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Organic Chemistry

Organic Chemistry. BELL RINGER. What makes a compound organic?. Origin of organic compounds. Naturally occurring organic compounds are found in plants, animals, and fossil fuels All of these have a plant origin All of these rely on the “fixing” of C from CO 2

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Organic Chemistry

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  1. Organic Chemistry

  2. BELL RINGER What makes a compound organic?

  3. Origin of organic compounds • Naturally occurring organic compounds are found in plants, animals, and fossil fuels • All of these have a plant origin • All of these rely on the “fixing” of C from CO2 • Synthetic organic compounds are derived from fossil fuels or plant material

  4. C C C C C Introduction • Most current research focuses on Organic • Originally from “organic” meaning life • Not just chemistry of life, chemistry of carbon • Exceptions: • oxides of carbon (CO2, CO) • carbonates,bicarbonates(NaHCO3,CaCO3) • cyanides (NaCN, etc) One C with no H, or with metal • Carbon can form four bonds…

  5. Properties of Organic Compounds • Covalently bonded • Low Melting Points • Non-electrolytes • Nonpolar • React slower than inorganic compounds • Require high activation energies • Insoluble in water ~ generally

  6. Carbon forms four bonds • Carbon can form four bonds, and forms strong covalent bonds with other elements • This can be represented in many ways …

  7. Functional groups • Functional groups are parts of molecules that result in characteristic features • About 100 functional groups exist, we will focus on about 10 • Useful to group the infinite number of possible organic compounds • Ex - the simplest group is hydrocarbons • Made up of only C and H • Not really a functional “group” • Further divided into: • Aliphatics - Alkanes, Alkenes, Alkynes • Aromatics

  8. C C C C C C Hydrocarbons Alkanes Alkenes CnH2n+2 CnH2n Alkynes Aromatics CnH2n-2

  9. Naming Hydrocarbons(nomenclature)

  10. Drawing structures: it’s all good 2-butene On a test, choose a method that shows all H’s This is called the “condensed structure” CH3CH=CHCH3 Using brackets can also shorten some formulas: CH3(CH2)4CH3vs. CH3CH2CH2CH2CH2CH3

  11. H H H H H H H H C C H H C C C C C C H H H H H H H H H H H H C C H H C C C C H H H H H H C C H C H H H H H H C C H H C C C H H H H H Draw/Name the following 2-pentene

  12. BELL RINGER What is the structural formula for 2-hexene CH3CHCHCH2CH2CH3

  13. Hydroxyl, carbonyl, carboxyl • There are other names that describe patterns of atoms that are parts of functional groups. • “Hydroxyl” refers to –OH • “Carbonyl” refers to C=O • “Carboxyl” refers to COOH

  14. Formic acid Acetone Acetylene Naming: common vs. IUPAC • Common names used in the 1800’s are still used for some compounds today: • The International Union of Pure and Applied Chemistry (IUPAC) was established in 1900s

  15. C2H4 CH3CH2CCCH2CH2CH2CH2CH3 Numbering carbons 1-pentene Q- draw pentene A- Where’s the bond? We number C atoms • Thus, naming compounds with multiple bonds is more complex than previously indicated • Only if 2+ possibilities exist, are #s needed • Always give double bond the lowest number • Try to name these: 2-butene Ethene 3-nonyne

  16. C H 3 H C C H 3 3 C H 3 Branched Hydrocarbons • 2,3-dimethylpentane • Names are made up of: side chains, root • Root is the longest possible HC chain • Must contain multiple bonds if present • Add -yl to get name of side chain • Common side chains include: CH3- methyl CH3CH2- ethyl CH3CH2CH2- propyl (CH3)2CH- isopropyl • Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)

  17. Naming side chains C H C H C H 3 2 3 CH C H C H C H C C H 3 2 2 3 C H 3 Rule 1: choose the correct ending -ane

  18. Naming side chains C H C H C H 3 2 3 C H C H CH C H C C H 3 2 2 3 C H 3 Rule 2: longest carbon chain ane

  19. Naming side chains C H C H C H 3 2 3 C H C H CH C H C C H 3 2 2 3 C H 3 Rule 3: attach prefix (according to # of C) ane Heptane

  20. Naming side chains C H C C H H C C H H 3 2 2 3 3 2 1 C C H H C C H H C CH C C H H C C C C H H 3 3 2 2 2 2 3 3 3 7 6 5 4 C C H H 3 3 Rule 4: Assign numbers to each carbon heptane

  21. 2 1 3 7 6 5 4 Naming side chains methyl C H C C H H C C H H 2 2 3 3 3 C C H H C C H H C CH C C H H C C C C H H 3 3 2 2 2 2 3 3 methyl C C H H methyl 3 3 Rule 5: Determine name for side chains heptane

  22. 2 1 3 7 6 5 4 Naming side chains methyl C H C H C H 3 2 3 C H C H CH C H C C H 3 2 2 3 methyl C H methyl 3 Rule 6: attach name of branches 3-methyl-3-methyl-5-methyl-heptane

  23. 2 1 3 7 6 5 4 Naming side chains methyl C H C H C H 3 2 3 C H C H CH C H C C H 3 2 2 3 methyl C H methyl 3 Rule 8,9: group similar branches 3-methyl-3-methyl-5-methyl-heptane

  24. 2 1 3 7 6 5 4 Naming side chains methyl C H C H C H 3 2 3 C H C H CH C H C C H 3 2 2 3 methyl C H methyl 3 Rule 8,9: group similar branches 3,3,5-trimethyl-heptane

  25. C BELL RINGER H H Name the hydrocarbon H H H C H C H C H H C H H H H H C – C – C – C = C – C H H H H H H H H 4-ethyl-3-methyl-4-octene

  26. Naming side chains 3-methylhexane 4-ethyl-2,3-dimethylheptane 5-ethyl-2,4,6-trimethyloctane

  27. Functional Groups Alcohols -OH Element Grouping: -name ends in –ol Naming: Example: 2-butanol

  28. H H HO C C OH H H Functional Groups Alcohols Ethylene glycol  1,2 Ethanediol Odorless, colorless, sweet and syrupy, toxic liquid

  29. O C H Functional Groups Aldehydes Element Grouping: -name ends in –al Naming: Example: ethanal

  30. O C Functional Groups Ketones Element Grouping: -name ends in –one Naming: Example: propanone

  31. O C OH Functional Groups Organic Acids Element Grouping: -name ends in–oic acid Naming: Example: butanoic acid

  32. O H H H H H C – C – C – C – C – C H H H H H H H Name the following organic compound: BELL RINGER 3-hexanone

  33. Functional Groups Ethers -O- Element Grouping: -name ends in ether Naming: Example: methyl propyl ether

  34. C C C C I F Cl Br Cl CH3-CH-CH-CH3 F Functional Groups Halides Element Grouping: Naming: -use prefix with o ending Example: 2-chloro-3-fluoro-butane

  35. N Functional Groups Amine Element Grouping: -name ends in–amine Naming: C H C H C H N H2 Example: 3 2 2 propanamine

  36. O X H C OH N H C H Functional Groups Amino Acids Element Grouping: Naming: TOO complicated Example:

  37. O C O Functional Groups Esters Element Grouping: -name ends in–oate Naming: Example: propyl methanoate

  38. O O C C NH2 H NH2 Functional Groups Amide Element Grouping: -name ends in–amide Naming: Example: methanamide

  39. CH3 CH3CH2CH2CH2CH2CH2-C-CH3 H H CH3 CH3 CH2CH3 H3C C C C H H CH2CHCH2CH2CH2-C-CH2 C C H H CH3CH2CH2 CH3 H H Drawing Side Chains 2,2-dimethyloctane 1,3-dimethylcyclopentane 6-ethyl-5-propyl-7-methyl-1-heptene

  40. O H H H H H C – C – C – O – C – C H H H H H BELL RINGER Name the hydrocarbon ethyl propanoate

  41. Isomers

  42. C H 3 C H C H C H C H C H C H C H 3 3 3 2 2 3 Structural Isomers Butane (C4H10) 2-methylpropane (C4H10) 1-butene 2-butene 2-methylpropene cyclobutane methylcyclopropane

  43. H H OH H OH H H C C C H H C C C H H H H H H H H H H H C C O C H H H H Structural Isomers 2-propanol 1-propanol ethyl-methyether

  44. Covalent Molecules Lab

  45. BELL RINGER Draw and name an isomer of butanal.

  46. Organic Reactions Generally organic reactions occur at a slower rate  covalent bonds Many reactions require a catalyst to lower the activation energy

  47. H H H H H –C=C– H F2 –C–C– H +  H F F Types of Reactions Addition -alkene or alkyne Reactants: -a double halogenated halocarbon Produces: Example: -only occurs with unsaturated hydrocarbons Special Info: -results in 2 atoms added

  48. H–C–C–C=C–H H H H H H H H H H–C–C–C–C–H H H H H H H Special type of Addition “Hydrogenation” + H2 Helps turn oils into margarine

  49. H H H H H H H H I2 + H–C–C–C–C–H H–C–C–C–C–H H H H H H I H H Types of Reactions Substitution Reactants: saturated hydrocarbon and halogen -a single halogenated halocarbon Produces: Example: HI + Special Info: -only occurs with alkanes, can add more by doing more than one substitution

  50. OH H yeast H + 2 CO2 2 H –C–C– H H Types of Reactions Fermentation -sugar and yeast Reactants: Produces: Alcohol and carbon dioxide Example:

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