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Organic Chemistry

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

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Organic Chemistry

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  1. Organic Chemistry Nomenclature: Alkanes

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

  3. Organic Compounds • Contain carbon • Have covalent bonds • Have low melting points • Have low boiling points • Burn in air (oxygen) • Are soluble in nonpolar solvents • Form large molecules

  4. http://www.ajsmidi.com/allsongs_1/bevrlyh.html Come and listen to a story about a man named Jed A poor mountaineer, barely kept his family fed, Then one day he was shootin at some food, And up through the ground came a bubblin crude.Oil that is, black gold, Texas tea. Well the first thing you know ol Jed's a millionaire, Kinfolk said "Jed move away from there" Said "Californy is the place you ought to be" So they loaded up the truck and moved to Beverly. Hills, that is. Swimmin pools, movie stars. Well now its time to say good by to Jed and all his kin. And they would like to thank you folks fer kindly droppin in. You're all invited back a gain to this locality To have a heapin helpin of their hospitality Hillybilly that is. Set a spell, Take your shoes off. Y'all come back now, y'hear?.

  5. Titusville, Pa 1859

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

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

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

  9. 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

  10. Sources of Organic Compounds Fractional Distillation of Crude Oil

  11. Barrel of crude oil 42 Gallons Priced by the Barrel $101 today 1 year ago: $90

  12. Alkanes • Hydrocarbon chains where all the bonds between carbons are SINGLE bonds • sp3 Hybridized Orbitals– tetrahedral,109.5o • Name uses the ending –ane • Examples: Methane, Propane, Butane, Octane, 2-methylpentane

  13. IUPAC Names Name # carbons Structural Formula Methane 1 CH4 Ethane 2 CH3CH3 Propane 3 CH3CH2CH3 Butane 4 CH3CH2CH2CH3 Pentane 5 CH3CH2CH2CH2CH3

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

  15. Prefixes for # of Carbons

  16. 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

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

  18. What is the General formula for Alkanes?

  19. Summary: IUPAC Rules for Alkane Nomenclature  1. Find and name the longest continuous carbon chain. AKA: parent chain.  2. Number the chain consecutively, starting at the end nearest an attached group (substituent). 3. Identify and name groups attached to this chain. (Examples: methyl-, bromo-, etc.) 4. Designate the location of each substituent group withthe number of the carbon parent chain on which the group is attached. Place a dash between numbers and letters. (Example: 3-chloropentane)  5. Assemble the name, listing groups in alphabetical order.    The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing. Place a comma between multiple numbers. (Example: 2,3-dichloropropane)

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

  21. Endings • Alkanes (all C-C single bonded parent chain) end in –ane • MethaneCH4 • EthaneC2H6 • PropaneC3H8 • Attached carbon groups (substituents) end in –yl • Methyl CH3 - • EthylCH3CH2- • Propyl CH3CH2CH2 –   3-ethylpentane

  22. 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

  23. Step 3. Name the attached groups. • Carbon (alkyl) groups • Methyl CH3 - • EthylCH3CH2- • Propyl CH3CH2CH2 – • Halogens • Fluoro (F-) • Chloro (Cl-) • Bromo (Br-) • Iodo (I-)

  24. 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

  25. 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

  26. Draw Some Simple Alkanes • 2-methylpentane • 3-ethylhexane • 2,2-dimethylbutane • 2,3-dimethylbutane

  27. 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

  28. Order of Priority • IN A TIE, halogens get the lower number before alkyl groups 4-chloro-2-methylpentane or2-chloro-4-methylpentane?

  29. 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 ?

  30. Isomers • Straight chain alkanes: • Alkane with straight carbon back bone • Branched chain alkanes: • Alkane with a branching connection of carbons. • Isomers: • Same molecular formula but different structures.

  31. Only one possible atom arrangement methane (CH4) ethane (C2H6) propane (C3H8)

  32. Butane (C4H10): 2 isomers linear alkane or branched alkane

  33. Isomers are completely different compounds. Varied Structures Physical properties (MP, BP)

  34. Types of Carbon Atoms • Primary carbon (1o) • a carbon bonded to one other carbon • Secondary carbon (2o) • a carbon bonded to two other carbons • Tertiary carbon (3o) • a carbon bonded to three other carbons

  35. Alkanes Example: Name the following compounds:

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

  37. Test Your Knowledge • http://chemed.chem.pitt.edu/Jeopardy/organic/index.htm

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