bond(s) is/are given thelowest number(s) possible.
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Alkenes
CC
CC
CC
H
H H
H
H
H
H
H
H
H
1,3-hexadiene
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Alkenes
CC
CC
CCH
H H
H
H
H
H
H
1,3,5-hexatriene
CC
CC
CCH
H H
C
C
H
H
H
H
H H
H
HH
2,3-dimethyl-1,3,5-hexatriene
CC
CC
CC
H
H H
H
H
H
H
H
H
H
1,3-hexadiene
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Cycloalkenes
Cycloalkenes have the general formula C nH2n-2 . Examples are: cyclopentene
C C
CC
C
HH
H
HH
H
H
H
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Cycloalkenes
cycloheptene
C C
CCC
C
CH
HH
H H
HHH
HHHH
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Alkynes
Alkynes contain C C bonds. The simplest alkyne is C 2H2, ethyne, or acetylene.
Alkynes with only one C C bond have the formula
CnH2n-2 . Each carbon atom in a C C bond is sp hybridized.
Each sp hybrid contains two bonds and two p bonds. The carbon atom will have one single bond and one
triple bond.
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Alkynes
Alkynes are named like the alkenes exceptthat the suffix -yne is used with thecharacteristic stem The alkyne stem is derived from the name of the
alkane with the same number of carbon atoms.
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Alkynes
Acetylene burns in a highly exothermic reaction The combustion produces temperatures of about 3000C. Acetylene is used in cutting torches for welding.
Alkynes are very reactive The two p bonds are sights of special reactivity.
Addition reactions, such as hydrogenation, are common.
g2g2g2g22 OH2CO45OH2C
g62g2g22 HC2HHC
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Hydrocarbons: A Summary
Carbon AtomHybridization C uses C forms Example
sp 3
tetrahedral 4 sp 3 hybrids4
bonds CH 4
sp 2
trigonal planar3 sp 2 hybrids& 1p orbital
3 bonds
1 p bondC2H4
sp linear 2 sp hybrids &2 p orbitals
2 bonds
2 p bonds
C2H2
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Aromatic Hydrocarbons
Historically, aromatic was used to describe pleasant smelling substances.
Now it refers to benzene, C 6H6, and derivativesof benzene. Other compounds that have similar chemical
properties to benzene are also called aromatic.
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Benzene
The structure of benzene, C 6H6, is:
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Other Aromatic Hydrocarbons
Coal tar is the common source of benzene andmany other aromatic compounds.
Some aromatic hydrocarbons that containfused rings are:
napthalene
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Other Aromatic Hydrocarbons
phenanthrene
CC
CC
C
CC
C
CC
C
CCC
H
H
H
H H
H
H
H
H
H
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Other Aromatic Hydrocarbons
Many aromatic hydrocarbons contain alkylgroups attached to benzene rings (as well as toother aromatic rings).
The positions of the substituents on benzenerings are indicated by the prefixes: ortho- ( o-) for substituents on adjacent C atoms
meta- ( m-) for substituents on C atoms 1 and 3 para- ( p-) for substituents on C atoms 1 and 4
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Functional Groups
Functional groups are groups of atoms thatrepresent potential reaction sites.
Compounds that contain a given functionalgroup usually undergo similar reactions.
Functional groups influence physical properties as well.
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Organic Halides
A halogen atom may replace almost any hydrogenatom in a hydrocarbon.
The functional group is the halide (-X) group.
Examples include: chloroform, CHCl 3
CCl Cl
Cl
H
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Organic Halides
1,2-dichloroethane, ClCH 2CH 2Cl
C CH
Cl
H
H
Cl
HH
CHH
H
http://localhost/var/www/apps/conversion/tmp/scratch_4/MEDIA/PDBs/1,2-dichloroethane.pdbhttp://localhost/var/www/apps/conversion/tmp/scratch_4/MEDIA/PDBs/1,2-dichloroethane.pdb8/13/2019 Lecture 9 Organic Chemistry and Polymerization
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Organic Halides
para-dichlorobenzene
Cl
Cl
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Alcohols and Phenols
The functional group in alcohols and phenols isthe hydroxyl (-OH) group.
Alcohols and phenols can be consideredderivatives of hydrocarbons in which one ormore H atoms have been replaced by -OHgroups.
Phenols are derivatives of benzene in which oneH has been replaced by replaced by -OH group.
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Alcohols and Phenols
Ethyl alcohol (ethanol), C 2H5OH, is the mostfamiliar alcohol.
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Alcohols and Phenols
Phenol, C 6H5OH, is the most familiar phenol.
OH
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Alcohols and Phenols
Alcohols are considered neutral compounds because they are only very slightly acidic. Alcohols can behave as acids but only in the presence
of very strong bases. Phenols are weakly acidic.
K a 1.0 x 10 -10 for phenol
Although phenols are very weakly acidic, theyare also very corrosive.
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Alcohols and Phenols
Alcohols can be classified into three classes:1. Primary (1) alcohols like ethanol have the -
OH group attached to a C atom that has one bond to another C atom.
CH3CH2
OH
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Alcohols and Phenols
2. Secondary(2) alcohols have the OH groupattached to a C atom that has bonds to 2 otherC atoms.
For example,2-propanol:
CH3
CHCH3
OH
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Alcohols and Phenols
3. Tertiary (3) alcohols have the OH groupattached to a C atom that is bonded to 3 otherC atoms.
For example, 2-methyl-2-propanol
CH3 C CH 3
OH
CH 3
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Alcohols and Phenols
The stem for the parent hydrocarbon plus an -ol suffix is the systematic name for an alcohol.
A numeric prefix indicates the position of the -OHgroup in alcohols with three or more C atoms.
Common names are the name of the appropriate
alkyl group plus alcohol.
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Alcohols and Phenols
Alcohols are named using the stem for the parenthydrocarbon plus an -ol suffix in the systematicnomenclature.
A numeric prefix indicates the position of the -OH groupin alcohols with three or more C atoms. Common alcohol names are the name of the appropriate
alkyl group plus the word alcohol.
CH 2C
H 2
CH 2
C
H 2
CH 3OH
CH 3CH C
H 2
CH
2
CH 3
OH
1-pentanol1-pentyl alcohol
2-pentanol2-pentyl alcohol
CH 2C
H 2
CH 2
C
H 2
CH 3OH
1-pentanol1-pentyl alcohol
CH 2C
H 2
CH 2
C
H 2
CH 3OH
CH 3CH C
H 2
CH
2
CH 3
OH
CH 3C
H 2
CH C
H 2
CH 3OH
1-pentanol1-pentyl alcohol
2-pentanol2-pentyl alcohol
3-pentanol3-pentyl alcohol
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Alcohols and Phenols
There are several isomeric monohydric acyclic(contains no rings) alcohols that contain morethan three C atoms.
There are four isomeric four-carbon alcohols.
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Alcohols and Phenols
There are eight isomeric five-carbon alcohols.You do it!
CH 2
CH 2
CH 2
CH 2
CH 3OH
CH 3CH C
H 2
CH 2
CH 3
OH
CH 3CH 2
CH C
H 2
CH 3OH
1-pentanol 2-pentanol 3-pentanol
CH 2
CH C
H 2
CH 3OHCH 3
CH 3 C CH 2CH 3
CH 3
OHCH 3
CH C
H CH 3
OH
CH 3
2-methyl-1-butanol 2-methyl-2-butanol 3-methyl-2-butanol
CH 3CH C
H 2
CH
2
CH 3
OH
3-methyl-1-butanol
CH 3 C CH 2CH 3
CH 3 OH
2,2-dimethyl-1-propanol
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Alcohols and Phenols
Polyhydric alcohols contain more than one -OHgroup per molecule.
CH2CH CH 2
OH
OH
OH
CH2
CH C
H CH C
H CH 2OHOH
OH
OH
OH
OH
glycerin sorbitol
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Alcohols and Phenols
Phenols are usually called by their common(trivial) names.
OH
OH
resorcinol
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Alcohols and Phenols
Phenols are usually called by their common(trivial) names.
OH
OH
OH
CH 3
resorcinol o-cresol
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Alcohols and Phenols
Phenols are usually called by their common(trivial) names.
OH
OH
OH
CH 3
OH
CH 3
resorcinol o-cresol m-cresol
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Alcohols and Phenols
Phenols are usually called by their common(trivial) names.
OH
OH
OH
CH 3
OH
CH 3
OH
CH 3resorcinol o-cresol m-cresol p-cresol
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Alcohols and Phenols
Because the -OH group is quite polar, the properties ofalcohols depend upon the number of -OH groups permolecule and the size of the organic group.
The boiling points of monohydric alcohols increase withincreasing molecular weight.
The solubility of monohydric alcohols in water decreasewith increasing molecular weight.
Polyhydric alcohols are more soluble in water because ofthe two or more polar groups (-OH).
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Ethers
Ethers may be thought of as derivatives of waterin which both H atoms have been replaced by
alkyl or aryl groups.
HO
H
water
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Ethers
Ethers may be thought of as derivatives of waterin which both H atoms have been replaced by
alkyl or aryl groups.
HO
H CH3O
H
water an alcohol
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Ethers
Ethers may be thought of as derivatives of waterin which both H atoms have been replaced by
alkyl or aryl groups.
HO
H CH3O
H CH3O
CH 3
water an alcohol an ether
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Ethers
Ethers are not very polar and not very reactive. They are excellent solvents.
Common names are used for most ethers.
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Aldehydes and Ketones
The functional group in aldehydes and ketones isthe carbonyl group.
O
R2R1 or H
carbonyl group
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Aldehydes and Ketones
Except for formaldehyde, aldehydes have one Hatom and one organic group bonded to a carbonylgroup.
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Aldehydes and Ketones
Ketones have two organic groups bonded to acarbonyl group.
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Aldehydes and Ketones
Common names for aldehydes are derived fromthe name of the acid with the same number of Catoms.
IUPAC names are derived from the parenthydrocarbon name by replacing -e with -al .
C
O
CH2
CH2
CH2
CH3 H
pentanal or pentyl aldehyde
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Aldehydes and Ketones
Common names for aldehydes are derived fromthe name of the acid with the same number of Catoms.
IUPAC names are derived from the parenthydrocarbon name by replacing -e with -al .
C
O
CH2
CH2
CH2
CH3 HC
O
C
CH3
CH3
CH 3
H
pentanal or pentyl aldehyde
2,3-dimethylproponal or 2,3-dimethylpropionaldehyde
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Aldehydes and Ketones
Common names for aldehydes are derived fromthe name of the acid with the same number of Catoms.
IUPAC names are derived from the parenthydrocarbon name by replacing -e with -al .
C
O
CH2
CH2
CH2
CH3 HC
O
CCH3
CH3
CH 3
HC
O
H
pentanal or pentyl aldehyde
2,3-dimethylproponal or 2,3-dimethylpropionaldehyde
benzanal or benzyl aldehyde
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Aldehydes and Ketones
The IUPAC name for a ketone is the characteristicstem for the parent hydrocarbon plus the suffix -one.
A numeric prefix indicates the position of thecarbonyl group in a chain or on a ring.
C
O
CH2
CH2
CH2
CH3 CH 3
2-hexanone or methyl pentyl ketone
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Aldehydes and Ketones
The IUPAC name for a ketone is the characteristicstem for the parent hydrocarbon plus the suffix -one.
A numeric prefix indicates the position of thecarbonyl group in a chain or on a ring.
C
O
CH2
CH2
CH2
CH3 CH 3
2-hexanone or methyl pentyl ketone
CH3CH2
CH2
CCH2
CH 3
O
3-hexanone or ethyl propyl ketone
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Aldehydes and Ketones
The IUPAC name for a ketone is the characteristicstem for the parent hydrocarbon plus the suffix -one.
A numeric prefix indicates the position of thecarbonyl group in a chain or on a ring.
C
O
CH
2
CH2
CH
2
CH3 CH 3
2-hexanone or methyl pentyl ketone
CH3CH2
CH
2
CCH
2
CH 3
O
3-hexanone or ethyl propyl ketone
CCH 3O
acetophenone or methyl phenyl ketone
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Aldehydes and Ketones
Many aldehydes and ketones occur in nature.
CHCH
COH
cinnamaldehyde
O
CH 3
CH 3 OH
testosterone
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Amines
Amines are derivatives of ammonia in which oneor more H atoms have been replaced by organicgroups (aliphatic or aromatic or a mixture of
both). There are three classes of amines.
H
N
HH
ammonia
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Amines
Amines are derivatives of ammonia in which oneor more H atoms have been replaced by organicgroups (aliphatic or aromatic or a mixture of
both). There are three classes of amines.
HN
H
H
CH3N
H
H
ammonia primaryamine
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Amines
Amines are derivatives of ammonia in which oneor more H atoms have been replaced by organicgroups (aliphatic or aromatic or a mixture of
both). There are three classes of amines.
HN
HH
CH3N
HH
CH3N
HCH 3
ammonia primaryaminesecondary
amine
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Amines
Amines are derivatives of ammonia in which oneor more H atoms have been replaced by organicgroups (aliphatic or aromatic or a mixture of
both). There are three classes of amines.
HN
HH
CH3N
HH
CH3N
HCH 3
CH3N
CH 3CH 3
ammonia primaryaminesecondary
aminetertiaryamine
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Amines
Aniline is the simplest aromatic amine. It ismuch less basic than NH 3.
Aniline is a very important industrial chemical.
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Amines
Heterocylic amines have one or more N atomsin a ring structure.
Many are important in living systems.
Npyridine
A i
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Amines
Heterocylic amines have one or more N atomsin a ring structure.
Many are important in living systems.
Npyridine
N
N
pyrimidine
A i
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Amines
Heterocylic amines have one or more N atomsin a ring structure.
Many are important in living systems.
Npyridine
N
N
pyrimidine
N
N
N
N
purine
C b li A id
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Carboxylic Acids
Carboxylic acids contain the carboxyl functionalgroup.
The general formula for carboxylic acids is: R represents an alkyl or an aryl group
COH
O
R1
COH
O
C b li A id
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Carboxylic Acids
IUPAC names for a carboxylic acid are derivedfrom the name of the parent hydrocarbon. The final -e is dropped from the name of the
parent hydrocarbon The suffix -oic is added followed by the word
acid.
Many organic acids are called by their common(trivial) names which are derived from Greek orLatin.
C b li A id
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Carboxylic Acids
Positions of substituents on carboxylic acid chainsare indicated by numeric prefixes as in othercompounds Begin the counting scheme from the carboxyl
group carbon atom. They are also often indicated by lower case Greek
letters.
= 1 st C atom = 2 nd C atom = 3 rd C atom, etc.
C b li A id
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Carboxylic Acids
CH C
OH
O
CH3
CH3
2-methylpropanoic acid or
-methylpropanoic acid
C b li A id
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Carboxylic Acids
CH C
OH
O
CH3
CH3
2-methylpropanoic acid or
-methylpropanoic acid
CH3CH C
H2
COH
OCH 3
3-methylbutanoic acid or
-methylbutanoic acid
C b li A id
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Carboxylic Acids
CH C
OH
OCH3
CH 3
2-methylpropanoic acid or -methylpropanoic acid
CH3CH C
H2
COH
OCH 3
3-methylbutanoic acid or -methylbutanoic acid
CH3 CH C
H2
CH2
COH
O
CH 3
4-methylpentanoic acid or -methylpentanoic acid
C b li A id
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Carboxylic Acids
Dicarboxylic acids contain two carboxyl groups permolecule.
OHC C
OHO
O
oxalic acid
Nomenclature of Carboxylic
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yAcids Dicarboxylic acids contain two carboxyl groups per
molecule.
OHC C
OHO
OOH C C
H2
C OH
O O
oxalic acid malonic acid
Nomenclature of Carboxylic
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yAcids Dicarboxylic acids contain two carboxyl groups per
molecule.
OHC C
OHO
OOH C C
H2
C OH
O O
OH C CH2
C
H2
C OH
O
O
oxalic acid malonic acid succinic acid
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Carboxylic Acids Aromatic acids are usually called by their
common names. Sometimes, they are named as derivatives of
benzoic acid which is considered to be the"parent" aromatic acid.
C b li A id
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Carboxylic Acids
OOHOOH
Clbenzoic acid p-chlorobenzoic acid
Carbo lic Acids
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Carboxylic Acids
OOHOOH
Cl
OOH
CH 3
O
OH
O
OH
benzoic acid p -chlorobenzoic acid
p -toluic acid phthalic acid
Carboxylic Acids
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Carboxylic Acids
Acid strengths of simple carboxylic acids varylittle with chain length.
However, substituents on a carbon atom in thechain can cause large variations in acidstrengths .
Carboxylic Acids
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Carboxylic Acids
COH
O
H
CH 3C
OH
O
OHC
CH 2
CH 3
O
Compound Name K a
formic acid
acetic acid
propionic acid
1.8 x 10 -4
1.8 x 10 -5
1.4 x 10 -5
Carboxylic Acids
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Carboxylic Acids
CH 2
COH
O
Cl
Compound Name K a
monochloroacetic acid 1.5 x 10 -3
CH 3C
OH
Oacetic acid 1.8 x 10 -5
CH C
OH
O
Cl
Cl dichloroacetic acid 5.0 x 10 -2
CC
OH
O
Cl Cl
Cltrichloroacetic acid 2.0 x 10 -1
Carboxylic Acids
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Carboxylic Acids
The -OH group in the carboxyl group ofcarboxylic acids, is displaced in many of theirreactions.
The non -OH portion of a carboxylic acid is calledan acyl group.
R1 C OH
O
R1 C
O
carboxyl group acyl group
Some Derivatives of
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Carboxylic Acids Four important classes of compounds contain
acyl groups They are all considered to be derivatives of
carboxylic acids. In these structures R's may represent either
alkyl or aryl groups.
Some Derivatives of
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Carboxylic Acids
R1C
OC
R1
O O
R1C
Cl
O
acid anhydride acid chloride
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Carboxylic Acids
R1C
OC
R1
O O
R1C
Cl
O
R1 C O R2
O
R1 C NH2
O
acid anhydride acid chloride
ester amide
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Carboxylic Acids Acid anhydrides are related to their parent acids as
follows: The word anhydride means without water.
CH3C
OH
O2
CH3 O CH 3
O O
+ H2O
acetic acid acetic anhydride
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Carboxylic Acids Acyl halides are much more reactive, and more
volatile, than their parent acids. They react with water to form their parent acids and a
hydrohalic acid.
CH3C
Cl
O
CH3 OH
O
+ HCl
acetyl chloride acetic acid
H2O+
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Carboxylic Acids Acyl halides are prepared by reacting their parent
acids with PCl 3, PCl 5, or SOCl 2. The more volatile acid halide is then distilled out of
the reaction mixture.
OOH
+ PCl 5
OCl
benzoic acid benzoyl chloride
Some Derivatives of
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Carboxylic Acids Esters are prepared by heating a carboxylic acid with
an alcohol in the presence of a small amount of aninorganic acid. The reaction mixture will contain some ester and water, as
well as unreacted acid and alcohol.
CH3C
OH
OCH2
OHCH3+
H2SO 4
CH3C
OCH2
CH 3
O+ H2O
ethanoic acid or acetic acid
ethanol or ethyl alcohol
ethyl ethanoate or ethyl acetate
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Carboxylic Acids
Esters are usually called by their common names. Many simple esters occur naturally and have pleasant
odors. Esters are frequently used in fragrances and as artificial
flavors.
CH2
CO
CH2
CH 3
O
CH2
CH3
ethyl butanoate or ethyl butyrateodor of pineapples
CH3 OCH2
CH2
CH2
CH2
CH2
CH2
CH2
CH 3
O
octyl ethanoate or octyl acetate odor of oranges
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Carboxylic Acids Fats are solid esters of glycerol and (mostly) saturated
acids at room temperature. Oils are liquid esters of glycerol and primarily
unsaturated acids at room temperature. The "acid" parts of fats and oils usually contain even
numbers of C atoms in naturally occurring fats and oils. 16 and 18 carbon chains are the most commonly found
chain sizes in nature.
Some Derivatives of
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Carboxylic Acids
Some acids that are found (as their esters) in fatsand oils include:
CH3CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
COH
O
palmitic acid CH 3(CH 2)14 COOH
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Carboxylic Acids
Stearic acid is often found in beef fat.
CH3CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
C
OH
O
stearic acid CH 3(CH 2)16 COOH
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Carboxylic Acids
Triglycerides are the triesters of glycerol. The common name for triglycerides is tri (acid
stem) plus an -in suffix. For example, tripalmitin.
Some Derivatives of
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Carboxylic Acids Waxes are esters of long chain fatty acids and
alcohols other than glycerol. Commonly, waxes are derived from
monohydric alcohols. Beeswax and carnauba wax are esters of myricyl
alcohol, C 30H61OH.
Some Derivatives of
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Carboxylic Acids
Carnauba wax is often used in car waxes.
carnauba wax
C
O
OC 25 H51C 30 H61
Some Derivatives of
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Carboxylic Acids
Dihydric alcohols (2 OHs per molecule) can reactwith dicarboxylic acids (2 COOHs per molecule) toform polyesters .
Ester linkages are formed at both ends of bothmolecules to give polymeric esters with very highmolecular weights.
COH
C
OH
O
O
+ CH2
CH2
OHOH
terephthalic aciddicarboxylic acid
ethylene glycoldihydric alcohol
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Carboxylic Acids
CO
CO
O
O
CH2 CH 2
O
*
*n
dacron
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Carboxylic Acids
Amides are derivatives of organic acids and primaryor secondary amines.
The functional groups of amides are:
CN
OR2
H
R1C
N
OR2
R3
R1or C
N
OH
H
R1 or
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Carboxylic Acids
Amides are also named as derivatives of carboxylicacids.
The suffix -amide is substituted for -ic acid or -oicacid .
CN
O
H
H
CH3
CNH2O
ethanamide or acetamide
benzamide
Some Derivatives ofb l d
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Carboxylic Acids
When an aryl or alkyl substituent is present on the Natom, the letter N and the name of the substituent are
prefixed to the name of the unsubstituted amide.
CN
O
CH 3
H
CH3
CNO
CH 3
CH2CH
3
N -ethylethanamide or N-ethylacetamide
N -ethyl- N -methylbenzamide
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Carboxylic Acids
Acetaminophen Tylenol - is an amide.
Summary of thei l G
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Functional Groups
A summary of the functional groups is:
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Substitution Reactions
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Subst tut o eact o s
In a substitution reaction an atom or group ofatoms attached to a carbon atom is replaced(substituted for) by another atom or group of
atoms. There is no change in the degree of saturation
at the reactive carbon atom.
Halogenation reactions are an important classof substitution reactions. Chlorine reacts with alkanes in free radical
chain reactions (also substitution reactions).
Substitution Reactions
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Free radical chain reactions The halogenation of methane is one example.
heat or uv light
Cl
.2
free radicals
Cl Cl
Substitution Reactions
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Cl
.+ H C
H
H
. + Cl
HH C H
H
H
heat or uv light
free radicals
Cl Cl
2 Cl
.
methyl radical
Substitution Reactions
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H C
H
H
. + Cl Cl
+ Cl .H C
H
H Cl
methyl radical
Cl
.+ H C
H
H
. + Cl
HH C H
H
H
heat or uv light
free radicals
2 Cl
.Cl Cl
methyl chloride
Substitution Reactions
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Free radical chain reactions Many substitution reactions of alkanes produce
more than one product.
C ClH
H
H
+ Cl Cl CH
H
ClCl + HCl
Substitution Reactions
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C ClH
H
H
+ Cl Cl CH
H
ClCl + HCl
CH
H
ClCl + Cl Cl CH
Cl
ClCl + HCl
Substitution Reactions
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HCl
C
H
ClClCl + Cl Cl C
Cl
ClClCl + HCl
C
H
H
ClCl + Cl Cl CH
Cl
ClCl +
C ClH
H
H
+ Cl Cl CH
H
ClCl + HCl
Substitution Reactions
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Nitration reaction of an aromatic hydrocarbonreplaces an H atom attached to an aromatic ringwith a nitro, -NO 2, group.
+ 2H SO 4HNO 2
NO2
Addition Reactions
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An addition reaction involves an increase inthe number of groups attached to carbon. The degree of saturation of the molecule is
increased.
C CH
H H
H
+ Cl C CH
Cl
H
HH
Cl
2
Addition Reactions
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Hydrogenation is a very important kind of addition reaction. Hydrogenation is used to convert unsaturated fats and oils to
saturated fats or oils.
C CH
H H
H+ H C CH
H
HHH
H2
Elimination Reactions
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An elimination reaction involves the removalof groups attached to carbon. The degree of unsaturation increases.
C CCH3 CH 3
HH
CH3
CH CH
Br Br
CH 3
Zn in
acetic acidor ethanol
C CCH3 H
CH 3H
+ ZnBr 2
mixture of cis & trans -2-butene
+
Elimination Reactions
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Dehydration is an important kind ofelimination reaction.
concentrated
2H SO 4
C CH H
HH
HCH CH
OHH
H+ H O2
Polymerization Reactions
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A polymer is a large molecule that consists ofa high-molecular weight chain of smallmolecules.
The small molecules that have been joined to formthe polymer are called monomers .
Synthetic polymers are a relatively new class
of molecules. The first one, bakelite, was discovered in 1909. Nylon, which is still extensively used, was
discovered in 1930s.
Polymerization Reactions
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Addition polymerization is a large commercial process in the United States.
Polyethylene is the addition polymer made inthe largest quantities in the United States. Polyethylene is used to make Coke bottles, plastic
bags, etc.
Polymerization Reactions
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Addition polymerization Polyethylene formation
CH2 CH 2n
ethylene
catalyst* CH 2 CH 2 *n
polyethylene
Polymerization Reactions
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Addition polymerization Teflon is the material used in nonstick frying pans
and other kitchen utensils.
C CF
F F
Fn
catalystC CF
F F
F** n
polytetrafluoroethylene or Teflon
tetrafluoroethylene
heat
Polymerization Reactions
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Formation of rubber Natural rubber is a polymer made of isoprene (2-
methyl-1,3-butadiene) units that form a uniquestereoisomeric structure.
2n
natural rubber isoprene
CH2
C CH
CH2
CH3
CH 2C
CHCH2
CH 2C
CHCH 2
*
CH 3 CH 3
*n
Polymerization Reactions
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Vulcanization of rubber Natural rubber is a sticky, soft compound when
heated which limited its commercial potential.
Charles Goodyear discovered in 1839 that heatingrubber with sulfur removed the stickiness andmade the substance elastic. This is the basis of modern tire production.
Vulcanization provides disulfide cross-linking bonds between the isoprene units.
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Polymerization Reactions
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Copolymers
3
styrenebutadiene
C CC C
H
H
H
H H
H CCH
H
H
+
Polymerization Reactions
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CH 2C
C
CH2 CH 2C
CCH2 CH 2
CCH2
CCCH 2
*
*
H
H
H
H
H H
H
n
Styrene - butadiene rubber (SBR)
Polymerization Reactions
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Condensation Polymers Condensation polymers occur when two molecules
react and eliminate a small molecule.
Molecules eliminated commonly are water and HCl. Important condensation polymers include nylon,
dacron, and kevlar.
Dacron is used in clothing to make it wrinkle free. Blood does not clot in contact with dacron thus it isused in artificial arteries.
Polymerization Reactions
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Condensation Polymers Dacron formation
terephthalic acidethylene glycol
CH2
CH2
OHOH
COOH
O OH
+
Polymerization Reactions
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CO OC
OOC
H2CH2
CH2
O HCH2
OH n
Dacron is a polyester
+ H2O
Polymerization Reactions
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Condensation Polymers Nylon was first made by Wallace Carothers in
the 1930s. Nylon is widely used in a variety of commercial
products including stockings, rope, guitar strings,fire-proof clothing.
Polymerization Reactions
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Condensation Polymers Nylon 66 formation
OHC
CH2
CH2
CH2
CH2
COH
O
O
NH2CH2
CH2
CH2
CH2
CH2
CH2
NH2+
adipic acid hexamethylene diamine
Polymerization Reactions
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+ H2ONH2C
CH2
CH2
CH2
CH2
CNH
CH2
CH2
CH2
CH2
CH2
CH2
NH
COH
O
O
O
n
Nylon is a polyamide