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Organic Chemistry Essentials

Organic Chemistry Essentials. Chemistry of carbon compounds Carbon can form 4 covalent bonds with other atoms. This allows it to make millions of different compounds. Carbon can form single, double, and triple bonds. Hydrocarbon. compound containing only hydrogen and carbon

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Organic Chemistry Essentials

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  1. Organic Chemistry Essentials • Chemistry of carbon compounds • Carbon can form 4 covalent bonds with other atoms. This allows it to make millions of different compounds. • Carbon can form single, double, and triple bonds.

  2. Hydrocarbon • compound containing only hydrogen and carbon • Ex. CH4 C2H6

  3. Hydrocarbon derivative • compound with some hydrogen atoms replaced by other elements (O, N, F, Cl, Br, I) • ex. CH3Br

  4. Straight chained hydrocarbon Ex. CH3CH2CH2CH2CH2CH3 or C6H14

  5. Branched hydrocarbon CH3 CH3CH2CHCH2CH3 or C6H14

  6. Saturated hydrocarbon • no double or triple bonds

  7. Unsaturated hydrocarbon • contains double and/or triple bonds • not “saturated” with hydrogen

  8. Structural formulas Condensed Structural formulas CH3-CH3

  9. Alkanes • hydrocarbons with only single bonds • General formula: CnH2n+2 • names end in -ane • boiling pt. increases with # of carbons

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

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

  12. Alkenes • contain at least one double bond • name ends in -ene • general formula: CnH2n

  13. Alkynes • contain at least one triple bond • name ends in -yne • general formula: CnH2n-2

  14. Nomenclature • naming system • IUPAC (International Union of Pure and Applied Chemistry)

  15. Rules for naming alkanes 1. Name the longest carbon chain in the structure. If the chain is cyclic, include the prefix cyclo. 2. Name, in alphabetical order, the kinds of groups which are attached to the chain you named in step 1. Use the appropriate prefix, such as di-, tri-, tetra-, etc., to indicate how many of each group are present.

  16. 3. Number the carbon atoms in the longest chain consecutively from the end of the chain which allows the attached groups to have the lowest numbers possible. Assign to each group you named in step 2 the number(s) indicating its position(s) on the main chain.

  17. Rules for naming alkenes and alkynes • Name the longest carbon chain containing the carbon-carbon double or triple bond. The name of the longest chain ends in –ene for an alkene; in –yne for an alkyne. The position of the double or triple bond in the carbon chain is indicated by a number before the name of the chain. • Name the groups attached as in alkanes.

  18. 3. When assigning numbers to atoms in the chain, start numbering from the end of the chain closest to the double or triple bond.

  19. Naming branched chain alkanes • substituent- atom or group of atoms that takes the place of hydrogen on a hydrocarbon molecule • ex. C, O, N, S, P, Cl, F, I, Br

  20. Alkyl Group • hydrocarbon substituent • alkane with one H removed • drop the -ane ending and add -yl H H C CH3 methyl H H H H C C CH3CH2 ethyl H H

  21. Name the following: 3,3-diethylhexane

  22. 4-ethyl-4,6-dimethyl-5-propylnonane

  23. 6-ethyl-4,5-dipropylnonane

  24. Draw the following: 2,2,4-trimethylpentane

  25. Draw the following: 3-ethyl-2-hexene

  26. Draw the following: 4-bromo-2,2-dichloro-3,5-diethyl-6-fluorooctane

  27. Properties of Hydrocarbons • nonpolar • not attracted to water

  28. Structural Isomers • compounds that have the same molecular formula but different molecular structures. • physical and chemical properties differ Butane2-methylpropane or isobutane CH3-CH2-CH2-CH3 CH3 CH3-CH-CH3

  29. Geometric Isomers • Each of the carbons of the double bond must have at least one substituent. • Ex. CH3CH=CHCH3 has 2 geometric isomers because the double bond is not free to rotate. Bond angle (sp2) is 120o.

  30. cis-2-butene trans-2-butene

  31. Stereoisomers • Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. • The two main types of stereoisomerism are: • cis-trans isomerism • optical isomerism

  32. Optical isomerism is a form of isomerism where the two different isomers are the same in every way except being non-superimposable mirror images of each other. Optical isomers are known as chiral molecules. A compound is chiral when it cannot be superimposed on its mirror image. The pair of mirror imaged non-superimposable compounds are known as enantiomers. Even though very similar still, different enantiomers of the same chiral drug can have very different pharmological effects, mainly because the proteins they bind to are also chiral. 4 different groups attached to the carbon The two enantiomers of bromochlorofluoromethane

  33. Cyclic hydrocarbons • compounds that contain a hydrocarbon ring • general formula is: CnH2n Cyclopropane Cyclobutane

  34. Aliphatic compounds • hydrocarbon compounds which do not contain rings

  35. Arenes • unsaturated cyclic hydrocarbons • Benzene, C6H6, is an arene. • Benzene is a flat molecule with resonance.

  36. Shorthand ways to draw benzene:

  37. Aromatic compound • any substance in which the bonding is like benzene • A benzene ring used as a substituent on a hydrocarbon chain is called a phenyl group. • Ex. methylbenzene (toluene)

  38. Nomenclature:

  39. Natural gas- 80% methane, 10% ethane, 4% propane, 2 % butane Petroleum = complex mixture of hydrocarbons Cracking= a controlled process by which hydrocarbons are broken down or rearranged into smaller, more useful molecules

  40. Functional Group • Chemically reactive part of an organic molecule • Learn these functional groups • R means the rest of the molecule (usually hydrocarbon

  41. The Common Functional Groups ClassGeneral Formula Halohydrocarbons RX Alcohols ROH Ethers ROR Aldehydes

  42. The Common Functional Groups ClassGeneral Formula Ketones Carboxylic Acids Esters Amines RNH2

  43. Halocarbons • Organic compounds containing F,Cl, Br, or I • Halogen groups are named as substituents just as alkyl groups are. Cl I I Cl-C-Cl CH3-CH-CH-CH3 H Cl-CH2-CH3CH3 bromobenzene 2,3-diiodobutane Trichloromethane (chloroform) chloromethane 1-chloropropane

  44. Alcohols Organic compounds with a hydroxyl group (-OH) Naming: drop “e”, add “-ol” Methanol Methyl alcohol “wood alcohol” Ethanol Ethyl alcohol “drinking alcohol”

  45. propanol propyl alcohol n-propanol 1-propanol 2-propanol isopropanol isopropyl alcohol “rubbing alcohol”

  46. Alcohols can be classified as primary, secondary or tertiary.

  47. antifreeze

  48. Glycerine 1,2,3-propantriol

  49. Phenol

  50. Properties of Alcohols • Hydrogen bonding • Short-chained alcohols are soluble in water Fermentation- production of ethanol from sugars by the action of yeast or bacteria C6H12O6 2CH3CH2OH + 2CO2 Denatured Alcohol- ethanol with an added substance to make it toxic

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