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VII. Organic

Organic Chemistry deals with carbon molecules attached to hydrogen and other elements. This discipline studies the properties and behavior of organic compounds, such as their low melting points, nonpolar nature, and slow reactivity. This knowledge is useful in various industries and fields.

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VII. Organic

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  1. VII. Organic

  2. What does organic chemistry have to do with my life?

  3. Organic Chemistry deals with carbon molecules attached to hydrogen and other elements.

  4. Properties of Organic Compounds • Low melting points and boiling points. Longer chains have higher melting and boiling points • Nonpolar (vdw forces) • React Slowly • Poor conductors of heat & electricity except for organic acids

  5. It can form up to 4 covalent bonds with other carbon atoms and make single double or triple bonds with itself.

  6. Each line represents a covalent bond - a shared pair of electrons. A structural formula show the way the atoms are arranged. • Methane Ethane H H H H C H H C C H H H H

  7. The double bonds makes this hydrocarbon an alkene The triple bonds makes this hydrocarbon an alkyne A structural formulas show the way the atoms are arranged. • propene H H H C C C H H H • ethyne H C C H

  8. Chemical or Molecular Formulas Tell the kind & number of atoms in a molecule.

  9. Hydrocarbons Compounds containing only carbon & hydrogen

  10. Saturated hydrocarbon Hydrocarbon containing only single carbon-carbon bonds

  11. Unsaturated hydrocarbon Hydrocarbon containing at least 1 double or triple carbon-carbon bond

  12. Homologous Series A group of related compounds in which each member differs from the one before it by the same additional unit. Properties vary in a predictable way.

  13. Table Q gives the general formula and examples (name and structure) of the homologous series of hydrocarbons.

  14. Table P gives the prefix used to name the first 10 hydrocarbons in an homologous series.

  15. Alkanes saturated hydrocarbons. All single bonds general formula CnH2n+2. end in “ane”

  16. Regents Question: 01/03 #25 In saturated hydrocarbons, carbon atoms are bonded to each other by (1) single covalent bonds, only (2) double covalent bonds, only (3) alternating single and double covalent bonds (4) alternating double and triple covalent bonds þ

  17. Alkenes Unsaturated Hydrocarbon Contain one double bond CnH2n End in “ene” # in front may give location of double bond.

  18. Alkynes Unsaturated hydrocarbon Contain one triple bond CnH2n-2 End in “yne” # in front gives location of triple bond.

  19. In a multiple covalent bond, more than one pair of electrons are shared between two atoms. Alkenes have one double bond H H C C H H Alkynes have one triple bond H C C H Ethene C2H4 Ethyne C2H2

  20. Chains of carbons can form rings • Use a prefix cyclo when a ring is formed • To make a ring, two Hydrogen atoms are removed Cyclopentane is a 5 carbon ring with all single bonds.

  21. The prefix of the name tells you how many carbons in the chain.The suffix tells you the type of hydrocarbon. Number of Carbons Prefix Example Alkane CnH2n+2 Alkyne CnH2n-2 Alkene CnH2n 1 Meth Methane CH4 2 Eth Ethane C2H6 Ethene C2H4 Ethyne C2H2 3 Prop Propane C3H8 Propene C3H6 Propyne C3H4 4 But Butane C4H10 Butene C4H8 Butyne C4H6 5 Pent Pentane C5H12 Pentene C5H10 Pentyne C5H8

  22. Regents Question: 06/03 #24 • Which element has atoms that can form single, double, and triple covalent bonds with other atoms of the same element? • hydrogen • (2) oxygen • (3) fluorine • (4) carbon þ

  23. Regents Question: 06/03 #21 Which hydrocarbon is saturated? (1) propene (2) ethyne (3) butene (4) heptane þ Alkanes are saturated hydrocarbons.

  24. Carbon always has 4 bonds. • Hydrogen always has 1 bond • Oxygen always has 2 bonds • Nitrogen always has 3 bonds C or C or C H O or O N

  25. The 4 single bonds of a carbon atom are directed to … the corners of a regular tetrahedron.

  26. Regents Question: 01/03 #13 The empirical formula of a compound is CH2 Which molecular formula is correctly paired with a structural formula for this compound? þ

  27. Regents Question: 08/02 #42 Which structural formula is incorrect? Carbon always has four bonds. þ

  28. Naming hydrocarbons with alkyl groups: • Find the longest continuous chain of carbons. This is the backbone. Find the name of the backbone. • Find the name of the alkyl group (or groups) attached to the backbone. • Name the alkyl group and then the name of the backbone. • Use a number to indicate which carbon the alkyl group is attached to if necessary.

  29. Chains of carbons can be branched • A carbon group connected to a chain is called an alkyl group. • To name the alkyl group, use the prefix for the number of carbons and add yl.

  30. Find the longest chain Find the alkyl group Find the name of this hydrocarbon. H H C H H H H H H H C C C C C C H H H H H H H 1 6 2 5 5 2 6 1 3 4 3 4 3- methyl hexane Counting from each direction find the carbon where the alkyl group is attached (the lower number)

  31. H H C H H C H H H H H H C C C C C H H H H H H The longest chain does not have to be drawn straight. H H C H H C H H H H H H C C C C C H H H H H H 3-methylhexane

  32. Isomers of organic compounds have the same molecular formula but different structures and properties. (3.1ii) Pentane C5H12 Methylbutane C5H12 H H H H H C C C C H H H H H C H H H H H H H H C C C C C H H H H H H

  33. Isomers # of possible isomers  as # of C atoms 

  34. 4 Carbon, 10 Hydrogen, 1 Oxygen 3 Carbon, 6 Hydrogen, 1 Oxygen Examples of isomers: 1-butanol (C4H9OH) diethyl ether (C2H5OC2H5) propanal (C2H5CHO) 2-propanone (CH3COCH3) Isomers have the same chemical formulas but different structural formulas.

  35. H H H H C C C H H H H C H H Regents Question: 08/02 #55 Given the structural formula for butane: Draw the structural formula for an isomer of butane.

  36. Regents Question: 06/03 #25 Which compound is an isomer of pentane? (1) butane (2) propane (3) methyl butane (4) methyl propane þ

  37. Regents Question: 01/03 #18 Which compound has an isomer? þ

  38. Regents Question: 06/02 #19 Which formula is an isomer of butane? þ

  39. Organic acids, alcohols, esters, aldehydes, ketones, ethers, halides, amines, amides, and amino acids are categories of organic molecules that differ in their structures. Functional groups impart distinctive physical and chemical properties to organic compounds.

  40. Naming Halocarbons (-X) • Halocarbons (or halides) have a halogen (F, Cl, Br, I) in place of a hydrogen • Name the halogen first (fluoro, chloro, bromo, iodo) then name the alkane • If there are more than 2 carbons in the chain, use a number to indicate which carbon the –X group is attached to. (Number from the direction that gives the smallest number) 1-chloropropane 2-bromobutane H H Cl H C C C H H H H H Br H H H C C C C H H H H H

  41. Reference Table R lists all the functional groups.

  42. Reference Table R Cont’d.

  43. Naming Alcohols (-OH) • Alcohols have the hydroxyl group -OH • Name the alkane drop the “e” and “ol” • If there are more than 2 carbons in the chain, use a number to indicate which carbon the –OH group is attached to. (Number from the direction that gives the smallest number) 1-propanol 2-propanol H H OH H C C C H H H H H OH H H C C C H H H H

  44. Regents Question: 08/02 #20 • Which compound is an alcohol? • propanal • (2) ethyne • (3) butane • (4) methanol þ

  45. Methyl ethyl ether Dimethyl ether H H H H C C O C H H H H H H H C O C H H H Naming Ethers (-O-) • Ethers have an Oxygen in the chain of carbons • Name the alkyl groups on either side of the O that is in the chain • If both alkyl groups are the same it is named once with the prefix DI in front of it.

  46. Naming Aldehydes (-CHO) • Aldehydes have a double bonded Oxygen on the last carbon in the chain. • Name the alkane, drop the e and add __al propanal methanal H H O H C C C H H H O H C H

  47. Regents Question: 01/03 #49 Which type of organic compound is represented by the structural formula shown below? (1) aldehyde (2) alcohol (3) ether (4) ester þ

  48. Naming Ketones (-CO-) • Ketones have a double bonded Oxygen on a carbon in the middle of the chain. (Not the last carbon) • Name the alkane, drop the e and add __one • If there are more than 4 carbons in the chain, use a number to indicate the location of the =O butanone 3-pentanone H H O H H C C C C H H H H H H O H H H C C C C C H H H H H

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