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

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How can we describe Hydrocarbons?

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• 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)

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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.

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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

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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!

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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

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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

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Aim: How do organic compounds react?

Do Now: Name the Functional Group:1. CH3COOH

2. CH3COOCH3

3. CH3CHO

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Which one is faster?

• Making Wine or Dissolving Alka Seltzer in water?

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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

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Fermentation

• A chemical process in which yeast cells secrete the enzyme zymase and break down glucose into carbon dioxide and ethanol:

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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:

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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

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Aim: How can we review Organic Chemistry for our test?

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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

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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.

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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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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

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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.

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Number of Possible Isomers for Selected

Alkanes

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Some Common Alkyl Groups

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Naming Alkanes

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Cis-Trans Isomerism

Does the term “trans” have anything to do withthe topic of “trans-fats” we have been hearing a lot about recently?

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Different Ways of Representing the Alkane Ethyne

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