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Introduction to Organic Chemistry

Introduction to Organic Chemistry. Ritalin. methyl 2-phenyl-2-piperidin-2-ylacetate. Common Elements in Organic Compounds. 24.1. Classification of Hydrocarbons. 24.1. Classification of Hydrocarbons. Aromatic: a hydrocarbon that contains one or more benzene rings. 24.1.

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Introduction to Organic Chemistry

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  1. Introduction to Organic Chemistry Ritalin methyl 2-phenyl-2-piperidin-2-ylacetate

  2. Common Elements in Organic Compounds 24.1

  3. Classification of Hydrocarbons 24.1

  4. Classification of Hydrocarbons Aromatic: a hydrocarbon that contains one or more benzene rings. 24.1

  5. Classification of Hydrocarbons Aliphatic: Relating to organic compounds in which carbon atoms DON’T HAVE BENZENE RINGS 24.1

  6. Alkaneshave the general formula CnH2n+2where n = 1,2,3,… • alkanes haveonly single covalent bonds • alkanes are called saturated hydrocarbons because they contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms in the molecule. (unsaturated hydrocarbons = alkenes & alkynes) CH4 C2H6 C3H8 methane ethane propane 24.2

  7. Alkane Nomenclature – Counting to Ten 1 Meth 2 Eth 3 Prop 4 But 5 Pent 6 Hex 7 Hept 8 Oct 9 Non 10 Dec

  8. Structural isomers are molecules that have the same molecular formula but different structures 24.2

  9. H H H H H C C C C C H H H CH3 H H H H H H C C C H H H CH3 H H H H CH3 C C C C H H H H H H How many structural isomers does pentane, C5H12, have? n-pentane 2,2-dimethylpropane 2-methylbutane 24.2

  10. CH3 CH2 CH2 CH CH2 CH2 CH3 CH3 Alkane Nomenclature • The parent name of the hydrocarbon is that given to the longest continuous chain of carbon atoms in the molecule.(Carbon backbone) 4-methylheptane 1 2 3 4 5 6 7 • An alkane less one hydrogen atom is an alkyl group. methane CH4 CH3 methyl 24.2

  11. Alkane Nomenclature Names of Common Substituent Groups Functional Group Name -F fluoro -Cl chloro -Br bromo -I iodo -NO2 nitro -OH hydroxyl (alcohol) -CH3 methyl -CH2CH3 ethyl -CH2CH2CH3 propyl -CH2CH2CH2CH3 butyl -NH2 amine -N=O amide

  12. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations (locants) of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locants of the branches. CH3 CH CH2 CH2 CH3 CH3 CH3 CH2 CH2 CH CH3 CH3 1 2 3 4 5 2-methylpentane 1 2 3 4 5 4-methylpentane 24.2

  13. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations (locants) of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locants of the branches. CH3 CH CH2 CH2 CH3 CH3 CH3 CH2 CH2 CH CH3 CH3 1 2 3 4 5 2-methylpentane 5 2 1 4 3 2-methylpentane 24.2

  14. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations (locants) of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locants of the branches. CH3 CH CH2 CH2 CH3 CH3 CH3 CH2 CH2 CH CH3 CH3 1 2 3 4 5 2-methylpentane 1 2 3 4 5 4-methylpentane 24.2

  15. CH3 CH3 CH CH CH2 CH2 CH3 CH3 1 2 3 4 5 6 CH3 CH2 C CH2 CH2 CH3 CH3 1 2 4 5 6 3 CH3 Alkane Nomenclature • Use prefixes di-, tri-, tetra-, when there is more than one alkyl branch of the same kind. 2,3-dimethylhexane Prefixes: di means double tri means triple tetra means quadruple 3,3-dimethylhexane 24.2

  16. Br Cl CH CH CH3 CH3 1 2 3 4 Br F CH2 CH CH3 CH2 1 2 3 4 Alkane Nomenclature • Use previous rules for other types of substituents. Names of Common Substituent Groups Functional Group Name -F fluoro -Cl chloro -Br bromo -I iodo -NO2 nitro 2-bromo-3-chlorobutane 1-bromo-3-fluorobutane 24.2

  17. CH3 CH2CH3 CH CH2 CH CH2 CH2 CH2 CH3 CH3 What is the structure of 2-chloro-4-methylhexane? Cl CH3 CH CH2 CH CH2 CH3 CH3 What is the IUPAC name of the following compound? methyl branch ethyl branch 1 2 3 4 5 6 7 8 …octane 4-ethyl-2-methyloctane Yes, the groups (branches) need to be listed alphabetical! 1 2 3 4 5 6 24.2

  18. Summary of rules for naming a basic alkane: • Assign a parent name based upon the longest continuous Carbon chain.(Find the longest C chain) • Assign location numbers (called locants) to all of the groups. Count along the parent chain in both directions: use the version that yields the lowest starting locant for the first branch. • Identify and name the branches coming off the parent chain. • Have same groups in different places? Use prefixes. (di for two, tri for three, or tetra for four) • Shove it all together alphabetically using commas and dashes!

  19. Now build n-heptane

  20. Draw the line angle formulas for: pentane butane decane hexane

  21. Practice Makes Perfect! Build this model (one model per table group), and write down the name. CH3 CH3 CH2 CH CH CH CH3 CH3 Br This drawing is called the condensed structuralformula 6 5 4 3 2 1 Locants 3-bromo-2,4-dimethylhexane

  22. This drawing is called the condensed structuralformula CH3 CH3 CH2 CH CH CH CH3 CH3 6 5 4 3 2 1 Locants The “complete structuralformula” shows all the H bonds too. Br 3-bromo-2,4-dimethylhexane This drawing is called The line-angleformula (aka the skeletal structure) Br 1 3 5 2 6 4 3-bromo-2,4-dimethylhexane Hold up your model and position it so that it looks like the line-angle formula. Do you see why it is drawn like this now?

  23. Build this model then name it. CH3 9 8 7 6 5 4 3 2 1 Locants Br Br 5,6-dibromo-7-chloro-4-ethyl-2-methylnonane Cl

  24. Draw 2-bromo-4-ethyl-3-methylheptane Draw 1-chloro-4,4-diethyloctane See white board for answers

  25. As I stamp your homework, build mirror images of these models: Part 1) CH2BrCl Part 2) CHBrClF We will use these to discuss chirality.

  26. Isomers of heptane • Heptane • 2-Methylhexane • 3-Methylhexane • 2,2-Dimethylpentane • 2,3-Dimethylpentane • 2,4-Dimethylpentane • 3,3-Dimethylpentane • 3-Ethylpentane • 2,2,3-Trimethylbutane • Please put poster on middle lab table CH2BrCl CHBrClF I NEED 2 of each built

  27. CH2BrCl Optical Isomers CHBrClF achiral Chiral (Handedness) 24.2

  28. not notsuperimposable on its mirror image notsuperimposable on its mirror image video Achiral (NOT Handedness) Chiral (Handedness) 24.2

  29. In the 1960’s, a drug called thalidomide was widely prescribed in the Western Europe to alleviate morning sickness in pregnant women. causes birth defects effective medication

  30. Alkanes whose carbon atoms are joined in rings are called cycloalkanes. They have the general formula CnH2n where n = 3,4,… 24.2

  31. Alkenes have the general formula CnH2n • contain at least one carbon-carbon double bond CH CH CH3 CH3 CH CH2 CH3 CH2 Cl Cl Cl H C C C C H H Cl H 1-butene 2-butene cis-dichloroethene trans-dichloroethene 24.2

  32. CH2 CH2 CH CH3 CH3 CH3 CH2 CH CH CH CH2 CH2 CH CH2 CH2 CH3 CH3 CH2 1-hexene 2-hexene 2-hexene

  33. Alkyneshave the general formula CnH2n-2 • contain at least one carbon-carbon triple bond C CH2 CH3 CH C C CH3 CH3 1-butyne 2-butyne 24.2

  34. H H C H H C H H C C C C C C C C H H C H H C H H Aromatic Hydrocarbons 24.3

  35. 1 6 2 5 3 4 Aromatic Compound Nomenclature 1- Number the benzene ring in the way that provides the lowest numbering system. 2- Identify the groups on benzene. If only one group is present, a number is not required (it is assumed to be located at #1) 3- Follow all naming rules for alkanes.

  36. CH2CH3 Cl NH2 NO2 Br Br Br Br Br 1 6 2 Br 5 3 4 Aromatic Compound Nomenclature aminobenzene ethylbenzene nitrobenzene chlorobenzene Br 1,2-dibromobenzene 1,2,4-tribromobenzene 1,3-dibromobenzene 24.3

  37. Model naming practice

  38. Organic Chemistry:Other Functional Groups

  39. Functional groups • Functional groups are parts of molecules that result in characteristic features • About 100 functional groups exist, we will focus on about 10

  40. 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

  41. Alcohols contain the hydroxyl functional group and have the general formula R-OH. OH or HO is stuck onto a Carbon chain of some sort. “R” means the Rest of the compound in that direction. 24.4

  42. Alcohols – OH replaces an a H R-OH • R group = CH3, C2H5 , C3H7 , etc. (some sort of carbon chain/ring) • Which compound shown is an alcohol ?

  43. How Do You Name Alcohols ? • Count the carbons and write the alkane name it would be then drop the “e” and replace with “ol” • Name the following: • Ethane • Ethanol Ethanol • Name the following: Propanol

  44. How Do You Name Alcohols ? • Special Note: If the OH is not on an end carbon, you must identify the locant of the carbon before the name. 2-Propanol 2-Butanol

  45. H2SO4 CH3OH + HOCH3 CH3OCH3 + H2O catalyst Ethers have the general formula R-O-R’. Condensation Reaction (not on exam) 24.4

  46. Ethers – a bad smelling compound, used to put people to sleep. General formula: ROR' Example: -O- is in the middle of carbon chain (breaks up the chain of C’s) Naming: Name the groups on each end (O is the middle) and add “ether“. If the same group appears twice use di in front of name. Dimethyl ether

  47. Using ethers on someone is a CRIME! You better pray for ROR.

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