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What is meant by the term Organic?. Page 2. Characteristics of organic compounds. Formed as a result almost exclusively of covalent bonding Generally nonpolar Generally insoluble in water usually soluble in nonpolar solvents (other organic compounds) - PowerPoint PPT Presentation
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What is meant by the term Organic?
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Page 2
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Characteristics of organic compounds
• Formed as a result almost exclusively of covalent bonding
• Generally nonpolar Generally insoluble in water– usually soluble in nonpolar solvents (other organic
compounds)• Non-electrolytes except organic acids which are
weak electrolytes• Have low melting points (due to weak
intermolecular forces that hold them together)– The great number of carbons leads to a higher melting
point.3
Characteristics of organic compounds, (continued)
• Have slower reaction rates than inorganic compounds– covalent bonds within organic molecules are strong– activation energies are high– catalysts are often used to increase reaction rates
4
How can we describe Hydrocarbons?
5
• Hydrocarbons– Definition - compounds composed of only
hydrogen and carbon– There are so many hydrocarbons found in nature;
nearly impossible to study all! They are grouped in Homologous series.
– Homologous series - group of organic compounds with similar properties and related structures (differ from each other by CH3)
6
3 Important Homologous Series of Hydrocarbons:
1. Alkanes2. Alkenes3. Alkynes
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• Aliphatic - hydrocarbon chains– Saturated
• Definition - has no bonds that can be broken to add extra hydrogen
• called Alkanes– family of hydrocarbons with all single bonds– general formula CnH2n+2
– named with suffix "ANE“– Table P – Organic Prefixes– As the number of carbons increases, the boiling point
increases.
8
TAKE OUT PAPER AND DRAW PLEASE
• Name and draw the first ten Alkanes– Go to table P and look at the prefix for the
number of carbons• 1 carbon is Meth
– All alkanes end in ‘ane’» ‘meth’ and ‘ane’» Methane
• 2 carbons is Eth– All alkanes end in ‘ane’
» ‘eth’ and ‘ane’» Ethane
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The First Ten Straight-Chain Hydrocarbons
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The First Ten Straight-Chain Hydrocarbons
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Page 3
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What are theUnsaturated Hydrocarbons?
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– Unsaturated - has double or triple bonds that can be broken to add more hydrogen
• Alkenes– family of hydrocarbons with at least one double bond– general formula CnH2n
– named with suffix "ENE“– Starts with Ethene.
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AlkenesTAKE OUT PAPER AND DRAW PLEASE
• Draw the first nine Alkenes– Go to table P and look at the prefix for the
number of carbons• 2 carbons is Eth
– All alkenes end in ‘ene’» ‘eth’ and ‘ene’» Ethene
• 3 carbons is Prop– All alkenes end in ‘ene’
» ‘prop’ and ‘ene’» Propene
15
Alkenes TAKE OUT PAPER AND DRAW PLEASE
• Draw the first nine Alkenes– Go to table P and look at the prefix for the
number of carbons• 4 carbons is But
– All alkenes end in ‘ene’» ‘but’ and ‘ene’» Butene
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Alkenes
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Alkynes
• Alkynes– family of hydrocarbons with one triple bond– general formula CnH2n-2
– named with suffix "YNE“– Starts with Ethyne.
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Alkynes
• Draw the first nine Alkynes– Go to table P and look at the prefix for the
number of carbons• 2 carbons is Eth
– All alkenes end in ‘yne’» ‘eth’ and ‘yne’» Ethyne
• 3 carbons is Prop– All alkenes end in ‘yne’
» ‘prop’ and ‘yne’» Propyne
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Packet Page 4
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With this ring I,get confused?
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The Benzene Series (Aromatic hydrocarbons)
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The benzene series consists of molecules which are cyclic in nature.The general formula is CnH2n-6.
Benzene HC
H C C HC6H6
H C C HCH
Although it appears that the structure has alternating double and single bonds, the bonding involves six identical bonds. A resonance structure is used to show structural formula of benzene.
H HC C
H C C H H C C H
H C C H H C C HC CH H
An abbreviated structural formula can be used in place of the above:
OR
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Toluene or Methylbenzene C7H8
HC
H C C CH3
H C C HCH
An abbreviated structural formula can be used in place of the above:
CH3 CH3
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Alkylderivatives of Benzene
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Page 5 Practice
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Aim: How can we name organic compounds?
We have rules!!!!YAY!!!!!!!!!!!
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• Rule 1: Find the longest continuous chain
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• Rule 2: Assign numbers to each C atom in the longest chain, starting at the end with the attached group.
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• Rule 3: If more than one of the same types of group is attached to the main chain prefixes are used to identify the attached groups.
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• Rule 4: When naming alkenes or alkynes the carbon with the double/triple bond, the carbon number with the double/triple bond must be identified in the name.
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Packet Pages 10-11
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Aim: How can we represent organic compounds?
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What are we showing in the following pictures?
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Different ways to represent one compound
• Molecular Formula• Structural Formula• Condensed Structural Formula• Ball-and-Stick Model• Space-Filling Model
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Molecular Formula
• Shows the kind and number of atoms in a compound.
• Example: CH4 or C2H6
• Tells us that there are carbon and hydrogen atoms. For methane, there are 4 hydrogens for 1 carbon atom.
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Structural Formula
• In addition, shows the bonding patterns and two-dimensional view.
• For example:
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Condensed Structural Formula
• Written structural formula• For example: Methane: CH4
• Ethane: CH3CH3
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Ball-and-Stick Model
• Shows a 3D structure of the compound• Example:
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Space-Filling Model
• Shows the actual structure of the compound• Example:
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Molecules Models of Organic Hydrocarbons Fig 8.4
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Isomers
• Isomers: When a molecular formula can be represented by more than one structural arrangement
• Isomers have the same molecular formula, but different physical and chemical properties.
• As the # of carbon atoms increases, so does the # of possible isomers
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Isomers• How would you draw the structural
formula for a 4 carbon hydrocarbon?
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Structural Isomers of Butane
Fig 8.544
Isomer Practice
•Draw 3 Isomers for 5 and 6 carbon Alkanes.•Be sure you have the correct number of hydrogens.
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What are the variousFunctional Groups?
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Functional Groups
• Atoms or groups of atoms that replace hydrogen atoms in a hydrocarbon.
• This will form new compounds?• They have distinct physical and chemical
properties.• There are 9 functional groups• All found on Table R!
47
C, H and O• Alcohols (R-OH)
– ethanol, isopropyl alcohol, (rubbing alcohol)• Ethers (R-O-R)
– dimethyl ether (old anaesthetic)• Ketones
– acetone (nail polish remover)• Aldehydes (a ketone with at least one R = H)
– formaldehyde • Esters
– many fine odours• Carboxylic acids
– acetic acid• Carbohydrates
– (CH2O)n, glucose, starch, cellulose48
R
O
R
R
O
O
R
H3C O CH3
H3C
C
O
CH3
H3C
C
O
OH
H
CHOC
OH
C
H
OH
C
OH
H
C
OH
H
HOH2C
1. Halides• A Halogen (F, Cl, Br, or I) replaces a hydrogen on a
hydrocarbon.• Used as organic solvents• General Formula: R-X (X= Halogen & R= Alkyl group)• Add fluoro for F Designate the location of
• Chloro for Cl the halide with 1,2 etc• Bromo for Br• Iodo for I
49
2-fluoropropane
2. AlcoholsOrganic compounds in which one or more hydrogen
atoms are replaced by an –OH group.-OH group is called a hydroxyl group.NOT A BASE!They are nonelectrolytes (Do not form ions in solution).Polar substancesGeneral Formula: R-OHNaming: Position of OH group must be assigned & -ANE
ending changes to –OL.
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Classification of AlcoholsThere are primary, secondary, and tertiary carbon
atoms:
Primary Carbon: Attached to one carbon onlySecondary: Attached to two carbon atomsTertiary: Attached to three carbon atoms.
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Alcohols “ol” ending
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3. Aldehydes
• Organic compounds in which a carbonyl group (C=O) is found on the end carbon (a primary carbon):
• Naming: Substitute –AL in place of final –E of alkane name.
• General Formula
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Propanal
4. Ketones
• C=O group is on the inside of a hydrocarbon:
• Naming: Substitute –ONE in place of final –E of alkane name.
• General Formula:
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Propanone
5. Ethers
• Two carbon chains are joined together by an oxygen atom:
• Naming: name the alkyl groups and add ether at the end.
• General Formula: R-O-R
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Methyl ethyl Ether
6. Organic Acids
• Organic compounds that have a Carboxyl group (-COOH):
• Naming: Substitute –OIC ACID in place of final –E in alkane name.
• Ethanoic acid= Acetic acid• General Formula:
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Ethanoic Acid
Carboxylic Acids
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3-methyl-2-hexanoic acid
armpit in a jar
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Isovaleric acid“locker room concentrate”
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4-ethyloctanoic acid“wet male goat”
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7. Esters
• General Formula:
• Have strong aromas; for example, flavorings in bananas, wintergreen, oranges.
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The fine smell of esters
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O
O
PINEAPPLE
O
O
BANANA
O
O
ORANGE
O
O
APRICOT
H O
O
ARTIFICIAL RUM FLAVOUR
8. Amines• Formed when one or more of the hydrogen’s in
ammonia is replaced by an alkyl group:
• Naming: Substitute –AMINE in place of final –E of alkane name.
• General Formula:
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9. Amides
• Formed by the combination of 2 amino acids:
• General Formula: • Form proteins• Naming: Replace final –E with -AMIDE
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Functional Groups
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Packet Pages 13-15
66
Aim: How do organic compounds react?
Do Now: Name the Functional Group:1. CH3COOH
2. CH3COOCH3
3. CH3CHO
67
Which one is faster?
• Making Wine or Dissolving Alka Seltzer in water?
68
Organic Reactions
• Occur more slowly than inorganic reactions because of the covalent bonds.
• There are 7 types of Organic Reactions.
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Substitution
• Involves the replacement of 1 or more of the hydrogen atoms in a saturated hydrocarbon with another atom or group:
• C2H6 + Cl2 C2H5Cl + HCl
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+
Addition• Involves adding 1 or more atoms at a double or triple bond:
• Ethene + Chlorine 1,2 dichloroethane
71
Fermentation
• A chemical process in which yeast cells secrete the enzyme zymase and break down glucose into carbon dioxide and ethanol:
72
Esterification
• Reaction between an organic acid and an alcohol to produce an ester plus water:
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Ethanoic acid + Ethanol Water + Ethyl ethanoate
Saponification
• When an ester reacts with an inorganic base to produce an alcohol and a soap:
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Fat + Base Glycerol + Soap
Combustion• Almost all organic compounds will combust , or
burn:
• Compound + Oxygen Carbon Dioxide + Water
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Polymerization
• Polymers: Organic compounds made up of chains of smaller units (monomers) covalently bonded together.
• Polymerization: Formation of these large polymer molecules.
• Examples of Natural Polymers: Cellulose, Proteins, & Starch
• Synthetic Polymers: Nylon & Rayon
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Addition Polymerization
• Joining of monomers of unsaturated compounds:
77
Condensation Polymerization
• Bonding of monomers by removing water from hydroxyl groups and joining monomers by an ether or ester linkage:
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Summary: Identify the Reaction
1. C2H6 + Cl2 C2H5Cl + HCl
2. C6H12O6 2C2H5OH + 2CO2
3. CH3COOH + CH3OH CH3COOCH3 + H2O
4. nC2H4 (C2H4)n
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Packet Pages 29-32
80
Aim: How can we review Organic Chemistry for our test?
81
Carbon • Carbon forms four bonds always!• Carbon can form single, double, or triple
bonds.• Single = Saturated• Double or Triple = Unsaturated• Carbon can covalently bond to other
carbon atoms.
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Hydrocarbons• Have hydrogen and carbon atoms only!• Homologous Series: Members that have
similar properties.• 3 Types: Alkanes, Alkenes, and Alkynes
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Alkane• All single bonds• All end in –ane• Each member differs by 1 carbon and 2
hydrogen atoms.• General Formula: Cn H2n + 2
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Alkene• Has at least one double bond• All end in –ene.• General Formula: CnH2n
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Alkyne• Has at least one triple bond• All end in –yne.• General Formula: CnH2n-2
86
Formulas• Molecular:• Shows the kind and
number of atoms in a compound.
• Example: CH4 or C2H6
• Structural:• In addition, shows the
bonding patterns and two-dimensional view.
87
Isomers• Isomers: When a molecular formula can
be represented by more than one structural arrangement
• Isomers have the same molecular formula, but different physical and chemical properties.
• As the # of carbon atoms increases, so does the # of possible isomers
88
Functional Groups
• Found on Table R!• Alcohols: Can be classified in two ways:1. Primary, Secondary, or Tertiary (with
ONE -OH group only)!2. 1 –OH: Monohydroxy• 2 -OH: Dihydroxy• 3 –OH: Trihydroxy
89
Organic Reactions
7 Types: Need to know reactants & products.CombustionSubstitutionAdditionEsterificationSaponificationFermentationPolymerization: Addition & Condensation
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Organic Reactions
• Occur more slower than inorganic reactions. Why?
• Review: Covalent bonds have low melting and boiling points, are poor conductors, and are nonpolar substances.
91
Number of Possible Isomers for Selected
Alkanes
92
Some Common Alkyl Groups
93
Naming Alkanes
94
Cis-Trans Isomerism
Does the term “trans” have anything to do withthe topic of “trans-fats” we have been hearing a lot about recently?
95
Different Ways of Representing the Alkane Ethyne
96