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Organic Chemistry Chapter 25

Organic Chemistry Chapter 25. Organic Chemistry. The chemistry of carbon compounds. Carbon has the ability to form long chains. Without this property, large biomolecules such as proteins, lipids, carbohydrates, and nucleic acids could not form. Structure of Carbon Compounds.

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Organic Chemistry Chapter 25

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  1. Organic ChemistryChapter 25

  2. Organic Chemistry • The chemistry of carbon compounds. • Carbon has the ability to form long chains. • Without this property, large biomolecules such as proteins, lipids, carbohydrates, and nucleic acids could not form.

  3. Structure of Carbon Compounds • There are three hybridization states and geometries found in organic compounds: • sp3Tetrahedral • sp2Trigonal planar • sp Linear

  4. Hydrocarbons • Four basic types: • Alkanes • Alkenes • Alkynes • Aromatic hydrocarbons

  5. Alkanes • Only single bonds. • Saturated hydrocarbons. • “Saturated” with hydrogens.

  6. Formulas • Lewis structures of alkanes look like this. • Also called structural formulas. • Often not convenient, though…

  7. Formulas …so more often condensed formulas are used.

  8. Properties of Alkanes • Only van der Waals force: London force. • Boiling point increases with length of chain.

  9. Structure of Alkanes • Carbons in alkanes sp3 hybrids. • Tetrahedral geometry. • 109.5° bond angles.

  10. Structure of Alkanes • Only -bonds in alkanes • Free rotation about C—C bonds.

  11. Isomers Have same molecular formulas, but atoms are bonded in different order.

  12. Organic Nomenclature • Three parts to a compound name: • Base: Tells how many carbons are in the longest continuous chain.

  13. Organic Nomenclature • Three parts to a compound name: • Base: Tells how many carbons are in the longest continuous chain. • Suffix: Tells what type of compound it is.

  14. Organic Nomenclature • Three parts to a compound name: • Base: Tells how many carbons are in the longest continuous chain. • Suffix: Tells what type of compound it is. • Prefix: Tells what groups are attached to chain.

  15. To Name a Compound… • Find the longest chain in the molecule. • Number the chain from the end nearest the first substituent encountered. • List the substituents as a prefix along with the number(s) of the carbon(s) to which they are attached.

  16. To Name a Compound… If there is more than one type of substituent in the molecule, list them alphabetically.

  17. Cycloalkanes • Carbon can also form ringed structures. • Five- and six-membered rings are most stable. • Can take on conformation in which angles are very close to tetrahedral angle. • Smaller rings are quite strained.

  18. Reactions of Alkanes • Rather unreactive due to presence of only C—C and C—H -bonds. • Therefore, great nonpolar solvents.

  19. Alkenes • Contain at least one carbon–carbon double bond. • Unsaturated. • Have fewer than maximum number of hydrogens.

  20. Structure of Alkenes • Unlike alkanes, alkenes cannot rotate freely about the double bond. • Side-to-side overlap makes this impossible without breaking -bond.

  21. Structure of Alkenes This creates geometric isomers, which differ from each other in the spatial arrangement of groups about the double bond.

  22. Properties of Alkenes Structure also affects physical properties of alkenes.

  23. Nomenclature of Alkenes • Chain numbered so double bond gets smallest possible number. • cis- alkenes have carbons in chain on same side of molecule. • trans- alkenes have carbons in chain on opposite side of molecule.

  24. Alkynes • Contain at least one carbon–carbon triple bond. • Carbons in triple bond sp-hybridized and have linear geometry. • Also unsaturated.

  25. Nomenclature of Alkynes 4-methyl-2-pentyne • Analogous to naming of alkenes. • Suffix is -yne rather than –ene.

  26. Functional Groups Term used to refer to parts of organic molecules where reactions tend to occur.

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