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CHAPTER 25 - CARBON AND ITS COMPOUNDS

CHAPTER 25 - CARBON AND ITS COMPOUNDS . Organic - pertaining to life Living or was once living Organic Chemistry - The chemistry of carbon compounds Carbon is well suited for life because it is the most versatile element in terms of bonding. Carbon can form four bonds.

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CHAPTER 25 - CARBON AND ITS COMPOUNDS

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  1. CHAPTER 25 - CARBON AND ITS COMPOUNDS

  2. Organic - pertaining to life • Living or was once living • Organic Chemistry - The chemistry of carbon compounds • Carbon is well suited for life because it is the most versatile element in terms of bonding.

  3. Carbon can form four bonds. • They can be single, double or triple bonds. • Carbon will not form diatomic molecules like other small atoms do. • It can form long carbon chains containing strong, short, covalent bonds.

  4. Allotropes • forms of the same element that differ in their bonding • There are several allotropes of carbon • Diamond – tetrahedral network of carbon atoms (every atom is locked into place (hardness) • Graphite – sheets can slide over each other (lubricant)

  5. Amorphous carbon – charcoal, soot, coke • Amorphous has not set arrangement of atoms. It has irregular patterns of high surface area, deep “caves” that can trap other molecules • Fullerenes – spherical molecules (60 atoms) see page 807, mostly experimental at this point.

  6. Hydrocarbons • molecules that contain only hydrogen and carbon

  7. Fossil Fuels • Natural gas - mostly methane • Crude oil - mixture of hydrocarbon chains from propane to butane, octane and longer Components separated using fractional distillation (see page 823) • Coal - mostly impure carbon (coke - pure carbon from coal, charcoal - pure carbon from wood)

  8. Types of Formulas (examples) Compound - hexane • Empirical formula • Molecular formula • Structural formula • Condensed structural formula

  9. CLASSIFICATION OF ORGANIC COMPOUNDS • ALKANES - Compounds that contain only hydrogen and single bonded carbons. (carbon chains surrounded by hydrogens) • Named with an ane ending that is preceded with a prefix which gives how many carbons that are in the carbon chain. • Memorize the IUPAC prefixes on page 816

  10. BRANCHED ALKANES • Give the name of the branch with a yl ending. • Indicate the number of the branch (keep numbers as low as possible). • Examples: • Problem assignment # 1 (first side of sheet)

  11. ALKANES SUBSTITUDED WITH HALOGENS • Give the position of the halogen (F, Cl, Br, or I) and then give the name of the halogen with an "o" ending. • 3-chloro-2-methylpentane • bromochloroiodomethane

  12. Conformational isomers - molecules with the same structure but with different bond rotation. • Molecules with single bonds can rotate about the single bond. • These are the same compound. They have the same melting point, the same boiling points and the same chemistry. • The higher the temperature the faster they change back and forth from one form to the other. • Example: cyclohexane (chair and boat conformation)

  13. http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch03/ch3-06.htmlhttp://www.chem.ucalgary.ca/courses/351/Carey5th/Ch03/ch3-06.html

  14. Structural isomers - molecules that have the same molecular formula but have different structural formulas. • These are different compounds with different melting points and different chemistry • Examples C5H12 (pentane, 1 methyl butane, 2,2 dimethyl propane)

  15. SUBSTITUTED ALKANES • Fisher Projection - a way to show the 3-dementional character of a molecule. • Examples: CHFClI • A carbon that has 4 different groups bonded to it is called a chiral carbon. • Enantiomers - (mirror image isomers) - two arrangements around a chiral carbon that cannot be rotated in such a way as to be superimposed on each other.

  16. They are different molecules that have the same formula, same boiling points and much of the same chemistry. • Their chemistry differs when they are reacting with molecules that also have chiral carbons. (biological systems) • They also rotate polarized light in opposite directions. • Vitamin C is an example of this type of molecule.

  17. UNSATURATED HYDROCARBONS • If the molecule is filled to capacity with hydrogen the compound is saturated (alkanes). • If the molecule is cyclic, contains a double bond or contains a triple bond it is unsaturated. • Saturated fats are from animals and are not good for you. • Unsaturated fats are from plants.

  18. Alkenes - contains a double bond. • Alkynes - contains a triple bond. • Use the same prefixes along with a number to give the position of the double or triple bond. • Example: 1 propene, 1 propyne, 3 chloro 1 butene, 3 chloro 1 butyne

  19. Hybridization and resonance • A double bonded carbon has 3 groups around it (sp2 hybridization) • Two of the p orbitals combine with the s orbital to form three sp2 hybrid orbitals. • The remaining p orbital is left unchanged and lies perpendicular to the flat molecule. • The overlap of the p orbitals forms a pi bond. • Sigma bond is the direct overlap of hybrid orbitals

  20. http://www.mhhe.com/physsci/chemistry/animations/chang_7e_esp/bom5s2_6.swfhttp://www.mhhe.com/physsci/chemistry/animations/chang_7e_esp/bom5s2_6.swf • Resonance is when several pi bonds lie in the same plane and all overlap • A pattern of alternating single and double bonds results in resonance. • Examples: 1,3 pentadiene, benzene (1,3,5 cyclohexatriene)

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