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Organic Chemistry

AP Notes Chapter 10. Organic Chemistry. Hydrocarbons. Alkanes and Cycloalkanes. Alkanes. Alkanes: hydrocarbons containing only carbon-carbon single bonds the first two alkanes are methane and ethane. Hydrocarbon: a compound composed of only carbon and hydrogen. Alkanes.

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Organic Chemistry

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  1. AP Notes Chapter 10 Organic Chemistry

  2. Hydrocarbons Alkanes and Cycloalkanes

  3. Alkanes • Alkanes: hydrocarbons containing only carbon-carbon single bonds • the first two alkanes are methane and ethane

  4. Hydrocarbon: a compound composed of only carbon and hydrogen

  5. Alkanes • the first 10 alkanes with unbranched chains Generic Alkane Formula: CnH2n+2

  6. Constitutional Isomerism Constitutional isomers:compounds that have the same molecular formula but different structural formulas (connected differently)

  7. Constitutional Isomerism

  8. Map of Organic Isomerization

  9. Nomenclature Example

  10. Cycloalkanes Cyclic hydrocarbon:a hydrocarbon that contains carbon atoms joined to form a ring

  11. Cycloalkanes

  12. Alkenes and Alkynes • Alkene: a hydrocarbon that contains one or more carbon-carbon double bonds • ethylene is the simplest alkene

  13. Alkenes and Alkynes • Alkyne: a hydrocarbon that contains one or more carbon-carbon triple bonds • acetylene is the simplest alkyne

  14. Alkenes • Cis-trans isomerism • because of restricted rotation about a carbon-carbon double bond, an alkene with two different groups on each carbon of the double bond shows cis-trans isomerism

  15. Benzene and its Derivatives

  16. Aromatic Compounds • Aromatic compound: a hydrocarbon that contains one or more benzene-like rings • arene: a term used to describe aromatic compounds • Ar-: a symbol for an aromatic group derived by removing an -H from an arene

  17. Kekulé structure for benzene (1872)

  18. The electrons of Benzene are Delocalized sp2 hybridized

  19. Nomenclature Example

  20. Functional Groups and Reactions of Organic Compounds

  21. Alkanes • They burn! • Hydrocarbon and Oxygen yields Carbon Dioxide and Water

  22. Reactions of Alkenes:ADDITION REACTIONS • Alkenes are unsaturated— more bonds can form to the C atoms • Molecules such as Br2, H2, HCl, HBr, and H2O add to the double bond

  23. An Addition Reaction Fat placed in Br2 vapor

  24. An Addition Reaction The fat in bacon is partially unsaturated. The fat adds Br2 to the C=C bonds.

  25. An Addition Reaction • Fats can be “hydrogenated” with H2. Saturated Fats Peanut butter has partially hydrogenated vegetable oil.

  26. C H 3 A l C l 3 + H C l + C H C l 3 Reactions of Aromatics • Substitutions — not additions — are typical. AlCl3 is a catalyst. Catalysts typically used in aromatic substitutions.

  27. Functional Groups See CD-ROM Screens 10.5 & 10.6

  28. Alcohols • Characterized by –OH group [R-OH • Name: add – ol to name of hydrocarbon Methanol Butanol

  29. Structures of Alcohols C3H5OH: how many structural isomers? Add -ol to name of 3-C hydrocarbon. Indicate position of OH with number.

  30. Alcohol Properties • Alcohols are a derivative of water • Many alcohols dissolve in water Methanol dissolves in water. Butanol is NOT soluble in water.

  31. “Sterno” • Alcohols burn in air • A mixture of ethanol + calcium acetate = STERNO

  32. Ethyleneglycol Propylene glycol GLYCOLSAlcohols with Two OH Groups

  33. Alcohol ReactionsScreen 11.6 Substitution Elimination

  34. C H O 1 O H O H H H H O H 2 4 H O H 4 O 5 5 H O H 3 H O H O 3 1 1 H 3 H O H O O H 4 H O H 2 H H O H 2 O H H O H H O H 5 H H C H O H b 2 - D - g l u c o s e a - D - g l u c o s e O p e n c h a i n f o r m Sugars: Related to Alcohols • Sugars are carbohydrates, compounds with the formula Cx(H2O)y.

  35. Amines Alcohols are derivatives of H2O (R–OH) and amines are derivatives of NH3. Trimethylamine Dimethylamine Methylamine

  36. Cadaverine Pyridine Amines Amines generally have terrible odors!

  37. + 2 - 2 C H N H ( a q ) + H S O ( a q ) 2 C H N H ( a q ) + S O ( a q ) 6 5 2 2 4 6 5 3 4 A n i l i n e A n i l i n i u m i o n Amines Amines, like NH3, are bases

  38. Amines Many natural products and drugs (such as nicotine and cocaine) are bases. Nicotine

  39. Structures of Aldehydes Odors from aldehydes and ketones Cinnamaldehyde

  40. carbonyl group

  41. H H methanal FORMALDEHYDE

  42. CH3CH2 H propanal

  43. R H an ALDEHYDE

  44. CH3 CH3 dimethylketone propanone ACETONE

  45. CH3 CH2CH2CH3 2-pentanone

  46. CH3CH2 CH2CH3 3-pentanone

  47. R R’ a KETONE

  48. Benzoic acid Acetic acid Carboxylic acid group with acidic H+ All are WEAK acids Carboxylic Acids Acids are found in many natural substances: bread, fruits, milk, wine

  49. Formic acid, HCO2H, gives the sting to ants. Carboxylic Acids

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