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Introduction to: Organic Chemistry

Introduction to: Organic Chemistry. H. H-C-H. H. Definition of Hydrocarbon. Compounds composed mainly of Carbon and Hydrogen. Carbon takes on a -4 charge with Hydrogen being a +4. Methane. H. H. H. H. H. H. H. H. H-C-C-C-C-C-C-C-C-H

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Introduction to: Organic Chemistry

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  1. Introduction to: Organic Chemistry

  2. H H-C-H H Definition of Hydrocarbon..... Compounds composed mainly of Carbon and Hydrogen. Carbon takes on a -4 charge with Hydrogen being a +4. Methane

  3. H H H H H H H H H-C-C-C-C-C-C-C-C-H H H H H H H H H Carbon can chemical bond with another Carbon, which is a very unusual capability! Carbon can make long chains of carbon atoms “hooked” together.

  4. Carbon has an s2p2 electron configuration and can accomplish four bonds.

  5. Carbon Chains are found in nature in many different arrangements Some are straight chains H H H H H- C - C - C - C - H H H H H Some are BRANCHED….. H H H H - C - C - C - H C H H H H A branch

  6. H H H H C C C C C C H H H H H H H H Some are in rings…….

  7. C C C C C C Hydrocarbon's Are NAMED by the type of bond between the Carbons: Carbons can share MULTIPLE number of electrons BETWEEN each atom DOUBLE BOND Single Bond Triple Bond

  8. HYDROCARBON CLASSIFICATIONS

  9. Hydrocarbon Classifications Hydrocarbons Aliphatic : Aromatic Benzene 1. Alkanes 2. Cycloalkanes 3. Alkenes 4. Alkynes “Chain” compounds “Ringed” compounds

  10. Alkanes Straight and Branched carbons with ONLY single bonds between the carbons. *Named with prefixes and suffixes Suffix name = ane (ending) Prefix name

  11. Alkanes Prefixes : 1 carbon meth 8 carbons oct 2 carbons eth 9 carbons non 3 carbons prop 10 carbons dec 4 carbons but 5 carbons pent 6 carbons hex 7 carbons hept

  12. Alkanes So ….. Methane is Ethane is Propane is

  13. Cycloalkanes Carbon compounds with single bonds that are arranged in a circle (cycle). H H H - C C -H H - C C -H H H Cyclobutane

  14. Alkenes Carbon compounds with a double bond between one or more carbons. H H - C = C - C - H H H H Propene

  15. Write Structure for: 2-pentene 2,3-pentadiene

  16. Naming Hints Count from either left or right of compound, that will give the double bond the LOWEST number. Assign number to the double bond. Place numbers in front of compound name, separating using commas. Place a hyphen between numbers and name. Add a numerical prefix BEFORE the ending suffix.

  17. Alkynes Carbon compounds with a triple bond! H H - C = C - C- H H Propyne

  18. Draw Structure for 2-pentyne 1,3-hexadiyne

  19. H C H - C C - H H - C C - H C H Aromatic Hydrocarbons “ringed” hydrocarbons that MUST contain alternating double bonds Not named with prefixes! BENZENE

  20. Aromatic Hydrocarbons Most of the time, the letters are not written in aromatic structures: A carbon is present at each point BENZENE

  21. Aromatic Hydrocarbons Alternating double bonds form SPECIAL arrangements called a PI bond. That is written as a circle…... BENZENE BENZENE

  22. Aromatic Hydrocarbons Two “benzenes” stuck together is a different compound Naphthalene

  23. Nomenclature The way to name a hydrocarbon

  24. Steps to naming a carbon compound: 1. Find the longest chain of connected Carbons! 2. Decide on the prefix by the carbon # 3. Decide the suffix by looking at the kind of bonds between the carbons • Circle any branches or • special groups

  25. 5. Name each branch, separately. Add -yl to ending of prefix. One carbon in branch = methyl prefix 6. Place the branch names IN FRONT of the prefix, having the least complex written FIRST !!!!! 7. Assign numbers to the branches, having the lowest total possible.

  26. Writing and Naming Isomers!

  27. Isomers are hydrocarbon compounds that have the SAME empirical formula but DIFFERENT structures!

  28. C-C-C C Easiest Isomer is Butane and iso-butane (isomer of butane) C-C-C-C Butane ( no H’s) C4H10 Methylpropane or Iso-butane C4H10

  29. There may be several isomers that can be written for one formula! Try writing some isomers for pentane……….

  30. C5H12 C-C-C-C-C-C Pentane C-C-C-C C C5H12 methylbutane C C-C-C C Dimethylpropane C5H12

  31. What are these structures isomers of ? C-C-C-C-C-C C C Octane C C C C-C-C-C-C-C-C Decane

  32. Special Types of Hydrocarbons

  33. A. Hydrocarbons with a Halogen ( family 17) B. Hydrocarbons with Oxygen: 1. Alcohols 2. Ethers 3. Aldehydes 4. Ketones 5. Acids 6. Esters

  34. C. Hydrocarbons with Nitrogen: 1. Amines 2. Amides 3. Amino Acids 4. Nitriles 5. Nitro compounds

  35. H Cl-C-Cl Cl H H-C-Br H H H-C-H H Hydrocarbons with Halogens Remove a hydrogen and replace it with chlorine, flourine, iodine or bromine. bromomethane methane Trichloromethane

  36. Oxygen Hydrocarbons Alcohols General Formula = R-OH NOT a Base! OH is a hydroxyl group, not a Hydroxide group. The Hydrogen gets removed only by strong metals. Alcohols with 1,2, and 3 Carbons dissolve in water, others do NOT.

  37. Oxygen Hydrocarbons Alcohols Suffix =- ol CH3OH Methanol CH3CH2OH Ethanol

  38. Oxygen Hydrocarbons Ethers Gen. Formula = R - O - R Suffix = - oxy CH3OCH2CH3 methoxyethane CH3CH2OCH2CH2CH3 ethoxypropane

  39. Oxygen Hydrocarbons Aldehydes Gen. Formula = O = Suffix = - al R- C - H O = Propanal CH3CH2C - H 3 carbons, single bonds!

  40. O = CH3CH2CCH2CH3 Oxygen Hydrocarbons Ketones Gen. Formula = R - C - R O = Suffix = - one 3-Pentanone O 2-pentanone = CH3CH2CH2CCH3

  41. Oxygen Hydrocarbons Organic Acid Gen. Formula = O = R - C- O - H Suffix = - noic acid Propanoic acid CH3CH2COOH CH3CH2CH2CH2COOH Pentanoic Acid

  42. Oxygen Hydrocarbons Esters O Gen. Formula = = R - C - O - R Suffix = - yl & -oate Name the two R groups with separate words CH3CH2COOCH3 Propyl methanoate

  43. CH3CHCH3 _ Nitrogen Hydrocarbons Amines Gen. Formula = R - NH2 Suffix = amine CH3CH2CH2NH2 Propanamine NH2 2- propanamine

  44. Nitrogen Hydrocarbons Amides Gen. Formula = O = R - C - NH2 Suffix = amide Butanamide CH3CH2CH2CONH2

  45. Nitrogen Hydrocarbons Amino Acids NH2 - Gen. Formula = R(or G) - CH - COOH Suffix = amino & noic CH3CH2CH(NH2)COOH 2-aminobutanoic Acid (NH2) means attached on top of previous carbon

  46. Nitrogen Hydrocarbons Nitriles _ R - C = N Gen. Formula = nitrile Suffix = CH3CH2CN Propanenitrile

  47. Nitrogen Hydrocarbons Nitro Compounds Gen. Formula = R - NO2 Prefix = Nitro Nitromethane CH3NO2 2-nitrobutane CH3CH2CH(NO2)CH3

  48. Benzene group Also called Phenyl group! OH Phenol

  49. When is benzene labeled like a branch? When you can’t name the “attachment” as one branch…… it has too many other items…..

  50. Cl Br C – C – C – C – C C C C 3-bromo-2-chloro-3-ethyl-2-methyl-1-phenylpentane

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