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Learning Objectives Chapter 11-15

Learning Objectives Chapter 11-15. Difference between organic and inorganic molecules Name characteristic features of organic compounds Draw organic compounds, including skeletal structures Identify common bond types, angles, and molecule shapes Name functional groups

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Learning Objectives Chapter 11-15

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  1. Learning Objectives Chapter 11-15 • Difference between organic and inorganic molecules • Name characteristic features of organic compounds • Draw organic compounds, including skeletal structures • Identify common bond types, angles, and molecule shapes • Name functional groups • Understand polarity and its effect on solubility and boiling point • Explain the difference between fat and water soluble vitamins • Describe alkane characteristics • Draw alkanes as full, condensed, and skeletal structures • Bond angle around alkane carbons • Draw constitutional isomers and ID longest carbon chain • ID 1°, 2°, 3°, 4° carbons • Name simple alkanes and cycloalkanes • Predict products of combustion & balance reaction equations • Identify unsaturated hydrocarbons: alkenes, alkynes, aromatic compounds • Alkene, Alkyne, Aromatic nomenclature • Stereoisomers • Addition Reactions • Polymers • Substitution Reactions • Name organic compounds with carbon-heteroatom single bonds (oxygen, halogens, sulfur) • Identify 1°, 2°, 3° alcohols and alkyl halides • Predict the products or reactants for following reactions: • Alcohol dehydration • Alcohol oxidation • Sulfur oxidation • Sulfur reduction • Understand the difference between Chiral and Achiral molecules • Identify chiral centers • Draw the enantiomers & diastereomers of a chiral molecule (using dashes & wedges to show geometry) • Draw fischer projections of chiral molecules • Explain the relevance of chiral centers in Biochemistry

  2. BONDING: Lewis Bond Theory strategy to tackle problems NH3 Start with the least electronegative element as the central element Surround the central element with the bonding elements and indicate their initial electrons Add extra electrons, from surrounding atoms, to the central atom to satisfy the octet rule Use multiple bonds if necessary   H N H      H     N H H     H   N H H H

  3. BONDING: Lewis Bond Theory strategy to tackle problems H    H  N  NH3   Initial electron bookkeeping: Find the difference, this is the number of electrons that must be shared ÷ 2 to know the # of bonds shared Arrange atoms around the most electronegative element Final electron bookkeeping: H  Need: 3x(1H x 2 e-) + (1N x 8 e-) = 14 e- Have: 3x(1H x 1 e-) + (1N x 5 e-) = 8 e- (14 e-) – (8 e-) = 6 e- (6 e-) ÷ 2 = 3 bonds      N H H  N H H     H H

  4. Drawing Chemical Structures .. Lewis Dot Structures Structural Formula or Complete Structure Structural Formula or Complete Structure with Geometry Indicated Condensed Structure Skeletal Structure H H H H H C C C C H H H H H H H H C C H C C H H H CH3CH2CH2=CH2

  5. Alkanes Longest Carbon Chain 1 2 1 1 3 3 4 2 2 4 5 3 5 6 4 6 7 5 Longest Carbon Chain Smith. General Organic & Biolocial Chemistry 2nd Ed.

  6. Alkanes 1°, 2°, 3°, 4° R H R R C C C C H R H R R R R R H H H R 1° 2° 3° 4° R = a Carbon atom Smith. General Organic & Biolocial Chemistry 2nd Ed.

  7. Alcohols & Alkyl Halides 1°, 2°, 3°

  8. ISOMERS Same chemical formula Stereoisomers Spatial Isomers Constitutional Isomers Structural Isomers Different connectivity between atoms Different spatial arrangement of atoms but with the same connectivity Enantiomers Diastereomers Mirror images of a chiral molecule that are not superimposable All stereoisomers that are not mirror images of one another Cis/Trans Isomers Conformational Isomers Rotation around C-C single bonds R R R R

  9. Functional Groups Overview Alkane Alkene Alkyne Aromatic C − C C = C C = C Hydrocarbon Functional Groups Smith. General Organic & Biolocial Chemistry 2nd Ed.

  10. Functional Groups Overview Alkyl halides Alcohols Ethers Amines Thiols Single Bond to a Heteroatom Functional Groups Smith. General Organic & Biolocial Chemistry 2nd Ed.

  11. Functional Groups Overview Aldehydes Carboxylic Acids Esters Ketones Amides Carbonyl Functional Groups Smith. General Organic & Biolocial Chemistry 2nd Ed.

  12. Nomenclature Alkanes 6 4 2 3 5 1 + + prefix parent suffix What, where are the substituents? Example: 2,4- dimethyl prefix How many carbons in longest chain? Example: hex parent What is the functional group? Example: ane suffix 2,4-dimethylhexane Smith. General Organic & Biolocial Chemistry 2nd Ed.

  13. Nomenclature Cycloalkanes 6 5 1 4 2 3 + cyclo- prefix + suffix + parent What, where are the substituents? Example: 1,3- dimethyl prefix How many carbons in the ring? Example: hex parent What is the functional group? Example: ane suffix 1,3-dimethylcyclohexane Smith. General Organic & Biolocial Chemistry 2nd Ed.

  14. Nomenclature Alkenes & Alkynes 6 4 2 3 5 1 + + prefix parent suffix First give location and type of substituents Second give location of double bond prefix How many carbons in longest chain? parent How many of the functional group and what is it? Alkene = ene; Alkyne = yne suffix 2,4-dimethyl 1,5- hexa diene * Note: when we have more then 1 multiple bond the parent name has an “a” added on: hexa instead of hex Smith. General Organic & Biolocial Chemistry 2nd Ed.

  15. Nomenclature Alkenes & Alkynes 1 3 2 4 5 + + prefix parent suffix First give location and type of substituents Second give location of double bond prefix How many carbons in longest chain? parent How many of the functional group and what is it? Alkene = ene; Alkyne = yne suffix 4-methyl 2- pent yne Smith. General Organic & Biolocial Chemistry 2nd Ed.

  16. Nomenclature Cyclo Alkenes & Alkynes 4 5 3 2 1 + + prefix parent suffix First give location and type of substituents Second give location of double bond prefix How many carbons in longest chain? parent How many of the functional group and what is it? Alkene = ene; Alkyne = yne suffix cyclo pent ene 3-methyl 1- Smith. General Organic & Biolocial Chemistry 2nd Ed.

  17. Nomenclature Aromatics: Benzene 5 6 o - m - p - 1 2 4 3 + prefix parent Give location, number, and type of substituent. You can also replace location & number with o, m, p prefix parent “Benzene” Polysubstituted Benzenes: Number to give lowest #s around ring Alphabetize substituents If part of common root name the molecule as a derivative of a monosubstituted benzene with common root at C1. 1,2-dimethyl benzene o-dimethyl benzene Smith. General Organic & Biolocial Chemistry 2nd Ed.

  18. Nomenclature Alcohols OH 6 4 2 3 5 1 + + prefix parent suffix First give location and type of substituents Second give location of double bond prefix How many carbons in longest chain? parent How many of the functional group and what is it? Alcohol = “ol” suffix 2-methyl 4- hexan ol *Note: after the greek root of the parent use “an”, iehexan * Second Note: when we have more then 1 multiple bond the parent name has an “a” after the greek root: hexa Smith. General Organic & Biolocial Chemistry 2nd Ed.

  19. Nomenclature Ethers 1 4 2 O 3 + + prefix parent suffix Use alkyl substitutant naming roots, but drop the “yl” and use “oxy” for the simplest alkyl group bonded to the ether oxygen. prefix parent How many carbons in longest chain? suffix Use alkane ending: ane 2-ethoxy but ane Smith. General Organic & Biolocial Chemistry 2nd Ed.

  20. Nomenclature Thiols SH 2 4 5 3 1 + + prefix parent suffix Give location and type of substituents, then give location of thiolgroup. prefix How many carbons in longest chain? parent Hydrocarbon functional group suffix + “thiol” suffix 2,4-dimethyl 1- pent anethiol Smith. General Organic & Biolocial Chemistry 2nd Ed.

  21. Nomenclature Alkyl Halides 1 2 6 4 Cl 3 5 + + prefix parent suffix Give location and type of substituents. Replace “ine” in halide name with “o”, ie Chlorine = chloro prefix parent How many carbons in longest chain? What is the hydrocarbon functional group? If alkane then “ane” suffix suffix 2-chloro 4-methyl hex ane Smith. General Organic & Biolocial Chemistry 2nd Ed.

  22. Properties of Organics Solubility LIKE DISSOLVES LIKE polar molecules dissolve in polar solvents nonpolar molecules dissolve in nonpolar solvents Polar Solvents Water: H2O Methanol: CH3OH Ethanol: CH3CH2OH Acetone: (CH3)2CO Acetic Acid: CH3CO2H Ammonia: NH3 Acetonitrile: CH3CN Nonpolar Solvents Pentane: C5H12 Hexane: C6H14 Cyclohexane: C6H12 Benzene: C6H6 Toluene: CH3C6H5 Smith. General Organic & Biolocial Chemistry 2nd Ed.

  23. Alkanes Combustion Complete Combustion heat + CH4 + 2O2 CO2 + 2H2O Incomplete Combustion heat + 2CH4 + 3O2 2CO + 4H2O Smith. General Organic & Biolocial Chemistry 2nd Ed.

  24. Alkene Reactions Addition H H H2 Metal catalyst Hydrogenation X X X2 X = Cl or Br Halogenation X H HX X = Cl or Br Hydrohalogenation H2O H2SO4 Hydration H OH

  25. Alkene Reactions Addition H H H2 Metal catalyst Hydrogenation X X X2 X = Cl or Br Halogenation X Markovnikov Rule: The major product in addition rxns is the molecule with the heteroatom bonded to the carbon with the most other groups bonded to it. H HX X = Cl or Br Hydrohalogenation H2O H2SO4 Hydration H OH

  26. Aromatic Reactions Substitution Cl Cl2 Clorination H NO2 HNO3 H2SO4 Nitration SO3H SO3 H2SO4 Sulfonation

  27. Rxns of Alcohols Elimination Reaction: Dehydration Zaitsev Rule: The major product in elimination is the alkene that has more alkyl groups bonded to it.

  28. Rxns of Alcohols Oxidations Oxidation requires breaking C-H bonds and forming new C-O bonds. When alcohol is the starting material the products always have a carbonyl group.

  29. Rxns of Thiols Oxidation & Reduction

  30. Stereo- isomers Chiral & Achiral For CHBrClF: CHIRAL Draw the molecule in 3 dimensions. Draw its mirror image. Try to align all bonds and atoms. Smith. General Organic & Biological Chemistry 2nd Ed.

  31. Chiral Molecules Fischer Projections A Fischer Projection takes a 3D tetrahedral shape, and re-draws it: Smith. General Organic & Biological Chemistry 2nd Ed.

  32. Stereo- isomers Multiple Chiral Centers chemwiki.ucdavis.edu

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