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CHEMISTRY II

6 12 C. CHEMISTRY II. Organic Chemistry The Chemistry of Carbon. It’s All About Carbon. Carbon is a unique element with the ability to bond to itself to form long chains that is the basis for all living things.

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CHEMISTRY II

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  1. 612C CHEMISTRY II Organic Chemistry The Chemistry of Carbon

  2. It’s All About Carbon • Carbon is a unique element with the ability to bond to itself to form long chains that is the basis for all living things. • Carbon with its sp3 hybrid orbital gives it the ability to form structured molecules that can combine with other elements. The most abundant of these is Hydrogen. This gives rise to Hydrocarbon chemistry or Organic Chemistry.

  3. Let’s Look a Hybrids H H H C2H4 C=C CH4 H -C- H H H H Methane General Formula and Structural Formula Ethene General and Structural Formula

  4. The Al’s • The three basic groups of hydrocarbons are • Alkanes – Single bonds between carbons with the general formula of CnH2n+2 • If n = 3 then the formula is C3H8 • Alkenes – Double bonds exist between at least two carbons. General formula CnH2n • If n = 3 then the formula is C3H6 • Alkynes – Triple bonds exist between at least two carbons. General formula CnH2n-2 • If n = 3 then the formula is C3H4

  5. Nomenclature • Prefixes for Hydrocarbons: • 1 – meth 8 - oct • 2 – eth 9 - non • 3 – prop 10 - dec • 4 – but 11 - undec • 5 – pent 12 - dodec • 6 – hex 13 - tridec • 7 – oct 14 – tetradec • We will start with the Alkanes - single bonds

  6. Let’s Explore! Methane is natural gas • The simplest Alkane is H | H -C- H | H Methane Meaning one carbon atom with all four bonds saturated with hydrogen's. The “meth” means one and the suffix “ane” means single bonds

  7. Others • Structures H H | | H-C--C-H Ethane | | H H H H H | | | H-C--C-C-H Propane | | | H H H CH3-CH3 Short hand method for ethane CH3-CH2-CH3 Short hand method for propane

  8. Let’s go a little longer • Butane has 4 carbon atoms and 10 Hydrogen’s C4H10 CH3-CH2-CH2-CH3 Butane But what about this? CH3 CH3-CH-CH3 This is a butane too but with a different structure. The same number of carbon’s and hydrogen’s but a different Structure is called an Isomer.

  9. Well, That Changes Things • In order to consistently name alkanes we need to define “Organic Groups” and establish some Rules. • GROUPS: All groups end in “yl” This x is where it -> is attached to another group x-CH3 One Carbon = meth. As a group it becomes methyl.

  10. And Again • So Name That Compound. CH3 CH3-CH-CH3 1 2 3 So Count the Carbon’s in the longest continuous chain There is 3 so it’s a propane. The methyl group is attached to the 2nd carbon. So the name is 2,methylpropane

  11. More Groups ☻ ☻ ☻ • -CH3 methyl • -CH2-CH3 ethyl • - CH2-CH2-CH3 n-propyl • CH3-CH2-CH3Iso-Propyl • -CH2-CH2-CH2-CH3 n-butyl • CH3-CH-CH2-CH3 sec-butyl • CH3-CH-CH3 tert-butyl • CH3 Indicates where group is attached ☻ ☻ ☻ ☻ ☻

  12. How About This? • Name That Compound • CH3 • CH3-CH2-CH-CH2-CH-CH2-CH3 • CH3-CH2-CH2-CH3 • Number the Longest continuous Chain from the end that gives the most complicated group the lowest number. • 2,4 Diethyloctane Ethyl Group Ethyl Group 1 4 3 2 5 6 7 8

  13. Seeing Double? • Alkenes have a double bond. When numbering start from the end that gives the double bond the lowest number. • CH3-CH2-CH=CH3 • When naming, identify the double bond by the number of the 1st carbon having it. The sufix becomes “ene.” • 1-butene 4 3 2 1

  14. Still Seeing Double • Name the following: Alkene CnH2n • CH3 • CH3-CH2-CH=CH-CH-CH3 • CH2 • CH • CH • CH3 Number the longest continuous chain with the most double bonds starting from the end that gives the first double bond the lowest number. Bonds get preference over groups. 7 6 5 9 8 4 3 2 1 5,8 – Dimethyl – 2,6 nonadiene

  15. Seeing in Triple • Alkynes: Triple Bonds • Double bonds are considered before triple bonds. • CH2=C-CH2-CH2-CH2-C C-CH=CH-CH3 • CH-CH3 • CH2 • CH3 1 9 10 2 3 4 5 6 7 8 = Number the longest continuous chain with the most double bonds including as many triple bonds as possible 2-Sec butyl-1,8-decadiene-6-yne

  16. ORGANIC GROUPS

  17. Functional Identity • 1. Alkyl Groups include Alkanes, Alkenes, and Alkynes. • 2. Cyclic hydrocarbons Cyclopentane H H H C H C C H H H H C C H H

  18. More, More! CH3 • Aromatic • Alcohol Methyl Benzene Ethanol CH3-CH2-OH R-OH R- Any alkyl group Isopropanol CH3-CH-CH3 OH

  19. More Groups • Ketone O O • R-C-R CH3-C-CH2-CH3 • Aldehyde O O • R-C-H CH3-C-H • Carboxylic Acid O O • R-C-OH CH3-C-OH Functional Group - Carboxyl Functional Group – Acid Group

  20. And Again • Alkyl Halide R-X where x = halogen • CH3-CH2-Br • Aryl Halide Ar-X (Aryl means an aromatic) • Glycol R-CH-CH-R CH2-CH2 • OH OH OH OH Cl Chlorobenzene Ethylene Glycol

  21. Continue OH OH OH • Phenol • Ester R – C – O – R • CH3-C-O-CH3 Ar - OH An Aromatic (benzene) can be represented in three ways O // O //

  22. Times 3 • Amine Primary Amine (10) • H • R-N-H • Secondary Amine (20) • H • R-N-R • Tertiary Amine (30) • R • R-N-R CH3-CH2-NH2 CH3-CH2-NH CH3 CH3 CH3-CH2-NH CH3

  23. Ether Ore • Ether Simple Ether • R-O-R • Ar-O-Ar • Mixed Ether • R-O-Ar CH3-O-CH3 -o- -O-CH3

  24. Lipids • Steroids: Cholesterol CH3 CH3 Cholesterol is the precursor to all steroids. Replace OH with=O and it becomes Testosterone. CH3 HO

  25. Triglycerides • Fats: Fatty Acids • H • H-C-O-C-CH3 • CH3-C-O-C-H • H-C-O-C-CH3 • H A Triglyceride is a tri-ester and the methyl groups can be any alkyl or aromatic group. O O O

  26. Carbo’s • Carbohydrates: Monosacchrides-Poly Glycocydic Bond CH2OH CH2OH CH2OH -D-glucose O O -D-fructose OH HO O OH OH OH OH Sucrose OH H2O -D-glucopryanosyl-1--D-fructofuranoside

  27. More Carbs • Polysaccharides: An Enzyme breaks the glycocidic bond. (Amylase) O O O O O O O O O Amylose (Starch) Humans cannot break the bonds in cellulose. O O O O O O O O O Cellulose

  28. Amino Acids • Amino Acids are the building blocks for proteins. • H • NH2-C-C-OH The “R” Group (Alkyl) • R (Ar) or (Aromatic) are the only • thing that is different in • the amino acid. O H NH2-C-C-OH CH3 O Alanine

  29. Let’s Join Hands  • Peptides Peptide chains can grow to make proteins. There are 20 natural amino acids and the order they are put together determines the kind of protein made. The order is controlled by DNA. HOH H NH2-C-C-OH CH3 H H N-C-C-OH H CH3 O O   Peptide bond Alanine Phenylalanine

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