What is meant by the term Organic?

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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.

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

How can we describe Hydrocarbons?

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)

3 Important Homologous Series of Hydrocarbons: Alkanes Alkenes Alkynes

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.

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 ‘eth’ and ‘ane’ Ethane

The First Ten Straight-Chain Hydrocarbons

The First Ten Straight-Chain Hydrocarbons

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What are the Unsaturated Hydrocarbons?

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.

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 2 carbons is Eth All alkenes end in ‘ene’ ‘eth’ and ‘ene’ Ethene 3 carbons is Prop ‘prop’ and ‘ene’ Propene

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

Alkenes

Alkynes Alkynes family of hydrocarbons with one triple bond general formula CnH2n-2 named with suffix "YNE“ Starts with Ethyne.

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 ‘prop’ and ‘yne’ Propyne

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With this ring I, get confused?

The Benzene Series (Aromatic hydrocarbons) The benzene series consists of molecules which are cyclic in nature. The general formula is CnH2n-6. Benzene H C H C C H C6H6 H

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 H C C H C C H H C C H An abbreviated structural formula can be used in place of the above: OR

Toluene or Methylbenzene C7H8 H C C CH3 H C C H C An abbreviated structural formula can be used in place of the above: CH3 CH3

Alkylderivatives of Benzene

Page 5 Practice

Aim: How can we name organic compounds? We have rules!!!! YAY!!!!!!!!!!!

Rule 1: Find the longest continuous chain

Rule 2: Assign numbers to each C atom in the longest chain, starting at the end with the attached group.

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.

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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Aim: How can we represent organic compounds?

What are we showing in the following pictures? Different symbols or signs to represent one thing- women! The bottom is written in braille.

Different ways to represent one compound Molecular Formula Structural Formula Condensed Structural Formula Ball-and-Stick Model Space-Filling Model

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.

Structural Formula In addition, shows the bonding patterns and two-dimensional view. For example:

Condensed Structural Formula Written structural formula For example: Methane: CH4 Ethane: CH3CH3

Ball-and-Stick Model Shows a 3D structure of the compound Example:

Space-Filling Model Shows the actual structure of the compound Example:

Molecules Models of Organic Hydrocarbons Fig 8.4

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

Isomers How would you draw the structural formula for a 4 carbon hydrocarbon?

Structural Isomers of Butane Fig 8.5

Isomer Practice Draw 3 Isomers for 5 and 6 carbon Alkanes. Be sure you have the correct number of hydrogens.

What are the various Functional Groups?

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!

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, cellulose

1. Halides 2-fluoropropane 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 2-fluoropropane

2. Alcohols Organic 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 substances General Formula: R-OH Naming: Position of OH group must be assigned & -ANE ending changes to –OL.

Classification of Alcohols There are primary, secondary, and tertiary carbon atoms: Primary Carbon: Attached to one carbon only Secondary: Attached to two carbon atoms Tertiary: Attached to three carbon atoms.

Alcohols “ol” ending

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 Propanal 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: Propanone 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 Methyl ethyl Ether Methoxyethane

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: Ethanoic Acid

Carboxylic Acids

3-methyl-2-hexanoic acid armpit in a jar

Isovaleric acid “locker room concentrate”

4-ethyloctanoic acid “wet male goat”

7. Esters General Formula: Have strong aromas; for example, flavorings in bananas, wintergreen, oranges.

The fine smell of esters

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:

9. Amides Formed by the combination of 2 amino acids: General Formula: Form proteins Naming: Replace final –E with -AMIDE propanamide

Functional Groups

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Aim: How do organic compounds react? Do Now: Name the Functional Group: 1. CH3COOH 2. CH3COOCH3 3. CH3CHO

Which one is faster? Making Wine or Dissolving Alka Seltzer in water?

Organic Reactions Occur more slowly than inorganic reactions because of the covalent bonds. There are 7 types of Organic Reactions.

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 +

Addition Involves adding 1 or more atoms at a double or triple bond: Ethene + Chlorine 1,2 dichloroethane

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

Esterification Reaction between an organic acid and an alcohol to produce an ester plus water: Ethanoic acid + Ethanol Water + Ethyl ethanoate

Saponification When an ester reacts with an inorganic base to produce an alcohol and a soap: Fat + Base Glycerol + Soap

Combustion Almost all organic compounds will combust , or burn: Compound + Oxygen Carbon Dioxide + Water

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

Addition Polymerization Joining of monomers of unsaturated compounds:

Condensation Polymerization Bonding of monomers by removing water from hydroxyl groups and joining monomers by an ether or ester linkage:

Summary: Identify the Reaction C2H6 + Cl2 C2H5Cl + HCl C6H12O6 2C2H5OH + 2CO2 CH3COOH + CH3OH CH3COOCH3 + H2O nC2H4 (C2H4)n

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

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.

Hydrocarbons Have hydrogen and carbon atoms only! Homologous Series: Members that have similar properties. 3 Types: Alkanes, Alkenes, and Alkynes

Alkane All single bonds All end in –ane Each member differs by 1 carbon and 2 hydrogen atoms. General Formula: Cn H2n + 2

Alkene Has at least one double bond All end in –ene. General Formula: CnH2n

Alkyne Has at least one triple bond All end in –yne. General Formula: CnH2n-2

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.

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

Functional Groups Found on Table R! Alcohols: Can be classified in two ways: Primary, Secondary, or Tertiary (with ONE -OH group only)! 1 –OH: Monohydroxy 2 -OH: Dihydroxy 3 –OH: Trihydroxy

Organic Reactions 7 Types: Need to know reactants & products. Combustion Substitution Addition Esterification Saponification Fermentation Polymerization: Addition & Condensation

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.

Number of Possible Isomers for Selected Alkanes

Some Common Alkyl Groups

Naming Alkanes

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

Different Ways of Representing the Alkane Ethyne