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12                                       Organic Chemistry








                                           Carbon
                   CONTENTS
                                           Atomic symbol                 C        Atomic mass                12.01 u
          ͻ Organic chemistry and organic
            compounds                      Atomic number                 6        Melting point              3800 K
          ͻ DŽĚĞƌŶ ĚĞĮŶŝƟŽŶ ŽĨ ŽƌŐĂŶŝĐ     'NGEVTQPKE EQPſIWTCVKQP    K L         Atomic radius              77 pm
                                                                       2 4
            chemistry
          ͻ hŶŝƋƵĞ ;Žƌ ǀĞƌƐĂƟůĞͿ ŶĂƚƵƌĞ ŽĨ   Carbon is an essential element in all organic compounds. It is a nonmetal.
            carbon                         An atom of carbon has four electrons in its outermost shell. So, it lies in
          ͻ dLJƉĞƐ ŽĨ ŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚƐ     Group 14 (or Group IVA) of the periodic table. It has two electronic shells
          ͻ Structure and isomerism        (K and L). So, it lies in the second period of the periodic table.
          ͻ Structural isomerism
          ͻ &ƵŶĐƟŽŶĂů ŐƌŽƵƉƐ
          ͻ Homologous series                              History of Organic Chemistry
          ͻ Hydrocarbons
                                            DŽƌĞ  ƚŚĂŶ  ϮϬϬϬ  LJĞĂƌƐ  ĂŐŽ͕  ŵĂŶLJ  ƉŚŝůŽƐŽƉŚĞƌƐ  ƌĞĐŽŐŶŝƐĞĚ  ŽƌŐĂŶŝĐ  ĐŽŵƉŽƵŶĚƐ  ĚŝƐƟŶĐƚ  ĨƌŽŵ
          ͻ  ůŬĂŶĞƐ͕ ĂůŬĞŶĞƐ ĂŶĚ ĂůŬLJŶĞƐ    ŝŶŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚƐ ĂŶĚ ĐůĂƐƐŝĮĞĚ ƚŚĞŵ ŝŶƚŽ ƚǁŽ ĐůĂƐƐĞƐ͗
          ͻ EŽŵĞŶĐůĂƚƵƌĞ ŽĨ ŽƌŐĂŶŝĐ         Ö dŚŽƐĞ ŚĂǀŝŶŐ ǀĞŐĞƚĂďůĞ ŽƌŝŐŝŶ͕ ƐƵĐŚ ĂƐ ƐƵŐĂƌ͕ ŵŽůĂƐƐĞƐ͕ ĨĞƌŵĞŶƚĞĚ ůŝƋƵŽƌƐ͕ ĨƌƵŝƚ ũƵŝĐĞƐ͕ ĞƚĐ͘
            ĐŽŵƉŽƵŶĚƐ͗ ŐĞŶĞƌĂů ƌƵůĞƐ ĨŽƌ /hW     Ö dŚŽƐĞ ŚĂǀŝŶŐ ĂŶŝŵĂů ŽƌŝŐŝŶ͕ Ğ͘Ő͘ ŵŝůŬ͕ ŚŽŶĞLJ͕ ĨĂƚ͕ ĞƚĐ͘
            nomenclature                    C.W. Scheele  ;ϭϳϰϮʹϴϲͿ  ŝƐŽůĂƚĞĚ  ƐĞǀĞƌĂů  ĂĐŝĚƐ  ĨƌŽŵ  ƉůĂŶƚƐ͘  A.L. Lavoisier  (1743–94) in 1784
          ͻ EĂŵŝŶŐ ĂŶ ŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚ ĨƌŽŵ   ƐŚŽǁĞĚ  ƚŚĂƚ  Ăůů  ŽƌŐĂŶŝĐ  ĐŽŵƉŽƵŶĚƐ  ;ĂƐ  ƚŚĞLJ  ǁĞƌĞ  ůĂƚĞƌ  ĐĂůůĞĚͿ  ĐŽŶƚĂŝŶĞĚ  ĐĂƌďŽŶ͕  ŚLJĚƌŽŐĞŶ͕
            ŝƚƐ ĨŽƌŵƵůĂ                     ŽdžLJŐĞŶ͕ ŶŝƚƌŽŐĞŶ͕ ĞƚĐ͘ /ƚ ǁĂƐ ůĂƚĞƌ ŽďƐĞƌǀĞĚ ƚŚĂƚ ǁŚŝůĞ ŝŶŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚƐ͕ ƐƵĐŚ ĂƐ ƐŽĚŝƵŵ
          ͻ ^ƚƌƵĐƚƵƌĂů ĨŽƌŵƵůĂ ĨƌŽŵ ƚŚĞ ŶĂŵĞ   ĐŚůŽƌŝĚĞ͕ ĐĂŶ ďĞ ƐLJŶƚŚĞƐŝnjĞĚ ĚŝƌĞĐƚůLJ ĨƌŽŵ ƚŚĞŝƌ ĞůĞŵĞŶƚƐ͕ ƚŚĞ ŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚƐ͕ ƐƵĐŚ ĂƐ ĞƚŚLJů
            ŽĨ Ă ĐŽŵƉŽƵŶĚ                   ĂůĐŽŚŽů͕ ĐŽƵůĚ ŶŽƚ ďĞ ƐŽ ƉƌĞƉĂƌĞĚ͘
          ͻ  ůŬĂŶĞƐ                         dŚĞ ĐŽŵƉůĞdž ŶĂƚƵƌĞ ŽĨ ŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚƐ ĂŶĚ ƚŚĞ ŽďƐĞƌǀĂƟŽŶƐ ŵĞŶƟŽŶĞĚ ĂďŽǀĞ ůĞĚ ƚŽ ƚŚĞ
          ͻ Methane                         ĐŽŵŵŽŶ ďĞůŝĞĨ ƚŚĂƚ ƚŚĞ ŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚƐ ǁĞƌĞ ƉƌŽĚƵĐĞĚ ƵŶĚĞƌ ƚŚĞ ŝŶŇƵĞŶĐĞ ŽĨ ƐŽŵĞ ŶĂƚƵƌĂů
          ͻ Ethane                          ĨŽƌĐĞƐ ĐĂůůĞĚ vital forces͘ dŚŝƐ ůĞĚ ƚŽ ƚŚĞ vital force theory ĨŽƌ ƚŚĞ ĨŽƌŵĂƟŽŶ ŽĨ ŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚƐ
                                            ŝŶ ƉůĂŶƚƐ ĂŶĚ ĂŶŝŵĂůƐ͘ Berzelius ǁĂƐ ŽŶĞ ŽĨ ƚŚĞ ƐƚƌŽŶŐ ƐƵƉƉŽƌƚĞƌ ƚŽ ƚŚŝƐ ƚŚĞŽƌLJ͘
          ͻ WŚLJƐŝĐĂů ĂŶĚ ĐŚĞŵŝĐĂů ƉƌŽƉĞƌƟĞƐ ŽĨ
                                            /Ŷ ϭϴϮϴ͕ Ă 'ĞƌŵĂŶ ƐĐŝĞŶƟƐƚ͕ F. Wöhler (1800–82) obtained urea (a typical organic compound and
            ethane
                                            ƉƌŽĚƵĐƚ ŽĨ ƚŚĞ ĂŶŝŵĂů ŵĞƚĂďŽůŝƐŵͿ ďLJ ŚĞĂƟŶŐ ĂŶ ŝŶŽƌŐĂŶŝĐ ĐŽŵƉŽƵŶĚ͕ ĂŵŵŽŶŝƵŵ ĐLJĂŶĂƚĞ Žƌ Ă
          ͻ  ůŬĞŶĞƐ
                                            ŵŝdžƚƵƌĞ ŽĨ ĂŵŵŽŶŝƵŵ ƐƵůƉŚĂƚĞ ĂŶĚ ƉŽƚĂƐƐŝƵŵ ĐLJĂŶĂƚĞ͘
          ͻ Ethene                                                         heat
          ͻ  ůŬLJŶĞƐ                                           NH CNO       o        NH ͘ K͘E, 2
                                                                                        2
                                                                4
                                                           ammonium cyanate             urea
          ͻ Ethyne                                                         heat
          ͻ Alcohols                            (NH ) SO 4  +  2KCNO       o         2NH CNO    +   K SO 4
                                                                                                      2
                                                  4 2
                                                                                         4
                                             ammonium sulphate    potassium cyanate
          ͻ ^ƚƌƵĐƚƵƌĂů ĂŶĚ ĞůĞĐƚƌŽŶŝĐ ĨŽƌŵƵůĂĞ                          rearrangement
            ŽĨ ƐŽŵĞ ĂůĐŽŚŽůƐ                                  NH CNO   o         NH ͘ K͘E, 2
                                                                                        2
                                                                4
                                                                           (heat)
          ͻ Ethanol (Ethyl alcohol, C H OH)                                         ammonium cyanate
                              2 ϱ
          ͻ Carboxylic acids                tƂŚůĞƌ ǁƌŽƚĞ ƚŽ  ĞƌnjĞůŝƵƐ͕ “I must tell you that I can make urea without the need of a kidney of
                                            any animal.” dŚŝƐ ƌĞĂĐƟŽŶ ŐŝǀĞ Ă ďŝŐ ďůŽǁ ƚŽ ƚŚĞ ǀŝƚĂů ĨŽƌĐĞ ƚŚĞŽƌLJ͘ /Ŷ ϭϴϰϰ͕ <ŽůďĞ ƉƌĞƉĂƌĞĚ ĂĐĞƟĐ
          ͻ  ƚŚĂŶŽŝĐ ĂĐŝĚ ;Žƌ ĂĐĞƟĐ ĂĐŝĚͿ
                                            ĂĐŝĚ ĨƌŽŵ ŝƚƐ ĞůĞŵĞŶƚƐ ĂŶĚ ŝŶ ϭϴϱϲ͕ Berthelot ƐLJŶƚŚĞƐŝnjĞĚ ŵĞƚŚĂŶĞ͘
                                            dŚƵƐ͕ ƚŚĞ ǀŝƚĂů ĨŽƌĐĞ ƚŚĞŽƌLJ ǁĂƐ ƌĞũĞĐƚĞĚ͕ ĂŶĚ ŝƚ ǁĂƐ ƌĞĐŽŐŶŝƐĞĚ ƚŚĂƚ Ăůů ĐŚĞŵŝĐĂů ĐŽŵƉŽƵŶĚƐ
                                            ǁŚĞƚŚĞƌ ŽƌŐĂŶŝĐ Žƌ ŝŶŽƌŐĂŶŝĐ͕ ŚĂǀĞ ƚŚĞ ƐĂŵĞ ĐŚĞŵŝĐĂů ĨŽƌĐĞƐ ŽƉĞƌĂƟŶŐ ŝŶ ƚŚĞŵ͘
                                           Organic Chemistry and Organic Compounds
                                           Sulphuric plant extracts, milk, oils, fats, sugar, starch, gums, alcohol,
                                           etc. were known to the ancient people. Beer was brewed as far back as
                                           7000 B.C. In order to differentiate products having vegetable and animal
                                           origin from those having mineral origin (nonliving source), a Swedish
                                           EJGOKUV   , ,  $GT\GNKWU      Ō       KP      UWIIGUVGF VJG ENCUUKſECVKQP QH
                                           all chemical compounds as:
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