Benzene and amine

Descrição

A level Chemistry (Cheminems) Mapa Mental sobre Benzene and amine, criado por Jumael Zafar em 01-09-2017.
Jumael Zafar
Mapa Mental por Jumael Zafar, atualizado more than 1 year ago
Jumael Zafar
Criado por Jumael Zafar mais de 7 anos atrás
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Resumo de Recurso

Benzene and amine
  1. Benzene
    1. Benzene is an aromatic compound with a formula of C6H6.
      1. It has a cyclic planar strucuture
        1. Each Carbon has a free electron on its p subshell and these electrons form a ring of delocalized electrons above and below the benzene. They are free to move.
          1. If benzene did have three double bonds, it would be called cyclohexa-1,3,5-triene, but this doesn't actually exist.
        2. Reasons why it does not have 3 double bonds which C6H6 is meant to have
          1. 1. All of its bond lengths are the same of 140 pm, unlike the length of a double bond.
            1. 2. If it had double bonds, it would have no delocalized electrons as there would be C=C bonds where the e-'s would remain.
              1. 3. The enthalpy of cyclohexene (has 1 double bond) is -120 kJ/mol. If benzene had 3 double bonds, you would expect its enthalpy to be 3 times higher of -360 kJ/mol.
                1. But benzene has a bond enthalpy of -208 kJ/mol, so it cannot have double bonds.
                2. Finally, if benzene had 3 double bonds, it would undergo electrophilic addition.
                  1. But it undergoes electrophilic substitution.
                3. Naming benzene
                  1. If a halogen, an alkyl group, or a nitrate ion (NO2-) is joined to benzene, the functional group will be the prefix and benzene is the suffix.
                    1. For example, nitrobenzene.
                      1. However, if an hydroxyl group (OH), an amine group (NH2, an acyl group or an alkene is joined to benzene, phyl- or phenol will be the prefix and the group willl be suffix.
                  2. Two types of electrophilic substitution.
                    1. Friedel-Crafts acylation
                      1. This is when you add an acyl group (-C(=O)R-). R is just an alkyl group.
                        1. This has to be done under reflux and using AlCl3 as a catalyst
                          1. The products are a phenylketone and Hydrochloric acid.
                      2. Nitration
                        1. You just need to add a nitronium ion to a benzene ring to replace a Hydrogen.
                          1. To form the nitronium ion, mix nitric acid with sulfuric acid.
                            1. You will get HSO4-, NH2+ and water.
                              1. The sulfuric acid acts as a catalyst. it reforms by the following reaction:
                                1. H+ + HSO4- makes H2SO4.
                                  1. This process can be used to make TNT explosives.
                      3. Amines
                        1. Naming them is easy.
                          1. If it is primary, secondary or tertiary amine, alkyl goes at the front and the suffix is amine.
                            1. If it has more than one functional group, the prefix goes in alphabetical order
                              1. There can also be quarternary ammonium ions.
                            2. Methylamine, propylamine, decylamine, decylpentylamine etc.
                            3. Cationic surfactants are compounds which are partially soluble and insoluble in water.
                              1. These are ammonium salts with a long hydrocarbon chain.
                                1. The long chain is insoluble and the ammonium head is soluble.
                                  1. This allows them to be used in detergents to remove grease
                            4. Bases
                              1. Amines can act as bases as they have a lone pair of e-'s on the Nitrogen
                                1. The availability of the lone pair depends on the alkyl group which pushes it so it is more available...
                                  1. ... Or the benzene ring which attracts the lone pair by it e- ring, making it less available.
                              2. Amides
                                1. These are basically carboxylic acids but with the o-H group replaced at the end by NH2
                                  1. The amide is always the suffix and the prefix depends on the acyl(R-C=O) group.

                                    Anotações:

                                    • If there are 3 carbon, the prefix would be propan-, if there is four, butan- etc.
                                    1. Prpanamide, pentanamide, decanethanamid

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