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Basic Organic Chemistry II

Review of Carbon Atom.

Biochem019
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Basic Organic Chemistry II

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  1. Organic Chemistry Review Part II

  2. Functional Groups Hydrocarbons Derivatives of Hydrocarbons

  3. Functional Groups • Organic molecules may have functional groups attached. • A functional group is a group of atoms of a particular arrangement that gives the entire molecule certain chemical characteristics. • Functional groups are named according to the composition of the group.

  4. Functional Groups • Organic chemists use the letter "R" to indicate an organic molecule. • The "R" can be any organic molecule.

  5. Hydrocarbons • The simplest organic compounds. • Contain only carbon and hydrogen, • Can be straight-chain, branched chain, or cyclic molecules. • Carbon tends to form four bonds in a tetrahedral geometry.

  6. Hydrocarbons • Two classifications: • Aliphatics • Aromatics • Aliphatic - hydrocarbons which do not contain an aromatic ring.

  7. Hydrocarbons • Aromatic- Aromatic hydrocarbons contain a set of covalently bound atoms with specific characteristics: • A delocalized conjugated π system, with the common arrangement of alternating single and double bonds

  8. Aliphatics Alkanes Cycloalkanes Alkenes Alkynes

  9. Alkanes IUPAC ending is …ane

  10. Alkanes • Saturated hydrocarbons. • Are hydrocarbons which contain only single bonds. • All alkanes are insoluble in water, but dissolve in organic solvents. • Density, viscosity, melting point & boiling points increase as the molecular weight/size of the hydrocarbon increases.

  11. Alkanes • Contain single covalent bonds. • Have the same structural formula: CnH2n+2 • All carbons have single bonds therefore the molecular geometry is tetrahedral.

  12. Alkanes • The names of alkanes start with the name of the alkane but end with the suffix –ane.

  13. Alkanes • Each atom in an alkane uses all its 4 valence electrons in forming single bonds with other atoms. • Alkyl groups may be used as substituents for hydrogens.

  14. Alkanes • Alkyl groups form the branches of straight chain hydrocarbons. • Can have more than one alkyl group for hydrogens. • For multiple substituents of the same type, use the following prefixes: • di- • tri- • tetra- • penta- • hexa-

  15. Alkanes

  16. Alkanes • Other functional groups can be used as substituents. • More than one substituent requires a prefix. • Any hydrogen can be substituted by: Halogens Alcohols Amines Nitriles Thiols Aldehydes Ketones

  17. Alkanes • Any carbon can be substituted by: • Carboxylic Acids • Esters • Amides • Thioesters • Addition of other atoms: • Ethers • Thioethers • Disulfides

  18. Cycloalkanes the prefix cyclo- and the ending …ane

  19. Cycloalkanes • Saturated hydrocarbons. • Form one or more rings fused together. • A single carbon in a ring may have two hydrogen atoms. • Are insoluble in water, but dissolve in organic solvents. • Have higher boiling points, melting points, and densities than alkanes.

  20. Cycloalkanes • All have the same general formula: CnH2n • The carbon atoms in cycloalkanes are sp3hybridized. • Each atom in a cycloalkane uses all its 4 valence electrons in forming covalent bonds with other atoms.

  21. Cycloalkanes • Can have more than one alkyl group to make straight chains. • For multiple alkyl groups of the same type, use prefixes.

  22. Cycloalkanes • Many functional groups can be used as substituents. • More than one substituent requires a prefix. • Any hydrogen or carbon atom can be substituted by:

  23. Cycloalkanes • The names follow those of the alkanes with the prefix cyclo- .

  24. Cycloalkanes

  25. Cycloalkanes

  26. Cycloalkanes

  27. Alkenes IUPAC ending is …ene

  28. Alkenes • Also known as olefins. • Are unsaturated hydrocarbons and are generally very reactive. • Are insoluble in water, but dissolve in organic solvents. • Ethene, propene and buteneare gases at room temperature. The remaining are liquids. • Boiling points increases with molecular mass (chain length). The higher the molecular mass, the higher the boiling point.

  29. Alkenes • Are hydrocarbons which contain one or more double bonds. • Double bonds are: • Have the same structural formula: CnH2n

  30. Alkenes • The main centers are the carbons of the double bond. • The geometry of each carbon in the center is trigonal planar. • This portion of the molecule is flat, with bond angles of 120 degrees.

  31. Alkenes All the alkenes with 4 or more carbon atoms in them show structural isomerism.

  32. Alkenes • The carbon-carbon double bond does not rotate. • Substituents groups on the molecule are locked on either one side of the molecule or opposite each other.

  33. Alkenes • The names of alkenes start with the name of the alkane but end with the suffix –ene. • For alkenes above propene, the position of the double bond must be specified in the name.

  34. Alkenes • Can have more than one alkyl group to form branches. • For more than one alkyl group, use prefixes.

  35. Alkenes • Many functional groups can be used as substituents. • More than one substituent requires a prefix. • Any hydrogen or carbon atom can be substituted by:

  36. Alkenes • For multiple double bonds, use the following prefixes: • di- • tri- • tetra- • penta- • hexa-

  37. Alkenes • A diene is a hydrocarbon chain that has two double bonds that may or may not be adjacent to each other.

  38. Alkenes: Examples

  39. Alkenes: Examples

  40. Alkynes IUPAC ending is …yne

  41. Alkynes • Also known as acetylenes. • Are unsaturated hydrocarbons and are generally very reactive. • Are insoluble in water; but quite soluble in organic solvents of low polarity (e.g. ligroin, ether, benzene, carbon tetrachloride, etc.). • Alkynes of four or fewer carbon atoms are gases. The rest are liquids. • Their boiling points increase with increasing number of carbons.

  42. Alkynes • Are hydrocarbons which contain one or more triple bonds. • Triple bonds are: • Have the same structural formula: CnH2n-2

  43. Alkynes • The main centers are the carbons of the triple bond. • The geometry of the center is linear. • This portion of the molecule is linear, with bond angles of 180 degrees.

  44. Alkynes All the alkynes with 4 or more carbon atoms in them show structural isomerism.

  45. Alkynes • The names of alkynes start with the name of the alkane but end with the suffix –yne. • For alkynes above propyne, the position of the triple bond must be specified in the name.

  46. Alkynes • Many functional groups can be used as substituents. • Only one substituent is allowed. • Any hydrogen or carbon atom can be substituted by:

  47. Alkynes • For multiple double bonds, use the following prefixes: • di- • tri- • tetra- • penta- • hexa-

  48. Alkynes: Examples

  49. Aromatics Structures that meet Huckel’s Rule

  50. Aromatics • Coplanar structures, with all the contributing atoms in the same plane. • Are arranged in one or more rings. • Benzene rings are not a common motif. • The three general requirements for a compound to be aromatic are: • The compound must be cyclic. • Each element within the ring must have a p-orbital that is perpendicularto the ring, hence the molecule is planar. • The compound must follow Hückel'sRule.

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