chapter 22, 23
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Chapter 22, 23. Organic Chemistry. Organic Chemistry. Organic chemistry The study of C-containing cpds Structures and rxns. Exceptions : oxides of C, carbonates, hydrocarbonates (inorganic). Millions and Millions of Organic Cpds. Carbon has 4 valence e- (group IV) - PowerPoint PPT PresentationTRANSCRIPT
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Chapter 22, 23
Organic Chemistry
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Organic Chemistry
Organic chemistry • The study of C-containing cpds• Structures and rxns
• Exceptions: oxides of C, carbonates, hydrocarbonates (inorganic)
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Millions and Millions of Organic Cpds
Carbon • has 4 valence e- (group IV)
• can bond (4 covalent bonds) to as many as 4 other atoms at once,
• can form C-chains (up to several thousand C) and rings of C
• → endless variety of cpds.
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• can bond strongly to elements such as O and N, halogens
• form double and triple bonds.
Millions and Millions of Organic Cpds
• millions of organic cpds
• classified into groups of cpds that have similar structures and properties.
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Hydrocarbons
Hydrocarbons• a group of organic cpds containing only H and C
Hydrocarbons
Saturated hydrocarbons• alkanes• all single bonds
−C−
Unsaturated hydrocarbons• alkenes—with
double bond −C=C−
• alkynes—with triple bond −C≡C−
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Saturated Hydrocarbons
Saturated hydrocarbon: (alkanes) • A hydrocarbon in which all the C atoms are
connected to each other by single bonds.
−C−C − C − C − C − C − C − C − C − C−
covalent
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Saturated Hydrocarbons
Uses of Alkanes
• the simplest hydrocarbons. (saturated)
• fuels e.g. methane (in town gas), propane (bottled fuel for BBQ), butane (lighter), gasoline
• as solvents in paint removers, glues, and other products.
• Other uses
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Alkanes
• The C in an alkane can be arranged in a chain or a ring.
• both chains and rings can have branches of other C chains attached to them.
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• Some alkanes have branched structures.
Alkanes
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• The condensed structural formula for propane can be written as CH3CH2CH3.
Alkanes
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Alkanes
CnH2n+2
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Energy source in the U.S.
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Fractionating column
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Fractions from Crude Oils
Fraction Compn of C chain
Boiling range (°C)
Natural gas C1 to C4 Below 20
Petroleum ether C5 to C6 30 to 60
Naphtha C7 to C8 60 to 90
Gasoline C6 to C12 40 to 175
Kerosene C12 to C15 150 to 275
Fuel oils, mineral oil C15 to C18 225 to 400
Petroleum jelly, wax, asphalt
C16 to C24 Over 400
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Unsaturated Hydrocarbons
Unsaturated hydrocarbon• A HC that has 1 or more −C=C− or −C≡C−
bonds• The other bonds are single bonds (−C−)• Alkenes (−C=C−), alkynes (−C≡C−)
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Alkenes
Alkenes
• A hydrocarbon containing 1 or more −C = C− bonds
• Unsaturated
• ending with -ene
• ethene• propene• butene• pentene
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Alkenes
• An unsaturated alkene can be converted into a saturated alkane by adding H to the C=C bond.
• hydrogenation.
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Alkynes
• Another type of unsaturated HC—alkyne, contains a triple bond (−C≡C−) between 2 C atoms.
• ending with -yne.• ethyne, propyne, butyne
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Alkynes
General formula: CnH2n-2
Ethyne C2H2 H—C≡C—H
H
|
Propyne C3H4 H—C—C≡C—H
|
H
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Aromatic Hydrocarbons
Aromatic hydrocarbon
• has a benzene ring
• most of them have distinctive aromas.
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Monomers and Polymers
A Polymer
• a giant molecule formed by covalent bonds
• hundreds or thousands of small individual repeating units (monomers), bonded together in chains.
• Monomers may all be alike, or they may be different.
• Properties of a polymer are different from those of the monomers that formed it.
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Synthetic Polymers
• Polymers are everywhere, making fabrics such as nylon and polyester, plastic wrap and bottles, rubber bands, and many more products you see every day.
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Structure of Polymers
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Structure of Polymers
Cellulose polymer found in the cell walls of plant cells
• monomer : glucose
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Structure of Polymers
• glucose
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Structure of Polymers
Starch
• natural plant polymer
• Monomer: glucose
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Rubber
• used in tires and rubber balls.
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Plastics
plastic ≠ polymer
not all polymers are plastics.
Plastics can be molded into different shapes.
must be heated enough to become liquefied if it is to be poured into a mold.
harden if it is allowed to cool.
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Functional Groups
A functional group in an organic molecule
• an atom or group of atoms that
• always reacts in a certain way (similiar chem properties)
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Functional Groups: Structure and Function
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Functional Groups
• The symbols R and R′ represent any C chains or rings bonded to the functional group.
• * represents a H atom, C chain, or C ring.
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Some Functional Groups
Compound type General Formula Functional groups
Halohydrocarbons R―X (F, Cl, Br, I) Halogens
Alkanols (Alcohols)
R―OH Hydroxyl e.g. methanol, ethanol
Alkanals(Aldehydes)
O ‖* C ―H
Carbonyl e.g. propanal
Alkanoic acids (Carboxylic acids)
O ‖* C ―OH
Carboxyl
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Cpd type Examples Condensed structural formula
Halohydro-carbon
Bromomethanetrichloromethane
CH3─Br (methyl bromide)CHCl3
Alkanols MethanolEthanolpropanol
CH3OHC2H5OH (CH3CH2OH)C3H7OH (CH3CH2CH2OH)
Alkanoic acid
Ethanoic acidPropanoic acid
C2H5COOH (CH3CH2 COOH)C3H7COOH (CH3CH2CH2COOH)
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Organic Cpds Containing Halogens
halohydrocarbon
• Any org cpd that contains a halogen substituent.
• one H in the methane is replaced by a halogen.
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Chloro-methane
CH3Cl H l H ─ C ─ Cl l H
Dichloro-methane
CH2Cl2 H l H ─ C ─ Cl l Cl
Trichloro-methane
CHCl3 H l Cl ─ C ─ Cl l Cl
Tetrachloro-methane
CCl4 Cl l Cl ─ C ─ Cl l Cl
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Alkanols (Alcohols)
• hydroxyl group (—OH).
• R─OH
Alcohol• An organic cpd in
which a hydroxyl gp replaces a H atom of a HC. Methanol
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Alkanols (Alcohols) CnH2n+1OH
Alkanol Condensed formula
Structural formula
Old name
Methanol
CH3OH H | H − C − OH | H
methyl alcohol
Ethanol
C2H5OH H H | | H − C − C − OH | | H H
ethyl alcohol
Propanol C3H7OH
Butanol C4H9OH
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Methanol(MethylAlcohol)
CH3OH H l H ─ C ─ OH l H
Ethanol C2H5OHCH3CH2OH
H H l l H ─ C ─ C─ OH l l H H
Propanol C3H7OHCH3CH2CH2OH
H H H l l l H ─ C ─ C ─ C ─ OH l l l H H H
Butanol C4H9OHCH3CH2CH2CH2OH
H H H H l l l l H ─ C ─ C ─ C ─ C ─ OH l l l l H H H H
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Alkanoic acids (Carboxylic Acids)
A alkanoic acid:
• an organic cpd that has a carboxyl group.
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Alkanoic Acids (Carboxylic Acids)
*COOH
Methanoic acid (formic acid) HCOOH
Ethanoic acid (acetic acid) CH3COOH
Propanoic acid C2H5COOH
Butanoic acid C3H7COOH
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Methanoic acid
HCOOH O ll H ─ C ─ OH
Ethanoic acid
CH3COOH H O l ll H ─ C ─ C─ OH l H
Propanoic acid
C2H5COOHCH3CH2COOH
H H O l l ll H ─ C ─ C ─ C ─ OH l l H H
Butanoic acid
C3H7COOHCH3CH2CH2COOH
H H H O l l l ll H ─ C ─ C ─ C ─ C ─ OH l l l H H H
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CST problem 1
For the polymer, polyvinyl chloride (PVC), ~CH2CH2CH(Cl)CH2CH(Cl)CH2CH(Cl)~
the repeat unit is
A CH(Cl)
B CH(Cl)CHCH2
C CH2CH
D CH2CH(Cl)
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The End