Organic Chemistry Why is it important?

What is Organic Chemistry? Study of hydrocarbons and derivatives 7 million Organic Compounds 1.5 million Inorganic Compounds Animal and plant matter, Foods, Pharmaceuticals, Cosmetics, Fertilizers, Plastics, Petrochemicals, Clothing

Organic Compounds Contain carbon Have covalent bonds Have low melting points Have low boiling points Burn in air (oxygen) Form large molecules

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Crude oil can have different components depending on where in the world it comes from

Where is the oil going? US Middle East Petroleum Reserves (%) 7 65 World Population (%) 5 3 World Petroleum 31 6 Consumption (%)

How is Crude Oil Refined? Distillation towers Separated by the physical property of … Boiling Point

Boiling Point Trends Small molecules low boiling points usually gases at room temperature Large molecules high boiling points usually liquids and solids at room temperature

Sources of Organic Compounds Fractional Distillation of Crude Oil

Products from Petroleum

Barrel of crude oil 42 Gallons Priced by the Barrel $120 today 1 year ago: $60

Petroleum products use 84% for Burning Fuel Transportation and Heating 16% for Building Products Medicine, plastic, dyes, lubricants, cosmetics, explosives

Alkanes Hydrocarbon chains where all the bonds between carbons are SINGLE bonds Name uses the ending –ane Examples: Methane, Propane, Butane, Octane, 2-methylpentane

Prefixes for # of Carbons 1 Meth 6 Hex 2 Eth 7 Hept 3 Prop 8 Oct 4 But 9 Non 5 Pent 10 Dec

IUPAC Names Methane 1 CH4 Ethane 2 CH3CH3 Propane 3 CH3CH2CH3 Name # carbons Structural Formula Methane 1 CH4 Ethane 2 CH3CH3 Propane 3 CH3CH2CH3 Butane 4 CH3CH2CH2CH3 Pentane 5 CH3CH2CH2CH2CH3 The names of organic compounds are determined by the IUPAC rules (International Union of Pure and Applied Chemistry). The stem of the name states the number of carbon atoms in the carbon chain of the compounds. The suffix, in this case –ane, indicates the alkane family.

IUPAC NAMES Hexane 6 CH3CH2CH2CH2CH2CH3 Name # carbons Structural Formula Hexane 6 CH3CH2CH2CH2CH2CH3 Heptane 7 CH3CH2CH2CH2CH2CH2CH3 Octane 8 CH3CH2CH2CH2CH2CH2CH2CH3 Nonane 9 CH3 CH2 CH2CH2CH2CH2CH2CH2CH3 Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

More Alkanes H H Condensed Structural Formulas H C C H CH3 CH3 H H Ethane H H H H C C C H CH3 CH2 CH3 H H H Propane The complete structural formula for ethane shows the single bonds between two carbon atoms and six H atoms. The complete structural formula of propane shows the 3-carbon chain with single bonds to the attached H atoms. To write a condensed structural formula, the H atoms are written as a group next to their respective C atoms.

Learning Check Alk1 A. What is the condensed formula for H H H H H C C C C H B. What is its molecular formula? C. What is its name?

What is the General formula for Alkanes? Cn H2n+2

Isomers Same formula with a different structure -C-C-C-C- VS -C-C-C- C straight branched Both are C4 H10, but they have different chemical and physical properties

Isomers Straight chain alkanes: Branched chain alkanes: Isomers: An alkane that has all its carbons connected in a row. Branched chain alkanes: An alkane that has a branching connection of carbons. Isomers: Compounds with same molecular formula but different structures.

Nomenclature or names of compounds Alkanes

IUPAC Rules for Alkane Nomenclature  Find and name the longest continuous carbon chain  Number the chain consecutively Identify and name groups attached to this chain  Designate the location of each substituent group with the number of the carbon parent chain  Assemble the name, listing groups in alphabetical order.    

Step 1. Find the parent chain. Where is the longest continuous chain of carbons?

Endings Alkanes (all C-C single bonded parent chain) end in –ane Methane CH4 Ethane C2H6 Propane C3H8 Attached carbon groups (substituents) end in –yl Methyl CH3 - Ethyl CH3CH2- Propyl CH3CH2CH2 –      3-ethylpentane

Step 2. Number the parent chain. Number the parent chain so that the attached groups are on the lowest numbers Methyl is on carbon #2 of the parent chain Methyl is on carbon #4 of the parent chain 1 2 3 4 5 GREEN is the right way for this one! 5 4 3 2 1 2 3 7 8 4 5 6 8 7 6 2 1 5 4 3 2 3 4 5 6 7 6 5 4 3 2 1 Groups on 2 and 5 Groups on 4, 6, and 7 Groups on 2, 3, and 5 Groups on 3 and 6

Step 3. Name the attached groups. Carbon (alkyl) groups Methyl CH3 - Ethyl CH3CH2- Propyl CH3CH2CH2 – Halogens Fluoro (F-) Chloro (Cl-) Bromo (Br-) Iodo (I-)

Step 4. Designate where the group is attached to the parent chain. Use the numbers of the parent chain from step 2 to designate the location of the attached groups to the parent chain. 2-methyl 1 2 3 4 5

Step 5. Alphabetize the groups, combine like groups, and assemble. The prefixes di, tri, tetra etc., used to designate several groups of the same kind Prefixes are not considered when alphabetizing (Example: dimethyl = m for alphabetizing) Parent chain goes LAST 1,1,1-trichloro-1-fluoromethane 1,1-dichloro-1,1-difluoromethane

Draw Some Simple Alkanes 2-methylpentane 3-ethylhexane 2,2-dimethylbutane 2,3-dimethylbutane

Structural Formulas “Lazy” way to write the Hydrogens Instead of drawing the bonds, just state how many hydrogens are attached NOTE: The bonds are between CARBONS in a parent chain, and not hydrogens! Structural Formula Lewis Structure

Order of Priority IN A TIE, halogens get the lower number before alkyl groups 4-chloro-2-methylpentane or 2-chloro-4-methylpentane?

Order of Priority IN A TIE between SIMILAR GROUPS, the group lower ALPHABETICALLY gets the lower number 4-bromo-2-chloropentane or 2-bromo-4-chloropentane ?

Alkanes Example: Name the following compounds:

Alkanes Example: Write the condensed structure for the following compounds: 3,3-dimethylpentane 2-methyl-4-sec-butyloctane 1,2-dichloro-3-methylheptane