‫ﻭﺯﺍﺭﺕ ﻣﻌﺎﺭﻑ‬

‫ﻣﻌﻴﻨﻴﺖ ﺍﻧﻜﺸﺎﻑ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ‪ ،‬ﺗﺮﺑﻴﺔ ﻣﻌﻠﻢ‬

‫ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ‬
‫ﻭ ﻣﺮﻛﺰ ﺳﺎﻳﻨﺲ‬
‫ﺭﻳﺎﺳﺖ ﻋﻤﻮﻣﻰ ﺍﻧﻜﺸﺎﻑ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ‬
‫ﻭ ﺗﺄﻟﻴﻒ ﻛﺘﺐ ﺩﺭﺳﻰ‬

‫ﺻﻨﻒ ﺩﻭﺍﺯﺩﻫﻢ‬

‫ﻛﻴﻤﻴﺎ ﺻﻨﻒ ﺩﻭﺍﺯﺩﻫﻢ‬

‫ﻛﺘﺎﺏ ﻫﺎﻯ ﺩﺭﺳﻰ ﻣﺘﻌﻠﻖ ﺑﻪ ﻭﺯﺍﺭﺕ ﻣﻌﺎﺭﻑ ﺑﻮﺩﻩ ﺧﺮﻳﺪ ﻭ ﻓﺮﻭﺵ ﺁﻥ ﺟﺪﺍ ً‬
‫ﻣﻤﻨﻮﻉ ﺍﺳﺖ‪ .‬ﺑﺎ ﻣﺘﺨﻠﻔﻴﻦ ﺑﺮﺧﻮﺭﺩ ﻗﺎﻧﻮﻧﻰ ﺻﻮﺭﺕ ﻣﻰ ﮔﻴﺮﺩ‪.‬‬

‫ﺳﺎﻝ ﭼﺎپ ‪1390‬ﻫـ ‪ .‬ﺵ‬

 ‫ﻭﺯﺍﺭﺕ ﻣﻌﺎﺭﻑ‬
‫ﻣﻌﻴﻨﻴﺖﺍﻧﻜﺸﺎﻑﻧﺼﺎﺏﺗﻌﻠﻴﻤﻲ‪،‬ﺗﺮﺑﻴﺔ‬
‫ﻣﻌﻠﻢ ﻭ ﻣﺮﻛﺰ ﺳﺎﻳﻨﺲ‬
‫ﺭﻳﺎﺳﺖ ﻋﻤﻮﻣﻲ ﺍﻧﻜﺸﺎﻑ ﻧﺼﺎﺏ‬
‫ﺗﻌﻠﻴﻤﻰ ﻭ ﺗﺄﻟﻴﻒ ﻛﺘﺐ ﺩﺭﺳﻰ‬
‫ﺳﺎﻝ ﭼﺎپ‪ 1390 :‬ﻫـ ‪ .‬ﺵ‬
‫ﺍﻟﻒ‬
 ‫ﻣﺆﻟﻔﻴﻦ‬
‫ﭘﻮﻫﻨﺪﻭﻯ ﺩﻳﭙﻠﻮﻡ ﺍﻧﺠﻴﻨﻴﺮ ﻋﺒﺪﺍﻟﻤﺤﻤﺪ »ﻋﺰﻳﺰ« ﺍﺳﺘﺎﺩ ﭘﻮﻫﻨﺘﻮﻥ ﻛﺎﺑﻞ‪.‬‬
‫ﭘﻮﻫﻨﻴﺎﺭ ﻣﺤﻤﺪ ﺍﻧﻮﺭ ﺷﺮﻳﻔﻰ ﺍﺳﺘﺎﺩ ﺍﻧﺴﺘﺘﻴﻮﺕ ﺗﺤﺼﻴﻼﺕ ﻋﺎﻟﻰ ﭘﺮﻭﺍﻥ‪.‬‬
‫ﻣﺆﻟﻒ ﻋﺘﻴﻖ ﺍﺣﻤﺪ ﺷﻴﻨﻮﺍﺭﻯ ﻋﻀﻮ ﻋﻠﻤﻰ ﺩﻳﭙﺎﺭﺗﻤﻨﺖ ﻛﻴﻤﻴﺎ‬
‫ﻣﻌﺎﻭﻥ ﻣﺆﻟﻒ ﻣﺤﻤﺪ ﺍﺟﻤﻞ ﻓﻴﺾ ﻋﻀﻮ ﻋﻠﻤﻰ ﺩﻳﭙﺎﺭﺗﻤﻨﺖ ﻛﻴﻤﻴﺎ‬
‫ﺍﻳﺪﻳﺖ ﻋﻠﻤﻰ‬
‫ﭘﻮﻫﻨﺪﻭﻯ ﺩﻳﭙﻠﻮﻡ ﺍﻧﺠﻴﻨﻴﺮ ﻋﺒﺪﺍﻟﻤﺤﻤﺪ »ﻋﺰﻳﺰ« ﺍﺳﺘﺎﺩ ﭘﻮﻫﻨﺘﻮﻥ ﻛﺎﺑﻞ‪.‬‬
‫ﺍﻳﺪﻳﺖ ﺯﺑﺎﻧﻰ‬
‫ﻣﺆﻟﻒ ﺳﻴﺪ ﻣﺤﻤﻮﺩ ﭘﺎﻳﻤﻨﺎﺭﻯ‬
‫ﻛﻤﻴﺘﺔ ﺩﻳﻨﻰ‪ ،‬ﺳﻴﺎﺳﻰ ﻭ ﻓﺮﻫﻨﮕﻰ‪:‬‬
‫ﺣﺒﻴﺐ ﺍﷲ ﺭﺍﺣﻞ ﻣﺸﺎﻭﺭ ﻭﺯﺍﺭﺕ ﻣﻌﺎﺭﻑ ﺩﺭ ﺭﻳﺎﺳﺖ ﺍﻧﻜﺸﺎﻑ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ‪.‬‬
‫ﻣﺆﻟﻒ ﻗﺎﺭﻯ ﻣﺎﻳﻞ ﺁﻗﺎ» ﻣﺘﻘﻰ« ﻋﻀﻮ ﻋﻠﻤﻰ ﺩﻳﭙﺎﺭﺗﻤﻨﺖ ﻋﻠﻮﻡ ﺍﺳﻼﻣﻰ‬
‫ﻛﻤﻴﺘﺔ ﻧﻈﺎﺭﺕ‬
‫ﺩﻛﺘﻮﺭ ﺍﺳﺪ ﺍﷲ ﻣﺤﻘﻖ ﻣﻌﻴﻦ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ‪ ،‬ﺗﺮﺑﻴﺔ ﻣﻌﻠﻢ ﻭ ﻣﺮﻛﺰ ﺳﺎﻳﻨﺲ‪.‬‬
‫ﺩﻛﺘﻮﺭ ﺷﻴﺮ ﻋﻠﻰ ﻇﺮﻳﻔﻰ ﻣﺴﺆﻭﻝ ﭘﺮﻭژﺓ ﺍﻧﻜﺸﺎﻑ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ‪.‬‬
‫ﻣﻌﺎﻭﻥ ﺳﺮﻣﺆﻟﻒ ﻋﺒﺪﺍﻟﻈﺎﻫﺮ ﮔﻠﺴﺘﺎﻧﻰ ﺭﺋﻴﺲ ﻋﻤﻮﻣﻰ ﺍﻧﻜﺸﺎﻑ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ ﻭ ﺗﺄﻟﻴﻒ ﻛﺘﺐ ﺩﺭﺳﻰ‬
‫ﻃﺮﺡ ﻭ ﺩﻳﺰﺍﻳﻦ‬
‫ﺣﻤﻴﺪﻛﺮﻳﻤﻰ)ﺳﻨﺠﺪﺩﺭﻩﻳﻰ(‬
‫ﺏ‬
‫ﺝ‬
 ‫ﺳﺮود ﻣﻠﯽ‬
‫دا ﻋﺰت د ﻫـــﺮ اﻓﻐـــﺎن دى‬
‫ﻫﺮ ﺑﭽﯽ ﻳ‪ ３‬ﻗﻬﺮﻣـــــــﺎن دى‬
‫د ﺑـﻠﻮ＇ــــﻮ‪ ،‬د ازﺑــــﮑـــــﻮ‬
‫د ﺗﺮﮐﻤﻨــــﻮ‪ ،‬د ﺗـﺎﺟـــﮑــــﻮ‬
‫ﭘﺎﻣﻴــﺮﻳﺎن‪ ،‬ﻧــﻮرﺳﺘﺎﻧﻴــــﺎن‬
‫ﻫـــﻢ اﻳﻤـــﺎق‪ ،‬ﻫﻢ ﭘﺸـﻪ ﻳﺎن‬
‫ﻟﮑــﻪ ﻟــﻤــﺮ ﭘﺮ ﺷﻨﻪ ﺁﺳﻤـﺎن‬
‫ﻟﮑـــﻪ زړه وي ﺟــﺎوﻳـــﺪان‬
‫واﻳﻮ اﷲ اﮐﺒﺮ واﻳﻮ اﷲ اﮐـــﺒﺮ‬
‫دا وﻃﻦ اﻓﻐﺎﻧﺴﺘـــﺎن دى‬
‫ﮐﻮر د ﺳﻮﻟ‪ ،３‬ﮐﻮر د ﺗﻮرې‬
‫دا وﻃﻦ د ！ﻮﻟﻮ ﮐـﻮر دى‬
‫د ﭘ‪＋‬ﺘــــﻮن او ﻫﺰاره وو‬
‫ورﺳﺮه ﻋﺮب‪－ ،‬ﻮﺟــﺮ دي‬
‫ﺑﺮاﻫﻮي دي‪ ،‬ﻗﺰﻟﺒﺎش دي‬
‫دا ﻫﻴـــﻮاد ﺑﻪ ﺗﻞ ‪＄‬ﻠـ‪８５‬ي‬
‫ﭘﻪ ﺳﻴﻨــﻪ ﮐ‪ ３‬د ﺁﺳﻴـــﺎ‪ ،‬ﺑـﻪ‬
‫ﻧﻮم د ﺣﻖ ﻣﻮ دى رﻫﺒـــﺮ‬
‫ﺩ‬
 ‫ﺑﺴﻢ ﺍﷲ ﺍﻟﺮﺣﻤﻦ ﺍﻟﺮﺣﻴﻢ‬
‫ﭘﻴﺎﻡ ﻭﺯﻳﺮ ﻣﻌﺎﺭﻑ‬
‫ﻣﻌﻠﻤﺎﻥ ﻭ ﺷﺎﮔﺮﺩﺍﻥ ﻋﺰﻳﺰ‪،‬‬
‫ﺗﻌﻠﻴﻢ ﻭ ﺗﺮﺑﻴﻪ ﺍﺳﺎﺱ ﺍﻧﻜﺸﺎﻑ ﻭ ﺗﻮﺳﻌﺔ ﻫﺮ ﻛﺸﻮﺭ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻰ ﺩﻫﺪ‪ ،‬ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ ﻳﻜﻰ ﺍﺯ ﻋﻨﺎﺻﺮ ﻣﻬﻢ ﺗﻌﻠﻴﻢ‬
‫ﻭ ﺗﺮﺑﻴﻪ ﻣﻰ ﺑﺎﺷﺪ ﻛﻪ ﻣﻄﺎﺑﻖ ﺍﻧﻜﺸﺎﻓﺎﺕ ﻋﻠﻤﻰ ﻣﻌﺎﺻﺮ ﻭ ﻧﻴﺎﺯﻣﻨﺪﻯﻫﺎﻯ ﺟﺎﻣﻌﻪ ﻭﺿﻊ ﻣﻰﮔﺮﺩﺩ‪ ،‬ﻭﺍﺿﺢ ﺍﺳﺖ ﻛﻪ‬
‫ﺍﻧﻜﺸﺎﻓﺎﺕ ﻋﻠﻤﻰ ﻭ ﻧﻴﺎﺯﻣﻨﺪﻯﻫﺎﻯ ﺟﺎﻣﻌﻪ ﻫﻤﻮﺍﺭﻩ ﺩﺭ ﺣﺎﻝ ﺗَ َﻄ ﱡﻮﺭ ﻣﻰﺑﺎﺷﺪ؛ ﺑﻨﺎ ًء ﻻﺯﻡ ﺍﺳﺖ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ ﻧﻴﺰ ﺑﻪ‬
‫ﺻﻮﺭﺕ ﻋﻠﻤﻰ ﻭ ﺩﻗﻴﻖ ﺍﻧﻜﺸﺎﻑ ﻧﻤﺎﻳﺪ‪ .‬ﺍﻟﺒﺘﻪ ﻧﺒﺎﻳﺪ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ ﺗﺎﺑﻊ ﺗﻐﻴﻴﺮﺍﺕ ﺳﻴﺎﺳﻰ‪ ،‬ﻧﻈﺮﻳﺎﺕ ﻭ ﺗﻤﺎﻳﻼﺕ‬
‫ﺍﺷﺨﺎﺹ ﮔﺮﺩﺩ‪.‬‬
‫ﻛﺘﺎﺑﻰ ﻛﻪ ﺍﻣﺮﻭﺯ ﺩﺭ ﺩﺳﺘﺮﺱ ﺷﻤﺎ ﻗﺮﺍﺭ ﺩﺍﺭﺩ ﺑﻨﺎﺑﺮ ﻫﻤﻴﻦ ﻣﺸﺨﺼﺎﺕ ﺗﻬﻴﻪ ﻭ ﺗﺮﺗﻴﺐ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪ ،‬ﻣﻮﺿﻮﻋﺎﺕ ﻋﻠﻤﻰ‬
‫ﻣﻔﻴﺪ ﺩﺭ ﺁﻥ ﺍﺿﺎﻓﻪ ﺷﺪﻩ‪ ،‬ﻓﻌﺎﻝ ﻧﮕﻪ ﺩﺍﺷﺘﻦ ﺷﺎﮔﺮﺩﺍﻥ ﺩﺭ ﻋﻤﻠﻴﺔ ﺗﺪﺭﻳﺲ ﺟﺰء ﭘﻼﻥ ﺗﺪﺭﻳﺲ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪.‬‬
‫ﺍﻣﻴﺪﻭﺍﺭﻡ ﺗﺪﺭﻳﺲ ﺍﻳﻦ ﻛﺘﺎﺏ ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯ ﺭﻭﺵﻫﺎﻯ ﺁﻣﻮﺯﺵ ﻓﻌﺎﻝ ﻣﻄﺎﺑﻖ ﺭﻫﻨﻤﻮﺩ ﻫﺎ ﻭ ﭘﻼﻥ ﺗﻌﻠﻴﻤﻰ ﺗﻌﻴﻴﻦ ﺷﺪﻩ‬
‫ﺻﻮﺭﺕ ﮔﻴﺮﺩ‪ ،‬ﻭ ﺍﻭﻟﻴﺎﻯ ﺷﺎﮔﺮﺩﺍﻥ ﻧﻴﺰ ﺩﺭ ﺗﻌﻠﻴﻢ ﻭ ﺗﺮﺑﻴﺔ ﺑﺎ ﻛﻴﻔﻴﺖ ﺩﺧﺘﺮﺍﻥ ﻭ ﭘﺴﺮﺍﻥ ﺧﻮﺩ ﻫﻤﻜﺎﺭﻯ ﻣﺘﺪﺍﻭﻡ ﻧﻤﺎﻳﻨﺪ‪ ،‬ﺗﺎ‬
‫ﺍﻫﺪﺍﻑ ﻭ ﺁﺭﻭﺯﻫﺎﻯ ﻧﻈﺎﻡ ﻣﻌﺎﺭﻑ ﺑﺮﺁﻭﺭﺩﻩ ﮔﺮﺩﻳﺪﻩ‪ ،‬ﻧﺘﺎﻳﺞ ﻭ ﺩﺳﺖ ﺁﻭﺭﺩﻫﺎﻯ ﺧﻮﺑﻰ ﺑﺮﺍﻯ ﺷﺎﮔﺮﺩﺍﻥ ﻭ ﻛﺸﻮﺭ ﻣﺎ ﺩﺍﺷﺘﻪ‬
‫ﺑﺎﺷﺪ‪.‬‬
‫ﺑﺎﻭﺭ ﺩﺍﺭﻡ ﻛﻪ ﻣﻌﻠﻤﺎﻥ ﮔﺮﺍﻧﻘﺪﺭ ﻣﺎ ﺩﺭ ﺗﻄﺒﻴﻖ ﻣﺆﺛﺮ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ ﻣﺴﺆﻭﻟﻴﺖ ﺧﻮﺩ ﺭﺍ ﺻﺎﺩﻗﺎﻧﻪ ﺍﺩﺍ ﻣﻰﻧﻤﺎﻳﻨﺪ‪.‬‬
‫ﻭﺯﺍﺭﺕ ﻣﻌﺎﺭﻑ ﻫﻤﻮﺍﺭﻩ ﺗﻼﺵ ﻣﻰ ﻧﻤﺎﻳﺪ ﺗﺎ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ ﻣﻌﺎﺭﻑ ﻣﻄﺎﺑﻖ ﺍﺳﺎﺳﺎﺕ ﺩﻳﻦ ﻣﺒﻴﻦ ﺍﺳﻼﻡ‪ ،‬ﺣﺲ ﻭﻃﻦ‬
‫ﺩﻭﺳﺘﻰ ﻭ ﻣﻌﻴﺎﺭ ﻫﺎﻯ ﻋﻠﻤﻰ ﺑﺎ ﺩﺭ ﻧﻈﺮﺩﺍﺷﺖ ﻧﻴﺎﺯﻣﻨﺪﻯ ﻫﺎﻯ ُﻣﺒﺮﻡ ﺟﺎﻣﻌﺔ ﻣﺎ ﺍﻧﻜﺸﺎﻑ ﻧﻤﺎﻳﺪ‪.‬‬
‫ﺩﺭ ﺍﻳﻦ ﻋﺮﺻﻪ ﺍﺯ ﺗﻤﺎﻡ ﺷﺨﺼﻴﺖﻫﺎﻯ ﻋﻠﻤﻰ ﻭ ﺩﺍﻧﺸﻤﻨﺪﺍﻥ ﺗﻌﻠﻴﻢ ﻭ ﺗﺮﺑﻴﺔ ﻛﺸﻮﺭ ﻭ ﺍﻭﻟﻴﺎﻯ ﻣﺤﺘﺮﻡ ﺷﺎﮔﺮﺩﺍﻥ ﺗﻤﻨﺎ‬
‫ﺩﺍﺭﻡ‪ ،‬ﺗﺎ ﺑﺎ ﺍﺭﺍﺋﺔ ﻧﻈﺮﻳﺎﺕ ﻭ ﭘﻴﺸﻨﻬﺎﺩﺍﺕ ﺳﺎﻟﻢ ﻭ ﻣﻔﻴﺪ ﺧﻮﻳﺶ ﻣﺆﻟﻔﺎﻥ ﻣﺎ ﺭﺍ ﺩﺭ ﺑﻬﺒﻮﺩ ﺑﻴﺸﺘﺮ ﺗﺄﻟﻴﻒ ﻛﺘﺐ ﺩﺭﺳﻰ ﻳﺎﺭﻯ‬
‫ﻧﻤﺎﻳﻨﺪ‪.‬‬
‫ﺍﺯ ﻫﻤﺔ ﺩﺍﻧﺸﻤﻨﺪﺍﻧﻰ ﻛﻪ ﺩﺭ ﺗﻬﻴﻪ ﻭ ﺗﺮﺗﻴﺐ ﺍﻳﻦ ﻛﺘﺎﺏ ﺳﻬﻢ ﮔﺮﻓﺘﻪ ﺍﻧﺪ‪ ،‬ﻭ ﺍﺯ ﻣﺆﺳﺴﺎﺕ ﻣﺤﺘﺮﻡ ﻣﻠﻰ ﻭ ﺑﻴﻦﺍﻟﻤﻠﻠﻰ ﻭ‬
‫ﺳﺎﻳﺮ ﻛﺸﻮﺭ ﻫﺎﻯ ﺩﻭﺳﺖ ﻛﻪ ﺩﺭ ﺗﻬﻴﻪ ﻭ ﺗﺪﻭﻳﻦ ﻧﺼﺎﺏ ﺗﻌﻠﻴﻤﻰ ﺟﺪﻳﺪ ﻭ ﻃﺒﻊ ﻭ ﺗﻮﺯﻳﻊ ﻛﺘﺐ ﺩﺭﺳﻰ ﻫﻤﻜﺎﺭﻯ ﻧﻤﻮﺩﻩ‬
‫ﺍﻧﺪ‪ ،‬ﺻﻤﻴﻤﺎﻧﻪ ﺍﻇﻬﺎﺭ ﺍﻣﺘﻨﺎﻥ ﻭ ﻗﺪﺭﺩﺍﻧﻰ ﻣﻰﻧﻤﺎﻳﻢ‪.‬‬
‫ﻭ ﻣﻦ ﺍﷲ ﺍﻟﺘﻮﻓﻴﻖ‬
‫ﻓﺎﺭﻭﻕ ﻭﺭﺩگ‬
‫ﻭﺯﻳﺮ ﻣﻌﺎﺭﻑ ﺟﻤﻬﻮﺭﻯ ﺍﺳﻼﻣﻰ ﺍﻓﻐﺎﻧﺴﺘﺎﻥ‬
‫ﻫـ‬
 ‫ﻓﻬﺮﺳﺖ ﻋﻨﺎﻭﻳﻦ‬
‫ﺻﻔﺤﻪ‬ ‫ﻋﻨﻮﺍﻥ‬
‫ﻣﻘﺪﻣﻪ‪1 .............................................................................................................................................‬‬
‫ﻓﺼﻞ ﺍﻭﻝ‬
‫ﺗﺸﻜﻴﻞ ﺭﻭﺍﺑﻂ ﻛﻴﻤﻴﺎﻭﻯ ﺩﺭ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ‪2 ......................................................................................‬‬
‫ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺘﺮﻭﻧﻴﻜﻰ ﻭﺳﺆﻳﻪ ﻫﺎﻯ ﺍﻧﺮژﻳﻜﻰ ﻛﺎﺭﺑﻦ‪3 ............................................................................‬‬
‫ﻭﻻﻧﺲ ﻛﺎﺭﺑﻦ ﻭ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ‪4 ...........................................................................................................‬‬
‫‪ :3-1‬ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ‪8 .........................................................................................................................‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﺍﻭﻝ ‪15 ..........................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭﺗﻤﺮﻳﻦ ﻓﺼﻞ ﺍﻭﻝ ‪16 ............................................................................................................‬‬
‫ﻓﺼﻞ ﺩﻭﻡ‬
‫ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻟﻰ‪18 ........................................................................................................................‬‬
‫‪ :1-2‬ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ‪19 ..................................................................................................................‬‬
‫‪ :2-2‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ‪22 ..........................................................................................................‬‬
‫‪: 3-2‬ﻃﺮﺯ ﻧﻮﺷﺘﻦ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ‪23 ........................................................................................‬‬
‫‪: 4-2‬ﺍﻳﺰﻭﻣﻴﺮﻫﺎ )‪32 ..........................................................................................................(Isomers‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﺩﻭﻡ‪34 ..........................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﺩﻭﻡ‪34 ............................................................................................................‬‬
‫ﻓﺼﻞ ﺳﺆﻡ‬
‫ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ‪36 ...........................................................................................................‬‬
‫‪ :1-3‬ﻣﻌﻠﻮﻣﺎﺕ ﻋﻤﻮﻣﻰ ‪37 ..................................................................................................................‬‬
‫‪ :2-3‬ﺻﻨﻒ ﺑﻨﺪﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ‪38 ................................................................................................‬‬
‫‪ :3-3‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻮﻯ ﺩﺭ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ‪39 ..............................................................................‬‬
‫‪ :4-3‬ﺳﻠﺴﻠﻪ ﻫﻮﻣﻮﻟﻮگ ﺍﻟﻜﺎﻧﻬﺎ ‪40 .......................................................................................................‬‬
‫‪ :5-3‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻭ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ) ﻣﺸﺘﻘﺎﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ( ‪41 ...................................‬‬
‫‪: 6-3‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺑﺎ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ‪42 ..............................................................................‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﺳﺆﻡ ‪48 .........................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﺳﺆﻡ ‪48 ..........................................................................................................‬‬
‫ﻓﺼﻞ ﭼﻬﺎﺭﻡ‬
‫ﺍﻟﻜﺎﻧﻬﺎ ﻭ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ‪50 ..................................................................................................................‬‬
‫‪: 1-4‬ﺍﻟﻜﺎﻥ ﻫﺎ )‪51 ........................................................................................................... (Alkanes‬‬
‫‪ :2-4‬ﻣﺮﻛﺒﺎﺕ ﺣﻠﻘﻮﻯ ) ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻥ ﻫﺎ (‪62 .......................................................................................‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﭼﻬﺎﺭﻡ‪68 .......................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﭼﻬﺎﺭﻡ‪68 .......................................................................................................‬‬
‫ﻓﺼﻞ ﭘﻨﺠﻢ‬
‫ﺍﻟﻜﻴﻨﻬﺎ ﻭ ﺍﻟﻜﺎﻳﻨﻬﺎ ‪70 ...........................................................................................................................‬‬
‫‪ :1-5‬ﺍﻟﻜﻴﻦ ﻫﺎ‪71 ...............................................................................................................................‬‬
‫ﻭ‬
 ‫ﻓﻬﺮﺳﺖ ﻋﻨﺎﻭﻳﻦ‬
‫ﺻﻔﺤﻪ‬ ‫ﻋﻨﻮﺍﻥ‬
‫‪: 2-5‬ﺍﻟﻜﺎﻳﻦ ﻫﺎ )‪80 ..........................................................................................................(Alkynes‬‬
‫‪: 3-5‬ﺍﺳﺘﻴﺘﻠﻴﻦ ‪86 ................................................................................................................................‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﭘﻨﺠﻢ‪89 ........................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭﺗﻤﺮﻳﻦ ﻓﺼﻞ ﭘﻨﺠﻢ ‪90 ..........................................................................................................‬‬
‫ﻓﺼﻞ ﺷﺸﻢ‬
‫ﻣﺮﻛﺒﺎﺕ ﺍﺭﻭﻣﺎﺗﻴﻚ )‪92 ......................................................................................................(Arenes‬‬
‫‪ :1-6‬ﺳﺎﺧﺘﻤﺎﻥ ﺑﻨﺰﻳﻦ ‪93 ......................................................................................................................‬‬
‫‪ 2-6‬ﻧﺎﻣﮕﺬﺍﺭﻯ ﻣﺮﻛﺒﺎﺕ ﺍﺭﻭﻣﺎﺗﻴﻚ ‪96 ................................................................................................‬‬
‫‪: 3-6‬ﺗﻌﺎﻣﻼﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﺍﺭﻭﻣﺎﺗﻴﻚ ‪96 ..................................................................................‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﺷﺸﻢ‪103 ......................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﺷﺸﻢ ‪104 .......................................................................................................‬‬
‫ﻓﺼﻞ ﻫﻔﺘﻢ‬
‫ﺍﻟﻜﺎﻳﻞ ﻫﻼﻳﺪ ﻫﺎ ‪106 ...........................................................................................................................‬‬
‫‪: 1-7‬ﺍﻟﻜﺎﻳﻞ ﻫﻼﻳﺪ ﻫﺎ ‪107 ..................................................................................................................‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﻫﻔﺘﻢ ‪116 ......................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﻫﻔﺘﻢ ‪116 .......................................................................................................‬‬
‫ﻓﺼﻞ ﻫﺸﺘﻢ‬
‫ﺍﻟﻜﻮﻝ ﻫﺎ ﻭ ﺍﻳﺘﺮ ﻫﺎ ‪119 .......................................................................................................................‬‬
‫‪: 1-8‬ﺍﻟﻜﻮﻝ ﻫﺎ )‪120 .......................................................................................................(Alcohols‬‬
‫‪: 2-8‬ﺍﻳﺘﺮﻫﺎ )‪134 .................................................................................................................(Ethers‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﻫﺸﺘﻢ ‪138 .....................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﻫﺸﺘﻢ ‪139 .......................................................................................................‬‬
‫ﻓﺼﻞ ﻧﻬﻢ‬
‫ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎ ﻭ ﻛﻴﺘﻮﻥ ﻫﺎ ‪142 ................................................................................................................‬‬
‫‪: 1-9‬ﺍﻟﺪﻳﻬﺎﻳﺪ ﻭ ﻛﻴﺘﻮﻥ ) ﻣﺮﻛﺒﺎﺕ ﮔﺮﻭﺏ ﻛﺎﺭﺑﻮﻧﻴﻞ (‪143 .....................................................................‬‬
‫‪ :1-9‬ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎ ‪143 .........................................................................................................................‬‬
‫‪: 2-9‬ﻛﻴﺘﻮﻥ ﻫﺎ )‪155 ......................................................................................................(Ketones‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﻧﻬﻢ ‪160 ........................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﻧﻬﻢ ‪161 .........................................................................................................‬‬
‫ﻓﺼﻞ ﺩﻫﻢ‬
‫ﺗﻴﺰﺍﺑﻬﺎﻯ ﻋﻀﻮﻯ ) ﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﺍﺳﻴﺪﻫﺎ ( ‪163 ....................................................................................‬‬
‫‪: 1-10‬ﺗﻴﺰﺍﺏ ﻫﺎﻯ ﻋﻀﻮﻯ‪164 ............................................................................................................‬‬
‫‪: 2-10‬ﺑﻌﻀﻰ ﺍﺯﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﺍﺳﻴﺪ ﻫﺎﻯ ﻣﻬﻢ‪172 ...............................................................................‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﺩﻫﻢ‪177 ........................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﺩﻫﻢ ‪178 ........................................................................................................‬‬
‫ﺯ‬
 ‫ﻓﻬﺮﺳﺖ ﻋﻨﺎﻭﻳﻦ‬
‫ﺻﻔﺤﻪ‬ ‫ﻋﻨﻮﺍﻥ‬
‫ﻓﺼﻞ ﻳﺎﺯﺩﻫﻢ‬
‫ﺍﻣﻴﻦ ﻫﺎ )‪181 .................................................................................................................... (Amines‬‬
‫‪ :1-11‬ﺳﺎﺧﺘﻤﺎﻥ ﻭ ﺻﻨﻒ ﺑﻨﺪﻯ ﺍﻣﻴﻦ ﻫﺎ‪182 .........................................................................................‬‬
‫‪ :2-11‬ﺍﻣﺎﻳﺪ ﻫﺎ )‪192 .........................................................................................................(Amides‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﻳﺎﺯﺩﻫﻢ ‪194 ...................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﻳﺎﺯﺩﻫﻢ‪195 ....................................................................................................‬‬
‫ﻓﺼﻞ ﺩﻭﺍﺯﺩﻫﻢ‬
‫ﭘﻮﻟﻰ ﻣﻴﺮ ﻫﺎﻯ ﻃﺒﻴﻌﻰ ‪197 ....................................................................................................................‬‬
‫‪ :12‬ﺻﻨﻒ ﺑﻨﺪﻯ ﭘﻮﻟﻴﻤﻴﺮ ﻫﺎﻯ ﻃﺒﻴﻌﻰ‪198 ..............................................................................................‬‬
‫‪ :1-12‬ﻗﻨﺪﻫﺎ ‪198 ...............................................................................................................................‬‬
‫‪ :2-12‬ﭘﺮﻭﺗﻴﻦ ﻫﺎ ‪214 .........................................................................................................................‬‬
‫‪ :3-12‬ﺩﻯ ﺍﻛﺴﻰ ﺭﺍﻳﺒﻮﺯ ﻧﻮﻛﻠﻴﻚ ﺍﺳﻴﺪ )‪ (D.N.A‬ﻭ ﺭﺍﻳﺒﻮﺯ ﻧﻮﻛﻠﻴﻚ ﺍﺳﻴﺪ )‪221 ....................(R.N.A‬‬
‫ﺧﻼﺻﻪ ﻓﺼﻞ ﺩﻭﺍﺯﺩﻫﻢ ‪224 ................................................................................................................‬‬
‫ﺳﺆﺍﻻﺕ ﻭ ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﺩﻭﺍﺯﺩﻫﻢ ‪225 .................................................................................................‬‬
‫ﻓﺼﻞ ﺳﻴﺰﺩﻫﻢ‬
‫ﭘﻮﻟﻰ ﻣﻴﺮ ﻫﺎﻯ ﻣﺼﻨﻮﻋﻰ ‪227 .............................................................................................................‬‬
‫‪ :1-13‬ﭘﻮﻟﻰ ﻣﻴﺮ ﻫﺎﻯ ﺟﻤﻌﻰ ﻣﺼﻨﻮﻋﻰ ‪228 ..........................................................................................‬‬
‫‪ :2-13‬ﭘﻮﻟﻰ ﻣﻴﺮ ﻫﺎﻯ ﻣﺘﺮﺍﻛﻢ ﺷﺪﻩ ‪234 ................................................................................................‬‬
‫‪ :3-13‬ﺳﺎﻳﻨﺲ‪ ،‬ﺗﻜﻨﺎﻟﻮﺟﻰ ﻭ ﺍﺟﺘﻤﺎﻉ‪236 ..............................................................................................‬‬
‫‪ :4-13‬ﺁﻟﻮﺩﻩ ﮔﻰ ﻣﺤﻴﻂ ﺯﻳﺴﺖ ﺩﺭ ﺍﺛﺮ ﺍﺳﺘﻌﻤﺎﻝ ﭘﻮﻟﻰ ﻣﻴﺮ ﻫﺎﻯ ﻣﺼﻨﻮﻋﻰ‪237 ..........................................‬‬
‫ﺧﻼﺻﺔ ﻓﺼﻞ ﺳﻴﺰﺩﻫﻢ ‪241 ..................................................................................................................‬‬
‫ﺗﻤﺮﻳﻦ ﻓﺼﻞ ﺳﻴﺰﺩﻫﻢ‪242 ....................................................................................................................‬‬
‫ﻣﺎﺧﺬ‪244 ...........................................................................................................................................‬‬
‫ﺡ‬
 ‫ﻣﻘﺪﻣﻪ‬
‫ﻛﺎﺭﺑﻦ ﻋﻨﺼﺮﻱ ﺩﺍﺭﺍﻯ ﺧﻮﺍﺹ ﻣﺮﺑﻮﻁ ﺑﻪ ﺧﻮﺩ ﺑﻮﺩﻩ ﻛﻪ ﻣﺮﻛﺒﺎﺕ ﻣﺨﺘﻠﻒ ﺭﺍ ﺩﺭ ﻃﺒﻴﻌﺖ ﺑﻪ ﻭﺟﻮﺩ ﺁﻭﺭﺩﻩ ﺍﺳﺖ‪،‬‬
‫ﻣﺮﻛﺒﺎﺕ ﺁﻥ ﺩﺭ ﻃﺒﻴﻌﺖ ﺑﻪ ﺍﻧﺪﺍﺯﺓ ﺯﻳﺎﺩ ﺍﺳﺖ ﻛﻪ ﻳﻚ ﺑﺨﺶ ﺧﺎﺻﻰ ﺭﺍ ﺩﺭ ﻛﻴﻤﻴﺎ ﺑﻪ ﺧﻮﺩ ﺍﺧﺘﺼﺎﺹ ﺩﺍﺩﻩ ﺍﺳﺖ ﻭﺁﻥ‬
‫ﻋﺒﺎﺭﺕ ﺍﺯ ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﻣﻴﺒﺎﺷﺪ‪ .‬ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﺑﺤﺸﻰ ﺍﺯ ﻛﻴﻤﻴﺎ ﺍﺳﺖ ﻛﻪ ﺍﺯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﻭﻣﺸﺘﻘﺎﺕ ﺁﻥ ﺑﺤﺚ‬
‫ﻣﻴﻜﻨﺪ‪ .‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﺩﺭ ﺻﻨﻌﺖ ﺍﻣﺮﻭﺯﻯ ﺭﻭﻝ ﺍﺳﺎﺳﻰ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ‪ ،‬ﺍﺩﻭﻳﻪ ﻫﺎ ‪،‬ﺭﻧﮕﻬﺎ ﻭﺩﻳﮕﺮ ﺳﺎﻣﺎﻥ‬
‫ﺁﻻﺕ ﻋﺼﺮﻯ ﻛﻨﻮﻧﻰ ﺍﺯﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺗﺸﻜﻴﻞ ﮔﺮﺩﻳﺪﻩ ﺍﻧﺪ‪ .‬ﻛﻴﻤﻴﺎﻯ ﺻﻨﻒ ﺩﻭﺍﺯﺩﻫﻢ ﺑﺨﺶ ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ‬
‫ﺑﻮﺩﻩ ﻭ ﻣﺮﻛﺒﺎﺗﻰ ﺭﺍ ﺗﺤﺖ ﻣﻄﺎﻟﻌﻪ ﻗﺮﺍﺭﻣﻴﺪﻫﺪ ﻛﻪ ﻋﻤﺪﺗﺎً ﺍﺯ ﻋﻨﺼﺮ ﻛﺎﺭﺑﻦ ﻭﻫﺎﻳﺪﺭﻭﺟﻦ ﺗﺸﻜﻴﻞ ﮔﺮﺩﻳﺪﻩ ﺍﻧﺪ؛ﻳﻌﻨﻰ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﻭ ﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﻣﻴﺒﺎﺷﺪ‪.‬‬
‫ﻛﻴﻤﻴﺎﻯ ﺻﻨﻒ ﺩﻭﺍﺯﺩﻫﻢ ﻣﺘﺸﻜﻞ ﺍﺯ ﺳﻴﺰﺩﻩ ﻓﺼﻞ ﺑﻮﺩﻩ ﻛﻪ ﻓﺼﻞ ﺍﻭﻝ ﺁﻥ ﺗﺸﻜﻴﻞ ﺭﻭﺍﺑﻂ ﻛﻴﻤﻴﺎﻭﻯ ﺭﺍ ﺩﺭ ﻣﺮﻛﺒﺎﺕ‬
‫ﻋﻀﻮﻯ ﺗﻮﺿﻴﺢ ﻣﻴﻨﻤﺎﻳﺪ‪ .‬ﻓﺼﻞ ﺩﻭﻡ ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻭ ﻓﻮﺭﻣﻮﻝ ﻫﺎ ﺭﺍ ﺍﺭﺍﻳﻪ ﻣﻴﺪﺍﺭﺩ ‪ .‬ﻓﺼﻞ ﺳﻮﻡ ﺩﺭﻣﻮﺭﺩ ﻃﺒﻘﻪ ﺑﻨﺪﻯ‬
‫ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺑﺤﺚ ﻧﻤﻮﺩﻩ ﻭ ﻓﺼﻞ ﭼﻬﺎﺭﻡ ﺍﻟﻜﺎﻧﻬﺎ ﻭﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺭﺍ ﺗﺸﺮﻳﺢ ﻣﻴﻜﻨﺪ ‪.‬ﻓﺼﻞ ﭘﻨﺠﻢ ﺍﻟﻜﻴﻦ ﻭﺍﻟﻜﺎﻳﻦ‬
‫‪،‬ﻓﺼﻞ ﺷﺸﻢ ﻣﺮﻛﺒﺎﺕ ﺍﺭﻭﻣﺎﺗﻴﻚ ‪ ،‬ﻓﺼﻞ ﻫﻔﺘﻢ ﺍﻟﻜﺎﻳﻞ ﻫﻼﻳﺪﻫﺎ‪ ،‬ﻓﺼﻞ ﻫﺸﺘﻢ ﺍﻟﻜﻮﻝ ﻫﺎ ﻭﺍﻳﺘﺮﻫﺎ‪ ،‬ﻓﺼﻞ ﻧﻬﻢ ﺩﺭﻣﻮﺭﺩ‬
‫ﺍﻟﺪﻳﻬﺎﻳﺪﻫﺎ ﻭﻛﻴﺘﻮﻥ ﻫﺎ ﻣﻌﻠﻮﻣﺎﺕ ﺍﺭﺍﻳﻪ ﻣﻴﺪﺍﺭﺩ ؛ ﺑﻪ ﻫﻤﻴﻦ ﺗﺮﺗﻴﺐ ﻓﺼﻞ ﺩﻫﻢ ﺗﻴﺰﺍﺑﻬﺎﻯ ﻋﻀﻮﻯ ‪ ،‬ﻓﺼﻞ ﻳﺎﺯﺩﻫﻢ ﺍﻣﻴﻨﻬﺎ‪،‬ﻓﺼﻞ‬
‫ﺩﻭﺍﺯﺩﻫﻢ ﭘﻮﻟﻰ ﻣﻴﺮﻫﺎﻯ ﻃﺒﻴﻌﻰ ﻭﻓﺼﻞ ﺳﻴﺰﺩﻫﻢ ﭘﻮﻟﻰ ﻣﻴﺮﻫﺎﻯ ﻣﺼﻨﻮﻋﻰ ﺭﺍ ﺗﻮﺻﻴﺢ ﻣﻴﻜﻨﺪ‪ .‬ﻣﻄﺎﻟﺐ ﻫﺮ ﻓﺼﻞ ﺟﻨﺒﻪ‬
‫ﻫﺎﻯ ﺣﻴﺎﺗﻰ ﺩﺍﺷﺘﻪ ﻭ ﺍﻫﺪﺍﻑ ﺍﺳﺎﺳﻰ ﺗﺪﺭﻳﺲ ﻫﺮ ﻓﺼﻞ ﺍﻳﻦ ﺍﺳﺖ ﻛﻪ ﺗﺎ ﺳﻄﺢ ﺁﻣﻮﺯﺵ ﺷﺎﮔﺮﺩﺍﻥ ﺩﺭﺍﻳﻦ ﻋﺮﺻﻪ ﺑﻠﻨﺪ‬
‫ﺭﻓﺘﻪ ﺍﺯ ﻣﻄﺎﻟﺐ ﺁﻣﻮﺯﺷﻰ ﺁﻥ ﺩﺭﻋﺮﺻﻪ ﻫﺎﻯ ﻣﺨﺘﻠﻒ ﺣﻴﺎﺗﻰ ﺧﻮﻳﺶ ﺍﺳﺘﻔﺎﺩﻩ ﻧﻤﺎﻳﻨﺪ ﻭﻫﻢ ﺩﺭ ﻣﺴﺎﻳﻞ ﺻﻨﻌﺘﻰ ﺩﺳﺘﺮﺳﻰ‬
‫ﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ‪.‬‬
‫ﺩﺭ ﺁﻏﺎﺯ ﻫﺮ ﻓﺼﻞ ﺍﻫﺪﺍﻑ ﺁﻣﻮﺯﺷﻰ ﺑﻪ ﺷﻜﻞ ﺳﺆﺍﻟﻬﺎ ﻃﺮﺡ ﻭ ﺩﺭ ﭘﺎﻳﺎﻥ ﻫﺮ ﻓﺼﻞ ﺧﻼﺻﺔ ﻓﺼﻞ ﺗﺤﺮﻳﺮ ﮔﺮﺩﻳﺪﻩ ﻛﻪ ﺗﺎ‬
‫ﺷﺎﮔﺮﺩﺍﻥ ﺭﺍ ﺍﺯ ﻣﻔﺎﻫﻴﻢ ﻭ ﺭﻭﺵ ﺁﻣﻮﺯﺵ ﺧﻮﺏ ﺑﻬﺮﻩ ﻣﻨﺪ ﺳﺎﺯﻧﺪ ؛ ﺑﻪ ﻫﻤﻴﻦ ﺗﺮﺗﻴﺐ ﺑﻌﺪ ﺍﺯ ﺧﻼﺻﺔ ﻫﺮ ﻓﺼﻞ ﺗﻤﺮﻳﻦ‬
‫ﻭﺳﺆﺍﻻﺕ ﺣﻞ ﻧﺎﺷﺪﻩ ﻃﺮﺡ ﺷﺪﻩ ﺍﺳﺖ ﺗﺎ ﺷﺎﮔﺮﺩﺍﻥ ﺧﻮﺩ ﺁﻧﻬﺎ ﺭﺍ ﺣﻞ ﻧﻤﺎﻳﻨﺪ ﺗﺎ ﺩﺭ ﺁﻣﻮﺯﺵ ﻣﻄﺎﻟﺐ ﻓﺼﻞ ﻣﺮﺑﻮﻁ ﺑﻪ‬
‫ﺁﻧﻬﺎ ﻛﻤﻚ ﻧﻤﺎﻳﻨﺪ‪ .‬ﻫﺮ ﻓﺼﻞ ﺑﻪ ﻛﻠﻤﺎﺕ ﺳﺎﺩﻩ ﻭﻋﺎﻡ ﻓﻬﻢ ﺗﺤﺮﻳﺮ ﮔﺮﺩﻳﺪﻩ ﺩﺭ ﺑﻴﻦ ﻣﺘﻦ ﻓﺼﻮﻝ ﻓﻌﺎﻟﻴﺖ ﻫﺎﻯ ﻋﻤﻠﻰ ﻭ‬
‫ﻧﻈﺮﻯ ﺍﺭﺍﻳﻪ ﺷﺪﻩ ﺗﺎ ﺷﺎﮔﺮﺩﺍﻥ ﺧﻮﺩ ﺑﻪ ﺍﺟﺮﺍﻯ ﺁﻥ ﺑﻪ ﻃﻮﺭﮔﺮﻭﭘﻰ ﻭ ﻳﺎ ﺍﻧﻔﺮﺍﺩﻯ ﺑﻪ ﻛﻤﻚ ﻣﻌﻠﻢ ﭘﺮﺩﺍﺧﺘﻪ ﻭ ﺍﻳﻦ ﻓﻌﺎﻟﻴﺘﻬﺎ‬
‫ﺩﺭ ﺁﻣﻮﺯﺵ ﻫﺮﭼﻪ ﺑﻴﺸﺘﺮ ﻭﺧﻮﺑﺘﺮ ﺷﺎﮔﺮﺩﺍﻥ ﻛﻤﻚ ﻣﻴﻨﻤﺎﻳﻨﺪ ‪.‬‬
‫ﻧﺎﮔﻔﺘﻪ ﻧﺒﺎﻳﺪ ﮔﺬﺍﺷﺖ ﺍﻳﻨﻜﻪ ﺗﺄﻟﻴﻒ ﺍﻳﻦ ﻛﺘﺎﺏ ﺑﻪ ﺍﺳﺎﺱ ﺗﺠﺎﺭﺏ ﻭﺩﺭﻙ ﻣﺸﻜﻞ ﺷﺎﮔﺮﺩﺍﻥ ﻋﺰﻳﺰ ﻧﻮﺟﻮﺍﻧﺎﻥ ﻭﺟﻮﺍﻧﺎﻥ‬
‫ﺩﺭﻋﺮﺻﺔ ﺗﻌﻠﻴﻢ ﻛﻴﻤﻴﺎ ‪ 20‬ﺳﺎﻟﺔ ﺑﻨﺪﻩ ﺑﻮﺩﻩ ﻭﻃﻮﺭﻯ ﺗﺎﻟﻴﻒ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ﺗﺎ ﻣﺸﻜﻞ ﺣﻴﺎﺗﻲ ﻭ ﭘﻮﻫﻨﺘﻮﻧﻲ ﺍﻳﺸﺎﻥ ﺩﺭ‬
‫ﻋﺮﺻﺔ ﻛﻴﻤﻴﺎ ﺣﻞ ﺷﺪﻩ ﺑﺎﺷﺪ‪.‬‬
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 ‫ﻓﺼﻞ ﺍﻭﻝ‬
‫ﺗﺸﻜﻴﻞ ﺭﻭﺍﺑﻂ ﻛﻴﻤﻴﺎﻭﻯ ﺩﺭﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ‬
‫ﺗﻌﺪﺍﺩ ﻣﺮﻛﺒﺎﺕ ﻛﺎﺭﺑﻦ ﺑﻪ ﺍﻧﺪﺍﺯﻩ ﺯﻳﺎﺩ ﺍﺳﺖ ﻛﻪ ﺑﺨﺶ ﻣﻬﻢ ﻋﻠﻢ ﻛﻴﻤﻴﺎ ﺭﺍ ﺑﻪ ﺍﻳﻦ ﻋﻨﺼﺮ ﺍﺧﺘﺼﺎﺹ ﺩﺍﺩﻩ‬
‫ﺍﻧﺪ ﻭ ﻋﻠﻤﻰ ﻛﻪ ﻣﺮﻛﺒﺎﺕ ﻛﺎﺭﺑﻦ ‪،‬ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎﺭﺍ ﻣﻴﺘﻮﺍﻧﻴﻢ ﺗﺤﺖ ﺁﻥ ﻣﻄﺎﻟﻌﻪ ﻧﻤﺎﺋﻴﻢ ‪ ،‬ﺑﻨﺎﻡ‬
‫» ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ« ﻳﺎﺩ ﻣﻴﺸﻮﺩ‪.‬‬
‫ﺑﺮﺍﻯ ﺷﻨﺎﺧﺖ ﻭﺍﻫﻤﻴﺖ ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﺩﺭﺻﻨﻌﺖ ﺑﻪ ﺍﻳﻦ ﺍﺭﻗﺎﻡ ﺗﻮﺟﻪ ﻧﻤﺎﻳﻴﺪ‪ ،‬ﻓﺮﻭﺵ ﻣﺮﻛﺒﺎﺕ ﻋﻀـــﻮﻯ‬
‫ﺩﺭﻳﻚ ﺳــــــــﺎﻝ ﺩﺭﻓــــــﺮﺍﻧﺴﻪ ﺩﺭﺳﺎﻝ‪1995‬ﻣﺒﻠﻎ ﻳﻜﺼﺪﻭﻫﺸﺘﺎﺩﻭﭘﻨﺞ ﻣﻠﻴﺎﺭﺩ )‪(185000000000‬‬
‫ﻓﺮﺍﻧﻚ ﻭ ﺣﺎﻝ ﺁﻧﻜﻪ ﺭﻗﻢ ﻓﺮﻭﺵ ﺳﺎﻻﻧﺔ ﻣﻮﺍﺩ ﻏﻴﺮﻋﻀﻮﻯ ) ﻣﻌﺪﻧﻰ ( ﻣﺘﺸﻜﻞ ﺍﺯ ﺗﻤﺎﻣﻰ ﻋﻨﺎﺻﺮ ﺟﺪﻭﻝ‬
‫ﺩﻭﺭﻩ ﻳﻰ ﺻــﺮﻑ ‪ 52‬ﻣﻴﻠﻴﺎﺭﺩ ﻓﺮﺍﻧﻚ ﺑﻮﺩﻩ ﺍﺳﺖ ‪ ،‬ﺑﻪ ﺍﻳﻦ ﺍﺳﺎﺱ ﺷﻨﺎﺧﺖ‪ ،‬ﺧﻮﺍﺹ‪ ،‬ﻧﺎﻣﮕﺬﺍﺭﻯ ﻭ‬
‫ﻣﻮﺭﺩ ﺍﺳﺘﻌﻤﺎﻝ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺍﺯ ﺍﻫﻤﻴﺖ ﺯﻳﺎﺩ ﺑﺮﺧﻮﺭﺩﺍﺭ ﺍﺳﺖ‪.‬ﺩﺭﺷﻨﺎﺧﺖ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﻭﺍﺑﻂ‬
‫ﻛﻴﻤﻴﺎﻭﻯ ﺭﻭﻝ ﺍﺳﺎﺳﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ؛ﺑﻨﺎﺑﺮﺍﻳﻦ ﺑﺎﻳﺪ ﺩﺍﻧﺴﺘﻪ ﺷﻮﺩ ﻛﻪ ﺭﺍﺑﻄﻪ ﭼﻴﺴﺖ ؟ ﺭﺍﺑﻄﻪ ﭼﻪ ﻃﻮﺭ ﺑﺮﻗﺮﺍﺭ‬
‫ﻣﻴﮕﺮﺩﺩ؟ ﻋﻮﺍﻣﻞ ﺑﺮﻗﺮﺍﺭﻯ ﺭﻭﺍﺑﻂ ﭼﻴﺴﺖ؟ ﺍﻧﻮﺍﻉ ﺭﻭﺍﺑﻂ ﻛﺪﺍﻡ ﻫﺎ ﺍﻧﺪ؟ ﺑﺎ ﻣﻄﺎﻟﻌﺔ ﺍﻳﻦ ﻓﺼﻞ ﺭﺍﺟﻊ ﺑﻪ‬
‫ﺭﻭﺍﺑﻂ ﻛﻴﻤﻴﺎﻭﻯ ﻣﻌﻠﻮﻣﺎﺕ ﺣﺎﺻﻞ ﺧﻮﺍﻫﻴﺪ ﻛﺮﺩ‪.‬‬
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 ‫‪ : 1-1‬ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻭﺳﻮﻳﻪ ﻫﺎﻯ ﺍﻧﺮژﻳﻜﻰ ﻛﺎﺭﺑﻦ‬
‫ﻛﺎﺭﺑﻦ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺘﺮﻭﻥ ‪ 1S 2 2S 2 2P 2‬ﺑﻮﺩﻩ ‪ ،‬ﺗﻌﺪﺍﺩ ﻣﺮﻛﺒﺎﺕ ﺁﻥ ﺯﻳﺎﺩ ﻭﺑﺎﺍﻫﻤﻴﺖ ﻣﻴﺒﺎﺷﺪ ﻭﺑﺨﺶ‬
‫ﻣﻬﻢ ﻛﻴﻤﻴﺎﻭﻯ ﻋﻀﻮﻯ ﺭﺍ ﺗﺸﻜﻴﻞ ﺩﺍﺩﻩ ﺍﺳﺖ‪ .‬ﺩﺭﺳﺎﻝ ‪ 1880‬ﺑﻪ ﺗﻌﺪﺍﺩ ‪ 1200‬ﻣﺮﻛﺐ ﻋﻀﻮﻯ ﻭﺗﺎ ﺳﺎﻝ‬
‫‪ 1998‬ﺍﺿﺎﻓﻪ ﺍﺯ ﺑﻴﺴﺖ ﻣﻴﻠﻴﻮﻥ ﻣﺮﻛﺐ ﻋﻀﻮﻯ ﻛﺸﻒ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ‪ .‬ﺩﺭﻫﻤﻴﻦ ﻣﺮﻛﺒﺎﺕ ﻛﺸﻒ ﺷﺪﻩ ﺑﻪ‬
‫ﺍﺭﻗﺎﻡ ﻓﻮﻕ ﺍﻟﺬﻛﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﻪ ﺷﻜﻞ ﺁﻳﻮﻥ ‪ C 4+‬ﻣﻮﺟﻮﺩ ﻧﺒﻮﺩﻩ‪ ،‬ﺑﻠﻜﻪ ﺑﻪ ﺻﻮﺭﺕ ﻋﻤﻮﻡ ﻣﻰ ﺗﻮﺍﻥ ﮔﻔﺖ‬
‫ﻛﻪ ﺩﺭﺗﻤﺎﻡ ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﻪ ﺣﺎﻟﺖ ﺗﺤﺮﻳﻚ ﻗﺮﺍﺭﺩﺍﺷﺘﻪ ﻭﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺘﺮﻭﻧﻰ ‪1S 2 2S1 2P 3‬‬
‫ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ‪.‬‬
‫ﺩﻳﺎﮔﺮﺍﻡ ﺳﻮﻳﺔ ﺍﻧﺮژﻯ ﺍﻟﻜﺘﺮﻭﻥ ﻫﺎﻯ ﻭﻻﻧﺴﻰ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﺷﻜﻞ )‪ (1-1‬ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ‪:‬‬
‫ﺷﻜﻞ )‪ (1-1‬ﺩﻳﺎﮔﺮﺍﻡ ﺳﻮﻳﻪ ﻫﺎﻯ ﺍﻧﺮژﻳﻜﻰ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ‬
‫‪+3‬‬
‫ﺩﺭﺑﻌﻀﻰ ﺍﺯﻣﺮﻛﺒﺎﺕ ﻏﻴﺮﻋﻀﻮﻯ ﻛﺎﺭﺑﻦ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﺷﻜﻞ ‪ C 4−‬ﻣﻼﺣﻈﻪ ﻛﺮﺩ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪، A l4C3− 4 ً :‬‬
‫‪ Be2C‬ﻭﻏﻴﺮﻩ ‪.‬‬
‫ﺑﻪ ﺻﻮﺭﺕ ﻋﻤﻮﻡ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﻪ ﻛﻮﻭﻻﻧﺴﻰ ﺭﺍ ﺑﺮﻗﺮﺍﺭﻧﻤﻮﺩﻩ ﻛﻪ ﺍﻛﺜﺮﺍ ً ﺯﻧﺠﻴﺮﻫﺎﻯ ﻃﻮﻝ ﻭﻳﺎ ﺣﻠﻘﻪ‬
‫ﻫﺎﻯ ﻛﻮﭼﻚ ﻭﺑﺰﺭگ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ؛ ﺩﺭﺍﻳﻦ ﺯﻧﺠﻴﺮﻫﺎ ﻭﻳﺎ ﺣﻠﻘﻪ ﻫﺎﻯ ﺑﻴﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ ﻳﻚ‬
‫ﮔﺎﻧﻪ ‪ ،‬ﺩﻭﮔﺎﻧﻪ ﻭﻳﺎ ﺳﻪ ﮔﺎﻧﻪ ﺑﻪ ﻣﻼﺣﻈﻪ ﻣﻰ ﺭﺳﺪ؛ﺣﺘﻰ ﺭﺍﺑﻄﻪ ‪ 1.5‬ﻧﻴﺰ ﻣﺸﺎﻫﺪﻩ ﺷﺪﻩ ﻛﻪ ﺁﻧﺮﺍ ﻣﻴﺘﻮﺍﻥ ﺩﺭﺑﻨﺰﻳﻦ‬
‫ﺑﻪ ﺣﺎﻟﺖ ﺭﻳﺰﻭﻧﺎﻧﺲ ﻣﻼﺣﻈﻪ ﮔﺮﺩﺩ‪ .‬ﺍﻧﺮژﻯ ﺭﺍﺑﻄﺔ ﻛﺎﺭﺑﻦ – ﻛﺎﺭﺑﻦ ‪ E(C−C) = 360 Kjoul mol‬ﺍﺳﺖ ‪.‬‬
‫ﻛﺎﺭﺑﻦ ﻃﺒﻴﻌﻰ ﺩﺍﺭﺍﻯ ﺩﻭ ﺍﻳﺰﻭﺗﻮپ ‪ 126C‬ﻭ ‪ 136C‬ﺑﻮﺩﻩ ﻛﻪ ﻓﻴﺼﺪﻯ ﺍﻧﺘﺸﺎﺭ ﺷﺎﻥ ﺩﺭ ﻃﺒﻴﻌﺖ ﺑﺘﺮﺗﻴﺐ ‪98.89%‬‬
‫ﻭ ‪ 0.11%‬ﺍﺳﺖ ؛ ﻻﻛﻦ ﺩﺭﻃﺒﻴﻌﺖ ﺍﻳﺰﻭﺗﻮپ ‪ C‬ﻧﻴﺰ ﻣﻮﺟﻮﺩﺍﺳﺖ ﻛﻪ ﺩﺭﻃﺒﻘﺎﺕ ﺑﻠﻨﺪ ﺍﺗﻤﻮﺳﻔﻴﺮ ﺩﺭﻧﺘﻴﺠﺔ‬
‫‪14‬‬
‫‪6‬‬
‫ﺗﻌﺎﻣﻞ ﻫﺴﺘﻮﻯ ﺫﻳﻞ ﺗﺸﻜﻴﻞ ﻣﻰ ﮔﺮﺩﺩ‪:‬‬
‫‪14 N + 1 n→1 H +14 C‬‬
‫‪7‬‬ ‫‪0‬‬ ‫‪1‬‬ ‫‪6‬‬
‫ﻧﺼﻒ ﻃﻮﻝ ﻋﻤﺮ ‪ 5568, 14 C‬ﺳﺎﻝ ﺍﺳﺖ ﻭﺩﺭﻧﺘﻴﺠﻪ ﺗﺸﻌﺸﻊ ‪ B‬ﺑﻪ ﻧﺎﻳﺘﺮﻭﺟﻦ ﻣﺒﺪﻝ ﻣﻴﮕﺮﺩﺩ‪:‬‬
‫‪6‬‬
‫‪14‬‬
‫‪14‬‬
‫‪6‬‬ ‫⎯‪C‬‬
‫‪⎯→7 N + 0−1 e‬‬
‫ﻭ ‪ 126C‬ﺩﺭﺣﺎﻟﺖ ﺗﻌﺎﺩﻝ ﺑﻮﺩﻩ ﻭﻧﺴﺒﺖ ﺗﻌﺎﺩﻝ ﺁﻥ‬ ‫‪14‬‬
‫‪6‬‬ ‫ﺩﺭﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻣﻮﺟﻮﺩﺍﺕ ﺣﻴﻪ ﺍﻳﺰﻭﺗﻮپ ‪C‬‬
‫‪3‬‬
 ‫‪14 C‬‬
‫ﻭﺛﺎﺑﺖ ﺍﺳﺖ ؛ﺍﻣﺎ ﺍﮔﺮﻣﻮﺟﻮﺩﺍﺕ ﺣﻴﻪ ﺍﻋﻢ ﺍﺯﻧﺒﺎﺗﺎﺕ ﻭﺣﻴﻮﺍﻧﺎﺕ ﺑﺎ ﻃﺒﻴﻌﺖ ﻗﻄﻊ ﺭﺍﺑﻄﻪ‬ ‫‪6 = 10−12‬‬
‫‪12 C‬‬
‫‪6‬‬
‫ﻧﻤﺎﻳﻨﺪ‪ .‬ﻧﺴﺒﺖ ﺗﻌﺎﺩﻟﻰ ﻓﻮﻕ ﺑﺮﻫﻢ ﺧﻮﺭﺩﻩ ‪ ،‬ﺗﺠﺰﻳﻪ ﻭﻛﺎﻫﺶ ‪ 146C‬ﺻﻮﺭﺕ ﮔﺮﻓﺘﻪ ﺣﻴﻮﺍﻧﺎﺕ ﻭﻧﺒﺎﺕ ﺑﻪ ﻣﺮگ‬
‫ﻣﻮﺍﺟﻪ ﺷﺪﻩ ﻭ ﻣﻘﺪﺍﺭﺁﻥ ﺍﺯﺑﻴﻦ ﻣﻰ ﺭﻭﺩ؛ ﺍﺯﺍﻳﻦ ﺧﺎﺻﻴﺖ ﺁﻥ ﺑﺮﺍﻯ ﺗﻌﻴﻦ ﻧﺼﻒ ﻃﻮﻝ ﻋﻤﺮﺍﺷﻴﺎ ﭼﻮﺑﻰ ‪ ،‬ﺟﺴﺪ‬
‫ﺍﻧﺴﺎﻧﻬﺎ ﻳﺎ ﺣﻴﻮﺍﻧﺎﺕ ﻛﻪ ﺍﺯ‪ 15‬ﺗﺎ ﺣﺪ ﺍﻋﻈﻤﻰ ‪ 30‬ﻫﺰﺍﺭ ﺳﺎﻝ ﻗﺒﻞ ﺍﻟﻰ ﺍﻛﻨﻮﻥ ﺯﻧﺪﻩ ﮔﻰ ﺩﺍﺷﺘﻪ ﺍﻧﺪ ‪ ،‬ﺑﺎﺩﻗﺖ‪10 %‬‬
‫ﻣﻴﺘﻮﺍﻥ ﺍﺳﺘﻔﺎﺩﻩ ﻛﺮﺩ‪.‬‬
‫ﻭﻻﻧﺲ ﻛﺎﺭﺑﻦ ﻭ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ‬
‫ﻗﻮﺓ ﺍﺗﺤﺎﺩ ﺍﺗﻮﻣﻬﺎﻯ ﻋﻨﺎﺻﺮ ﻛﻴﻤﻴﺎﻭﻯ ﺭﺍ ﺩﺭ ﺗﻌﺎﻣﻼﺕ ﻭ ﺗﻌﺪﺍﺩ ﺭﺍﺑﻄﻪ ﻫﺎﻯ ﻛﻪ ﻳﻚ ﺍﺗﻮﻡ ﺗﺸﻜﻴﻞ ﺩﺍﺩﻩ ﻣﻴﺘﻮﺍﻧﺪ‬
‫ﺑﻪ ﻧﺎﻡ ﻭﻻﻧﺲ ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ ؛ ﭘﺲ ‪ ،‬ﻭﻻﻧﺲ ﻛﺎﺭﺑﻦ ﭼﻨﺪ ﺍﺳﺖ؟ ﺷﻤﺎ ﻣﻴﺘﻮﺍﻧﻴﺪ ﺑﻄﻮﺭ ﺳﺎﺩﻩ ﺑﻪ ﺳﻮﺍﻝ ﻓﻮﻕ‬
‫ﺑﻪ ﺍﺳﺎﺱ ﺳﺎﺧﺘﻤﺎﻥ ﻭﺳﻤﺒﻮﻝ ﻟﻴﻮﻳﺲ )‪ (Lewis‬ﺟﻮﺍﺏ ﺑﺪﻫﻴﺪ؛ ﻃﻮﺭﻳﻜﻪ ﺩﺭ ﺁﻥ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻭﻻﻧﺴﻰ ﺑﻪ‬
‫ﻧﻘﺎﻁ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﻣﻴﺸﻮﺩ‪ ،‬ﭼﻮﻥ ﻛﺎﺭﺑﻦ ﺩﺍﺭﺍﻯ ﭼﻬﺎﺭﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺍﺳﺖ ‪ ،‬ﺳﻤﺒﻮﻝ ﻟﻴﻮﻳﺲ ﺁﻥ ﻗﺮﺍﺭ ﺫﻳﻞ‬
‫ﺗﺤﺮﻳﺮﻣﻴﮕﺮﺩﺩ‪:‬‬
‫ﺷﻜﻞ )‪ (1-2‬ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﻭ ﺳﺎﺧﺘﻤﺎﻥ ﻓﻀﺎﻳﻰ ﻛﺎﺭﺑﻦ‬ ‫ﻛﺎﺭﺑﻦ ‪C‬‬
‫ﺑﺮﺍﻯ ﭘﻮﺭﻩ ﻛﺮﺩﻥ )‪ (octate‬ﺣﺎﻟﺖ ﻫﺸﺖ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻗﺸﺮ ﺍﻟﻜﺘﺮﻭﻥ ﻫﺎﻯ ﻭﻻﻧﺴﻰ‪ ،‬ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎﻳﺪ ﭼﻬﺎﺭ‬
‫ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺧﻮﺩ ﺭﺍ ﺑﺎ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎ ﺑﻪ ﺷﻤﻮﻝ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺷﺮﻳﻚ ﻣﻴﺴﺎﺯﺩ‪ ،‬ﺩﺭ ﻧﺘﻴﺠﺔ‬
‫ﻭﻻﻧﺲ ﻛﺎﺭﺑﻦ ﭼﻬﺎﺭ ﺍﺳﺖ‪.‬‬
‫ﺩﺭ ﺗﻤﺎﻡ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﭼﻬﺎﺭ ﺭﺍﺑﻄﻪ ﺍﺷﺘﺮﺍﻛﻰ ﺭﺍ ﺑﺎ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻳﺎ ﺍﺗﻮﻡ ﻫﺎﻯ‬
‫ﻋﻨﺎﺻﺮﺩﻳﮕﺮ ؛ﺍﺯﻗﺒﻴﻞ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺁﻛﺴﻴﺠﻦ‪ ،‬ﻧﺎﻳﺘﺮﻭﺟﻦ ﻭ ﻫﻠﻮﺟﻦ ﻫﺎ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ‪.‬‬
‫ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯﺟﺪﻭﻝ ﺩﻭﺭﻩ ﻳﻰ ﻋﻨﺎﺻﺮ‪،‬ﻭﻻﻧﺲ ﺁﻛﺴﻴﺠﻦ‪ ،‬ﻧﺎﻳﺘﺮﻭﺟﻦ ﻭﻫﻠﻮﺟﻦ ﻫﺎ ﺩﺭ ﻳﺎﻓﺖ ﻣﻴﮕﺮﺩﺩ‪.‬‬
‫ﺟﺪﻭﻝ ﺫﻳﻞ ﻣﻮﻗﻒ ﻛﺎﺭﺑﻦ ﺭﺍ ﺩﺭ ﺑﻴﻦ ﻋﻨﺎﺻﺮﺩﻳﮕﺮ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪:‬‬
‫‪4‬‬
 ‫ﺸﺎﻥ ﺩﻫﻨﺪﺓ ﻣﻮﻗﻒ ﻛﺎﺭﺑﻦ‬
‫ﻧﺸﺎﻥ‬
‫ﺩﻭﺭﺓ ﻋﻨﺎﺻﺮ ﻧﺸ‬
‫‪ (1‬ﺩﻭﺭﺭﺓ‬
‫ﺟﺪﻭﻝ)‪(1 - 1‬‬
‫ﻛﺎﺭﺑﻦ ﻣﻴﺘﻮﺍﻧﺪ ﺭﺍﺑﻄﻪ ﻫﺎ ﻯ ﻳﮕﺎﻧﻪ‪ ،‬ﺩﻭﮔﺎﻧﻪ ﻭ ﺳﻪ ﮔﺎﻧﻪ ﺭﺍ ﺩﺍﺭﺍ ﺑﺎﺷﺪ ﻛﻪ ﺩﺭ ﺫﻳﻞ ﺗﻮﺿﻴﺢ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫ﭼﻮﻥ ﻛﺎﺭﺑﻦ ﺩﺭ ﻗﺸﺮ ﻭﻻﻧﺴﻰ ﺧﻮﺩ ﺩﺍﺭﺍﻯ ﭼﻬﺎﺭ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺍﺳﺖ ؛ ﺑﻨﺎﺑﺮﺍﻳﻦ ﺑﺮﺍﻯ ﺗﻜﻤﻴﻞ ﺍﻛﺘﻴﺖ ﺧﻮﺩ‬
‫ﺑﻪ ﭼﻬﺎﺭ ﺍﻟﻜﺘﺮﻭﻥ ﺩﻳﮕﺮ ﺿﺮﻭﺭﺕ ﺩﺍﺭﺩ ‪ ،‬ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﺎﻥ ) ‪ (C2 H 6‬ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎﻳﻚ ﺍﺗﻮﻡ ﺩﻳﮕﺮ‬
‫ﻛﺎﺭﺑﻦ ﻭ ﺑﺎ ﺳﻪ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺭﺍﺑﻄﻪ ﺩﺍﺭﺩ‪،‬ﺑﻴﻦ ﻫﺮﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭ ﻫﺮ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻳﻚ ﺭﺍﺑﻄﻪ ﺑﺮﻗﺮﺍﺭﺑﻮﺩﻩ‬
‫ﻛﻪ ﻳﻚ ‪،‬ﻳﻚ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﻣﺸﺘﺮﻙ ﺑﻴﻦ ﺁﻧﻬﺎ ﻣﻮﺟﻮﺩ ﻣﻴﺒﺎﺷﺪ ‪ ،‬ﻋﻠﻤﺎﻯ ﻧﺠﻮﻡ ﺑﺎﻭﺭ ﺩﺍﺭﻧﺪ ﻛﻪ ﺳﻄﺢ ﺯﺣﻞ‬
‫ﺭﺍ ﺍﻳﺘﺎﻥ ﻣﺎﻳﻊ ﺗﺸﻜﻴﻞ ﺩﺍﺩﻩ ﺍﺳﺖ ‪:‬‬
‫‪H‬‬
‫ﺷﻜﻞ )‪ ( 3 - 1‬ﻧﺸﺎﻥ ﺩﻫﻨﺪﺓ ﺍﻳﺘﺎﻥ ﻣﺎﻳﻊ ﺩﺭ ﺳﻄﺢ ﺯﺣﻞ‬
‫ﻋﻼﻭﻩ ﺑﺮﺍﻳﻦ ﻛﺎﺭﺑﻦ ﻭﻋﻨﺎﺻﺮ ﺩﻳﮕﺮ ﺍﺯ ﺟﻤﻠﻪ ﻧﺎﻳﺘﺮﻭﺟﻦ ‪،‬ﺁﻛﺴﻴﺠﻦ ﻭ ﺳﻠﻔﺮ ﻣﻴﺘﻮﺍﻧﻨﺪ ﺑﺎ ﺍﺗﻮﻣﻬﺎﻯ ﺩﻳﮕﺮ ﺑﺎ ﺭﻋﺎﻳﺖ‬
‫ﻗﺎﻋﺪﺓ ﺍﻛﺘﻴﺖ ﺑﻴﺶ ﺍﺯ ﻳﻚ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ‪،‬ﺩﻭﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ )ﭼﻬﺎﺭﺍﻟﻜﺘﺮﻭﻥ ( ﺭﺍ ﻣﺸﺘﺮﻙ ﻗﺮﺍﺭﺩﻫﻨﺪ ﻛﻪ‬
‫ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ‪ .‬ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﻴﻠﻴﻦ ﺩﺍﺭﺍﻯ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭﭼﻬﺎﺭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺑﻮﺩﻩ ﻛﻪ‬
‫ﺭﺍﺑﻄﻪ ﺑﻴﻦ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ – ﻛﺎﺭﺑﻦ ﺁﻥ ﺩﻭﮔﺎﻧﻪ ﻣﻴﺒﺎﺷﺪ ‪ .‬ﺍﻳﺘﻴﻠﻴﻦ ﺑﻪ ﺷﻜﻞ ﻫﺎﺭﻣﻮﻥ ﺩﺭ ﺍﻛﺜﺮ ﻧﺒﺎﺗﺎﺕ ﺑﻪ ﻃﻮﺭ‬
‫ﻣﺸﺨﺺ ﺑﺎﺩﻧﺠﺎﻥ ﺭﻭﻣﻰ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﺩﺭ ﻣﻮﻗﻊ ﭘﺨﺘﻪ ﺷﺪﻥ ﺁﻧﺮﺍ ﺁﺯﺍﺩ ﻣﻴﺴﺎﺯﺩ ﻭﺑﺎﻋﺚ ﭘﺨﺘﻦ ﺑﺎﺩﻧﺠﺎﻥ ﻫﺎﻯ‬
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 ‫ﺭﻭﻣﻰ ﺩﻳﮕﺮﻣﻴﮕﺮﺩﺩ ؛ ﺑﻨﺎﺑﺮﺍﻳﻦ ﺩﺭ ﺯﺭﺍﻋﺖ ﺩﺭﻋﺮﺻﺔ ﭘﺨﺘﻦ ﺑﺎﺩﻧﺠﺎﻥ ﺭﻭﻣﻰ ﺍﺯ ﺍﻳﺘﻴﻠﻴﻦ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﻨﻤﺎﻳﻨﺪ‪:‬‬
‫ﺷﻜﻞ ) ‪ ( 4 - 1‬ﺑﺎﺩﻧﺠﺎﻥ ﺭﻭﻣﻰ ﻣﻨﺒﻊ ﺍﻳﺘﻠﻴﻦ‬
‫ﻫﻤﭽﻨﺎﻥ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻣﻴﺘﻮﺍﻧﻨﺪ ﺭﺍﺑﻄﺔ ﺳﻪ ﻛﺎﻧﻪ ﺭﺍ ﺑﺎﻫﻢ ﺑﺮﻗﺮﺍﺭ ﺳﺎﺧﺘﻪ ﺳﻪ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﺭﺍﺑﺎﻫﻢ ﻣﺸﺘﺮﻙ‬
‫ﻗﺮﺍﺭ ﺩﻫﻨﺪ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺍﺳﺘﻠﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﻴﻦ ﻫﻢ ﺭﺍﺑﻄﺔ ﺳﻪ ﮔﺎﻧﻪ ﺭﺍ ﺑﺮﻗﺮﺍﺭ ﻧﻤﻮﺩﻩ ‪ ،‬ﺩﺭ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﻦ ﻣﺮﻛﺐ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺷﺎﻣﻞ ﺍﺳﺖ ‪ .‬ﺩﺭ ﭼﺮﺍﻍ ﻫﺎﻯ ﻣﻌﺪﻥ ﺷﻨﺎﺳﻰ‬
‫ﺍﺯ ﺳﻨﮓ ﻛﻠﺴﻴﻢ ﻛﺎﺭﺑﺎﻳﺪ ﺍﺳﺘﻔﺎﺩﻩ ﻧﻤﻮﺩﻩ ‪،‬ﻃﻮﺭﻳﻜﻪ ﺑﺎﻻﻯ ﻛﻠﺴﻴﻢ ﻛﺎﺭﺑﺎﻳﺪ ﺁﺏ ﺭﺍ ﻋﻼﻭﻧﻤﻮﺩﻩ ‪ ،‬ﺩﺭﻧﺘﻴﺠﺔ‬
‫ﻫﺎﻳﺪﺭﻭﻟﻴﺰ ﺁﻥ ﺍﺳﻴﺘﻴﻠﻴﻦ ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ ‪.‬‬
‫ﺷﻜﻞ )‪ ( 1-5‬ﺍﺳﺘﻌﻤﺎﻝ ﮔﺎﺯ ﺍﺳﻴﺘﻴﻠﻴﻦ ﺩﺭ ﭼﺮﺍﻍ ﻫﺎﻯ ﺍﻛﺴﻰ ﺍﺳﻴﺘﻠﻴﻦ ﻣﻌﺎﺩﻥ ﺷﻨﺎﺳﺎﻥ‬
‫ﻳﻜﻰ ﺍﺯ ﺧﺼﻮﺻﻴﺎﺕ ﻣﻬﻢ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻋﺒﺎﺭﺕ ﺍﺯ ﺗﺸﻜﻴﻞ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎﻯ ﺯﻧﺠﻴﺮﻯ ﻭ‬
‫ﺯﻧﺠﻴﺮ ﺑﺴﺘﻪ )ﺣﻠﻘﻮﻯ( ﺍﺳﺖ ﻛﻪ ﻛﺎﺭﺑﻦ ﺑﺎ ﻛﺎﺭﺑﻦ ﺩﺭ ﺁﻧﻬﺎ ﺑﺎ ﻫﻢ ﺭﺍﺑﻄﻪ ﺩﺍﺭﻧﺪ‪ .‬ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺫﻳﻞ ﺍﺳﻜﻠﻴﺖ‬
‫ﻛﺎﺭﺑﻨﻰ ﻣﺮﻛﺒﺎﺕ ﺯﻧﺠﻴﺮﻯ ﻭ ﺣﻠﻘﻮﻯ ﻋﻀﻮﻯ ﺭﺍ ﻧﺸﺎﻥ ﻣﻴﺪﻫﻨﺪ ‪:‬‬
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‫ﺑﺮﺧﻼﻑ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎ؛ ﻣﺎﻧﻨﺪ‪ :‬ﻧﺎﻳﺘﺮﻭﺟﻦ ﻭﺁﻛﺴﻴﺠﻦ ‪ ،‬ﺭﻭﺍﺑﻂ ﻣﺘﻌﺪﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻗﻮﺕ ﺭﺍﺑﻄﻪ ﻫﺎﻯ‬
‫ﻛﺎﺭﺑﻦ – ﻛﺎﺭﺑﻦ ﺭﺍ ﻛﻢ ﻧﻪ ﻣﻰ ﺳﺎﺯﺩ‪.‬‬
‫ﺩﺭﺯﻧﺠﻴﺮ ﻫﺎ ﻭﺣﻠﻘﻪ ﻫﺎ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻧﻴﺰ ﻣﻴﺘﻮﺍﻧﻨﺪ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻭ ﺳﻪ ﮔﺎﻧﻪ ﺭﺍ ﺑﺎ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ‬
‫ﻭ ﻋﻨﺎﺻﺮﺩﻳﮕﺮ ﺑﺮﻗﺮﺍﺭ ﻧﻤﺎﻳﻨﺪ ؛ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪:‬‬
‫ﻃﺮﻳﻘﻪ ﻫﺎﻯ ﻣﺨﺘﻠﻒ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﺔ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺑﺎﻋﺚ ﻣﻮﺟﻮﺩﻳﺖ ﺗﻌﺪﺍﺩ ﻭ ﺍﻧﻮﺍﻉ ﺯﻳﺎﺩ ﻣﺮﻛﺐ ﻛﺎﺭﺑﻦ‬
‫ﻣﻴﮕﺮﺩﺩ‪.‬‬
‫ﻣﺜﺎﻝ ‪ :‬ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﻣﺮﻛﺐ ﻓﺎﺭﻡ ﺍﻟﺪﻳﻬﺎﻳﺪ )‪ (CH 2O‬ﺭﺍ ﺗﺤﺮﻳﺮﺩﺍﺭﻳﺪ ‪.‬‬
‫ﺣﻞ ‪ :‬ﺍﻭﻻ« ﺗﻌﺪﺍﺩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻣﺠﻤﻮﻋﻰ ﻭﻻﻧﺴﻰ ﺭﺍ ﻣﺤﺎﺳﺒﻪ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫ﻫﺮﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺩﺍﺭﺍﻯ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺑﻮﺩﻩ ؛ﭘﺲ ﺩﻭﺍﺗﻮﻡ ﺁﻥ ﺩﺍﺭﺍﻯ ﺩﻭ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﻣﻴﺒﺎﺷﺪ؛ﺑﻪ‬
‫ﻫﻤﻴﻦ ﺗﺮﺗﻴﺐ ﻳﻚ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺍﺭﺍﻯ ﭼﻬﺎﺭﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﻭﻳﻚ ﺍﺗﻮﻡ ﺁﻛﺴﻴﺠﻦ ﺩﺍﺭﺍﻯ ﺷﺶ ﺍﻟﻜﺘﺮﻭﻥ‬
‫ﺑﻮﺩﻩ ﻛﻪ ﺑﻪ ﺻﻮﺭﺕ ﻛﻞ ﺩﺭ ﺍﻳﻦ ﻣﺮﻛﺐ ﺩﻭﺍﺯﺩﻩ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﻣﻮﺟﻮﺩ ﺍﺳﺖ‪ .‬ﺑﺎﺩﺭ ﻧﻈﺮ ﺩﺍﺷﺖ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ‬
‫ﻭﻻﻧﺴﻰ ﺍﺗﻮﻣﻬﺎﻯ ﻣﺘﺸﻜﻠﺔ ﻣﺎﻟﻴﻜﻮﻝ ﻓﺎﺭﻡ ﺍﻟﺪﻳﻬﺎﻳﺪ ‪،‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻣﺘﺸﻜﻠﺔ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ ﻣﺬﻛﻮﺭﺍ ﺑﺎﻫﻢ ﻧﺰﺩﻳﻚ‬
‫ﻗﺮﺍﺭ ﺩﻫﻴﺪ‪ ،‬ﻛﺎﺭﺑﻦ ﻛﻪ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ ﺑﻮﺩﻩ ‪،‬ﺩﺭ ﻭﺳﻂ ﻗﺮﺍﺭ ﮔﺮﻓﺘﻪ ‪ ،‬ﺩﺭﺍﻳﻦ ﺻﻮﺭﺕ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻭﻻﻧﺴﻰ ﻫﺮ‬
‫ﻳﻚ ﺍﺯ ﺍﺗﻮﻣﻬﺎ ﺭﺍ ﺑﻪ ﻧﺰﺩﻳﻚ ﺁﻧﻬﺎ ﻗﺮﺍﺭ ﺩﺍﺩﻩ ﻗﺎﻋﺪﺓ ﻟﻴﻮﻳﺲ ﺗﻄﺒﻴﻖ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫ﺩﺭ ﻓﻮﺭﻣﻮﻝ ﻓﻮﻕ ﺗﻌﺪﺍﺩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺗﺤﺮﻳﺮ ﺷﺪﻩ ﺩﻭﺍﺯﺩﻩ ﻋﺪﺩ ﻭ ﺗﻌﺪﺍﺩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻭﻻﻧﺴﻰ ﻧﻴﺰ ﺩﻭﺍﺯﺩﻩ ﻋﺪﺩ‬
‫ﺍﻧﺪ ﻛﺎﺭﺑﻦ ﺩﻭﺭﺍﺑﻄﺔ ﻳﮕﺎﻧﻪ ﻭﻳﻚ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺩﺍﺷﺘﻪ ﻭ ﺩﺭ ﻣﺠﻤﻮﻉ ﭼﻬﺎﺭ ﺭﺍﺑﻄﺔ ﻛﻮﻟﻨﺖ ﺭﺍ ﺗﺸﻜﻴﻞ ﺩﺍﺩﻩ ﺍﺳﺖ ‪.‬‬
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 ‫ﺍﮔﺮ ﺭﺍﺑﻄﻪ ﻫﺎ ﺭﺍ ﺑﻪ ﻳﻚ ﺧﻂ ﺍﻓﺎﺩﻩ ﻧﻤﺎﻳﻢ ﻓﺮﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺯﻳﺮ ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ ‪:‬‬
‫ﺩﺭﺍﻳﻦ ﻓﻮﺭﻣﻮﻝ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻧﻤﺎﻳﺎﻥ ﮔﺮ ﭼﻬﺎﺭﺍﻟﻜﺘﺮﻭﻥ ﻣﺸﺘﺮﻙ ﺑﻴﻦ ﻛﺎﺭﺑﻦ ﻭﺁﻛﺴﻴﺠﻦ ﺍﺳﺖ؛ ﺑﻨﺎﺑﺮﺍﻳﻦ‬
‫ﻗﺎﻋﺪﺓ ﻫﺸﺘﺎﻳﻰ ﺭﻋﺎﻳﺖ ﺷﺪﻩ ﺍﺳﺖ ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﺯﻳﺮ ﺭﺍ ﺗﺮﺳﻴﻢ ﻧﻤﺎﻳﻴﺪ‪:‬‬
‫ﺍﻟﻒ ‪ -‬ﻛﺎﺭﺑﻦ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ ) ‪ (CO‬ﺏ‪ -‬ﻛﺎﺭﺑﻦ ﺗﺘﺮﺍ ﻛﻠﻮﺭﺍﻳﺪ ) ‪ (CCl 4‬ﺝ – ﺍﻣﻮﻧﻴﺎ ) ‪( NH 3‬‬
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‫ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ) ‪( Hybridization‬‬
‫ﻃﻮﺭﻳﻜﻪ ﺩﺭ ﻓﻮﻕ ﻣﻄﺎﻟﻌﻪ ﺷﺪ ‪ ،‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ ﻳﮕﺎﻧﻪ‪ ،‬ﺩﻭﮔﺎﻧﻪ ﻭ ﺳﻪ ﮔﺎﻧﻪ ﺭﺍ ﺗﺸﻜﻴﻞ ﺩﺍﺩﻩ ﻣﻴﺘﻮﺍﻧﻨﺪ‪،‬‬
‫ﺑﺎﻳﺪ ﺩﺍﻧﺴﺘﻪ ﺷﻮﺩ ﻛﻪ ﭼﻄﻮﺭ ﺍﻳﻦ ﺭﺍﺑﻄﻪ ﻫﺎ ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﻧﺪ؟ ﻛﺪﺍﻡ ﻧﻮﻉ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ﺩﺭﺗﺸﻜﻴﻞ ﺁﻧﻬﺎ ﺩﺧﻴﻞ‬
‫ﺍﻧﺪ؟ ﺑﻪ ﺧﺎﻃﺮ ﺟﻮﺍﺏ ﺑﻪ ﺳﺆﺍﻻﺕ ﻓﻮﻕ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻫﺎﺑﻴﺮﻳﺪ ﺷﺪﻩ ﺭﺍ ﻣﻄﺎﻟﻌﻪ ﻣﻴﻨﻤﺎﻳﻢ ‪.‬‬
‫ﻛﻠﻤﻪ ‪ Hybrid‬ﺩﺭﻳﻮﻧﺎﻧﻰ ﺑﻪ ﻣﻌﻨﻰ ﺍﺧﺘﻼﻁ ﺧﻮﻥ ﺑﻮﺩﻩ ‪،‬ﻳﻌﻨﻰ ﻧﺴﻠﻰ ﻛﻪ ﺍﺯﺩﻭﻧﺴﻞ ﻣﺨﺘﻠﻒ ﺣﺎﺻﻞ ﺷﺪﻩ ﺑﺎﺷﺪ‬
‫ﻭﻣﻔﻬﻮﻡ ﺍﻣﺘﺰﺍﺝ ﻳﺎ ﺍﺧﺘﻼﻁ ﺭﺍ ﻣﻴﺮﺳﺎﻧﺪ ‪ .‬ﺩﺭﺍﻳﻨﺠﺎ ﻣﻨﻈﻮﺭ ﺍﺯﺍﺧﺘﻼﻁ ﺩﻭﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﺍﺗﻮﻣﻰ ﻣﺨﺘﻠﻒ‬
‫ﺑﻮﺩﻩ ﻛﻪ ﺩﻭ ﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪﻯ ﺟﺪﻳﺪ ﺭﺍ ﺑﻪ ﻣﻴﺎﻥ ﻣﻴﺂﻭﺭﺩ ‪.‬‬
‫ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻭﻻﻧﺴﻰ ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﻛﻴﻤﻴﺎﻭﻯ ﻣﻴﺘﻮﺍﻧﺪ ﺩﺭﺍﻭﺭﺑﻴﺘﺎﻝ ‪ d ، p ، s ، f‬ﻭﻏﻴﺮﻩ ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ‬
‫ﻛﻪ ﺩﺭﺍﻳﻨﺼﻮﺭﺕ ﺗﻤﺎﻡ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻣﺬﻛﻮﺭﺍﺯ ﻟﺤﺎﻅ ﺍﻧﺮژﻯ ﻫﻢ ﺍﺭﺯﺵ ﻧﺒﻮﺩﻩ ﻭ ﺭﻭﺍﺑﻂ ﺁﻧﻬﺎ ﻧﻴﺰ ﻫﻢ ﺍﺭﺯﺵ‬
‫ﻧﻤﻴﺒﺎﺷﺪ؛ ﻻﻛﻦ ﺗﺠﺮﺑﻪ ﺑﻪ ﺍﺛﺒﺎﺕ ﺭﺳﺎﻧﻴﺪﻩ ﻛﻪ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺍﺗﻮﻡ ﻫﺎﻯ ﻣﺮﻛﺰﻯ ﺁﻧﻬﺎ ﺩﺍﺭﺍﻯ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ‬
‫ﻣﺨﺘﻠﻒ ﻭﻻﻧﺴﻰ )‪ ( ..... d ، p ، s‬ﺑﻮﺩﻩ ﻭﺍﺯﻟﺤﺎﻅ ﺭﺍﺑﻄﻪ ﻫﻢ ﺍﺭﺯﺵ ﻣﻴﺒﺎﺷﻨﺪ ‪ ،‬ﺍﻳﻦ ﻣﻄﻠﺐ ﺗﻮﺳﻂ ﻋﻠﻤﺎ ﻫﺮﻳﻚ‬
‫‪ Cleyster‬ﻭ ‪ Pamling‬ﺗﻮﺿﻴﺢ ﮔﺮﺩﻳﺪ ‪ .‬ﻋﻠﻤﺎﻯ ﻣﺬﻛﻮﺭ ﺍﺭﺍﻳﻪ ﺩﺍﺷﺘﻪ ﺍﻧﺪ‪ :‬ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻛﻪ ﺍﺯﻟﺤﺎﻅ‬
‫ﺍﻧﺮژﻯ ﺍﺧﺘﻼﻑ ﺯﻳﺎﺩﻯ ﻧﺪﺍﺷﺘﻪ ﻭﺩﺭﻋﻴﻦ ﻗﺸﺮ ﺍﺻﻠﻰ ﻭﺍﻗﺸﺎﺭﺍﺧﻴﺮﺍﺗﻮﻣﻬﺎ ﻗﺮﺍﺭﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ‪ ،‬ﻣﻄﺎﺑﻖ ﺑﻪ ﺗﻌﺪﺍﺩ‬
‫ﺍﻭﻟﻰ ﺷﺎﻥ ﺑﺎ ﻫﻢ ‪ Hybridization‬ﻧﻤﻮﺩﻩ ﻭﺑﻪ ﺗﻌﺪﺍﺩ ﺍﻭﻟﻰ ﺧﻮﺩ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﻩ ﺭﺍ ﺗﻮﻟﻴﺪ‬
‫ﻣﻴﻨﻤﺎﻳﺪ ﻛﻪ ﺩﺭﻳﻚ ﺳﻄﺢ ﺍﻧﺮژﻯ ﻗﺮﺍﺭﺩﺍﺭﻧﺪ ﻭﻋﻴﻦ ﺳﺎﺧﺘﻤﺎﻥ ﺍﺑﺮ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍ ﺩﺍﺭﺍ ﻣﻴﺒﺎﺷﻨﺪ‪ .‬ﺍﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ‬
‫ﻫﺎ ﺑﻪ ﺳﻤﺖ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﻛﺶ ﺷﺪﻩ ﻭﺗــﺪﺍﺧﻞ ﺁﻧﻬﺎ ﺍﻋﻈﻤﻰ ﺑﻮﺩﻩ ﺯﻣﻴﻨﺔ ﺗﺸﻜﻴﻞ ﺭﻭﺍﺑﻂ ﻣﺴﺎﻋﺪ ﻣﻴﮕﺮﺩﺩ‪.‬‬
‫ﺩﺭﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﺍﺗﻮﻣﻰ ﻳﻚ ﻣﻘﺪﺍﺭ ﺍﻧﺮژﻯ ﺑﻪ ﻣﺼﺮﻑ ﺭﺳﻴﺪﻩ؛ ﺑﻨﺎﺑﺮﺍﻳﻦ ﻫﻤﭽﻮﺍﻭﺭﺑﻴــــﺘﺎﻝ ﻫﺎ‬
‫ﺑﻰ ﺛﺒﺎﺕ ﺑﻪ ﻧﻈﺮﻣﻴﺮﺳﻨﺪ ؛ ﺍﻣﺎ ﺩﺭﺍﺛﻨﺎﻯ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺍﻧﺮژﻯ ﺭﺍ ﺍﺯﺩﺳﺖ ﺩﺍﺩﻩ ‪ ،‬ﺛﺒﺎﺕ ﻻﺯﻣﻪ ﺭﺍ ﺣﺎﺻﻞ ﻣﻴﻨﻤﺎﻳﻨﺪ‪.‬‬
‫ﮔﺮ ﭼﻪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺗﻨﻬﺎ ﺩﺍﺭﺍﻯ ﺩﻭ ﺍﻟﻜﺘﺮﻭﻥ ﺗﺎﻗﻪ ﺩﺭ ﻗﺸﺮ ﻭﻻﻧﺲ ﺍﺳﺖ؛ ﺍﻣﺎ ﭼﻬﺎﺭ ﺭﺍﺑﻄﻪ ﺭﺍ ﺑﺎ ﺍﺗﻮﻡ ﻫﺎﻯ‬
‫ﻫﺎﻳﺪﺭﻭﺟﻦ ﺗﺸﻜﻴﻞ ﺩﺍﺩﻩ ﻣﻰ ﺗﻮﺍﻧﺪ‪ ،‬ﺑﻪ ﺍﻳﻦ ﻣﻌﻨﻰ ﺍﺳﺖ ﻛﻪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻧﻴﻤﻪ ﭘﻮﺭﻩ ﺷﺪﺓ‬
‫ﺍﻟﻜﺘﺮﻭﻧﻰ ﺧﻮﺩ ﺭﺍ ﺩﺭ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺑﺎ ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺑﻪ ﻛﺎﺭ ﺑﺮﺩﻩ ﺍﺳﺖ‪ .‬ﺑﺮﺍﻯ ﺗﺸﺮﻳﺢ ﺗﺸﻜﻴﻞ ﭼﻬﺎﺭ‬
‫ﺭﺍﺑﻄﺔ ﻛﺎﺭﺑﻦ‪ ،‬ﺗﻴﻮﺭﻯ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﻭﺍﻧﻤﻮﺩ ﻣﻰ ﺳﺎﺯﺩ ﻛﻪ ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻭﻻﻧﺴﻰ ﻛﺎﺭﺑﻦ ) ‪ ( 2s,2p‬ﺑﺎﻫﻤﺪﻳﮕﺮ‬
‫‪8‬‬
 ‫ﻣﺨﻠﻮﻁ ﮔﺮﺩﻳﺪﻩ‪ ،‬ﺑﺎﻋﺚ ﺗﺸﻜﻴﻞ ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻛﻪ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﺷﻜﻞ ﻭ ﺍﻧﺮژﻯ ﺍﻧﺪ‪ ،‬ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﻧﺪ‪.‬‬
‫‪ sp 3‬ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ‪ :‬ﺍﻳﻦ ﻧﻮﻉ ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺭﺍ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎ ﺭﺑﻦ ﺩﺭﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻯ ﻣﺸﺒﻮﻉ‬
‫ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻭﻃﻮﺭﻯ ﺍﺳﺖ ﻛﻪ ﻳﻚ ﺍﻭﺭ ﺑﻴﺘﺎﻝ‪ s‬ﺑﺎ ﺳﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ‪p‬ﺩﺭﻧﺘﻴﺠﺔ ﺟﺬﺏ ﺍﻧﺮژﻯ ﺑﺎﻫﻢ ﻣﺨﺘﻠﻂ ﮔﺮﺩﻳﺪﻩ‬
‫ﻭﭼﻬﺎﺭﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﻩ ‪ sp 3‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ﻛﻪ ﻣﻮﺍﺟﻪ ﺑﻪ ﺭﺃﺱ ﻫﺎﻯ ﭼﻬﺎﺭﻭﺟﻬﻰ ﺑﻮﺩﻩ ﻭﺯﺍﻭﻳﻪ ﺑﻴﻦ‬
‫‪o‬‬
‫ﺁﻧﻬﺎ ‪ 109.5‬ﺩﺭﺟﻪ ﺍﺳﺖ‪،‬ﺍﻳﻦ ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ‪ CCl4 ، CH ،‬ﻭﻏﻴﺮﻩ ﻣﻼﺣﻈﻪ ﻛﺮﺩ ‪.‬‬
‫‪4‬‬ ‫‪1‬‬
‫ﺳﻬﻢ‪ s‬ﺩﺭ ‪ sp 3‬ﻭﺳﻬﻢ ‪ p‬ﺩﺭﺁﻥ ‪ 3‬ﺍﺳﺖ‪.‬‬
‫‪4‬‬ ‫‪4‬‬
‫ﺷﻜﻞ )‪ ( 6 - 1‬ﻫﺎﻳﺒﺮﻳﺪ ‪Sp 3‬‬
‫ﺑﺮﺍﻯ ﻛﺴﺐ ﻣﻌﻠﻮﻣﺎﺕ ﺑﻴﺸﺘﺮ ﺩﺭ ﺑﺎﺭﺓ ﻧﻮﻉ ﻫﻴﺒﺮﻳﺪﻳﺰﺷﻦ‪ ،‬ﺗﺸﻜﻴﻞ ‪ CH 4‬ﺭﺍ ﺑﻪ ﺻﻮﺭﺕ ﻣﻔﺼﻞ ﻣﻄﺎﻟﻌﻪ‬
‫ﻣﻴﻜﻨﻴﻢ‪ .‬ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺩﺭ ﻣﻴﺘﺎﻥ ﺑﺎ ﻋﺚ ﺑﻪ ﻣﻴﺎﻥ ﺁﻣﺪﻥ ﭼﻬﺎﺭ ﺭﺍﺑﻄﺔ ﻣﻌﺎﺩﻝ ‪ C − H‬ﻭ ﺗﺸﻜﻞ ﺗﻴﺘﺮﺍﻫﻴﺪﺭﺍﻝ‬
‫)‪ (tetrahedral‬ﺩﺭﻣﺎﻟﻴﻜﻮﻝ ﺁﻥ ﻣﻴﮕﺮﺩﺩ‪ .‬ﺗﺮﺗﻴﺐ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻗﺸﺮ ﻭﻻﻧﺴﻰ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺗﺘﺮﺍﻫﺎﻳﺪﺭﺍﻝ ﻭ ﺯﺍﻭﻳﺔ‬
‫ﺷﻜﻞ ﻞ‬
‫ﺫﻳﻞ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ‪:‬‬ ‫ﻭﻻﻧﺴﻰ ﺁﻥ ﺩﺭ ﻞ‬
‫ﻰ‬
‫ﺷﻜﻞ )‪ ( 7 - 1‬ﻫﺎﻳﺒﺮﻳﺪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭﺗﺸﻜﻴﻞ ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻥ‬
‫‪9‬‬
‫ﻼ ﺷﻜﻞ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﻴﺒﺮﻳﺪ ﺭﺍ ﻣﺸﺎﻫﺪﻩ ﻛﺮﺩﻳﺪ ﻭﺩﺭ ﺑﺎﺭﺓ ﻣﻮﻗﻌﻴﺖ ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﺩﺭ ﻓﻀﺎﻯ ﺑﻪ ﺍﻃﺮﺍﻑ‬ ‫ﺷﻤﺎ ﻗﺒ ً‬
‫ﻫﺴﺘﻪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻣﻌﻠﻮﻣﺎﺕ ﺣﺎﺻﻞ ﻛﺮﺩﻳﺪ ﻭ ﺩﻳﺪﻳﺪ ﻛﻪ ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﻴﺒﺮﻳﺪ ﺩﺭ ﭼﻬﺎﺭ ﻛﻨﺞ ﺗﻴﺘﺮﺍﻫﻴﺪﺭﺍﻝ‬
‫ﻛﻪ ﺯﺍﻭﻳﻪ ﺑﻴﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ‪ 109.4o‬ﺍﺳﺖ ﻗﺮﺍﺭ ﺩﺍﺭﺩ ‪.‬‬
‫ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻫﻴﺒﺮﻳﺪ ‪ sp 3‬ﺑﺎﻋﺚ ﺟﺪﺍﺷﺪﻥ ﺍﻋﻈﻤﻰ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ﺍﺯ ﻫﻤﺪﻳﮕﺮ ﮔﺮﺩﻳﺪﻩ ﻭ ﺭﺍﺑﻄﻪ ﻫﺎ ﺍﺯﻳﻜﺪﻳﮕﺮ‬
‫ﻓﺎﺻﻠﺔ ﺍﻋﻈﻤﻰ ﺩﺍﺭﻧﺪ‪ .‬ﻭﻗﺘﻴﻜﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ‪ 1s‬ﭼﻬﺎﺭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺑﺎ ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp 3‬ﻛﺎﺭﺑﻦ ﺗﺪﺍﺧﻞ‬
‫ﻣﺴﺘﻘﻴﻢ ﻣﻰ ﻧﻤﺎﻳﻨﺪ‪ ،‬ﻳﻚ ﻣﺎﻟﻴﻜﻮﻝ ﺗﻴﺘﺮﺍﻫﻴﺪﺭﺍﻝ ﺑﺎ ﭼﻬﺎﺭ ﺭﺍﺑﻄﺔ ﻣﻌﺎﺩﻝ ‪) C − H‬ﺷﻜﻞ‪ (7 - 1‬ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ‬
‫ﻛﻪ ﺑﺎ ﺳﺎﺧﺘﻤﺎﻥ ‪ CH 4‬ﻛﻪ ﺩﺭ ﺗﺠﺮﺑﻪ ﺛﺎﺑﺖ ﮔﺮﺩﻳﺪﻩ‪ ،‬ﻣﻄﺎﺑﻘﺖ ﺩﺍﺭﺩ‪.‬‬
‫ﺷﻜﻞ ‪ 7 - 1‬ﺗﺪﺍﺧﻞ ﻣﺴﺘﻘﻴﻢ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ‪ sp 3‬ﺑﺎ ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ 1s‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﺷﻜﻞ ﺗﻴﺘﺮﺍ ﻫﻴﺪﺭﺍﻝ‬
‫‪ CH 4‬ﺭﺍ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﻭ ﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﻳﺸﻦ ‪ sp 3‬ﺭﺍﺑﺮﺍﻯ ﺗﺸﺮﻳﺢ ﺩﻳﮕﺮ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻭﻏﻴﺮﻋﻀﻮﻯ ﺍﺯﻗﺒﻴﻞ‬
‫‪ NH 3‬ﻭ ‪ H 2O‬ﺑﻪ ﻛﺎﺭ ﻣﻰ ﺑﺮﺩ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ ‪ :‬ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺩﺭ ﺍﻳﺘﺎﻥ‬
‫ﺳﺎﻣﺎﻥ ﻭ ﻣﻮﺍﺩ ﻣﻮﺭﺩ ﺿﺮﻭﺭﺕ ‪ :‬ﻳﻚ ﺳﻴﺖ ﻣﻮﺩﻝ ﻫﺎﻯ ﻣﺎﻟﻴﻜﻮﻟﻰ‬
‫ﺷﻤﺎ ﺩﺭﺍﻳﻦ ﻓﻌﺎﻟﻴﺖ ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﺎﻥ ﺭﺍ ﺩﺭ ﺷﻜﻞ ﺫﻳﻞ ﻣﻼﺣﻈﻪ ﻧﻤﻮﺩﻩ ‪ ،‬ﺑﻪ ﺳﺆﺍﻻﺕ‬
‫ﺯﻳﺮ ﺟﻮﺍﺏ ﺍﺭﺍﻳﻪ ﻧﻤﺎﻳﻴﺪ‪:‬‬
‫ﺷﻜﻞ )‪ ( 8 - 1‬ﺗﺪﺍﺧﻞ ﻣﺴﺘﻘﻴﻢ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﺓ ﺍﻳﺘﺎﻥ‬
‫‪ - 1‬ﺗﻌﺪﺍﺩ ﺭﺍﺑﻄﻪ ﻫﺎ ﺩﺭﺍﻃﺮﺍﻑ ﻫﺮ ﻛﺎﺭﺑﻦ ﭼﻨﺪ ﺍﺳﺖ؟‬
‫‪ - 2‬ﻫﻴﺒﺮﻳﺪﺍﺯﻳﺰﺷﻦ ﻫﺮﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﭼﻪ ﻧﻮﻉ ﺍﺳﺖ؟‬
‫‪ - 3‬ﺗﺮﺗﻴﺐ ﺳﻪ ﺑﻌﺪﻯ ﺍﺗﻮﻡ ﻫﺎ ﺩﺭ ﺍﻃﺮﺍﻑ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﻪ ﻛﺪﺍﻡ ﻣﻨﻮﺍﻝ ﺍﺳﺖ ؟‬
‫‪ - 4‬ﻳﻚ ﻣﻮﺩﻝ ﺍﻳﺘﺎﻥ ﺭﺍ ﺑﺴﺎﺯﻳﺪ‪.‬‬
‫‪ - 5‬ﺩﻭ ﺍﺭﺑﻴﺘﺎﻝ ﻛﻪ ﺩﺭ ﺍﺛﺮ ﺗﻤﺎﺱ ﺁﻧﻬﺎ ﺭﺍﺑﻄﻪ ﺑﻴﻦ ﻛﺎﺭﺑﻦ ﻭ ﻛﺎﺭﺑﻦ ﺩﺭ ﺍﺗﻴﺎﻥ ﺑﻪ ﻭﺟﻮﺩ ﻣﻰ ﺁﻳﺪ ﭼﻪ ﻧﺎﻡ ﺩﺍﺭﺩ؟‬
‫‪10‬‬
‫ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺍﺭﺍﻯ ﭼﻬﺎﺭ ﺭﺍﺑﻄﻪ ﺑﻮﺩﻩ ﻛﻪ ﺑﺎ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎ ﺑﺮﻗﺮﺍﺭﻧﻤﻮﺩﻩ ﻭ ﺷﻜﻞ ﺗﻴﺘﺮﺍﻫﻴﺪﺭﺍﻝ ﺭﺍ ﺗﺸﻜﻴﻞ‬
‫ﻣﻴﺪﻫﺪ‪ .‬ﺑﺮﺍﻯ ﺗﺸﻜﻴﻞ ﭼﻬﺎﺭ ﺭﺍﺑﻄﻪ‪ ،‬ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ‪ ،‬ﭼﻬﺎﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪ ‪ sp 3‬ﺧﻮﺩ ﺭﺍ ﺑﻪ ﻛﺎﺭﺑﺮﺩﻩ ﻭﺍﺯﺗﺪﺍﺧﻞ‬
‫ﻣﺴﺘﻘﻴﻢ ﺁﻧﻬﺎ ﺑﺎ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﺍﺗﻮﻣﻬﺎﻯ ﺩﻳﻜﺮ‪،‬ﺭﺍﺑﻄﻪ ﺳﮕﻤﺎ )‪ (S ) (Sigma‬ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ ﻛﻪ ﺑﺎﻋﺚ ﺗﺸﻜﻴﻞ‬
‫ﺭﺍﺑﻄﻪ ﻫﺎ ﺑﺸﻜﻞ ﺗﻴﺘﺮﺍﻫﻴﺪﺭﺍﻝ ﺩﺭ ﺍﻃﺮﺍﻑ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻣﻴﮕﺮﺩﺩ‪.‬ﺩﺭ ﺍﻳﻨﺠﺎ ﺳﻮﺍﻝ ﭘﻴﺪﺍ ﻣﻰ ﺷﻮﺩ ﻛﻪ ﺁﻳﺎ ﺍﺗﻮﻡ‬
‫ﻛﺎﺭﺑﻦ ﺩﻳﮕﺮ ﻧﻮﻉ ﻫﻴﺒﺮﻳﺪﻳﺰﺷﻦ ﺭﺍ ﺩﺭ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺑﻪ ﻛﺎﺭ ﺑﺮﺩﻩ ﻣﻴﺘﻮﺍﻧﺪ؟ﺟﻮﺍﺏ ﺳﺆﺍﻝ ﺭﺍ ﺗﻮﺿﻴﺤﺎﺕ ﺫﻳﻞ ﺍﺭﺍﻳﻪ ﻣﻴﻜﻨﺪ ‪.‬‬
‫‪ sp 2‬ﻫﺎﻳﺒﺮﻳﺪ ﻳﺰﻳﺸﻦ ‪ :‬ﺩﺭ ﺍﻳﻦ ﻧﻮﻉ ﻫﺎﻳﺒﺮﻳﺪ ﻳﻚ ﺍﻭﺭﺑﻴﺘﺎﻝ‪ s‬ﻭﺩﻭ ﺍﻭﺭﺑﻴﺘﺎ ﻝ‪ p‬ﺑﺎ ﻫﻢ ﺍﻣﺘﺰﺍﺝ ﻧﻤﻮﺩﻩ‪ ،‬ﺩﺭﻧﺘﻴﺠﻪ‬
‫ﺳﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﺓ ‪ sp 2‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ‪ ،‬ﺍﻳﻦ ﺍﻭﺭ ﺑﻴﺘﺎﻝ ﻫﺎ ﺩﺭ ﻳﻚ ﺳﻄﺢ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﻛﻪ ﺳﻬﻢ ‪ s‬ﺩﺭ‬
‫‪2‬‬
‫ﻫﺮ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp 2‬ﻣﺴﺎﻭﻯ ﺑﻪ ‪ 1‬ﻭﺍﺯ‪ p‬ﻣﻴﺒﺎﺷﺪ ‪،‬ﺯﺍﻭﻳﺔ ﻭﻻﻧﺴﻰ ﺩﺭﺑﻴﻦ ﺍﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ‪ 120o‬ﺩﺭﺟﻪ ﺍﺳﺖ‪.‬‬
‫‪3‬‬ ‫‪3‬‬
‫ﺷﻜﻞ )‪ (9 – 1‬ﻫﺎﻳﺒﺮﻳﺪ ‪sp 2‬‬
‫ﻫﺎﻳﺒﺮﻳﺪ ‪ sp 2‬ﺭﺍ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻏﻴﺮﻣﺸﺒﻮﻉ ﻓﺎﻣﻴﻞ ﺍﻳﺘﻴﻠﻴﻦ ﺩﺍﺭﺍ ﺍﻧﺪ ‪ .‬ﺩﺭﻣﺎﻟﻴﻜﻮﻝ‬
‫‪ BF3‬ﺍﺗﻮﻡ ﺑﻮﺭﻭﻥ ﻫﺎﻳﺒﺮﻳﺪ ‪ sp 2‬ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ ‪:‬‬
‫ﺷﻜﻞ )‪ sp 2 (10 - 1‬ﻫﺎﻳﺒﺮﻳﺪ ﺍﺗﻮﻡ ﺑﻮﺭﻭﻥ ﺩﺭ ‪: BF3‬‬
‫ﺩﺭﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻧﻴﻤﻪ ﭘﺮﺷﺪﻩ ﻭﻳﺎ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﭘﺮﺷﺪﻩ ﻣﻜﻤﻞ ﺳﻬﻢ ﺩﺍﺷﺘﻪ‪ ،‬ﻣﺎﻟﻴﻜﻮﻝ ﺍﻭﺭﺑﻴﺘﺎﻝ‬
‫ﺭﺍﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ؛ ﺩﺭ ﻫﺎﻳﺒﺮﻳﺪ ﻳﺰﻳﺸﻦ ﻧﻪ ﺗﻨﻬﺎ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ‪ s‬ﻭ‪ p‬ﺳﻬﻢ ﮔﺮﻓﺘﻪ ؛ ﺑﻠﻜﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ‪ d‬ﻭ‪ f‬ﻧﻴﺰ‬
‫ﺳﻬﻴﻢ ﻣﻴﺒﺎﺷﻨﺪ ‪.‬‬
‫ﻫﻴﺒﺮﻳﺪﺍﺯﻳﺰﺷﻦ ‪ sp 2‬ﺩﺭ ﻣﺮﻛﺒﺎﺕ ﻛﺎﺭﺑﻦ ﻛﻪ ﺑﺎﻋﺚ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻣﻴﮕﺮﺩﻧﺪ‪ ،‬ﻣﻮﺟﻮﺩﺍﺳﺖ‪ .‬ﺳﺎﺩﻩ ﺗﺮﻳﻦ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﻋﻀﻮﻯ ﻛﻪ ﺩﺍﺭﺍﻯ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺍﺳﺖ‪ ،‬ﻋﺒﺎﺭﺕ ﺍﺯ ﻣﺮﻛﺐ ﺍﻳﺘﻴﻠﻴﻦ ﺑﻮﺩﻩ ﻛﻪ‬
‫ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺫﻳﻞ ﺍﺳﺖ‪:‬‬
‫ﺷﻜﻞ )‪ (11 - 1‬ﺳﺎﺧﺘﻤﺎ ﻟﻴﻮﻳﺲ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﻴﻠﻴﻦ‬
‫‪11‬‬
‫ﺗﺠﺮﺑﻪ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ﻛﻪ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﻴﻠﻴﻦ ﺳﺎﺧﺘﻤﺎﻥ ﻣﺴﻄﺢ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻭ ﺯﻭﺍﻳﺎﻯ ﺭﺍﺑﻄﻪ ﻭﻯ ﺩﺭ ﺁﻥ ﺩﺭ ﺣﺪﻭﺩ‬
‫‪ 120o‬ﺍﺳﺖ‪.‬‬
‫ﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﻳﺸﻦ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﻣﺮﻛﺐ ﺍﻳﺘﻠﻴﻦ ﭼﻪ ﻧﻮﻉ ﺍﺳﺖ؟‬
‫ﺩﺭ ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺍﻳﺘﻴﻠﻴﻦ ﺩﻳﺪﻩ ﻣﻴﺸﻮﺩ ﻛﻪ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎ ﻳﻚ ﺍﺗﻮﻡ ﺩﻳﮕﺮ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﻪ ﺑﺮ ﻗﺮﺍﺭ ﻧﻤﻮﺩﻩ‬
‫ﺍﺳﺖ‪ .‬ﺳﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﻴﺒﺮﻳﺪ ﺷﺪﻩ ﺑﺮﺍﻯ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﺔ ﻫﺎﻯ ﻫﺮﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎ ﺳﻪ ﺍﺗﻮﻡ ﺩﻳﮕﺮ ﺩﺭ ﺍﻃﺮﺍﻑ ﺁﻥ‬
‫)ﻳﻚ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭ ﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ( ﺿﺮﻭﺭﺕ ﺍﺳﺖ ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺑﺎﻋﺚ ﺗﺸﻜﻴﻞ ﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﻳﺸﻦ ‪sp 2‬‬
‫ﻣﻴﮕﺮﺩﺩ‪.‬‬
‫ﺷﻜﻞ ﻓﻀﺎﻯ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ‪ sp 2‬ﺑﻪ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﭼﻄﻮﺭ ﺍﺳﺖ؟ ﻫﺮ ﺳﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻣﺬﻛﻮﺭ ﺩﺭ ﻳﻚ ﺳﻄﺢ‬
‫ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﻭ ﺯﻭﺍﻳﺎﻯ ﺑﻴﻦ ﺁﻧﻬﺎ ‪ 120o‬ﺍﺳﺖ‪ ،‬ﻃﻮﺭﻳﻜﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ p‬ﻫﺎﻳﺒﺮﻳﺪﺍﺯﻳﺰﺷﻦ ﻧﺎﺷﺪﻩ ﺑﻪ ﺷﻜﻞ ﻋﻤﻮﺩ ﺑﺎﻻﻯ‬
‫ﺳﻄﺢ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﻛﻪ ﺩﺭ ﺷﻜﻞ )‪ ( 12 - 1‬ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ‪.‬‬
‫ﺷﻜﻞ )‪ (12 - 1‬ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﺔ ﻣﺮﻛﺐ ﺍﻳﺘﻴﻠﻴﻦ ﺩﻭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﻴﺒﺮﻳﺪ ‪sp 2‬‬
‫ﺩﺭﺗﺸﻜﻴﻞ ﺭﻭﺍﺑﻂ ﺩﺭ ﻣﺮﻛﺐ ﺍﻳﺘﻴﻠﻴﻦ ﺩﻭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﻴﺒﺮﻳﺪ ‪ sp 2‬ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻫﺮﻳﻚ ﺑﺎ ﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ﺭﺍﺑﻄﻪ ﺑﺮﻗﺮﺍﺭ ﻧﻤﻮﺩﻩ ﻭ ﺩﻭ ﺭﺍﺑﻄﺔ ‪ C − H‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ‪ .‬ﻳﻚ ﻫﻴﺒﺮﻳﺪ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp 2‬ﺑﺎﻗﻴﻤﺎﻧﺪﻩ ﺩﺭ ﻫﺮ ﺍﺗﻮﻡ‬
‫ﻛﺎﺭﺑﻦ ﺑﺎ ﻫﻤﺪﻳﮕﺮ ﺗﺪﺍﺧﻞ ﻣﺴﺘﻘﻴﻢ ﻧﻤﻮﺩﻩ ﻭ ﺑﺎﻋﺚ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﺔ ‪ S‬ﺩﺭ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﮔﺮﺩﻳﺪﻩ ﻭ ﻃﻮﺭﻳﻜﻪ‬
‫ﻼ ﺩﺭ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﺔ ﺍﻳﺘﻴﻠﻴﻦ ﻣﺸﺎﻫﺪﻩ ﻧﻤﻮﺩﻳﺪ‪،‬ﺭﺍﺑﻄﺔ ﺩﻭﻡ ﺩﺭ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﺍﺛﺮ ﺗﺪﺍﺧﻞ ﺟﺎﻧﺒﻰ‬ ‫ﺷﻤﺎ ﻗﺒ ً‬
‫ﺍﻭﺭﺑﻴﺘﺎﻟﻬﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻫﻴﭙﺮﻳﺪ ﻧﺎﺷﺪﺓ‪p‬ﺁﻧﻬﺎ ﺑﻪ ﻭﺟﻮﺩ ﻣﻴﺂﻳﺪ ﻛﻪ ﺩﺭ ﺷﻜﻞ )‪ (13 - 1‬ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ‪:‬‬
‫ﺷﻜﻞ )‪ :(13 - 1‬ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﻫﺎ ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯ ﺍﻭﺭﺑﻴﺘﺎﻟﻬﺎ ﺩﺭ ﻣﺮﻛﺐ ﺍﻳﺘﻠﻴﻦ‬
‫ﺍﺯ ﺗﺪﺍﺧﻞ ﺟﺎﻧﺒﻰ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ‪ p‬ﺩﺭ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ ﺑﻪ ﻣﻴﺎﻥ ﻣﻴﺂﻳﺪ ﻛﻪ ﺑﻨﺎﻡ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ) ‪ ( P‬ﻳﺎﺩ‬
‫ﻣﻰ ﺷﻮﺩ‪ .‬ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ p z‬ﻏﻴﺮﻫﺎﺑﻴﺮﻳﺪ ﺷﺪﺓ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﻗﺴﻤﺖ ﺑﺎﻻ ﻭ ﭘﺎﻳﻴﻦ ﺳﻄﺢ ﻣﺎﻟﻴﻜﻮﻝ‬
‫‪12‬‬
‫ﺑﺎ ﻫﻤﺪﻳﮕﺮ ﺷﺮﻳﻚ ﺷﺪﻩ ‪،‬ﺭﺍﺑﻄﺔ ‪ P‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ‪ .‬ﻫﻤﻴﺸﻪ ﻳﻚ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺷﺎﻣﻞ ﻳﻚ ﺭﺍﺑﻄﺔ ‪ σ‬ﻭ‬
‫ﻳﻚ ﺭﺍﺑﻄﺔ ‪ P‬ﻣﻴﺒﺎﺷﺪ‪ .‬ﺭﺍﺑﻄﺔ ‪ P‬ﺍﺯ ﺗﺪﺍﺧﻞ ﺟﺎﻧﺒﻰ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻏﻴﺮ ﻫﺎﺑﺒﺮﻳﺪ ﺷﺪﺓ ‪ p z‬ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ)ﺷﻜﻞ‬
‫‪ 13 - 1‬ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ (‪.‬‬
‫ﻓﻜﺮ ﻛﻨﻴﺪ‬
‫ﺑﻪ ﻧﻈﺮ ﺷﻤﺎ ﺭﺍﺑﻄﺔ ‪ σ‬ﻗﻮﻯ ﻭ ﻣﺴﺘﺤﻜﻢ ﺍﺳﺖ ﻭﻳﺎ ﺍﻳﻨﻜﻪ ﺭﺍﺑﻄﺔ ‪ P‬ﻗﻮﻯ ﺍﺳﺖ ؟ ﺗﺸﺮﻳﺢ ﻛﻨﻴﺪ‪.‬‬
‫‪ sp‬ﻫﺎﻳﺒﺮﻳﺪ ‪:‬ﺩﺭ ﻓﻮﻕ ﻣﻄﺎﻟﻌﻪ ﻧﻤﻮﺩﻳﺪ ﻛﻪ ﭼﻄﻮﺭ ﻣﻴﺘﻮﺍﻧﻴﻢ ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯ ﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﻳﺸﻦ ‪ sp‬ﺭﺍﺑﻄﺔ‬
‫ﺩﻭﮔﺎﻧﻪ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍ ﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﻢ ‪ ،‬ﺣﺎﻻ ﻣﻰ ﺁﻣﻮﺯﻳﻢ ﻛﻪ ﭼﻄﻮﺭ ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯ ﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﻳﺸﻦ‬
‫‪ sp‬ﻣﻴﺘﻮﺍﻧﻴﻢ ﺭﺍﺑﻄﺔ ﺳﻪ ﮔﺎﻧﻪ ﺭﺍ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﻢ ؛ ﺩﺭﺍﻳﻦ ﻧﻮﻉ ﻫﺎﻳﺒﺮﻳﺪ ﻳﻚ ﺍﻭﺭﺑـــــﻴﺘﺎﻝ‪s‬‬
‫ﻭﻳﻚ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ p‬ﺑﺎ ﻫﻢ ﺍﻣﺘــــﺰﺍﺝ ﻧﻤﻮﺩﻩ ‪ ،‬ﺩﺭﻧﺘﻴﺠﻪ ﻫﺎﻳﺒﺮﻳﺪ ‪ ( sp − hybrid ) sp‬ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ‬
‫ﻛﻪ ﺯﺍﻭﻳﻪ ﻭﻻﻧﺴﻰ ﺭﻭﺍﺑﻂ ‪ 180 o‬ﺑﻮﺩﻩ ‪ ،‬ﻣﺜﺎﻝ ﺁﻥ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﻫﺎﻳﺒﺮﻳﺪ ‪ sp‬ﻋﻨﺎﺻﺮ ‪Hg , Cd , Zn , Be‬‬
‫ﺩﺭﻣﺮﻛﺒﺎﺕ ﻫﻠﻮﺟﻨﻴﺪ ﻫﺎ ﺍﺭﺍﻳﻪ ﻛﺮﺩ ‪ .‬ﻧﺘﺎﻳﺞ ﺗﺠﺮﺑﻰ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ﻛﻪ ‪ Hg ، Cd , Zn, Be‬ﻫﺎﻳﺒﺮﻳﺪ ‪ sp‬ﺭﺍ‬
‫ﺩﺭﻫﻠﻮﺟﻨﻴﺪ ﻫﺎﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻭ ﻣﺮﻛﺒﺎﺕ ﺁﻧﻬﺎ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﻫﻨﺪﺳﻰ ﺧﻄﻰ ﻣﻴﺒﺎﺷﺪ ‪ .‬ﺳﻬﻢ‪s‬ﻭ ‪ p‬ﻫﺮ ﻳﻚ ‪ 1‬ﺍﺳﺖ‪.‬‬
‫‪2‬‬
‫ﺷﻜﻞ )‪ ( 14 - 1‬ﻫﺎﻳﺒﺮﻳﺪ ‪: sp‬‬
‫ﻫﺎﻳﺒﺮﻳﺪ ‪ sp‬ﻭﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺳﻪ ﮔﺎﻧﻪ ﺭﺍ ﺩﺭ ﻣﺮﻛﺐ ﺍﺳﺘﻴﻠﻴﻦ ) ‪ ( C2 H 2‬ﻛﻪ ﺳﺎﺩﻩ ﺗﺮﻳﻦ ﻣﺮﻛﺐ ﻋﻀﻮﻯ ﺍﺳﺖ‬
‫ﻢ‪:‬‬‫‪ ،‬ﺑﺎ ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺁﻥ ﻗﺮﺍﺭ ﺫﻳﻞ ﻣﻄﺎﻟﻌﻪ ﻣﻴﻨﻤﺎﻳﻢ‬
‫ﺷﻜﻞ )‪ (15 - 1‬ﻣﺮﻛﺐ ﺍﺳﺘﻴﻠﻴﻦ ﺑﺎ ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺁﻥ‬
‫ﻃﻮﺭﻳﻜﻪ ﺩﺭ ﺷﻜﻞ ﺩﻳﺪﻩ ‪،‬ﺍﺳﻴﺘﻴﻠﻴﻦ ﻳﻚ ﻣﺎﻟﻴﻜﻮﻝ ﺧﻄﻰ ﺑﻮﺩﻩ ﻛﻪ ﺯﻭﺍﻳﺔ ﺭﺍﺑﻄﺔ ﺁﻥ ﻣﺴﺎﻭﻯ ﺑﻪ ‪ 180 o‬ﺍﺳﺖ‪.‬‬
‫ﻛﺪﺍﻡ ﻧﻮﻉ ﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﺷﻦ ﺩﺭ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻣﺮﻛﺐ ﺍﺳﺘﻴﻠﻴﻦ ﻣﻮﺟﻮﺩ ﺍﺳﺖ؟ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﺍﺳﺘﻴﻠﻴﻦ ﺑﻪ ﺩﻭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪ ﺿﺮﻭﺭﺕ ﺩﺍﺭﺩ ﻛﻪ ﺑﻴﻦ ﻫﻢ ﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺭﺍﺑﻄﻪ ﻫﺎ ﺭﺍ ﺑﺮﻗﺮﺍﺭ ﻧﻤﺎﻳﻨﺪ‪:‬‬
‫‪13‬‬
 ‫ﺷﻜﻞ )‪ (16 - 1‬ﻫﺎﺑﻴﺮﻳﺪ ‪ sp‬ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﺍﺳﻴﺘﻴﻠﻴﻦ‬
‫ﺩﺭﺷﻜﻞ ‪16 - 1‬ﻣﻮﻗﻌﻴﺖ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ﺩﺭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭﻫﻴﺒﺮﻳﺮﺍﺯﺷﻦ ‪ sp‬ﻣﻼﺣﻈﻪ ﻣﻴﮕﺮﺩﺩ ﻛﻪ ﺩﻭ ﺍﻭﺭﺑﻴﺘﺎﻝ‬
‫‪ sp‬ﺣﺎﻟﺖ ﺧﻄﻰ ﺩﺍﺷﺘﻪ ﻭ ﺯﺍﻭﻳﺔ ‪ 180 o‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ‪ .‬ﺩﺭ ﺣﺎﻟﻴﻜﻪ ﺩﻭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﻴـــﺒﺮﻳﺪﺍﺯﻳﺰﺷﻦ ﻧﺎﺷﺪﺓ‬
‫ﻫﺮﻳﻚ ﺍﺯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺑﺎﻻﻯ ﻫﻤﺪﻳﮕﺮ ﻭ ﺑﺎﻻﻯ ﺧﻄﻰ ﻛﻪ ﺩﻭ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp‬ﺭﺍ ﺍﺭﺗﺒﺎﻁ ﻣﻴﺪﻫﺪ‪ ،‬ﻋﻤﻮﺩ‬
‫ﻭﺍﻗﻊ ﻣﻴﺒﺎﺷﺪ‪.‬‬
‫ﺑﺮﺍﻯ ﺗﺸﻜﻴﻞ ﺍﺳﺘﻴﻠﻴﻦ‪ ،‬ﻳﻚ ﻫﺎﻳﺒﺮﻳﺪ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp‬ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎ ﻳﻚ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ 1S‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ﺗﺪﺍﺧﻞ ﻣﺴﺘﻘﻴﻢ ﻧﻤﻮﺩﻩ ﻭ ﺭﺍﺑﻄﺔ ‪ C − H‬ﺭﺍ ﺑﺮﻗﺮﺍﺭ ﻣﻴﻨﻤﺎﻳﻴﺪ‪ .‬ﺩﻭ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp‬ﺑﺎﻗﻴﻤﺎﻧﺪﻩ ﺩﺭ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ‬
‫ﺗﺪﺍﺧﻞ ﻣﺴﺘﻘﻴﻢ ﻧﻤﻮﺩﻩ ﺭﺍﺑﻄﺔ ‪ S‬ﺭﺍ ﺩﺭ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ﻭ ﺩﻭ ﺍﻟﻜﺘﺮﻭﻥ ﻫﺮﻳﻚ ﺍﺯ ﺍﺗﻮﻣﻬﺎﻯ‬
‫ﻛﺎﺭﺑﻦ ﻛﻪ ﺩﺭ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻏﻴﺮ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﺓ‪ p‬ﻗﺮﺍﺭ ﺩﺍﺭﻧﺪ ‪ ،‬ﺍﺯ ﺗﺪﺍﺧﻞ ﺟﺎﻧﺒﻰ ﺍﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ﺑﺎ ﻫﻤﺪﻳﮕﺮ‬
‫ﺩﻭ ﺭﺍﺑﻄﺔ ‪ P‬ﺭﺍ ﺩﺭ ﺑﻴﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺍﺳﺘﻠﻴﻦ ﺑﻪ ﻭﺟﻮﺩ ﻣﻰ ﺁﻭﺭﻧﺪ ﻛﻪ ﺩﺭ ﺷﻜﻞ ﺫﻳﻞ ﻧﺸﺎﻥ‬
‫ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ‪:‬‬
‫ﺷﻜﻞ)‪ ( 17 - 1‬ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﻫﺎ ﺩﺭ ﺍﺳﺘﻠﻴﻦ ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﺓ‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺑﺎﺩﺭﻧﻈﺮﺩﺍﺷﺖ ﺳﺎﺣﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺒﺎﺕ ﻭﺗﺮﺳﻴﻢ ﺁﻧﻬﺎ ‪ ،‬ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺁﻛﺴﻴﺠﻦ ﺭﺍ ﺩﺭﻣﺎﻟﻴﻜﻮﻝ‬
‫‪4‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪1‬‬
‫ﺁﺏ ﻭﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺷﻤﺎﺭﻩ‪ 4 - 1‬ﺭﺍ ﺩﺭﻣﺎﻟﻴﻜﻮﻝ ‪ C H 3− C H = C = C H 2‬ﻣﺸﺨﺺ‬
‫ﺳﺎﺯﻳﺪ ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ ‪:‬‬
‫ﺷﻜﻞ ﻓﻀﺎﻳﻰ ﻣﺎﻟﻴﻜﻮﻝ ‪ SO3‬ﺭﺍ ﺗﺤﺮﻳﺮ ﻭﺑﻪ ﺳﻮﺍﻻﺕ ﺫﻳﻞ ﺟﻮﺍﺏ ﺍﺭﺍﻳﻪ ﻧﻤﺎﻳﺪ ‪.‬‬
‫‪ - 1‬ﭼﻨﺪ ﺟﻮﺭﻩ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺍﺗﻮﻡ ﺳﻠﻔﺮ ﺭﺍ ﺍﺣﺎﻃﻪ ﻣﻰ ﻧﻤﺎﻳﺪ‬
‫‪14‬‬
 ‫ﺧﻼﺻﺔ ﻓﺼﻞ ﺍﻭﻝ‬
‫‪
t‬ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﻋﺒﺎﺭﺕ ﺍﺯ ﻛﻴﻤﻴﺎﻯ ﻣﺮﻛﺒﺎﺕ ﻛﺎﺭﺑﻦ ‪ ،‬ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﻣﺸﺘﻘﺎﺕ ﺁﻥ ﺍﺳﺖ ‪.‬‬
‫‪
t‬ﻛﺎﺭﺑﻦ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺘﺮﻭﻧﻰ ‪ 1S 2 2S 2 2P 2‬ﺑﻮﺩﻩ ﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﻪ ﺣﺎﻟﺖ ﺗﺤﺮﻳﻚ ﺳﺎﺧﺘﻤﺎﻥ‬
‫ﺍﻟﻜﺘﺮﻭﻧﻰ ‪ 1S 2S1 2P 3‬ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ‬
‫‪
t‬ﺑﺮﺍﻯ ﭘﻮﺭﻩ ﻛﺮﺩﻥ ﺣﺎﻟﺖ ﻫﺸﺖ ﺍﻟﻜﺘﺮﻭﻧﻰ)‪ (octate‬ﻗﺸﺮ ﺍﻟﻜﺘﺮﻭﻥ ﻫﺎﻯ ﻭﻻﻧﺴﻰ‪ ،‬ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﭼﻬﺎﺭ‬
‫ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺧﻮﺩ ﺭﺍ ﺑﺎ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎ ﺑﻪ ﺷﻤﻮﻝ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺷﺮﻳﻚ ﺳﺎﺧﺘﻪ‪ ،‬ﺩﺭ ﻧﺘﻴﺠﺔ‬
‫ﻭﻻﻧﺲ ﻛﺎﺭﺑﻦ ﭼﻬﺎﺭ ﺍﺳﺖ‪.‬‬
‫‪
t‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻣﻴﺘﻮﺍﻧﺪ ﺭﺍﺑﻄﺔ ﻳﮕﺎﻧﻪ‪ ،‬ﺩﻭﮔﺎﻧﻪ ﻭ ﺳﻪ ﮔﺎﻧﻪ ﺭﺍ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪ‪.‬‬
‫‪ Hybridization
t‬ﻋﺒﺎﺭﺕ ﺍﺯﺍﺧﺘﻼﻁ ﺩﻭﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﺍﺗﻮﻣﻰ ﻣﺨﺘﻠﻒ ﺑﻮﺩﻩ ﻛﻪ ﺩﻭ ﻭﻳﺎ ﭼﻨﺪﻳﻦ‬
‫ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪﻯ ﺟﺪﻳﺪ ﺭﺍ ﺑﻪ ﻣﻴﺎﻥ ﻣﻴﺂﻭﺭﻧﺪ ‪.‬‬
‫‪ sp 3 t‬ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ‪ :‬ﺍﻳﻦ ﻧﻮﻉ ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺭﺍ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﻯ ﻣﺸﺒﻮﻉ ﺩﺍﺭﺍ‬
‫ﺑﻮﺩﻩ ﻭﻃﻮﺭﻯ ﺍﺳﺖ ﻛﻪ ﻳﻚ ﺍﻭﺭ ﺑﻴﺘﺎﻝ‪ s‬ﺑﺎ ﺳﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ‪ p‬ﺩﺭﻧﺘﻴﺠﺔ ﺟﺬﺏ ﺍﻧﺮژﻯ ﺑﺎﻫﻢ ﻣﺨﺘﻠﻂ ﮔﺮﺩﻳﺪﻩ‬
‫ﻭﭼﻬﺎﺭﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﻩ ‪ sp 3‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ‪.‬‬
‫‪ sp 2 t‬ﻫﺎﻳﺒﺮﻳﺪ ﻳﺰﻳﺸﻦ ‪ :‬ﺩﺭ ﺍﻳﻦ ﻧﻮﻉ ﻫﺎ ﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﻳﻚ ﺍﻭﺭﺑﻴﺘﺎﻝ‪ s‬ﻭﺩﻭ ﺍﻭﺭﺑﻴﺘﺎ ﻝ‪ p‬ﺑﺎ ﻫﻢ ﺍﻣﺘﺰﺍﺝ ﺣﺎﺻﻞ‬
‫ﻧﻤﻮﺩﻩ ‪ ،‬ﺩﺭﻧﺘﻴﺠﻪ ﺳﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﺓ ‪ sp 2‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ‪.‬‬
‫‪ sp t‬ﻫﺎﻳﺒﺮﻳﺪ ‪ :‬ﺩﺭﺍﻳﻦ ﻧﻮﻉ ﻫﺎﻳﺒﺮﻳﺪ ﻳﻚ ﺍﻭﺭﺑـــــﻴﺘﺎﻝ‪ s‬ﻭﻳﻚ ﺍﻭﺭﺑﻴﺘﺎﻝ‪ p‬ﺑﺎ ﻫﻢ ﺍﻣﺘــــﺰﺍﺝ ﻧﻤﻮﺩﻩ ‪ ،‬ﺩﺭﻧﺘﻴﺠﻪ‬
‫ﻫﺎﻳﺒﺮﻳﺪ ‪ ( sp − hybrid ) sp‬ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫‪
t‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻣﻴﺘﻮﺍﻧﺪ ﺯﻧﺠﻴﺮﻫﺎﻯ ﻛﺎﺭﺑﻨﻰ ‪ ،‬ﺯﻧﺠﻴﺮﻫﺎﻯ ﻣﻨﺸﻌﺐ ﻭ ﺣﻠﻘﻪ ﻫﺎ ﺭﺍ ﺑﺎ ﻫﻤﺪﻳﮕﺮ ﺗﺸﻜﻴﻞ‬
‫ﺩﻫﻨﺪ ‪.‬‬
‫‪
t‬ﺭﺍﺑﻄﻪ ﺳﮕﻤﺎ ‪ :‬ﺍﮔﺮﭘﻮﺷﺶ ﺍﺑﺮﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺑﻪ ﺍﻣﺘﺪﺍﺩ ﺧﻄﻰ ﻛﻪ ﻫﺴﺘﻪ ﻫﺎﻯ ﺩﻭ ﺍﺗﻮﻡ ﺭﺍ ﻭﺻﻞ ﻣﻴﺴﺎﺯﺩ ‪،‬‬
‫ﺻﻮﺭﺕ ﺑﮕﻴﺮﺩ ‪ ،‬ﻳﻌﻨﻰ ﺗﺪﺍﺧﻞ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ﻣﺴﺘﻘﻴﻢ ﻭﺍﻋﻈﻤﻰ ﺑﺎﺷﺪ ﺭﺍﺑﻄﻪ ﻣﺴﺘﺤﻜﻢ ﺑﻮﺩﻩ ﻭﺑﻨﺎﻡ ﺭﺍﺑﻄﻪ ﺳﮕﻤﺎ‬
‫) ‪ ( S‬ﻳﺎﺩ ﻣﻴﺸﻮﺩ‬
‫‪
t‬ﺭﺍﺑﻄﻪ ‪ : π‬ﺭﺍﺑﻄﻪ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﺩﺭﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﻣﻴﺘﻮﺍﻧﺪ ﺩﻭﮔﺎﻧﻪ ﻭﻳﺎ ﺳﻪ ﮔﺎﻧﻪ ﺑﺎﺷﺪ‪ .‬ﺍﻳﻦ ﻧﻮﻉ ﺭﺍﺑﻄﻪ ﺗﻮﺳﻂ‬
‫ﺑﻴﺸﺘﺮﺍﺯ ﻳﻚ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎ ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ ؛ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪ :‬ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺁﻛﺴﻴﺠﻦ ﺭﺍﺑﻄﻪ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ‬
‫ﺁﻛﺴﻴﺠﻦ ﺩﻭﮔﺎﻧﻪ ﻭﺩﺭﻣﺎﻟﻴﻜﻮﻝ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺭﺍﺑﻄﻪ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺳﻪ ﮔﺎﻧﻪ ﺍﺳﺖ ‪ .‬ﺍﮔﺮﺗﺪﺍﺧﻞ ﺍﻭﺭﺑﻴﺘﺎﻝ‬
‫ﻫﺎﻯ ﺍﺗﻮﻣﻰ ﺟﺎﻧﺒﻰ ﺑﺎﺷﺪ؛ ﻳﻌﻨﻰ ﭘﻮﺷﺶ ﺍﺑﺮﺍﻟﻜﺘﺮﻭﻧﻰ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ‪ P‬ﺟﺎﻧﺒﻰ ﺑﻮﺩﻩ ﺑﺎﺷﺪ ﻭﺑﺎﻻﻯ ﻣﺤﻮﺭ ‪X‬‬
‫ﻋﻤﻮﺩ ﻗﺮﺍﺭﮔﻴﺮﺩ ‪ ،‬ﺍﻳﻦ ﺭﺍﺑﻄﻪ ﺗﺸﻜﻴﻞ ﺷﺪﻩ ﺑﻨﺎﻡ ﺭﺍﺑﻄﻪ ‪ P‬ﻳﺎﺩ ﻣﻴﺸﻮﺩ ‪.‬‬
‫‪
t‬ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻣﺘﺸﻜﻞ ﺍﺯ ﻳﻚ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ) ‪ (S‬ﻭ ﻳﻚ ﺭﺍﺑﻄﺔ ‪ P‬ﻭﺭﺍﺑﻄﺔ ﺳﻪ ﮔﺎﻧﻪ ﻣﺘﺸﻜﻞ ﺍﺯ ﻳﻚ ﺳﮕﻤﺎ‬
‫) ‪ (S‬ﻭ ﺩﻭ ﭘﺎﻯ) ‪ ( P‬ﻣﻴﺒﺎﺷﺪ‪.‬‬
‫‪15‬‬
 ‫ﺳﺆﺍﻻﺕ ﻓﺼﻞ ﺍﻭﻝ‬
‫ﺳﺆﺍﻻﺕ ﭼﻬﺎﺭ ﺟﻮﺍﺑﻪ‬
‫‪ - 1‬ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﻪ ﺣﺎﻟﺖ ﺗﺤﺮﻳﻚ ﻗﺮﺍﺭﺩﺍﺷﺘﻪ ﻭﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺘﺮﻭﻧﻰ ‪ ------‬ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ‪:‬‬
‫ﺍﻟﻒ ‪ 1S 2 2S 2 2P 2 -‬ﺏ ‪ 1S 2S1 2P 3 -‬ﺝ ‪ 1S 2 2S1 2P 3 -‬ﺩ ‪1S 2S1 2P 2 -‬‬
‫‪ - 2‬ﻧﺼﻒ ﻃﻮﻝ ﻋﻤﺮ ‪ --- 14 C‬ﺳﺎﻝ ﺍﺳﺖ ﻭﺩﺭﻧﺘﻴﺠﻪ ﺗﺸﻌﺸﻊ ‪ ----‬ﺑﻪ ﻧﺎﻳﺘﺮﻭﺟﻦ ﻣﺒﺪﻝ ﻣﻴﮕﺮﺩﺩ‪:‬‬
‫‪6‬‬
‫ﺍﻟﻒ‪ B + ، 5568, -‬ﺏ‪ B ، 5568, -‬ﺝ‪ G ، 5580 -‬ﺩ‪A ،5580 -‬‬
‫‪ - 3‬ﺩﺭ ﺗﻤﺎﻡ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ‪ - --‬ﺭﺍﺑﻄﻪ ﺍﺷﺘﺮﺍﻛﻰ ﺭﺍ ﺑﺎ ﺩﻳﮕﺮ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻳﺎ ﺍﺗﻮﻡ ﻫﺎﻯ‬
‫ﻋﻨﺎﺻﺮﺩﻳﮕﺮ ؛ﺍﺯﻗﺒﻴﻞ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺁﻛﺴﻴﺠﻦ‪ ،‬ﻧﺎﻳﺘﺮﻭﺟﻦ ﻭ ﻫﻠﻮﺟﻦ ﻫﺎ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ‪.‬‬
‫ﺍﻟﻒ ‪ -‬ﺩﻭ ﺭﺍﺑﻄﻪ ﺏ ‪ -‬ﺳﻪ ﺭﺍﺑﻄﻪ ﺝ ‪ -‬ﭼﻬﺎﺭ ﺭﺍﺑﻄﻪ ﺩ – ﻳﻚ ﺭﺍﺑﻄﻪ‬
‫‪ - 4‬ﻛﺎﺭﺑﻦ ﻣﻴﺘﻮﺍﻧﺪ ﺭﺍﺑﻄﻪ ﻫﺎ ﻯ ‪ -------‬ﺩﺍﺭﺍ ﺑﺎﺷﺪ‬
‫ﺍﻟﻒ ‪ -‬ﻳﮕﺎﻧﻪ‪ ،‬ﺏ‪ -‬ﺩﻭﮔﺎﻧﻪ ‪ ،‬ﺝ ‪ -‬ﺳﻪ ﮔﺎﻧﻪ ﺩ – ﻫﺮ ﺳﻪ ﺟﻮﺍﺏ ﺩﺭﺳﺖ ﺍﺳﺖ ‪.‬‬
‫‪ - 5‬ﺑﻴﻦ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭ ﻫﺮ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻳﻚ ﺭﺍﺑﻄﻪ ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ﻛﻪ ‪ ---‬ﺍﻟﻜﺘﺮﻭﻥ ﻣﺸﺘﺮﻙ ﺑﻴﻦ ﺁﻧﻬﺎ‬
‫ﻣﻮﺟﻮﺩ ﻣﻴﺒﺎﺷﺪ ‪،‬‬
‫ﺍﻟﻒ ‪ -‬ﻳﻚ ﺟﻮﺭﻩ ﺏ – ﺩﻭ ﺟﻮﺭﻩ ﺝ‪-‬ﺳﻪ ﺟﻮﺭﻩ ﺩ‪ -‬ﭼﻬﺎﺭ ﺟﻮﺭﻩ‬
‫‪ Hybrid - 6‬ﻋﺒﺎﺭﺕ ﺍﺯﺍﺧﺘﻼﻁ ﺩﻭﻭﻳﺎ ﭼﻨﺪﻳﻦ ‪ ----‬ﻣﺨﺘﻠﻒ ﺑﻮﺩﻩ ﻛﻪ ﺩﻭ ﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪----‬ﺟﺪﻳﺪ‬
‫ﺭﺍ ﺑﻪ ﻣﻴﺎﻥ ﻣﻴﺂﻭﺭﺩ ‪.‬‬
‫ﺍﻟﻒ‪ -‬ﺍﻭﺭﺑﻴﺘﺎﻝ ﺍﺗﻮﻣﻰ ‪ ،‬ﻫﺎﻳﺒﺮﻳﺪﻯ ﺏ‪ -‬ﺍﻭﺭﺑﻴﺘﺎﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ‪ ،‬ﻫﺎﻳﺒﺮﻳﺪﻯ ﺝ –ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭ‬
‫ﺩ‪ -‬ﻫﻴﭽﻜﺪﺍﻡ‬
‫‪ – 7‬ﺍﮔﺮ ﻳﻚ ﺍﻭﺭ ﺑﻴﺘﺎﻝ‪ s‬ﺑﺎ ﺳﻪ ﺍﻭﺭﺑﻴﺘﺎﻝ‪ p‬ﺩﺭﻧﺘﻴﺠﺔ ﺟﺬﺏ ﺍﻧﺮژﻯ ﺑﺎﻫﻢ ﻣﺨﺘﻠﻂ ﮔﺮﺩﻳﺪﻩ‪ ،‬ﻛﺪﺍﻡ ﺍﻭﺭﺑﻴﺘﺎﻝ‬
‫ﻫﺎﻳﺒﺮﻳﺪ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ؟‬
‫ﺍﻟﻒ ‪ sp -‬ﺏ‪ sp -‬ﺝ ‪ sp -‬ﺩ‪sp 3 -‬‬
‫‪2‬‬ ‫‪4‬‬
‫‪ - 8‬ﺳﻬﻢ ‪ s‬ﺩﺭﻫﺮﺍﻭﺭﺑﻴﺘﺎﻝ ‪ 2‬ﻣﺴﺎﻭﻯ ﺑﻪ ‪ ---‬ﻭﺯﺍﻭﻳﺔ ﻭﻻﻧﺴﻰ ﺩﺭﺑﻴﻦ ﺍﻳﻦ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ‪ -----‬ﺍﺳﺖ‪.‬‬
‫‪sp‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺍﻟﻒ‪ 1 -‬ﻭ ‪ 120o‬ﺏ‪ -‬ﻭ ‪ 120o‬ﺝ‪ -‬ﻭ ‪ 180 o‬ﺩ‪ -‬ﻭ ‪180 o‬‬
‫‪5‬‬ ‫‪3‬‬ ‫‪3‬‬ ‫‪3‬‬
‫‪ - 9‬ﺍﮔﺮﻳﻚ ﺍﻭﺭﺑـــــﻴﺘﺎﻝ‪ s‬ﻭﻳﻚ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ p‬ﺑﺎ ﻫﻢ ﺍﻣﺘــــﺰﺍﺝ ﻧﻤﺎﻳﻨﺪ ﻛﺪﺍﻡ ﻫﺎﻳﺒﺮﻳﺪ ﺣﺎﺻﻞ ﻣﻴﺸﻮﻧﺪ؟‬
‫ﺍﻟﻒ ‪ sp -‬ﺏ ‪ sp 2 -‬ﺝ ‪ sp3 -‬ﺩ‪، spd -‬‬
‫‪ - 10‬ﺍﮔﺮﺗﺪﺍﺧﻞ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎ ﻣﺴﺘﻘﻴﻢ ﻭﺍﻋﻈﻤﻰ ﺑﺎﺷﺪ ‪ ،‬ﺭﺍﺑﻄﻪ ﻣﺴﺘﺤﻜﻢ ﺑﻮﺩﻩ ﻭﺑﻨﺎﻡ ﺭﺍﺑﻄﻪ ‪ ----‬ﻳﺎﺩ ﻣﻴﺸﻮﺩ‪.‬‬
‫ﺍﻟﻒ‪ -‬ﺳﮕﻤﺎ ﺏ‪ S -‬ﺝ ‪ -‬ﺍﻟﻒ ﻭﺏ ﺩ ‪ -‬ﻫﻴﭽﻜﺪﺍﻡ‬
‫‪ - 11‬ﺩﺭ ﻣﺮﻛﺐ ‪ CH − CH = CH = CH − C ≡ CH‬ﭼﻨﺪ ﺭﺍﺑﻄﺔ ‪ P‬ﻣﻮﺟﻮﺩ ﺍﺳﺖ؟‬
‫‪3‬‬
‫ﺍﻟﻒ – ﺳﻪ ﺏ‪ -‬ﭼﻬﺎﺭ ﺝ – ﭘﻨﺞ ﺩ – ﺩﻭ‬
‫‪16‬‬
 ‫ﺳﺆﺍﻻﺕ ﺗﺸﺮﻳﺤﻰ‬
‫‪ - 1‬ﭼﺮﺍ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺑﺎ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ‪ CH 3‬ﻳﺎ ‪ C2 H 5‬ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ﻧﻪ ﻣﻰ ﺗﻮﺍﻧﻨﺪ؟‬
‫‪ - 2‬ﭼﻨﺪ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺑﺎ ﻫﺮ ﻳﻚ ﺍﺯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭ ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ ‪C − C = C − C ≡ C‬‬
‫ﺗﺮﻛﻴﺐ ﺷﺪﻩ ﻣﻰ ﺗﻮﺍﻧﺪ؟‬
‫‪ – 3‬ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﻭ ﺭﻭﺍﺑﻂ ﺧﻄﻰ ﺍﻳﺘﺎﻳﻞ ﺍﻟﺪﻳﻬﺎﻳﺪ ) ‪ (CH 3CHO‬ﺭﺍ ﺭﺳﻢ ﻧﻤﺎﻳﻴﺪ‪.‬‬
‫‪ – 4‬ﺳﺎﺧﺘﻤﺎﻥ ﺭﻭﺍﺑﻂ ﺧﻄﻰ ﭘﺮﻭﭘﻴﻦ ) ‪ (CH CH = CH‬ﺭﺍ ﺑﺎ ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﻭ ﺯﻭﺍﻳﺎﻯ ﺭﻭﺍﺑﻂ ﺁﻥ‬
‫‪3‬‬ ‫‪2‬‬
‫ﺗﺮﺳﻴﻢ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪ - 5‬ﻫﻴﺒﺮﻳﺪﺍﺯﻳﺰﺷﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺒﺎﺕ ﺫﻳﻞ ﻣﺸﺨﺺ ﺳﺎﺯﻳﺪ‪:‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫‪H‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪Cl ، H‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪H‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫‪ - 6‬ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﺷﻦ ‪ ،‬ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﻫﺎﺭﺍ ﺩﺭﻣﺮﻛﺐ ‪ CCl 4‬ﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪ - 7‬ﻫﺎﻳﺒﺮﻳﺪﺍﻳﺰﺷﻦ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ ﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺒﺎﺕ ﺫﻳﻞ ﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫‪ BF3 , BH 2 , H 2O‬ﻭ ‪CO2‬‬
‫‪ - 8‬ﺯﺍﻭﻳﺔ ﺭﺍﺑﻄﻪ ﻭﻯ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﺫﻳﻞ ﺑﻪ ﺻﻮﺭﺕ ﺗﻘﺮﻳﺒﻰ ﭼﻨﺪ ﺧﻮﺍﻫﺪ ﺑﻮﺩ ؟‬
‫‪H‬‬ ‫‪Cl‬‬ ‫‪Cl‬‬
‫‪H‬‬ ‫‪C‬‬ ‫‪Cl‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪H‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪H‬‬
‫‪H‬‬ ‫‪Cl‬‬ ‫‪Cl‬‬
‫‪ –9‬ﻣﻮﺩﻝ ﻣﺎﻟﻴﻜﻮﻝ ﺍﺳﭙﺮﻳﻦ ﺭﺍ ﻗﺮﺍﺭ ﺫﻳﻞ ﺑﻪ ﺩﻗﺖ ﻣﻼﺣﻈﻪ ﻧﻤﻮﺩﻩ ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻧﺮﺍ ﺑﻪ ﺍﺳﺎﺱ ﺭﻭﺍﺑﻂ‬
‫ﺧﻄﻰ ﺗﺮﺳﻴﻢ ﻭ ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍ ﺩﺭ ﺁﻥ ﻣﺸﺨﺺ ﺳﺎﺯﻳﺪ ‪.‬‬
‫)ﺩﺭ ﻣﻮﺩﻝ ﺍﺳﭙﺮﻳﻦ ﮔﻠﻮﻟﺔ ﻧﺼﻮﺍﺭﻯ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ‪ ،‬ﺳﺮﺥ ﺍﺗﻮﻡ ﺁﻛﺴﻴﺠﻦ ﻭﺳﺮﺥ ﻣﺎﻳﻞ ﺑﻪ ﺳﻔﻴﺪ ﺍﺗﻮﻡ ﻫﺎﻯ‬
‫ﻫﺎﻳﺪﺭﻭﺟﻦ ﺭﺍ ﺍﻓﺎﺩﻩ ﻣﻴﻜﻨﺪ (‪:‬‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﺍﺳﭙﺮﻳﻦ ‪:‬‬
‫‪ - 10‬ﺩﺭ ﻣﺮﻛﺒﺎﺕ ﺫﻳﻞ ﭼﻨﺪ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﻭﭼﻨﺪ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ؟ ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺁﻧﺮﺍ ﺗﺤﺮﻳﺮ‬
‫ﺩﺍﺷﺘﻪ ﻭﻫﻢ ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﺗﻤﺎﻣﻰ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍ ﺗﻮﺿﻴﺢ ﺑﺪﺍﺭﻳﺪ‪:‬‬
‫ﺍﻟﻒ ‪ 1,3 − butadiene-‬ﺏ ‪ – 1-pentyne‬ﺝ ‪propadiene - 1,2 -‬‬
‫‪17‬‬
 ‫ﻓﺼﻞ ﺩﻭﻡ‬
‫ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻭﻓﻮﺭﻣﻮﻝ ﻫﺎ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﻛﻴﻤﻴﺎﻭﻯ ﺍﺯ ﺟﻤﻠﻪ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺩﺍﺭﺍﻯ ﺗﺮﻛﻴﺐ ﺧﺎﺹ‬
‫ﻣﺮﺑﻮﻁ ﺑﻪ ﺧﻮﺩ ﺑﻮﺩﻩ ﻭﺍﺯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺑﻪ ﺍﺷﻜﺎﻝ ﻣﺨﺘﻠﻒ ﻭ ﺑﺎ ﻗﻮﻩ ﻫﺎﻯ ﻣﺨﺘﻠﻒ ﺗﺸﻜﻴﻞ ﮔﺮﺩﻳﺪﻩ‬
‫ﺍﻧﺪ ‪ .‬ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﺑﺎ ﺗﺮﻛﻴﺐ ﻣﺨﺘﻠﻒ ﺩﺍﺭﺍﻯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﻣﺨﺘﻠﻒ ﺑﻮﺩﻩ ﻛﻪ ﻃﺮﺯ ﺭﻭﺍﺑﻂ‬
‫ﺍﺗﻮﻣﻬﺎ ﻧﻴﺰ ﺑﻪ ﺍﺷﻜﺎﻝ ﻣﺨﺘﻠﻒ ﻣﻼﺣﻈﻪ ﻣﻴﮕﺮﺩﻧﺪ ‪ .‬ﺑﺎﻳﺪ ﺑﺪﺍﻧﻴﻢ ﻛﻪ ﻣﺎﻟﻴﻜﻮﻝ ﭼﻴﺴﺖ ﻭ ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﻫﺎ ﭼﻪ ﻧﻮﻉ ﺍﺳﺖ؟ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﺗﻮﺳﻂ ﻛﺪﺍﻡ ﺍﺷﻜﺎﻝ ﻭ ﺳﻤﺒﻮﻟﻬﺎ ﺍﺭﺍﺋﻪ ﻣﻴﺸﻮﺩ ؟ ﻓﻮﺭﻣﻮﻝ‬
‫ﭼﻴﺴﺖ ﻭ ﻛﺪﺍﻡ ﻣﺸﺨﺼﺎﺕ ﻣﺎﻟﻴﻜﻮﻝ ﺭﺍ ﺍﺭﺍﺋﻪ ﻣﻜﻨﺪ ؟ ﻓﻮﺭﻣﻮﻝ ﻫﺎ ﭼﻨﺪ ﻧﻮﻉ ﺍﻧﺪ ؟ ﻭﭼﮕﻮﻧﻪ ﻓﻮﺭﻣﻮﻟﻬﺎ‬
‫ﺗﺤﺮﻳﺮ ﻣﻴﮕﺮﺩﻧﺪ؟ ﺍﻳﺰﻭﻣﻴﺮﻯ ﭼﻴﺴﺖ ﻭﭼﻄﻮﺭ ﻣﻔﻬﻮﻡ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺭﺍ ﺗﻮﺿﻴﺢ ﻛﺮﺩﻩ ﻣﻴﺘﻮﺍﻧﻴﻢ ؟ ﺑﺎ ﻣﻄﺎﻟﻌﺔ‬
‫ﺍﻳﻦ ﻓﺼﻞ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﺳﺆﺍﻻﺕ ﻓﻮﻕ ﺟﻮﺍﺏ ﺍﺭﺍﺋﻪ ﻛﺮﺩ ‪.‬‬
‫‪18‬‬
 ‫‪ : 1- 2‬ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‬
‫ﻳﻚ ﻣﺮﻛﺐ ﻛﻴﻤﻴﺎﻭﻯ ﺭﺍ ﻣﻌﻤﻮﻻ" ﺗﻮﺳﻂ ﻃﺮﺯ ﺗﺮﺗﻴﺐ ﺳﻤﺒﻮﻝ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﺓ ﺁﻥ ﺑﺎ ﺿﺮﺍﻳﺐ ﻧﺴﺒﺘﻰ‬
‫ﻛﻪ ﺑﻪ ﻧﺎﻡ ﺿﺮﺍﻳﺐ ﺳﺘﻴﻜﻴﻮ ﻣﺘﺮﻯ )‪(Stoichiometry‬ﻧﻴﺰ ﻳﺎﺩ ﻣﻴﺸﻮﺩ ‪ ،‬ﻧﺸﺎﻥ ﻣﻴﺪﻫﻨﺪ‪ ،‬ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪ NaCl :‬ﻧﺸﺎﻥ‬
‫ﺩﻫﻨﺪﺓ ﻧﻤﻚ ﻃﻌﺎﻡ ﻭ ‪ H 2O‬ﻧﺸﺎﻥ ﺩﻫﻨﺪﻩ ﺁﺏ ﺍﺳﺖ ﻛﻪ ﻃﺮﺯ ﺗﺮﺗﻴﺐ ﺳﻤﺒﻮﻝ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﻩ ﺑﺎ ﺿﺮﺍﻳﺐ‬
‫ﻧﺴﺒﺘﻰ ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻳﺎﺩ ﻣﻴﻨﻤﺎﻳﻨﺪ‪ .‬ﻳﻚ ﻣﺎﻟﻴﻜﻮﻝ ﺁﺏ ﺍﺯ ﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﻳﻚ ﺍﺗﻮﻡ‬
‫ﺍﻛﺴﻴﺠﻦ ﺗﺸﻜﻴﻞ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ‪ ،‬ﺑﻪ ﺍﻳﻦ ﺍﺳﺎﺱ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﺏ ‪ H 2O‬ﺍﺳﺖ‪.‬‬
‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﺍﺳﺎﺱ ﺗﺠﺰﻳﻪ ﻛﻴﻤﻴﺎﻭﻯ ﺗﻌﻴﻴﻦ ﻧﻤﻮﺩ ‪ .‬ﻧﻮﻉ ﺩﻳﮕﺮﻯ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ‬
‫ﻛﻴﻤﻴﺎﻭﻯ ﻋﺒﺎﺭﺕ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ ﺍﺳﺖ ‪ ،‬ﺩﺭﺍﻳﻦ ﻓﻮﺭﻣﻮﻝ ﺗﻌﺪﺍﺩ ﻧﺴﺒﺘﻰ ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﻣﺨﺘﻠﻒ ﺩﺭ ﻳﻚ‬
‫ﻣﺮﻛﺐ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﻣﻴﺸﻮﺩ‪).‬ﻛﻠﻤﻪ ﺗﺠﺮﺑﻰ ﺩﺭﻳﻦ ﺟﺎ ﺑﻪ ﺍﻳﻦ ﻣﻌﻨﻰ ﺍﺳﺖ ﻛﻪ ﻓﻮﺭﻣﻮﻝ ﺍﺭﺍﺋﻪ ﺷﺪﻩ ﺗﻨﻬﺎ ﺑﻪ ﺍﺳﺎﺱ‬
‫ﻣﺸﺎﻫﺪﻩ ﻭ ﺍﻧﺪﺍﺯﻩ ﮔﻴﺮﻯ؛ ﻳﻌﻨﻰ ﺗﺤﻠﻴﻞ ﺗﻮﺻﻴﻔﻰ ﻭﻣﻘﺪﺍﺭﻯ ﻣﺸﺨﺺ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ(‪ .‬ﻣﺎﻟﻴﻜﻮﻝ ﮔﻠﻮﻛﻮﺯ ﺩﺍﺭﺍﻯ‬
‫‪ 6‬ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ‪ 12 ،‬ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ‪ 6‬ﺍﺗﻮﻡ ﺁﻛﺴﻴﺠﻦ ﺑﻮﺩﻩ ﻭ ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ ﺁﻥ ‪ CH 2 O‬ﺍﺳﺖ ﻛﻪ ﺗﻨﻬﺎ‬
‫ﻧﺴﺒﺖ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ‪ ،‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﺍﺗﻮﻡ ﻫﺎﻯ ﺁﻛﺴﻴﺠﻦ ﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﮔﻠﻮﻛﻮﺯ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪.‬‬
‫ﭼﻮﻥ ﺍﻳﻦ ﻧﺴﺒﺖ ﻫﺎ ﻫﻤﻮﺍﺭﻩ ﺳﺎﺩﻩ ﺗﺮﻳﻦ ﺷﻜﻞ ﻳﻚ ﻣﺎﺩﻩ ﺭﺍ ﺁﺷﻜﺎﺭ ﻣﻴﺴﺎﺯﺩ ‪ ،‬ﺍﺯﻳﻦ ﺳﺒﺐ ﺍﻳﻦ ﻓﻮﺭﻣﻮﻝ ﺭﺍ ﺑﻪ ﻧﺎﻡ‬
‫ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ ﻧﻴﺰ ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪ ‪.‬ﺩﺭ ﺷﻜﻞ ﺫﻳﻞ ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﮔﻠﻮﻛﻮﺯ ﺑﻪ ﭼﻨﺪﻳﻦ ﺷﻜﻞ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ‪:‬‬
‫ﺷﻜﻞ )‪ : ( 1 - 2‬ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﮔﻠﻮﻛﻮﺯ‬
‫ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺗﺠﺮﺑﻰ‬
‫ﺩﺭ ﺟﺪﻭﻝ ﺯﻳﺮ ﻣﺜﺎﻟﻬﺎﻯ ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ ﻭ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺍﺭﺍﺋﻪ ﺷﺪﻩ ﺍﺳﺖ ‪:‬‬
‫ﺟﺪﻭﻝ )‪ :( 1 - 2‬ﻣﻘﺎﻳﺴﺔ ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ ﻭ ﻣﺎﻟﻴﻜﻮﻟﻰ‬
‫ﻃﺮﺯ ﻧﻤﺎﻳﺶ‬ ‫ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ‬ ‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‬ ‫ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ‬ ‫ﻣﺮﻛﺐ‬
‫‪30.03‬‬ ‫‪CH O‬‬ ‫‪CH O‬‬ ‫ﻓﺎﺭﻡ ﺍﻟﺪﻳﻬﺎﻳﺪ‬
‫‪2‬‬ ‫‪2‬‬
‫‪60.06‬‬ ‫‪C2 H 4 O2‬‬ ‫‪CH O‬‬ ‫ﺍﺳﺘﻴﻚ ﺍﺳﻴﺪ‬
‫‪2‬‬
‫‪180‬‬ ‫‪C H O‬‬ ‫‪CH O‬‬ ‫ﮔﻠﻮﻛﻮﺯ‬
‫‪6 12 6‬‬ ‫‪2‬‬
‫‪19‬‬
‫ﺑﺮﺍﻯ ﺍﻳﻦ ﻛﻪ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﺓ ﻭﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺑﻪ ﺩﺭﺳﺘﻰ ﺗﺤﺮﻳﺮ ﻭ ﺩﺭﻳﺎﻓﺖ ﻧﻤﻮﺩﻩ ﺑﺎﺷﻴﻢ ‪،‬ﻻﺯﻡ‬
‫ﺍﺳﺖ ﺗﺎ ﺗﺤﻠﻴﻞ ﺗﻮﺻﻴﻔﻰ ﻭ ﻣﻘﺪﺍﺭﻯ ﻣﺮﻛﺐ ﺭﺍ ﺑﺪﺍﻧﻴﻢ ‪ .‬ﺑﺎ ﺩﺍﻧﺴﺘﻦ ﺗﺤﻠﻴﻞ ﺗﻮﺻﻴﻔﻰ ﻭ ﻣﻘﺪﺍﺭﻯ ﻣﺮﻛﺐ ﻣﻴﺘﻮﺍﻥ‬
‫ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ ﺁﻥ ﺭﺍ ﻗﺮﺍﺭ ﻣﻮﺍﺩ ﺫﻳﻞ ﺗﺤﺮﻳﺮ ﻭ ﺩﺭﻳﺎﻓﺖ ﻛﺮﺩ ‪:‬‬
‫‪ - 1‬ﻛﻤﻴﺖ ﻫﺎﻯ ﻣﻘﺪﺍﺭﻯ ﻫﺮﻋﻨﺼﺮ ﺭﺍﻛﻪ ﺩﺭﺍﺛﺮ ﺍﻧﺎﻟﻴﺰ)ﺗﺠﺰﻳﻪ ( ﺣﺎﺻﻞ ﺷﺪﻩ ﺍﺳﺖ ‪ ،‬ﺑﻪ ﻣﻮﻝ ﺗﺒﺪﻳﻞ ﻣﻴﻜﻨﻴﻢ‪.‬‬
‫‪ - 2‬ﻣﻘﺪﺍﺭ ﻣﻮﻝ ﻫﺎﻯ ﻫﺮ ﻋﻨﺼﺮ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﺓ ﻣﺮﻛﺐ ﺭﺍ ﻛﻪ ﻗﺮﺍﺭ ﻣﺎﺩﺓ ‪ 1‬ﺣﺎﺻﻞ ﻧﻤﻮﺩﻳﻢ ‪ ،‬ﺩﻗﻴﻘﺎ"ﻣﻼﺣﻈﻪ‬
‫ﻧﻤﻮﺩﻩ‪ ،‬ﻛﻤﻴﺖ ﻛﻮﭼﻚ ﺁﻧﻬﺎ ﺭﺍ ﺑﺮﻣﻼ ﻣﻴﺴﺎﺯﻳﻢ ‪ ،‬ﺳﭙﺲ ﺗﻤﺎﻡ ﻛﻤﻴﺖ ﻣﻮﻟﻰ ﻋﻨﺎﺻﺮ ﻣﺘﺸﻜﻠﻪ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ‬
‫ﻣﻄﻠﻮﺏ ﺭﺍ ﺗﻘﺴﻴﻢ ﺑﺮ ﻫﻤﻴﻦ ﻛﻤﻴﺖ ﻛﻮﭼﻚ ﻣﻮﻟﻰ ﻧﻤﻮﺩﻩ ‪ ،‬ﺍﺭﻗﺎﻡ ﺑﺪﻭﻥ ﻭﺍﺣﺪ ﻫﺎﻯ ﻗﻴﺎﺳﻰ ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ‪.‬‬
‫‪ - 3‬ﻛﻤﻴﺖ ﻫﺎﻯ ﺭﻗﻤﻰ ﻛﻪ ﻃﺒﻖ ﻣﺎﺩﺓ ‪ 2‬ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪ ،‬ﺩﻗﻴﻘﺎ" ﻣﻄﺎﻟﻌﻪ ﺷﺪﻩ‪ ،‬ﺩﺭ ﺻﻮﺭﺕ ﻛﻪ ﺍﻋﺪﺍﺩ ﺗﺎﻡ‬
‫ﺑﺎﺷﺪ ‪ ،‬ﺿﺮﺍﻳﺐ ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﻣﺘﺸﻜﻠﻪ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ ﺭﺍ ﺩﺭ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﻭ ﺍﮔﺮ ﺍﺭﻗﺎﻡ ﺗﺎﻡ‬
‫ﻧﺒﺎﺷﻨﺪ ‪ ،‬ﺁﻧﻬﺎ ﺭﺍ ﺑﻪ ﻃﺮﻳﻘﻪ ﺭﻭﻧﺪﺍﻑ ﻭ ﻳﺎ ﺿﺮﺏ ﻧﻤﻮﺩﻥ ﻛﻮﭼﻜﺘﺮﻳﻦ ﻋﺪﺩ ﺗﺎﻡ ‪ ،‬ﺑﻪ ﺍﻋﺪﺍﺩ ﺗﺎﻡ ﺗﺒﺪ ﻳﻞ ﻧﻤﻮﺩﻩ‪،‬‬
‫ﺍﻳﻦ ﺍﻋﺪﺍﺩ ﺗﺎﻡ ﻧﺴﺒﺖ ﺍﺗﻮﻣﻰ ﻋﻨﺎﺻﺮ ﺭﺍ ﺩﺭ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ ﺍﻓﺎﺩﻩ ﻣﻴﻜﻨﺪ ‪ ،‬ﺍﺭﻗﺎﻡ ﻧﺴﺒﺘﻰ ﻋﻨﺎﺻﺮ ﺭﺍ ﺑﺎ ﺩﺭﻧﻈﺮ ﺩﺍﺷﺖ‬
‫ﻃﺮﺯ ﺗﺤﺮﻳﺮ ﺩﺭﺳﺖ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺑﻪ ﺳﻤﺒﻮﻝ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﻛﻴﻤﻴﺎﻭﻯ ﺿﻤﻴﻤﻪ ﺳﺎﺧﺘﻪ ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ‬
‫ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ‪.‬‬
‫‪ - 4‬ﻏﺮﺽ ﺗﺤﺮﻳﺮ ﺩﺭﺳﺖ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺐ‪ ،‬ﻋﻼﻭﻩ ﺍﺯ ﺩﺍﺷﺘﻦ ﺗﺤﻠﻴﻞ ﺗﻮﺻﻴﻔﻰ ﻭ ﻣﻘﺪﺍﺭﻯ ﺑﺎﻳﺪ‬
‫ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺐ ﻧﻴﺰ ﻣﻌﻠﻮﻡ ﺑﺎﺷﺪ‪ ،‬ﺑﺪﻳﻦ ﺍﺳﺎﺱ ﺑﺎ ﺩﺭ ﻧﻈﺮ ﺩﺍﺷﺖ ﺗﺤﻠﻴﻞ ﺗﻮﺻﻴﻔﻰ ﻭ ﻣﻘﺪﺍﺭﻯ ﻗﺮﺍﺭ ﻣﻮﺍﺩ‬
‫ﻓﻮﻕ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻭ ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺐ ﻣﻄﻠﻮﺏ ﺭﺍ ﺑﻪ ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻧﺴﺒﺘﻰ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ‬
‫ﺗﻘﺴﻴﻢ ﻭ ﻋﺪﺩ ﺗﺎﻡ ﺣﺎﺻﻞ ﺧﻮﺍﻫﺪ ﺷﺪﻛﻪ ﺍﻳﻦ ﻋﺪﺩ ﺭﺍ ﺑﻪ ﻧﺴﺒﺖ ﻋﻨﺎﺻﺮ ﺩﺭ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ ﺿﺮﺏ ﻧﻤﻮﺩﻩ ﻭﺩﺭ‬
‫ﻧﺘﻴﺠﻪ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺐ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ‪:‬‬
‫ﻛﺘﻠﺔ ﻓﻮﺭﻣﻮﻟﻰ‬
‫=‪X‬‬
‫ﻛﺘﻠﺔ ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ‬
‫ﻣﺜﺎﻝ ﺍﻭﻝ‪ :‬ﺑﻪ ﻣﻘﺪﺍﺭ ‪ 7.2g‬ﻳﻚ ﻣﺮﻛﺐ ﻋﻀﻮﻯ ﺑﺎ ﺍﻛﺴﺎﻳﺪ ﻣﺲ ﺩﺭ ﻧﻞ ﺍﻣﺘﺤﺎﻧﻰ ﺣﺮﺍﺭﺕ ﺩﺍﺩﻩ‬
‫ﺷﺪﻩ ﺍﺳﺖ ﻭ ﺩﺭ ﻧﺘﻴﺠﻪ ‪ 10.52‬ﮔﺮﺍﻡ ﻛﺎﺭﺑﻦ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ ﻭ ‪4.32‬ﮔﺮﺍﻡ ﺑﺨﺎﺭﺍﺕ ﺁﺏ ﺣﺎﺻﻞ ﮔﺮﺩﻳﺪﻩ‬
‫ﺍﺳﺖ ﺍﮔﺮ ﺑﻪ ﻣﻘﺪﺍﺭ ‪ 1.8‬ﮔﺮﺍﻡ ﺁﻥ ﺩﺭ‪ 50‬ﮔﺮﺍﻡ ﺁﺏ ﺣﻞ ﮔﺮﺩﺩ ‪،‬ﻣﺤﻠﻮﻝ ﺣﺎﺻﻞ ﺑﻪ ﺣﺮﺍﺭﺕ ‪− 0.37o C‬‬
‫ﻣﻨﺠﻤﺪ ﻣﻴﮕﺮﺩﺩ ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﺓ ﻣﺮﻛﺐ ﻣﺬﻛﻮﺭ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪.‬‬
‫‪10.52g CO 2‬‬ ‫‪−‬‬ ‫‪7.2g‬‬ ‫ﺣﻞ ‪:‬‬
‫‪x‬‬ ‫‪−‬‬ ‫‪100‬‬
‫‪10.52g ⋅ 100‬‬
‫=‪X‬‬ ‫‪= 146.11%‬‬
‫‪7.3g‬‬
‫‪146.11gCO 2 ⋅ 12gC‬‬
‫‪44gCO 2‬‬ ‫‪− 12gC‬‬ ‫=‪X‬‬ ‫‪= 40%C‬‬
‫‪44CO 2‬‬
‫‪146.11gCO 2 − X‬‬
‫‪20‬‬
4.32g H 2O − 7.2g
x − 100
4.32g ⋅ 100
X= = 59.2%
7.3g
59,2gH 2O⋅2gH
18gH 2O − 2gH X= = 7%H
18H 2O
59.2gH 2O − X
6.6g H 2O − 7.2g
x − 100
6.6g ⋅ 100
X= = 59.2%
7.3g
59,2gH 2O ⋅ 16gO
18gH 2O − 16gO X= = 52 .6%O
18H 2O
59 .2gH 2O − X
C = 40g/12g ⋅ mol −1 = 3.33mol
H =7g/1g⋅mol −1 =7mol
O =52.6g/16g⋅mol −1 = 3.3mol
C = 3.33mol/3. 33mol = 1
H = 7mol/3.33m ol = 2
O = 3.3mol/3.3 3mol =1
C =1
H =2 CH 2O ‫ﻓﻮﺭﻣﻮﻝ ﺑﺴﻴﻂ‬
O =1
: ‫ ﺍﺳﺖ ﺍﺯﺍﻳﻦ ﺟﺎ ﺩﺍﺭﻳﻢ ﻛﻪ‬Δt = K ⋅ C = K ⋅ m⋅1000g⋅molal ‫ﺍﺯ ﺻﻨﻒ ﻳﺎﺯﺩﻫﻢ ﻣﻴﺪﺍﻧﻴﻢ ﻛﻪ‬
m M⋅m′
m⋅1000g⋅molal
⋅M = K ⋅
Δt⋅m′
CKg 1.8g⋅1000g⋅molal
M = 1.85 o ⋅ = 180
mol 0.37o ⋅50g
M = 180
M(CH O)n = 180
2
(12 +1⋅2 +16)n =180
180
(30)n =180 ⇒n = = 6⇒ n = 6
30
(CH O)n = (CH O)6 ⇒ C H O
2 2 6 12 6
21
 ‫ﻣﺸﻖ ﻭﺗﻤﺮﻳﻦ ﻛﻨﻴﺪ‬
‫ﺗﺤﻠﻴﻞ ﺗﺗﻮﺻﻴﻔﻰ ﻭﻣﻘﺪﺍﺭﻯ ﻳﻚ ﻣﺮﻛﺐ ﻋﻀﻮﻯ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﺍﺳﺖ ﻛﻪ ﺩﺭ ﺗﺮﻛﻴﺐ ﺁﻥ ﺑﻪ ﻣﻘﺪﺍﺭ ‪6g‬‬ ‫ﺗ ﻠﻞ‬
‫ﻛﺎﺭﺑﻦ ﻭ‪1.2g‬ﻫﺎﻳﺪﺭﻭﺟﻦ ﺷﺎﻣﻞ ﺍﺳﺖ ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﺑﺴﻴﻂ ﺁﻥ ﺭﺍ ﺗﺤﺮﻳﺮ ﻧﻤﺎﻳﻴﺪ‪.‬ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻥ‪72‬‬
‫ﺍﺳﺖ ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻥ ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻛﻨﻴﺪ ‪.‬‬
‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‪ ،‬ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺑﻪ ﺯﺑﺎﻥ ﻛﻴﻤﻴﺎﻭﻯ ﻣﻌﺮﻓﻰ ﻣﻴﻨﻤﺎﻳﺪ ‪ .‬ﻓﻮﺭﻣﻮﻝ ﻧﻪ ﺗﻨﻬﺎ ﻧﻮﻉ ﺍﺗﻮﻣﻬﺎ ﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﻧﺸﺎﻥ ﺩﺍﺩﻩ ؛ﺑﻠﻜﻪ ﺗﻌﺪﺍﺩ ﻭﺍﻧﻮﺍﻉ ﺍﺗﻮﻡ ﻫﺎ ﺭﺍ ﻧﻴﺰ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪.‬ﻣﻴﺘﺎﻥ ﺳﺎﺩﻩ ﺗﺮﻳﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﺍﻟﻜﺎﻥ ﺑﻮﺩﻩ ﻭ ﺩﻭ‬
‫ﻣﺮﻛﺐ ﺩﻳﮕﺮ ﺍﻟﻜﺎﻧﻬﺎ ﻋﺒﺎﺭﺕ ﺍﺯ ﺍﻳﺘﺎﻥ ‪ C2H 6‬ﻭﭘﺮﻭﭘﺎﻥ ‪ C3H 8‬ﻣﻴﺒﺎﺷﺪ ‪.‬ﺁﻳﺎ ﻣﻴﺘﻮﺍﻧﻴﺪ ﻓﺮﻣﻮﻝ ﺍﻟﻜﺎﻥ ﺩﺍﺭﻧﺪﺓ‬
‫ﭼﻬﺎﺭ ﻛﺎﺭﺑﻦ ﺭﺍ ﺗﺤﺮﻳﺮ ﻧﻤﺎﻳﻴﺪ ؟ ﺑﺮﺍﻯ ﺍﻳﻦ ﻛﺎﺭ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﺳﻪ ﺍﻟﻜﺎﻥ ﺍﻭﻟﻰ ﻛﻤﻚ ﮔﺮﻓﺘﻪ ﻭﺭﺍﺑﻄﻪ ﺑﻴﻦ ﺗﻌﺪﺍﺩ‬
‫ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻭﻫﺎﻳﺪﺭﻭﺟﻦ ﺭﺍ ﺩﺭ ﻫﺮﻳﻚ ﺁﻥ ﺩﺭﻳﺎﻓﺖ ﻧﻤﺎﻳﻴﺪ ؛ ﺑﻨﺎﺑﺮ ﺍﻳﻦ ﺗﻤﺎﻣﻰ ﺍﻟﻜﺎﻧﻬﺎ ﺩﺍﺭﺍﻯ ﻓﻮﺭﻣﻮﻝ‬
‫ﻋﻤﻮﻣﻰ ‪ Cn H 2n + 2‬ﺍﻧﺪ ‪ ،‬ﺩﺭ ﺍﻳﻦ ﻓﻮﺭﻣﻮﻝ ‪ n‬ﺗﻌﺪﺍﺩ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍ ﺩﺭ ﻫﺮ ﺍﻟﻜﺎﻥ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪.‬‬
‫( ﺗﻌﻴﻴﻦ ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺍﻟﻜﺎﻧﻬﺎ ‪n 2n + 2‬‬ ‫ﺟﺪﻭﻝ )‪3 - 2‬‬
‫‪C H‬‬
‫‪CH‬‬ ‫‪C H‬‬ ‫‪C H‬‬ ‫‪C H‬‬
‫‪4‬‬ ‫‪2 6‬‬ ‫‪3 8‬‬ ‫? ‪4‬‬
‫ﺗﻌﺪﺍﺩ‬ ‫‪ C=2‬ﺗﻌﺪﺍﺩ‬ ‫‪ C=3‬ﺗﻌﺪﺍﺩ‬ ‫‪ C=4‬ﺗﻌﺪﺍﺩ‬
‫‪ H=2(1)+2=4‬ﺗﻌﺪﺍﺩ‬ ‫‪ H=2(2)+2=6‬ﺗﻌﺪﺍﺩ‬ ‫‪ H=2(3)+2=8‬ﺗﻌﺪﺍﺩ‬ ‫‪ H=2(4)+2=10‬ﺗﻌﺪﺍﺩ‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﻓﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺍﻟﻜﺎﻧﻬﺎﻯ ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻛﻨﺒﺪ ﻛﻪ ﺗﻌﺪﺍﺩ ﻛﺎﺭﺑﻦ ﺁﻥ ﻗﺮﺍﺭ ﺟﺪﻭﻝ ﺯﻳﺮ ﺑﻮﺩﻩ ﺑﺎﺷﺪ ‪:‬‬
‫ﺗﻌﺪﺍﺩﻛﺎﺭﺑﻦ )‪ (n‬ﻫﺮ ﺍﻟﻜﺎﻥ‬ ‫‪5‬‬ ‫‪6‬‬ ‫‪7‬‬ ‫‪8‬‬ ‫‪9‬‬ ‫‪10‬‬
‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‬
‫‪ :2- 2‬ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ‬
‫ﻓﺮﻣﻮﻝ ﻫﺎﻯ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺒﺎﺕ ﺑﺮﺍﻯ ﻣﺎ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ﻛﻪ ﻛﺪﺍﻡ ﻋﻨﺎﺻﺮ ﺩﺭ ﺗﺮﻛﻴﺐ ﻳﻚ ﻣﺮﻛﺐ ﺷﺎﻣﻞ‬
‫ﺍﺳﺖ ﻭ ﺗﻌﺪﺍﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺮ ﻣﺮﻛﺐ ﺩﺭﺗﺮﻛﻴﺐ ﻋﻨﺎﺻﺮ ﻣﺬﻛﻮﺭ ﺑﻪ ﭼﻪ ﺗﻌﺪﺍﺩ ﺍﺳﺖ ؛ ﺍﻣﺎ ﺑﺮﺍﻯ ﺍﻳﻦ ﻛﻪ ﺑﺪﺍﻧﻴﻢ‬
‫ﺍﺗﻮﻣﻬﺎﻯ ﻋﻨﺎﺻﺮ ﻣﺘﺸﻜﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﻣﺮﻛﺒﺎﺕ ﭼﻄﻮﺭ ﺑﺎﻫﻢ ﻣﺘﻮﺻﻞ ﺷﺪﻩ ﺍﻧﺪ ‪ ،‬ﺑﺎﻳﺪ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ‬
‫ﺁﻧﻬﺎﺭﺍ ﻧﻮﺷﺘﻪ ﻛﺮﺩﻩ ﺑﺘﻮﺍﻧﻴﻢ ‪ .‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻣﻌﻠﻮﻣﺎﺕ ﺯﻳﺎﺩﻯ ﺭﺍ ﺩﺭﻣﻮﺭﺩ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ ﺑﺮﺍﻯ ﻣﺎ‬
‫ﺍﺭﺍﻳﻪ ﻣﻴﻜﻨﺪ ﻭ ﻣﻮﻗﻌﻴﺖ ﺍﺗﻮﻡ ﻫﺎﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺑﺮﺍﻯ ﻣﺎ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪.‬‬
‫ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻋﻼﻭﻩ ﺍﺯ ﻧﻮﻉ ‪ ،‬ﺗﻌﺪﺍﺩ ﺍﺗﻮﻣﻬﺎﻯ ﻫﺮ ﻋﻨﺼﺮ‪ ،‬ﺷﻴﻮﺓ ﺍﺗﺼﺎﻝ ﺍﺗﻮﻡ ﻫﺎ ﺭﺍ ﺑﺎﻳﻚ ﺩﻳﮕﺮ ﻧﻴﺰ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪.‬‬
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 ‫ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺗﺠﺮﺑﻰ ‪ ،‬ﻣﺎﻟﻴﻜﻮﻟﻰ ﻭﺳﺎﺧﺘﻤﺎﻧﻰ ﺩﻭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺮﻳﻚ ﻣﺮﻛﺐ ﺍﻳﺘﺎﻳﻞ ﺍﻟﻜﻮﻝ ﻭ ﺩﺍﻯ ﻣﻴﺘﺎﻳﻞ ﺍﻳﺘﺮ‬
‫ﺭﺍﻛﻪ ﺩﺭ ﺟﺪﻭﻝ ) ‪ ( 2 - 2‬ﺩﺭﺝ ﺍﺳﺖ ‪ ،‬ﺑﺎﻫﻢ ﻣﻘﺎﻳﺴﻪ ﻧﻤﺎﻳﻴﺪ ‪ .‬ﻧﻮﻉ ﻭﺗﻌﺪﺍﺩ ﺍﺗﻮﻣﻬﺎﺩﺭ ﻫﺮﺩﻭ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﻣﺮﻛﺒﺎﺕ ﻳﻜﺴﺎﻥ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻃﺮﺯ ﺭﻭﺍﺑﻂ ﺍﺗﻮﻣﻬﺎ ﻭ ﺳﺎﺧﺘﻤﺎﻥ ﺁﻧﻬﺎ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺭﺩ ‪ .‬ﻫﻤﻴﻦ ﻓﺮﻕ ﻛﻮﭼﻚ‬
‫ﺳﺎﺧﺘﻤﺎﻧﻰ ﺑﺎﻋﺚ ﺗﻔﺎﻭﺕ ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺁﻧﻬﺎ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ‪.‬ﺩﺍﻯ ﻣﻴﺘﺎﻳﻞ ﺍﻳﺘﺮ ﮔﺎﺯﻯ ﺍﺳﺖ ﻛﻪ ﺩﺭ‬
‫ﻳﺨﭽﺎﻝ ﻫﺎ ﺑﻪ ﻛﺎﺭﻓﺘﻪ ﻭﻣﺎﺩﺓ ﺑﻰ ﻫﻮﺵ ﻛﻨﻨﺪﻩ ﻣﻴﺒﺎﺷﺪ؛ ﺍﻣﺎ ﺍﻳﺘﺎﻧﻮﻝ ﻣﺎﻳﻌﻰ ﺍﺳﺖ ﻛﻪ ﺑﻪ ﺣﻴﺚ ﻣﺤﻠﻞ ﻣﻮﺍﺩ‬
‫ﻋﻀﻮﻯ ﺩﺭ ﺻﻨﻌﺖ ﺍﺯ ﺁﻥ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﮕﺮﺩﺩ ﻭﻳﻚ ﻣﺎﺩﺓ ﻳﻰ ﻧﺸﻪ ﺁﻭﺭ ﺑﻮﺩﻩ ‪ ،‬ﺑﻪ ﺍﻧﺴﺎﻥ ﺑﻰ ﺧﻮﺩﻯ ﺭﺍ ﺑﺎﺭ ﻣﻰ‬
‫ﺁﻭﺭﺩ ‪ .‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻧﻬﺎ ﻣﺎﻧﻨﺪ ﺳﺎﺧﺘﻤﺎﻥ ﻫﺎﻯ ﻟﻴﻮﻳﺲ ﺍﺳﺖ ﻭﻳﻚ ﺧﻂ ﻛﻮﺗﺎﻩ ﻧﻤﺎﻳﺎﻧﮕﺮ ﻳﻚ‬
‫ﺭﺍﺑﻄﺔ ﺳﺎﺩﻩ ﻣﻴﺒﺎﺷﺪ ﻛﻪ ﺗﺼﻮﺭ ﻳﻚ ‪،‬ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﺩﺭ ﺍﻧﺠﺎﻡ ﻫﺎﻯ ﺍﻳﻦ ﺧﻂ ﻣﺘﺼﻮﺭ ﺍﺳﺖ ‪.‬‬
‫ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﺗﺮﻛﻴﺐ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻓﺮﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺷﺎﻥ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺍﻳﺰﻭﻣﻴﺮ ﻳﻚ‬
‫ﺩﻳﮕﺮ ﻳﺎﺩ ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫ﺟﺪﻭﻝ )‪ :( 2-2‬ﻣﻘﺎﻳﺴﺔ ﺧﻮﺍﺹ ﺍﻳﺘﺎﻧﻮﻝ ﻭ ﺩﺍﻯ ﻣﻴﺘﺎﻳﻞ ﺍﻳﺘﺮ‬
‫ﻧﻘﻄﺔ ﻏﻠﻴﺎﻥ ﻛﺜﺎﻓﺖ‬ ‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ‬ ‫ﻓﻮﺭﻣﻮﻝ‬ ‫ﻣﺮﻛﺐ‬
‫ﺳﺎﺩﻩ‬
‫‪78o C‬‬ ‫ﺍﻳﺘﺎﻧﻮﻝ‬
‫‪H H‬‬ ‫‪C H O‬‬
‫‪0.816g/cm 3‬‬ ‫| |‬ ‫‪C H O‬‬
‫‪2 6‬‬
‫‪H − C− C− O − H‬‬ ‫‪2 6‬‬
‫| |‬
‫‪H H‬‬
‫‪0.661g/cm 3 − 24.5o C‬‬ ‫ﺩﺍﻯ ﻣﻴﺘﺎﻳﻞ‬
‫‪H‬‬ ‫‪H‬‬ ‫‪C H O‬‬ ‫‪C H O‬‬
‫|‬ ‫|‬ ‫‪2 6‬‬ ‫‪2 6‬‬
‫‪H − C− O − C− H‬‬
‫|‬ ‫|‬ ‫ﺍﻳﺘﺮ‬
‫‪H‬‬ ‫‪H‬‬
‫‪ : 3 – 2‬ﻃﺮﺯ ﻧﻮﺷﺘﻦ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ‬
‫ﭼﻄﻮﺭ ﻣﻴﺘﻮﺍﻥ ﺍﺷﻜﺎﻝ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺭﺍ ﭘﻴﺸﺒﻴﻨﻰ ﻛﺮﺩ ﻭﺁﻥ ﺭﺍ ﻧﻮﺷﺖ ؟‬
‫ﺗﺎﺣﺎﻝ ﻣﻄﺎﻟﺐ ﺯﻳﺎﺩﻯ ﺭﺍ ﺩﺭﻣﻮﺭﺩ ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺁﻣﻮﺧﺘﻴﺪ ؛ ﺍﻣﺎ ﺟﻬﺖ ﮔﻴﺮﻯ ﺳﻪ ﺑﻌﺪﻯ ﻳﺎ ﺳﺎﺧﺘﻤﺎﻥ‬
‫ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺭﺍ ﻣﻄﺎﻟﻌﻪ ﻧﻪ ﻛﺮﺩﻩ ﺍﻳﺪ ‪ .‬ﺍﺷﻜﺎﻝ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﻋﺎﻣﻞ ﺑﺴﻴﺎﺭ ﻣﻬﻤﻰ ﺩﺭ ﺗﻌﻴﻴﻦ ﺧﻮﺍﺹ‬
‫ﻛﻴﻤﻴﺎﻭﻯ ﺁﻧﻬﺎ ﺍﺳﺖ ‪.‬ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﺳﺎﺩﻩ ﺩﺍﺭﺍﻯ ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﺳﺎﺩﻩ ﺍﻧﺪ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﺩﻭ ﺍﺗﻮﻣﻰ ﻣﺎﻧﻨﺪ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺩﺍﺭﺍﻯ ﻳﻚ ﺷﻜﻞ ﺳﺎﺩﻩ ﺑﻮﺩﻩ ﻛﻪ ﻗﺮﺍﺭ ﺫﻳﻞ ﻧﻤﺎﻳﺶ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ ؛ ﺍﻣﺎ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ‬
‫ﻛﻪ ﺑﻴﺸﺘﺮ ﺍﺯ ﺩﻭﺍﺗﻮﻡ ﺭﺍ ﺩﺍﺭﻧﺪ ‪ ،‬ﺩﺍﺭﺍﻯ ﺍﺷﻜﺎﻝ ﻫﻨﺪﺳﻰ ﻣﻐﻠﻖ ﺑﻮﺩﻩ ﻭ ﺑﺎﻳﺪ ﻣﻌﻠﻮﻣﺎﺕ ﺯﻳﺎﺩﻯ ﺭﺍ ﺍﺭﺍﺋﻪ ﮔﺮﺩﺩ ‪.:‬‬
‫ﺷﻜﻞ )‪ ( 2-2‬ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﺩﻭ ﺍﺗﻮﻣﻰ ﻣﺎﻧﻨﺪ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ﺑﻪ ﺻﻮﺭﺕ ﻋﻤﻮﻡ ﺑﻴﻦ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻳﻚ ﻣﺮﻛﺐ ﻭ ﺷﻜﻞ ﻫﻨﺪﺳـﻰ ﺁﻥ ﺭﺍﺑﻄﺔ ﺭﻭﺷـــــﻦ ﻣﻮﺟﻮﺩ ﻧﻴﺴﺖ ؛‬
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‫ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪ :‬ﺩﻭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺒﺎﺕ ﻫﺮ ﻳﻚ ﻛﺎﺭﺑﻦ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ ) ‪ (CO 2‬ﻭ ﺳﻠﻔﺮﺩﺍﻯ ﻛﺴﺎﻳﺪ ) ‪ (SO 2‬ﺭﺍ ﺩﺭ‬
‫ﻧﻈﺮ ﻣﻴﮕﻴﺮﻳﻢ ‪ ،‬ﺩﺭ ﻫﺮ ﺩﻭ ﻣﺮﻛﺐ ﺳﻪ ﺍﺗﻮﻡ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﺩﻭ ﺍﺗﻮﻡ ﺁﻥ ﺁﻛﺴﻴﺠﻦ ﺍﺳﺖ ؛ ﺍﻣﺎ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ‬
‫ﺍﻳﻦ ﺩﻭ ﻣﺮﻛﺐ ﺩﺍﺭﺍﻯ ﺍﺷﻜﺎﻝ ﻣﺨﺘﻠﻒ ﻫﻨﺪﺳﻰ ﺍﻧﺪ ‪ ،‬ﻣﺎﻟﻴﻜﻮﻝ ‪ CO 2‬ﺧﻄﻰ ﻭﻣﺎﻟﻴﻜﻮﻝ ‪ SO 2‬ﺧﻤﻴﺪﻩ ﺍﺳﺖ‬
‫ﭼﺮﺍ ؟ ﺟﻮﺍﺏ ﺍﻳﻦ ﺳﺆﺍﻝ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺩﺭ ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻭﻻﻧﺴﻰ‪،‬ﺧﺎﺻﺘﺎ" ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺁﺯﺍﺩ ﺍﺗﻮﻡ‬
‫ﻫﺎﻯ ﺁﻧﻬﺎ ﺟﺴﺘﺠﻮﻛﺮﺩ ‪:‬‬
‫ﺷﻜﻞ )‪ : ( 3 - 2‬ﻣﻮﺩﻝ ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻝ ﻛﺎﺭﺑﻦ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ ﻭ ﺳﻠﻔﺮ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ‬
‫ﻳﻜﻰ ﺍﺯ ﻧﻈﺮﻳﺎﺗﻰ ﻛﻪ ﺑﺮﺍﻯ ﭘﻴﺸﺒﻴﻨﻰ ﺍﺷﻜﺎﻝ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺍﺭﺍﺋﻪ ﺷﺪﻩ ﺍﺳﺖ ‪ ،‬ﻋﺒﺎﺭﺕ ﺍﺯ ﻧﻈﺮﻳﺔ ﻗﻮﺓ‬
‫ﺩﺍﻓﻌﺔ ﺟﻔﺖ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻗـــﺸﺮﻭﻻﻧـــــﺴﻰ )‪(Vaoleance shell Electronpairs Repulsion‬‬
‫ﺍﺳـــــﺖ ﻛﻪ ﺑﻪ )‪ (VSEPR‬ﺍﺭﺍﺋﻪ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﻣﻄﺎﺑﻖ ﺑﻪ ﺍﻳﻦ ﻧﻈﺮﻳﻪ ‪ ،‬ﻗﻮﻩ ﻫﺎﻯ ﺩﺍﻓﻌﺔ ﺍﻟﻜﺘﺮﻭﺳﺘﺎﺗﻴﻜﻰ ﻣﻮﺟﻮﺩ‬
‫ﺑﻴﻦ ﺟﻔﺖ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ ﻭﻳﺎ ﻧﺎﺭﺍﺑﻄﻪ ﻳﻰ ﺩﺭ ﻳﻚ ﻣﺎﻟﻴﻜﻮﻝ ﺳﺒﺐ ﻣﻴﺸﻮﺩ ﺗﺎ ﺍﻳﻦ ﺍﻟﻜﺘﺮﻭﻧﻬﺎ ﺣﺪ ﺍﻣﻜﺎﻥ‬
‫ﺍﺯ ﻫﻢ ﻓﺎﺻﻠﻪ ﮔﺮﻓﺘﻪ ﻭ ﺟﻬﺖ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ ﻭﺍﻳﻦ ﺟﻬﺖ ﮔﻴﺮﻯ ﺟﻔﺖ ﺍﻟﻜﺘﺮﻭﻧﻬﺎ ﻃــــﻮﺭﻯ ﺍﺳــﺖ ﻛﻪ ﭘﺎﻳﺪﺍﺭ‬
‫ﺗﺮﻳﻦ ﺳﺎﺧﺘﻤﺎﻥ ﻫﻨﺪﺳﻰ ﺭﺍ ﺑﻪ ﻣﺎﻟﻴﻜﻮﻝ ﻓﺮﺍﻫﻢ ﻣﻴﻜﻨﺪ ‪ .‬ﺳﺎﺧﺘﻤﺎﻥ ﺧﺎﺻﻰ ﺍﺯ ﺍﺗﻮﻡ ﻫﺎ ﻛﻪ ﺑﺎﻋﺚ ﻣﻴﺸﻮﺩ ﺗﺎﺑﻴﻦ‬
‫ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﻫﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ ﻭﻏﻴﺮ ﺭﺍﺑﻄﻪ ﻳﻰ ﻣﺎﻟﻴﻜﻮﻟﻬﺎ ﻛﻤﺘﺮﻳﻦ ﺩﻓﻌﻪ ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ‬
‫ﻳﺎﺩ ﻣﻴﺸﻮﺩﻭ ﻋﺒﺎﺭﺕ ﺍﺯ ﺳﺎﺣﺔ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ ﺍﺳﺖ ﻛﻪ ﺍﻟﻜﺘﺮﻭﻧﻬﺎ ﺻﺮﻑ ﻧﻈﺮ ﺍﺯ ﺗﻌﺪﺍﺩ ﺩﺭﺁﻧﺠﺎ ﻣﻮﺟﻮﺩ‬
‫ﺑﺎﺷﺪ ‪ .‬ﺑﻪ ﺍﺳﺎﺱ ﺍﻳﻦ ﺗﻌﺮﻳﻒ ﺭﺍﺑﻄﻪ ﻫﺎﻯ ﻳﮕﺎﻧﻪ ‪،‬ﺩﻭﮔﺎﻧﻪ ﻭﺳﻪ ﮔﺎﻧﻪ ﻳﻚ ﺳﺎﺣﻪ ﺑﻪ ﺷﻤﺎﺭ ﻣﻴﺮﻭﺩ ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺑﺮﺍﻯ ﻧﺸﺎﻥ ﺩﺍﺩﻥ ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﻣﻴﺘﻮﺍﻥ ﺍﺯ ﭘﻮﻗﺎﻧﻪ ﻫﺎﻯ ﺑﺎﺩ ﺩﺍﺭ ﺍﺳﺘﻔﺎﺩﻩ ﻛﺮﺩ ‪ .‬ﭼﻨﺪﻳﻦ ﭘﻮﻗﺎﻧﻪ‬
‫ﺭﺍ ﺗﻬﻴﻪ ﻭﺗﺠﺎﺭﺏ ﺯﻳﺮ ﺭﺍ ﺍﻧﺠﺎﻡ ﺩﻫﻴﺪ ‪:‬‬
‫‪ - 1‬ﺍﺑﺘﺪﺍ ﺩﻭ ﭘﻮﻗﺎﻧﺔ ﻛﻮﭼﻚ ﺭﺍ ﺑﻪ ﻋﻴﻦ ﺍﻧﺪﺍﺯﻩ ﺑﺎﺩ ﭘﺮ ﻧﻤﺎﻳﻴﺪ ‪ ،‬ﺳﭙﺲ ﺑﺎ ﺍﺳﺘﻔﺎﺩﻩ ﺍﺯ ﻧﺦ ﺳﺮ ﭘﻮﻗﺎﻧﻪ ﻫﺎ ﺭﺍﺑﺎ‬
‫ﻫﻢ ﺩﻳﮕﺮ ﻃﻮﺭﻯ ﺑﺴﺘﻪ ﻛﻨﻴﺪ ﻛﻪ ﺑﺎﻫﻢ ﻧﺰﺩﻳﻚ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﺁﺯﺍﺩ ﺑﺎﺷﻨﺪ ‪ .‬ﭘﻮﻗﺎﻧﻪ ﻫﺎ ﺭﺍ ﺭﻭﻯ ﭘﺎﺭﭼﺔ ﺍﺑﺮﻳﺸﻤﻰ‬
‫ﻣﺎﻟﺸﺪﺍﺩﻩ ﺗﺎ ﭼﺎﺭﺝ ﺑﺮﻗﻰ ﺣﺎﺻﻞ ﻧﻤﺎﻳﻨﺪ ؛ ﺳﭙﺲ ﺁﻧﻬﺎ ﺭﺍ ﺭﻭﻯ ﻣﻴﺰ ﺭﻫﺎ ﻧﻤﺎﻳﻴﺪ ﺗﺎﺣﺎﻟﺖ ﺛﺎﺑﺖ ﺭﺍ ﺑﻪ ﺧﻮﺩ ﺍﺧﺘﻴﺎﺭ‬
‫ﻛﻨﻨﺪ ‪ ،‬ﭘﻮﻗﺎﻧﻪ ﻫﺎ ﻛﺪﺍﻡ ﻳﻚ ﺍﺯ ﺣﺎﻟﺖ ﻫﺎﻯ ﺯﻳﺮ ﺭﺍ ﺑﻪ ﺧﻮﺩ ﺍﺧﺘﻴﺎﺭ ﺧﻮﺍﻫﺪ ﻛﺮﺩ؟‬
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 ‫ﺷﻜﻞ )‪(4 - 2‬‬
‫‪ – 2‬ﺍﮔﺮ ﺩﺭ ﺁﺯﻣﺎﻳﺶ ﻓﻮﻕ ﺳﻪ ﭘﻮﻗﺎﻧﻪ ﺭﺍ ﺑﻪ ﻛﺎﺭ ﺑﺒﺮﻳﺪ ‪ ،‬ﻛﺪﺍﻡ ﺳﺎﺧﺘﻤﺎﻥ ﺯﻳﺮ ﺑﻪ ﺁﻧﻬﺎ ﻣﻨﺎﺳﺐ ﺧﻮﺍﻫﺪ ﺑﻮﺩ ؟‬
‫ﺷﻜﻞ )‪( 5 – 2‬‬
‫‪ - 3‬ﺍﮔﺮ ﺩﺭ ﺁﺯﻣﺎﻳﺶ ﻓﻮﻕ ﭼﻬﺎﺭ ﭘﻮﻗﺎﻧﻪ ﺭﺍ ﺑﻪ ﻛﺎﺭ ﺑﺒﺮﻳﺪ ‪ ،‬ﻛﺪﺍﻡ ﺳﺎﺧﺘﻤﺎﻥ ﺯﻳﺮ ﺑﻪ ﺁﻧﻬﺎ ﻣﻨﺎﺳﺐ ﺧﻮﺍﻫﺪ ﺑﻮﺩ ؟‬
‫ﺷﻜﻞ )‪( 6 - 2‬‬
‫ﭼﻄﻮﺭ ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺑﻪ ﺍﺳﺎﺱ ﺳﺎﺧﺘﺎﺭ ﻟﻴﻮﻳﺲ ﺁﻧﻬﺎ ﺗﻌﻴﻴﻦ ﻣﻴﮕﺮﺩﻧﺪ ؟‬
‫ﺑﺮﺍﻯ ﺍﻳﻦ ﻣﻘﺼﺪ ﻃﺒﻖ ﺷﻴﻮﻫﺎﻯ ﺯﻳﺮ ﻋﻤﻞ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫‪ – 1‬ﺳﺎﺧﺘﺎﺭ ﻟﻴﻮﻳﺲ ﻣﺎﻟﻴﻜﻮﻝ ﺭﺳﻢ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫‪ – 2‬ﺗﻌﺪﺍﺩ ﺳﺎﺣﻪ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺩﺭ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ ﻣﻌﻴﻴﻦ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫‪– 3‬ﺳﺎﺧﺘﻤﺎﻥ ﻫﻨﺪﺳﻰ ﻣﻨﺎﺳﺐ ﺭﺍ ﺑﺮ ﺍﺳﺎﺱ ﺗﻌﺪﺍﺩ ﺳﺎﺣﻪ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻣﺸﺨﺺ ﺳﺎﺯﻳﺪ ‪.‬‬
‫ﺯﺍﻭﻳﺔ ﺭﺍﻛﻪ ﺳﻪ ﺍﺗﻮﻡ ﻣﺮﺗﺒﻂ ﺷﺪﻩ ﺑﺎﻫﻢ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺯﺍﻭﻳﺔ ﺭﺍﺑﻄﻪ ﻳﻰ ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪ ﻛﻪ ﺣﺪ ﺍﻛﺜﺮ‬
‫ﺍﻳﻦ ‪ 180 o‬ﺯﺍﻭﻳﻪ ﺍﺳﺖ ‪.‬‬
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 ‫ﺩﻭ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ )ﺳﺎﺧﺘﺎﺭ ﺧﻄﻰ(‬
‫ﻣﺎﻟﻴﻜﻮﻝ ‪ CO 2‬ﺭﺍﻛﻪ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺍﺳﺖ ‪ ،‬ﺩﺭ ﻧﻈﺮ ﻣﻴﮕﻴﺮﻳﻢ ‪:‬‬
‫‪..‬‬ ‫‪..‬‬
‫‪:O = C = O :‬‬
‫ﺩﺭ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ ﺩﻭﺳﺎﺣﺔﺍﻟﻜﺘﺮﻭﻧﻰ )ﭼﭗ ﻭﺭﺍﺳﺖ ( ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪.‬‬
‫ﺗﻨﻬﺎ ﺟﻬﺖ ﮔﻴﺮﻯ ﻣﻤﻜﻨﻪ ﻛﻪ ﻣﻴﺘﻮﺍﻧﺪ ﺩﻭ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍ ﺗﺎ ﺣﺪ ﺍﻣﻜﺎﻥ ﺩﻭﺭ ﺍﺯ ﻳﻚ‬
‫ﺩﻳﮕﺮ ﻗﺮﺍﺭ ﺩﻫﺪ ‪ ،‬ﻋﺒﺎﺭﺕ ﺍﺯ ﺳﺎﺧﺘﻤﺎﻥ ﺧﻄﻰ ﻣﻴﺒﺎﺷﺪ ‪.‬ﺷﻜﻞ ﺯﻳﺮ ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫ﺷﻜﻞ )‪ ( 7 - 2‬ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻝ ﺧﻄﻰ‬
‫ﻣﻄﺎﺑﻖ ﺑﻪ ﻧﻈﺮﻳﺔ )‪ (VSEPR‬ﻣﺎﻟﻴﻜﻮﻟﻰ ﻛﻪ ﺩﺍﺭﺍﻯ ﺩﻭﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺩﺭ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ‬
‫‪o‬‬
‫ﺍﻧﺪ ‪ ،‬ﻃﻮﺭﻯ ﻛﻪ ﺩﺭ ﻛﺎﺭﺑﻦ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ ﺩﻳﺪﻩ ﻣﻴﺸﻮﺩ ‪ ،‬ﺳﺎﺧﺘﻤﺎﻥ ﺧﻄﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ ﻭ ﺯﺍﻭﻳﺔ ﻭﻻﻧﺴﻰ ‪18 0‬‬
‫ﺍﺳﺖ ‪.‬‬
‫ﺳﻪ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ )ﺳﺎﺧﺘﺎﺭ ﺳﻪ ﺿﻠﻌﻰ ﻳﺎ ﻣﺴﻄﺢ (‬
‫ﺩﺭ ﺍﻳﻦ ﻣﻮﺭﺩ ﺳﺎﺧﺘﻤﺎﻥ ﺳﻠﻔﺮ ﺗﺮﺍﻯ ﺍﻛﺴﺎﻳﺪ ) ‪ (SO‬ﺭﺍ ﻣﻼﺣﻈﻪ ﻣﻴﻨﻤﺎﻳﻴﻢ ‪:‬‬
‫‪.. 3‬‬
‫‪:O:‬‬
‫‪..‬‬ ‫‪| ..‬‬
‫‪:O = S −O:‬‬
‫‪..‬‬
‫ﺩﺭ ‪ SO 3‬ﺳﺎﺣﺔ ﺳﻪ ﺑﻌﺪﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺩﺭ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ )‪ (S‬ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪ .‬ﺳﺎﺧﺘﻤﺎﻥ ﻫﻨﺪﺳﻰ ﺍﻳﻦ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﻛﻪ ﺳﻪ ﺿﻠﻌﻰ ﻳﺎ ﺢ‬
‫ﻣﺴﻄﺢ ﺍﺳﺖ ﻗﺮﺍﺭ ﺫﻳﻞ ﻣﻴﺒﺎﺷﺪ ‪:‬‬
‫ﺷﻜﻞ )‪ ( 8 - 2‬ﺳﺎﺧﺘﻤﺎﻥ ﻣﺴﻄﺢ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﻣﺎﻧﻨﺪ ‪ ، SO 3‬ﺯﻣﺎﻧﻰ ﻛﻪ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ ﺗﻮﺳﻂ ﺳﻪ ﺍﺗﻮﻡ ﺩﻳﮕﺮ ﺍﺣﺎﻃﻪ ﺷﺪﻩ ﺑﺎﺷﺪﻭﺟﻮﺭﻩ‬
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‫ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺩﺭ ﺁﻥ ﻧﻮﻉ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ ﺑﺎﺷﺪ ‪ ،‬ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺴﻄﺢ ﺑﻮﺩﻩ ﻭﺯﺍﻭﻳﺔ ﻭﻻﻧﺴﻰ ﺁﻥ‬
‫‪ 120‬ﺩﺭﺟﻪ ﺍﺳﺖ ‪.‬‬
‫ﭼﻬﺎﺭ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ )ﺳﺎﺧﺘﺎﺭ ﭼﻬﺎﺭ ﻭﺟﻬﻰ (‬
‫ﻭﺿﻴﻌﺖ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﻛﻪ ﭼﻬﺎﺭ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ‪ ،‬ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻝ ﺁﻧﻬﺎ ﻛﻤﻰ ﭘﻴﭽﻴﺪﻩ ﺍﺳﺖ‬
‫ﻛﻪ ﻣﺜﺎﻝ ﺁﻥ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﻣﻴﺘﺎﻥ ‪ CH 4‬ﺍﺭﺍﺋﻪ ﻛﺮﺩ ؛ ﺯﻳﺮﺍ ﺑﻪ ﻋﻮﺽ ﻳﻚ ﺷﻜﻞ ﻣﺴﻄﺢ ﻛﻪ ﺩﺭ ﺻﻔﺤﺔ ﻛﺎﻏﺬ‬
‫ﻧﻤﺎﻳﺶ ﺩﺍﺩﻩ ﻣﻴﺸﻮﺩ ؛ ﺩﺍﺭﺍﻯ ﻳﻚ ﺷﻜﻞ ﺳﻪ ﺑﻌﺪﻯ ﻣﻮﺳﻮﻡ ﺑﻪ ﭼﻬﺎﺭ ﻭﺟﻬﻰ ﺍﺳﺖ ‪ .‬ﭼﻨﺪ ﻃﺮﻳﻘﺔ ﻧﻤﺎﻳﺶ‬
‫ﻣﺨﺘﻠﻒ ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻥ ﺩﺭ ﺷـــﻜﻞ )‪ (9 – 2‬ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ ‪.‬ﺍ ﺷﻜﺎﻝ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﺻﻮﺭﺕ ﺳﻪ ﭘﺎﻳﻪ‬
‫ﺩﺭﻧﻈﺮﮔﺮﻓﺖ ﻛﻪ ﭘﺎﻳﺔ ﭼﻬﺎﺭﻣﻰ ﺁﻥ ﺑﻪ ﺳﻤﺖ ﺑﺎﻻ ﺑﺮﺁﻥ ﺍﺳﺘﻮﺍﺭ ﺍﺳﺖ ‪ .‬ﺩﺭﺍﻳﻦ ﻧﻮﻉ ﺳﺎﺧﺘﻤﺎﻥ ﺟﻮﺭﻩ ﻫﺎﻯ‬
‫ﺯﺍﻭﻳﺔ ‪ 109.5o‬ﺍﺳﺖ ‪.‬‬
‫ﺩﻳﮕﺮﺮ ﺯ ﻭﻳ‬
‫ﺑﺎﻳﻚ ﻳ‬
‫ﻰ ﺑﻳ‬
‫ﺍﻟﻜﺘﺮﻭﻧﻰ‬
‫ﺮﻭ‬
‫ﺷﻜﻞ )‪ ( 9 - 2‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﻴﺘﺎﻥ‬
‫‪ – 4‬ﺩﺭ ﺻﻮﺭﺕ ﻣﻮﺟﻮﺩﻳﺖ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻏﻴﺮ ﺭﺍﺑﻄﻪ ﻳﻰ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ‪ ،‬ﺯﻭﺍﻳﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ ﺭﺍ‬
‫ﻃﻮﺭﻯ ﺗﻨﻈﻴﻢ ﻛﻨﻴﺪﻛﻪ ﺑﺮﺍﻯ ﺳﺎﺣﻪ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻣﺮﺑﻮﻁ ﺑﻪ ﺟﻮﺭﻩ ﻫﺎﻯ ﻏﻴﺮ ﺭﺍﺑﻄﻪ ﻳﻰ ﻓﻀﺎﻯ ﺑﺰﺭﮔﺘﺮﻯ ﺑﺎﺯ‬
‫‪SO‬‬
‫ﮔﺮﺩﺩ ‪ .‬ﺍﺗﻮﻡ ﺳﻠﻔﺮ ﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ‪ 2‬ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫‪..‬‬
‫‪S‬‬
‫‪: :‬‬
‫‪:O :‬‬ ‫‪O‬‬
‫ﺑﻪ ﺍﻃﺮﺍﻑ ﺍﻳﻦ ﺍﺗﻮﻡ ﺳﻪ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺳﺎﺧﺘﺎﺭ ﺁﻥ ﺑﻪ ﮔﺮﻭپ ﺳﻪ ﺿﻠﻌﻰ‬
‫ﻣﺴﻄﺢ ﻣﺮﺑﻮﻁ ﺍﺳﺖ ‪ .‬ﺩﺭ ﺍﻳﻦ ﺳﺎﺧﺘﻤﺎﻥ ﺳﺎﺣﻪ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺑﺎ ﻫﻢ ﺯﺍﻭﻳﺔ ‪ 120‬ﺩﺭﺟﻪ ﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ؛ ﺍﻣﺎﻳﻚ‬
‫ﺟﻮﺭﺓ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻏﻴﺮ ﺭﺍﺑﻄﻮﻯ ﺩﺭ ﻣﻘﺎﻳﺴﻪ ﺑﺎ ﻳﻚ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﺭﺍﺑﻄﻪ ﻳﻰ ﻓﻀﺎﻯ ﺯﻳﺎﺩ ﺭﺍ ﺍﺷﻐﺎﻝ ﻣﻴﻨﻤﺎﻳﺪ ؛‬
‫ﺯﻳﺮﺍ ﺟﻮﺭﻩ ﺍﻟﻜــﺘﺮﻭﻧﻬﺎﻯ ﻏﻴﺮﺭﺍﺑﻄﻮﻯ ﺗﺤﺖ ﺗﺄﺛﻴﺮ ﻳﻚ ﻫﺴﺘﻪ ﺑﻮﺩﻩ ﻭ ﺩﺭ ﺣﺎﻟﻰ ﻛﻪ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺭﺍﺑﻄﻪ‬
‫ﻳﻰ ﺗﺤﺖ ﺗﺄﺛﻴﺮ ﺩﻭﻫﺴﺘﻪ ﻗﺮﺍﺭ ﺩﺍﺭﻧﺪ ‪ .‬ﻗﻮﺓ ﺩﺍﻓﻌﻪ ﺑﻴﻦ ﺟﻮﺭﻩ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﻏﻴﺮ ﺭﺍﺑﻄﻪ ﻳﻰ – ﺭﺍﺑﻄﻪ ﻳﻰ ﻛﻤﻰ‬
‫ﺑﻴﺸﺘﺮ ﺍﺯ ﻗﻮﺓ ﺩﺍﻓﻌﺔ ﺑﻴﻦ ﺟﻮﺭﻩ ﺍﻟﻜــﺘﺮﻭﻧﻬﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ – ﺭﺍﺑﻄﻪ ﻳﻰ ﺍﺳﺖ ‪.‬ﺩﺭ ﺍﺛﺮ ﺍﻳﻦ ﻗﻮﺓ ﺩﻓﻊ ﺑﻴﺸﺘﺮ ‪ ،‬ﺟﻮﺭﻩ‬
‫‪SO‬‬
‫‪2‬‬
‫ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ ﻛﻤﻰ ﺍﺯ ﻫﻤﺪﻳﮕﺮ ﺩﻭﺭ ﺷﺪﻩ ‪ ،‬ﺍﺯ ﺍﻳﻦ ﺳﺒﺐ ﺍﺳﺖ ﻛﻪ ﺯﺍﻭﻳﺔ ﺭﺍﺑﻄﻪ ﻳﻰ ﻣﺎﻟﻴﻜﻮﻝ‬
‫‪27‬‬
‫ﻛﻪ ﺑﺎﻳﺪ ‪ 120‬ﺩﺭﺟﻪ ﺑﺎﺷﺪ ‪ ،‬ﺑﻪ ‪ 119.5‬ﺩﺭﺟﻪ ﺗﻘﻠﻴﻞ ﻧﻤﻮﺩﻩ ﺍﺳﺖ ‪ .‬ﺩﺭ ﻣﻮﺭﺩ ‪ SO 2‬ﺑﺎﻳﺪ ﮔﻔﺖ ﻛﻪ ﺩﺭ ﺁﻥ‬
‫ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻭﺳﻪ ﮔﺎﻧﻪ ﻧﻴﺰ ﺑﻪ ﻫﻤﻴﻦ ﺗﺮﺗﻴﺐ ﺑﻮﺩﻩ ؛ ﺯﻳﺮﺍ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺁﻧﻬﺎ ﻧﺴﺒﺖ ﺑﻪ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ‬
‫ﺭﺍﺑﻄﺔ ﻳﮕﺎﻧﻪ ﺑﻪ ﻓﻀﺎﻯ ﺑﻴﺸﺘﺮ ﻧﻴﺎﺯ ﺩﺍﺭﺩ ‪ .‬ﺍﺷﻜﺎﻝ ﺫﻳﻞ ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺍﻳﺘﻴﻠﻴﻦ ﻭ ﺍﺳﺘﻴﻠﻴﻦ ﺭﺍ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪﻛﻪ‬
‫ﺑﻴﻦ ﺩﻭﻛﺎﺭﺑﻦ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺷﺎﻥ ﺑﻪ ﺗﺮﺗﻴﺐ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻭﺳﻪ ﮔﺎﻧﻪ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪:‬‬
‫ﺷﻜﻞ )‪ ( 10 - 2‬ﺳﺎﺧﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﻴﻠﻴﻦ‬
‫ﺷﻜﻞ )‪ : ( 11– 2‬ﻓﻮﺭﻣﻮﻝ ﻭﺳﺎﺧﺘﻤﺎﻥ ﺧﻄﻰ ﻣﺎﻟﻴﻜﻮﻝ ﺍﺳﻴﺘﻴﻠﻴﻦ‬
‫ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺑﻌﻀﻰ ﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﺟﺪﻭﻝ ﺯﻳﺮ ﺗﺤﺮﻳﺮ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ‪:‬‬
‫ﺟﺪﻭﻝ )‪ ( 3 - 2‬ﻧﺎﻡ ﻭﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺑﻌﻀﻰ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﻧﺎﻡ ﺍﻟﻜﺎﻥ‬ ‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‬ ‫ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ‬
‫ﭘﺮﻭﭘﺎﻥ‬ ‫‪C H‬‬
‫‪3 8‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H − C| − C| − C| − H‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﺑﻴﻮﺗﺎﻥ‬ ‫‪C H‬‬
‫‪4 10‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H H‬‬
‫|‬ ‫|‬
‫‪H − C| − C| − C| − C| − H‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H H‬‬
‫‪28‬‬
 ‫ﭘﻨﺘﺎﻥ‬ ‫‪C H‬‬
‫‪5 12‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H − C| − C| − C| − C| − C| − H‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﻫﮕﺰﺍﻥ‬ ‫‪C H‬‬
‫‪6 14‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H − C| − C| − C| − C| − C| − C| − H‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﻫﭙﺘﺎﻥ‬ ‫‪C H‬‬
‫‪7 16‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H − C− C− C − C− C− C− C| − H‬‬
‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﺍﻭﻛﺘﺎﻥ‬ ‫‪C H‬‬
‫‪8 18‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H − C− C− C − C− C− C− C− C| − H‬‬
‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﻧﻮﻧﺎﻥ‬ ‫‪C H‬‬
‫‪9 20‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H − C− C− C − C− C− C− C− C− C| − H‬‬
‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﺩﻳﻜﺎﻥ‬ ‫‪C H‬‬
‫‪10 22‬‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H‬‬
‫|‬
‫‪H − C− C− C − C− C− C− C− C− C − C| − H‬‬
‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﺍﮔﺮ ﺑﻪ ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﺎﻧﻬﺎﻯ ﺟﺪﻭﻝ ﻓﻮﻕ ﺗﻮﺟﻪ ﺷﻮﺩ ‪ ،‬ﺩﻳﺪﻩ ﻣﻴﺸﻮﺩﻛﻪ ﺍﻳﻨﻬﺎ ﺑﻪ ﺍﻧﺪﺍﺯﺓ ﻳﻚ ﮔﺮﻭپ ﻣﺘﻠﻴﻦ‬
‫)‪ (−CH 2 −‬ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺭﻧﺪ ‪ .‬ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺑﻪ ﺍﻧﺪﺍﺯﺓ ﻳﻚ )‪ (−CH 2 −‬ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ‪ ،‬ﺑﻪ ﻧﺎﻡ‬
‫ﻫﻮﻣﻮﻟﻮگ ﻳﻚ ﺩﻳﮕﺮ )‪(homolog‬ﻳﺎﺩ ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫ﺁﻳﺎ ﻣﻴﺘﻮﺍﻧﻴﺪ ﺑﻪ ﺍﺳﺎﺱ ﺳﺎﺧﻤﺎﻥ ﻫﺎﻯ ﺯﻳﺮ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺗﺤﺮﻳﺮ ﻧﻤﺎﻳﻴﺪ ؟‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H H‬‬
‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬ ‫|‬
‫‪H − C−‬‬
‫|‬
‫‪C‬‬
‫|‬
‫‪− C− H‬‬
‫|‬ ‫ﺏ‪-‬‬ ‫ﺍﻟﻒ ‪، H − C| − C| − C| − C| − H -‬‬
‫‪H H −C−H H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H H‬‬
‫|‬
‫‪H‬‬
‫ﻃﻮﺭﻯ ﻛﻪ ﺩﻳﺪﻩ ﻣﻴﺸﻮﺩ ﺍﻟﻜﺎﻥ ﺍﻟﻒ ﻭﺏ ﻫﺮ ﺩﻭ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻝ ) ‪ (C4H10‬ﺑﻮﺩﻩ ؛ ﺍﻣﺎ‬
‫ﺳﺎﺧﺘﻤﺎﻥ ﺯﻧﺠﻴﺮ ﻛﺎﺭﺑﻨﻰ ﺁﻧﻬﺎ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺭﺩ ‪ ،‬ﻃﻮﺭﻯ ﻛﻪ ﺍﻭﻟﻰ) ﺍﻟﻒ( ﺯﻧﺠﻴﺮ ﻧﺎﺭﻣﻞ ﻭﻣﺴﺘﻘﻴﻢ ﺩﺍﺷﺘﻪ ‪ ،‬ﺩﺭ‬
‫ﺣﺎﻟﻴﻜﻪ ﺩﻭﻣﻰ )ﺏ( ﺯﻧﺠﻴﺮ ﻣﻨﺸﻌﺐ ﺩﺍﺭﺩ ‪ .‬ﺍﺯ ﺗﻮﺿﻴﺤﺎﺕ ﻓﻮﻕ ﻧﺘﻴﺠﻪ ﮔﻴﺮﻯ ﻣﻴﺸﻮﺩ ﻛﻪ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‬
‫ﺑﺮﺍﻯ ﻣﺎ ﺗﻤﺎﻣﻰ ﺍﻃﻼﻋﺎﺕ ﺭﺍ ﺩﺭﻣﻮﺭﺩ ﻣﺮﻛﺐ ﺍﺭﺍﺋﻪ ﻧﺪﺍﺷﺘﻪ ؛ ﺍﻣﺎ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻃﺮﺯ ﺭﻭﺍﺑﻂ ﺍﺗﻮﻡ ﻫﺎﻯ‬
‫ﺷﺎﻣﻞ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ ﺑﺮﺍﻯ ﻣﺎ ﻣﻌﻠﻮﻣﺎﺕ ﺍﺭﺍﺋﻪ ﻣﻴﻜﻨﺪ ‪.‬‬
‫ﻣﺜﺎﻝ‬
‫ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﺁﺏ ) ‪ ( H O‬ﻭ ﺍﻣﻮﻧﻴﺎ ) ‪ (NH 3‬ﺭﺍ ﭘﻴﺸﺒﻴﻨﻰ ﻧﻤﻮﺩﻩ‪،‬ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪.‬‬
‫‪2‬‬
‫‪29‬‬
 ‫ﺣﻞ‬
‫‪..‬‬
‫‪H:N:H‬‬ ‫‪..‬‬ ‫‪ – 1‬ﺳﺎﺧﺘﻤﺎﻥ ﻟﻴﻮﻳﺲ ﺁﻧﻬﺎ ﺭﺍ ﺗﺤﺮﻳﺮ ﻣﻴﻨﻤﺎﻳﻴﻢ ‪:‬‬
‫‪..‬‬ ‫‪H : O:‬‬
‫‪..‬‬
‫‪H‬‬ ‫‪H‬‬
‫‪ - 2‬ﺗﻌﺪﺍﺩ ﺳﺎﺣﻪ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍ ﺑﻪ ﺍﻃﺮﺍﻑ ﺍﺗﻮﻡ ﻣﺮﻛﺰﻯ ﻫﺮﺩﻭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺸﻤﺎﺭﻳﻢ‬
‫ﺍﻟﻒ‪ -‬ﺍﺗﻮﻡ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺩﺭ ‪ NH 3‬ﺳﻪ ﺭﺍﺑﻄﻪ ﺭﺍ ﺑﺎ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺩﺍﺭﺍﺑﻮﺩﻩ ﻭ ﻳﻚ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﺁﺯﺍﺩ ﺭﺍ ﺩﺍﺭﺩ ؛‬
‫ﺑﻨﺎﺑﺮﺍﻳﻦ ﭼﻬﺎﺭ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ ‪.‬‬
‫ﺏ ‪ -‬ﺍﺗﻮﻡ ﺁﻛﺴﻴﺠﻦ ﺩﺭ ‪ H 2O‬ﺩﻭ ﺭﺍﺑﻄﻪ ﺭﺍ ﺑﺎ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺩﺍﺭﺍﺑﻮﺩﻩ ﻭ ﺩﻭﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﺁﺯﺍﺩ ﺭﺍ ﺩﺍﺭﺩ ؛‬
‫ﺑﻨﺎﺑﺮﺍﻳﻦ ﭼﻬﺎﺭ ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ ‪.‬‬
‫‪ – 3‬ﺳﺎﺧﺘﻤﺎﻥ ﻫﻨﺪﺳﻰ ﻣﻨﺎﺳﺐ ﺭﺍ ﺑﺮ ﺍﺳﺎﺱ ﻧﻈﺮﻳﺔ ‪ VSEPR‬ﺗﻌﻴﻴﻦ ﻣﻰ ﻧﻤﺎﻳﻴﻢ ‪:‬‬
‫ﺍﻟﻒ‪ -‬ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺩﺭ ﻫﺮﺍﺗﻮﻡ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﭼﻬﺎﺭ ﻭﺟﻬﻰ ﺧﻮﺍﻫﺪ ﺑﻮﺩ ﻭﺯﺍﻭﻳﺔ ﺭﺍﺑﻄﻪ ﻳﻰ‪ 109.5‬ﺩﺭﺟﻪ ﺍﺳﺖ ‪.‬‬
‫‪ – 4‬ﻭﺿﻌﻴﺖ ﺟﻮﺭﻩ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍ ﻣﺸﺨﺺ ﻣﻴﻨﻤﺎﻳﻴﻢ ‪.‬‬
‫ﺍﻟﻒ ‪ -‬ﺩﺭﻣﻮﺭﺩ ﺍﻣﻮﻧﻴﺎ ﭼﻬﺎﺭ ﻭﺟﻬﻰ ﺭﺍ ﺑﻪ ﺷﻜﻞ ﺳﻪ ﭘﺎﻳﺔ ﺩﺭ ﻧﻈﺮ ﻣﻴﮕﻴﺮﻳﻢ ﻛﻪ ﭘﺎﻳﺔ ﭼﻬﺎﺭﻣﻰ ﺁﻥ ﺑﻪ ﺳﻤﺖ ﺑﺎﻻ‬
‫ﺑﺎﻻﻯ ﺁﻥ ﺍﺳﺘﻮﺍﺭ ﺍﺳﺖ ‪ .‬ﺍﮔﺮ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﺁﺯﺍﺩ ﺭﺍ ﭘﺎﻳﺔ ﭼﻬﺎﺭﻣﻰ ﻗﺒﻮﻝ ﻧﻤﺎﻳﻴﻢ ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﺑﻪ ﺩﺳﺖ ﺁﻣﺪﻩ‬
‫ﻳﻚ ﻫﺮﻡ ﺑﺎ ﻗﺎﻋﺪﺓ ﺳﻪ ﺿﻠﻌﻰ ﺧﻮﺍﻫﺪ ﺑﻮﺩ‪ ) .‬ﺷﻜﻞ )‪ 12 – 2‬ﺍﻟﻒ (‬
‫ﺏ – ﺩﺭﻣﻮﺭﺩ ﺁﺏ‪،‬ﺷﻜﻞ ﻣﺎﻟﻴﻜﻮﻝ ﺁﺏ ﺧﻤﻴﺪﻩ ﺑﻮﺩﻩ ﻭ ﺩﻭﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺁﺯﺍﺩ ﺩﻭﭘﺎﻳﺔ ﺟﻬﺎﺭ ﻭﺟﻬﻰ ﺭﺍ‬
‫ﺍﺷﻐﺎﻝ ﻣﻴﻨﻤﺎﻳﺪ ‪.‬‬
‫ﺝ – ﺑﻨﺎﺑﺮ ﻣﻮﺟﻮﺩﻳﺖ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻧــﻬﺎﻯ ﻏﻴﺮ ﺭﺍﺑﻄﻪ ﻳﻰ – ﻏﻴﺮﺭﺍﺑﻄﻪ ﻳﻰ ‪ ،‬ﻏﻴﺮﺭﺍﺑﻄﻪ ﻳﻰ – ﺭﺍﺑـــﻄﻪ ﻳﻰ ‪،‬ﻭ‬
‫ﺭﺍﺑﻄﻪ ﻳﻰ – ﺭﺍﺑﻄﻪ ﻳﻰ ﻛﻪ ﺑﻪ ﺗﺮﺗﻴﺐ ﻗﻮﺓ ﺩﺍﻓﻌﺔ ﺑﻴﻦ ﺁﻧﻬﺎﻛﻢ ﻣﻰ ﺷﻮﺩ ‪ ،‬ﺯﺍﻭﻳﺔ ﺭﻭﺍﺑﻂ ﻣﺎﻟﻴﻜﻮﻝ ﺁﺏ ﻭﺍﻣﻮﻧﻴﺎ‬
‫ﻛﻤـــﻰ ﺍﺯ ﺯﺍﻭﻳﺔ ﻧﻮﺭﻣﺎﻝ ﻛﻮﭼﻚ ﺷﺪﻩ ) ﺯﺍﻭﻳﺔ ﺭﻭﺍﺑﻂ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻣﻮﻧﻴﺎ ﻭﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺁﺏ ﺍﺳﺖ(‬
‫ﺍﺷﻜﺎﻝ ﺫﻳﻞ ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫‪104 / 5°‬‬ ‫‪107 °‬‬
‫ﺷﻜﻞ )‪ ( 12 - 2‬ﺳﺎﺧﺘﻤﺎﻥ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺍﻣﻮﻧﻴﺎ ﻭﺁﺏ‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﺯﻳﺮ ﺭﺍ ﭘﻴﺸﺒﻴﻨﻰ ﻭﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪.‬‬
‫‪SiCl2 ، PCl2 ، H 2S‬‬
‫‪30‬‬
 ‫ﻃﺮﻳﻘﺔ ﺳﺎﺩﻩ ﺳﺎﺧﺘﻦ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ‬
‫ﺍﮔﺮ ﺑﻪ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﺟﺪﻭﻝ )‪ ( 3 – 2‬ﻧﻈﺮ ﺍﻧﺪﺍﺯﻳﻢ ‪ ،‬ﺩﺭ ﻳﺎﻓﺖ ﻣﻴﺪﺍﺭﻳﻢ ﻛﻪ ﺗﺤﺮﻳﺮ‬
‫ﻭﺗﺮﺳﻴﻢ ﺍﻳﻦ ﻫﺎ ﻣﺸﻜﻞ ‪ ،‬ﻏﻴﺮ ﺍﻗﺘﺼﺎﺩﻯ ﻭ ﺩﺷﻮﺍﺭ ﺍﺳﺖ ؛ ﺍﺯﻳﻦ ﺳﺒﺐ ﻃﺮﻳﻘﻪ ﻫﺎﻯ ﺩﻳﮕﺮﻯ ﺑﺮﺍﻯ ﻧﻤﺎﻳﺶ ﻭ‬
‫ﺗﺤﺮﻳﺮ ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺑﻨﺎ ﮔﺬﺍﺷﺘﻪ ﺷﺪ ﻛﻪ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ ‪:‬‬
‫‪ -‬ﺑﺮﺍﻯ ﺗﺤﺮﻳﺮ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺑﻪ ﻃﻮﺭ ﻓﺸﺮﺩﻩ ‪،‬ﺭﻭﺍﺑﻂ ﺳﺎﺩﻩ ﺑﻴﻦ ﻛﺎﺭﺑﻨﻬﺎﻭﻫﺎﻳﺪﺭﻭﺟﻦ ﺭﺍ ﻧﻤﺎﻳﺶ‬
‫ﻧﻤﻴﺪﻫﻨﺪ ﻭﺑﻌﻀﻰ ﺍﻭﻗﺎﺕ ﺭﻭﺍﺑﻂ ﺑﻴﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍ ﻧﻴﺰ ﺗﺤﺮﻳﺮ ﻧﻤﻰ ﻧﻤﺎﻳﻨﺪ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪:‬‬
‫‪H H H H H H‬‬
‫|‬ ‫|‬ ‫| |‬ ‫|‬ ‫|‬
‫⎯ ‪H − C− C− C − C− C− C− H‬‬
‫‪⎯→ CH 3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 3‬‬
‫|‬ ‫|‬ ‫| |‬ ‫|‬ ‫|‬
‫‪H H H H H H‬‬
‫‪Hexane‬‬
‫‪H 3CCH 2CH 2CH 2CH 2CH 3‬‬
‫‪ -‬ﻧﻤﺎﻳﺶ ﻋﻼﻣﻪ ﻫﺎﻯ ﻛﻴﻤﻴﺎﻭﻯ ‪ :‬ﺩﺭﺍﻳﻦ ﺭﻭﺵ ﺗﻤﺎﻣﻰ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﻭﻫﺎﻳﺪﺭﻭﺟﻦ ﺍﺯ ﻓﻮﺭﻣﻮﻝ‬
‫ﺳﺎﺧﺘﻤﺎﻧﻰ ﺣﺬﻑ ﻣﻴﺸﻮﺩ ﻭﺗﻨﻬﺎ ﺭﻭﺍﺑﻂ ﻛﻪ ﺗﻮﺳﻂ ﺧﻄﻮﻁ)‪ (-‬ﺯﺍﻭﻳﻪ ﺩﺍﺭ ﺍﺭﺍﺋﻪ ﻣﻴﮕﺮﺩﺩ ‪ ،‬ﻧﻤﺎﻳﺶ ﺩﺍﺩﻩ ﻣﻴﺸﻮﺩ ‪.‬‬
‫ﺍﻳﻦ ﻧﻮﻉ ﺳﺎﺧﺘﻤﺎﻥ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺳﺎﺧﺘﻤﺎﻥ ﺍﺳﻜﻠﻴﺘﻰ ﻭﻳﺎﺳﺎﺧﺘﻤﺎﻥ ﺧﻂ– ﺯﺍﻭﻳﻪ ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪ ‪ ،‬ﺩﺭﺍﻳﻦ ﺳﺎﺧﺘﻤﺎﻥ ﺗﻨﻬﺎ‬
‫ﺭﺍﺑﻄﻪ ﻫﺎﻯ ﻛﺎﺭﺑﻦ – ﻛﺎﺭﺑﻦ )‪ (C-C‬ﻧﻤﺎﻳﺶ ﺩﺍﺩﻩ ﻣﻴﺸﻮﺩ ‪ ،‬ﻃﻮﺭﻯ ﻛﻪ ﻣﻮﻗﻌﻴﺖ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭ ﻣﺤﻞ‬
‫ﺗﻘﺎﻃﻊ ﺧﻄﻮﻁ ‪ ،‬ﺍﺑﺘﺪﺍﻭ ﺍﻧﺠﺎﻡ ﺧﻄﻮﻁ ﺗﺼﻮﺭ ﻣﻴﮕﺮﺩﺩ ﻭ ﺍﺯ ﺭﺳﻢ ﺭﺍﺑﻄﻪ ﻫﺎﻯ‪ C-H‬ﺧﻮﺩﺩﺍﺭﻯ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫ﺍﮔﺮ ﺍﺯ ﻋﺪﺩ ‪ 4‬ﺗﻌﺪﺍﺩ ﺭﻭﺍﺑﻂ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺗﻔﺮﻳﻖ ﮔﺮﺩﺩ ‪ ،‬ﺗﻌﺪﺍﺩ ﺍﺗﻮﻣﻬﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻣﺘﻮﺻﻞ ﺑﻪ ﻫﻤﺎﻥ‬
‫‪H H‬‬
‫|‬ ‫|‬
‫‪H H H‬‬
‫| |‬ ‫|‬ ‫ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ‪:‬‬
‫⎯ ‪H − C− C− C − C− C− H‬‬
‫‪⎯→ CH 3 − CH 2 − CH 2 − CH 2 − CH 3‬‬
‫⎯‬
‫|‬ ‫|‬ ‫| |‬ ‫|‬
‫‪H H‬‬ ‫‪H H H‬‬
‫‪Pentane‬‬ ‫‪H 3C‬‬ ‫‪CH 2‬‬ ‫‪CH 3‬‬
‫‪CH 2‬‬ ‫‪CH 2‬‬
‫‪CH 3‬‬ ‫ﻣﺤﻞ ﺗﻘﺮﺭ‬
‫ﻣﺤﻞ ﺗﻘﺮﺭ ‪C H2‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫‪ - 1‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻥ ﻧﻴﻤﻪ ﻣﺸﺮﺡ ‪ ،‬ﻣﺸﺮﺡ ﻧﺎﻗﺺ ﻭ ﺍﺳﻜﻠﻴﺘﻰ ﻣﺮﻛﺒﺎﺕ ﺯﻳﺮﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ‪:‬‬
‫‪C‬‬ ‫‪H‬‬ ‫‪,C H‬‬ ‫‪, C H‬‬ ‫‪, C H‬‬
‫‪6‬‬ ‫‪14‬‬ ‫‪6 12‬‬ ‫‪7 16‬‬ ‫‪4‬‬ ‫‪10‬‬
‫‪ – 2‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻣﻜﻤﻞ ﻣﺮﻛﺒﺎﺕ ﺯﻳﺮ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪:‬‬
‫‪CH 3 (CH 2 ) 4 CH 3‬‬
‫‪CH 3 CH 2 C (CH 2 ) 2 CH 3‬‬ ‫‪, C (CH 3 )3 (CH 2 )3 CH 3‬‬
‫‪31‬‬
‫ﻧﺎﻡ ﻛﻴﻤﻴﺎﻭﻯ ﺁﺳﭙﺮﻳﻦ‪ ،‬ﺍﺳﻴﺘﺎﻳﻞ ﺳﺎﻟﻴﺴﻴﻠﻴﻚ ﺍﺳﻴﺪ ﺍﺳﺖ ‪ ،‬ﭼﻮﻥ ﻧﻤﺎﻳﺶ ﻛﺎﻣﻞ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻥ ﻣﺸﻜﻞ‬
‫ﺍﺳﺖ ؛ ﺑﻨﺎﺑﺮﺍﻳﻦ ﻛﻴﻤﺎﺩﺍﻥ ﻫﺎ ﻣﻌﻤﻮﻻ" ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﺍﺳﻜﻠﻴﺘﻰ ﺁﻥ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﻨﻤﺎﻳﻨﺪﻛﻪ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ ‪:‬‬
‫‪.‬‬
‫‪OH‬‬ ‫‪O‬‬
‫‪/‬‬ ‫||‬
‫‪O = C‬‬ ‫‪O − C−‬‬ ‫‪.‬‬
‫‪OH‬‬ ‫‪O‬‬
‫‪/‬‬ ‫||‬
‫‪O = C‬‬
‫‪O − C − CH 3‬‬
‫ﺷﻜﻞ )‪ (13-2‬ﺍﺳﭙﺮﻳﻦ ﻭ ﻓﻮﺭﻣﻮﻝ ﺁﻥ‬
‫ﺑﻴﺸﺘﺮ ﺑﺪﺍﻧﻴﺪ‬
‫ﺯﺍﻭﻳﺔ ﻧﻮﺭﻣﺎﻝ ﺑﻴﻦ ﺭﻭﺍﺑﻂ ﻭﻻﻧﺴﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺒﺎﺕ ‪109.5°‬ﺑﻮﺩﻩ ﻭﺩﺭ ﺗﻤﺎﻡ ﻣﺎﻟﻴﻜﻮﻟﻬﺎ ﺑﺎﻳﺪ ﺑﻪ ﻫﻤﻴﻦ ﺍﻧﺪﺍﺯﻩ‬
‫ﺑﻮﺩﻩ ﺑﺎﺷﻨﺪ ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﺯﻧﺠﻴﺮﻯ ﺑﻪ ﺷﻜﻞ ﺯﮔﺰﺍگ ﻣﻼﺣﻈﻪ ﻣﻴﺸﻮﻧﺪ‬
‫‪ : 4 – 2‬ﺍﻳﺰﻭﻣﻴﺮﻫﺎ )‪(Isomers‬‬
‫ﺩﺭ ﻛﻴﻤﻴﺎ ﺧﺎﺻﺘﺎ"ﺩﺭﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﻣﺮﻛﺒﺎﺕ ﺯﻳﺎﺩﻯ ﻣﻮﺟﻮﺩﺍﺳﺖ ﻛﻪ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﺁﻧــــﻬﺎﺩﺍﺭﺍﻯ ﭼﻨﺪﻳﻦ‬
‫ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻳﻚ ﻓﻮﺭﻣﻮﻝ ﺗﺮﻛﻴﺒﻰ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪ :‬ﺍﻳﺘﺎﻳﻞ ﺍﻟــــﻜﻮﻝ ﻭ‬
‫ﺩﺍﻯ ﻣﻴﺘﺎﻳﻞ ﺍﻳﺘﺮ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻧﻬﺎ ﺍﺯﻫﻢ ﻓﺮﻕ ﺩﺍﺭﻧﺪ ‪:‬‬
‫‪H H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫|‬ ‫|‬ ‫|‬ ‫|‬
‫‪H − C− C− O − H‬‬ ‫‪H − C− O − C− H‬‬
‫|‬ ‫|‬ ‫|‬ ‫|‬
‫‪H H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫‪Ethanol‬‬ ‫‪imethylete r‬‬
‫ﻃﻮﺭﻯ ﻛﻪ ﺩﻳﺪﻩ ﻣﻴﺸﻮﺩ ‪،‬ﺩﺭ ﺍﻳﺘﺎﻧﻮﻝ ﺍﺗﻮﻡ ﺁﻛﺴﻴﺠﻦ ﺑﺎ ﻳﻚ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭﻳﻚ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺭﺍﺑﻄﻪ ﺩﺍﺷﺘﻪ ؛‬
‫ﺩﺭ ﺣﺎﻟﻰ ﻛﻪ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺩﺍﻯ ﻣﻴﺘﺎﻳﻞ ﺍﻳﺘﺮ ﺍﺗﻮﻡ ﺁﻛﺴﻴﺠﻦ ﺑﺎ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﻪ ﺑﺮﻗﺮﺍﺭ ﻧﻤﻮﺩﻩ ﺍﺳﺖ؛ ﭘﺲ‪:‬‬
‫ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻧﻬﺎ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ ؛ﻳﻌﻨﻰ‬
‫ﻃﺮﺯ ﺭﻭﺍﺑﻂ ﺍﺗﻮﻣﻬﺎ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﺷﺎﻥ ﺍﺯﻫﻢ ﻣﺘﻔﺎﻭﺕ ﺑﺎﺷﻨﺪ ‪ ،‬ﺍﻳﺰﻭﻣﻴﺮ )‪ (Isomers‬ﻫﻢ ﺩﻳﮕﺮ ﮔﻔﺘﻪ‬
‫ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫ﺑﺮﺍﻯ ﺍﺳﺘﺨﺮﺍﺝ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺍﻳﺰﻭﻣﻴﺮﻫﺎ ﺗﻮﺻﻴﻪ ﻣﻴﮕﺮﺩﺩ ﺗﺎ ﺑﻪ ﺻﻮﺭﺕ ﻣﻘﺪﻣﺎﺗﻰ ﺷﻴﻤﺎﻫﺎﻯ ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ‬
‫ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺗﺤﺮﻳﺮ ﻧﻤﻮﺩﻩ ﻭﺑﻌﺪ ﺍﺯ ﺁﻥ ﺑﻪ ﺗﺪﺭﻳﺞ ﺯﻧﺠﻴﺮ ﺍﺻﻠﻰ) ﻋﻤﺪﻩ ( ﺭﺍ ﻛﻮﺗﺎﻧﻤﻮﺩﻩ ﻭ ﺍﺗﻮﻡ‬
‫ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺣﺬﻑ ﺷﺪﻩ ﺍﺯ ﺯﻧﺠﻴﺮ ﺍﺻﻠﻰ ﺭﺍﺑﻪ ﺷﻜﻞ ﺯﻧﺠﻴﺮ ﻣﻨﺸﻌﺐ ) ﺯﻧﺠﻴﺮ ﺟﺎﻧﺒﻰ( ﺩﺭ ﺗﻤﺎﻡ ﺣﺎﻻﺕ ﻣﻤﻜﻨﻪ‬
‫ﺗﺤﺮﻳﺮ ﻛﺮﺩ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪ :‬ﺷﻴﻤﺎﻯ ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ ﺍﻳﺰﻭﻣﻴﺮ ﻫﺎﻯ ﻫﭙﺘﺎﻥ ) ‪ (C 7 H16‬ﺭﺍ ﻣﻄﺎﻟﻌﻪ ﻣﻴﻨﻤﺎﻳﻢ‪:‬‬
‫‪32‬‬
‫‪1− C − C − C − C − C − C − C‬‬ ‫‪2−‬‬ ‫‪C − C− C − C − C − C‬‬
‫|‬
‫‪C‬‬
‫‪3 − C − C − C− C − C − C‬‬ ‫‪4−‬‬ ‫‪C − C− C− C − C‬‬
‫|‬ ‫| |‬
‫‪C‬‬ ‫‪C C‬‬
‫‪5 − C − C− C − C− C‬‬ ‫‪6−‬‬ ‫‪C −C − C−C −C‬‬
‫|‬ ‫|‬ ‫|‬
‫‪C‬‬ ‫‪C‬‬ ‫‪C- C‬‬ ‫‪C‬‬
‫‪C‬‬ ‫‪C‬‬ ‫|‬
‫|‬ ‫|‬
‫‪7 − C − C− C − C − C‬‬ ‫‪8−‬‬ ‫‪C − C − C− C − C‬‬ ‫‪9−‬‬ ‫‪C − C− C− C‬‬
‫|‬ ‫|‬ ‫| |‬
‫‪C‬‬ ‫‪C‬‬ ‫‪C C‬‬
‫ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﻣﻜﻤﻞ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﺑﻌﺪ ﺍﺯ ﺗﻜﻤﻴﻞ ﺷﻴﻤﺎ ﻫﺎﻯ ﺍﺳﻜﻠﻴﺖ ﻫﺎﻯ ﻛﺎﺭﺑﻨﻰ ﺑﺎ ﻋﻼﻭﻩ ﻧﻤﻮﺩﻥ ﺗﻌﺪﺍﺩ‬
‫ﻻﺯﻣﻰ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻫﺎ ﺑﻪ ﺩﺳﺖ ﻣﻰ ﺁﻳﺪ‪.‬‬
‫ﺍﻳﺰﻭﻣﻴﺮﻯ ﺩﺭ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺯﻳﺎﺩ ﺑﻮﺩﻩ ﻛﻪ ﺩﺭ ﻫﺮ ﻣﺒﺤﺚ ﻣﺮﻛﺒﺎﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ‬
‫ﻣﻄﺎﻟﻌﻪ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫ﺍﻟﻜﻴﻨﻬﺎ ﻋﻼﻭﻩ ﺍﺯ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻭﺍﻳﺰﻭﻣﻴﺮﻯ ﻧﻈﺮ ﺑﻪ ﻣﻮﻗﻌﻴﺖ ﺭﺍﺑﻄﻪ ﺩﻭﮔﺎﻧﻪ ‪ ،‬ﺩﺍﺭﺍﻯ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻓﻀﺎﻳﻰ ﻧﻴﺰ ﺍﻧﺪ ‪.:‬‬
‫ﺍﻟﻒ ‪ :‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻭ ﻣﻮﻗﻌﻴﺖ ﺭﺍﺑﻂ ﺩﻭﮔﺎﻧﻪ‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫ﻣﺮﻛﺒﺎﺕ ﺫﻳﻞ ﺭﺍ ﺩﺭﻧﻈـﺮ ﺑﮕﻴﺮﻳﺪ ‪.‬‬
‫‪C H2 = C H − C H2 C H3‬‬ ‫‪1 − Butene.‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫‪C H3 − C H = C H − C H3‬‬ ‫‪2 − Butene‬‬
‫ﻓﻮﺭﻣﻮﻝ ﺟﻤﻌﻰ ﻫﺮﺩﻭ ﻣﺮﻛﺐ ﻓﻮﻕ ‪ C4 H 8‬ﺑﻮﺩﻩ ‪ ،‬ﺍﻣﺎ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻫﺮﺩﻭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ ﺍﺯﻫﻢ‬
‫ﻣﺘﻔﺎﻭﺕ ﺑﻮﺩﻩ ‪ ،‬ﻣﻮﻗﻌﻴﺖ ﺭﺍﺑﻂ ﺩﻭﮔﺎﻧﻪ ﺩﺭﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺭﺩ ‪ ،‬ﺍﻳﻦ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻳﺰﻭﻣﻴﺮﻯ‬
‫ﺳﺎﺧﺘﻤﺎﻧﻰ ﺍﺯﻟﺤﺎﻅ ﻣﻮﻗﻌﻴﺖ ﺭﺍﺑﻂ ﺩﻭﮔﺎﻧﻪ ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪ ‪.‬‬
‫ﺏ – ﺍﻳﺰﻭﻣﻴﺮﻯ ﻓﻀﺎﻳﻰ ‪( Stereo isomeris ) :‬‬
‫‪ Stereo‬ﻛﻠﻤﻪ ﻳﻮﻧﺎﻧﻰ ﺑﻮﺩﻩ ﻛﻪ ﺑﻪ ﻣﻌﻨﻰ ﺟﺎﻣﺪ ﻭﺍﺟﺴﺎﻡ ﺳﺨﺖ ﻣﻴﺒﺎﺷﺪ ‪ ،‬ﺑﻨﺎﺑﺮﺍﻳﻦ ‪Stereo isomeris‬‬
‫ﻣﺮﺑﻮﻁ ﺑﻪ ﻣﺮﻛﺒﺎﺗﻰ ﺍﺳﺖ ﻛﻪ ﺳﺎﺧﺘﻤﺎﻥ ﻓﻀﺎﻳﻰ ﻣﺴﺘﺤﻜﻢ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻭ ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﺁﻥ ﺩﺭﻓﻀـﺎ ﺗﻐﻴﻴﺮ ﻧﻤﻴﻜﻨﺪ‪.‬‬
‫ﺯﻳﺎﺩﺗﺮﺑﺪﺍﻧﻴﺪ‬
‫ﺍﻟﻜﻴﻦ ﻫﺎ ﺑﺎ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺍﻳﺰﻭﻣﻴﺮ ﺑﻮﺩﻩ ﻭﺍﻟﻜﺎﻳﻦ ﻫﺎ ﺑﺎ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﻴﻦ ﻫﺎ ﺍﻳﺰﻭﻣﻴﺮ ﻣﻴﺒﺎﺷﻨﺪ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪:‬‬
‫ﻣﺮﻛﺐ ﺩﺍﺭﺍﻯ ﻓﻮﺭﻣﻮﻝ ﺟﻤﻌﻰ ‪ C 3 H 6‬ﻣﻴﺘﻮﺍﻧﺪ ﭘﺮﻭﭘﻴﻦ ﺑﺎﺷﺪ ﻭﻳﺎﺍﻳﻨﻜﻪ ﺳﺎﻳﻜﻠﻮ ﭘﺮﻭﭘﺎﻥ ﺑﻮﺩﻩ ﺑﺎﺷﺪ ‪:‬‬
‫‪H 2C‬‬ ‫‪C 2‬‬
‫‪CH‬‬
‫‪CH‬‬ ‫‪− CH = CH‬‬
‫‪3‬‬ ‫‪2‬‬
‫‪CH 2‬‬ ‫‪1 − propene‬‬
‫‪Cyclo propane‬‬
‫‪33‬‬
 ‫ﺧﻼﺻﺔ ﻓﺼﻞ ﺩﻭﻡ‬
‫* ﻳﻚ ﻣﺮﻛﺐ ﻛﻴﻤﻴﺎﻭﻯ ﺭﺍ ﻣﻌﻤﻮﻻ" ﺗﻮﺳﻂ ﻃﺮﺯ ﺗﺮﺗﻴﺐ ﺳﻤﺒﻮﻝ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﺓ ﺁﻥ ﺑﺎ ﺿﺮﺍﻳﺐ‬
‫ﻧﺴﺒﺘﻰ ﻛﻪ ﺑﻪ ﻧﺎﻡ ﺿﺮﺍﻳﺐ ﺍﺳﺘﻴﻜﻴﻮ ﻣﺘﺮﻯ )‪(Stoichiometry‬ﻧﻴﺰ ﻳﺎﺩ ﻣﻴﺸﻮﺩ ‪ ،‬ﻧﺸﺎﻥ ﻣﻴﺪﻫﻨﺪﻛﻪ ﻃﺮﺯ ﺗﺮﺗﻴﺐ‬
‫ﺳﻤﺒﻮﻝ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﻩ ﺑﺎ ﺿﺮﺍﻳﺐ ﻧﺴﺒﺘﻰ ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻳﺎﺩ ﻣﻴﻨﻤﺎﻳﻨﺪ‪..‬‬
‫* ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﺍﺳﺎﺱ ﺗﺠﺰﻳﻪ ﻛﻴﻤﻴﺎﻭﻯ ﺗﻌﻴﻴﻦ ﻧﻤﻮﺩ ‪ .‬ﻧﻮﻉ ﺩﻳﮕﺮﻯ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ‬
‫ﻛﻴﻤﻴﺎﻭﻯ ﻋﺒﺎﺭﺕ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ ﺍﺳﺖ ‪ ،‬ﺩﺭﻳﻦ ﻓﻮﺭﻣﻮﻝ ﺗﻌﺪﺍﺩ ﻧﺴﺒﺘﻰ ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﻣﺨﺘﻠﻒ ﺩﺭ ﻳﻚ‬
‫ﻣﺮﻛﺐ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ﻣﻴﺸﻮﺩ‪).‬ﻛﻠﻤﻪ ﺗﺠﺮﺑﻰ ﺩﺭﺍﻳﻦ ﺟﺎ ﺑﻪ ﺍﻳﻦ ﻣﻌﻨﻰ ﺍﺳﺖ ﻛﻪ ﻓﻮﺭﻣﻮﻝ ﺍﺭﺍﺋﻪ ﺷﺪﻩ ﺗﻨﻬﺎ ﺑﻪ ﺍﺳﺎﺱ‬
‫ﻣﺸﺎﻫﺪﻩ ﻭ ﺍﻧﺪﺍﺯﻩ ﮔﻴﺮﻯ؛ ﻳﻌﻨﻰ ﺗﺤﻠﻴﻞ ﺗﻮﺻﻴﻔﻰ ﻭ ﻣﻘﺪﺍﺭﻯ ﻣﺸﺨﺺ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ(‪..‬‬
‫* ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‪ ،‬ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺑﻪ ﺯﺑﺎﻥ ﻛﻴﻤﻴﺎﻭﻯ ﻣﻌﺮﻓﻰ ﻣﻴﻨﻤﺎﻳﺪ ‪ .‬ﻓﻮﺭﻣﻮﻝ ﻧﻪ ﺗﻨﻬﺎ ﻧﻮﻉ ﺍﺗﻮﻣﻬﺎ ﺭﺍ ﺩﺭ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﻧﺸﺎﻥ ﺩﺍﺩﻩ ؛ﺑﻠﻜﻪ ﺗﻌﺪﺍﺩ ﻭ ﺍﻧﻮﺍﻉ ﺍﺗﻮﻡ ﻫﺎ ﺭﺍ ﻧﻴﺰ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ‬
‫* ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻣﻌﻠﻮﻣﺎﺕ ﺯﻳﺎﺩﻯ ﺭﺍ ﺩﺭﻣﻮﺭﺩ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ ﺑﺮﺍﻯ ﻣﺎ ﺍﺭﺍﻳﻪ ﻣﻴﻜﻨﺪ‪ ،‬ﻣﻮﻗﻌﻴﺖ ﺍﺗﻮﻡ‬
‫ﻫﺎﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺑﺮﺍﻯ ﻣﺎ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪.‬‬
‫* ﺍﺷﻜﺎﻝ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﻋﺎﻣﻞ ﺑﺴﻴﺎﺭ ﻣﻬﻤﻰ ﺩﺭ ﺗﻌﻴﻴﻦ ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺁﻧﻬﺎ ﺍﺳﺖ ‪.‬‬
‫* ﻳﻜﻰ ﺍﺯ ﻧﻄﺮﻳﺎﺗﻰ ﻛﻪ ﺑﺮﺍﻯ ﭘﻴﺸﺒﻴﻨﻰ ﺍﺷﻜﺎﻝ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﺍﺭﺍﺋﻪ ﺷﺪﻩ ﺍﺳﺖ ‪ ،‬ﻋﺒﺎﺭﺕ ﺍﺯ ﻧﻈﺮﻳﺔ ﻗﻮﺓ‬
‫ﺩﺍﻓﻌﺔ ﺟﻔـــﺖ ﺍﻟﻜﺘﺮﻭﻧـــــﻬﺎﻯ ﻗﺸﺮ ﻭﻻﻧـــﺴﻰ )‪(Vaoleance shell Elctronpairs Repulsion‬‬
‫ﺍﺳﺖ ﻛﻪ ﺑﻪ )‪ (VSEPR‬ﺍﺭﺍﺋﻪ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﻣﻄﺎﺑﻖ ﺑﻪ ﺍﻳﻦ ﻧﻈﺮﻳﻪ ‪ ،‬ﻗﻮﻩ ﻫﺎﻯ ﺩﺍﻓﻌﺔ ﺍﻟﻜﺘﺮﻭﺍﺳﺘﺎﺗﻴﻜﻰ ﻣﻮﺟﻮﺩ‬
‫ﺑﻴﻦ ﺟﻔﺖ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ ﻭﻳﺎ ﻏﻴﺮ ﺭﺍﺑﻄﻪ ﻳﻰ ﺩﺭ ﻳﻚ ﻣﺎﻟﻴﻜﻮﻝ ﺳﺒﺐ ﻣﻴﺸﻮﺩ ﺗﺎ ﺍﻳﻦ ﺍﻟﻜﺘﺮﻭﻧﻬﺎ ﺣﺪ‬
‫ﺍﻣﻜﺎﻥ ﺍﺯ ﻫﻢ ﻓﺎﺻﻠﻪ ﮔﺮﻓﺘﻪ ﻭ ﺟﻬﺖ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ ﻭﺍﻳﻦ ﺟﻬﺖ ﮔﻴﺮﻯ ﺟﻔﺖ ﺍﻟﻜﺘﺮﻭﻧﻬﺎ ﻃﻮﺭﻯ ﺍﺳﺖ ﻛﻪ ﭘﺎﻳﺪﺍﺭ‬
‫ﺗﺮﻳﻦ ﺳﺎﺧﺘﻤﺎﻥ ﻫﻨﺪﺳﻰ ﺭﺍ ﺑﻪ ﻣﺎﻟﻴﻜﻮﻝ ﻓﺮﺍﻫﻢ ﻣﻴﻜﻨﺪ ‪.‬‬
‫*ﺯﺍﻭﻳﺔ ﺭﺍﻛﻪ ﺳﻪ ﺍﺗﻮﻡ ﻣﺮﺗﺒﻂ ﺷﺪﻩ ﺑﺎﻫﻢ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺯﺍﻭﻳﺔ ﺭﺍﺑﻄﻪ ﻳﻰ ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪﻛﻪ ﺣﺪ ﺍﻛﺜﺮ ﺍﻳﻦ‬
‫‪ 180 o‬ﺯﺍﻭﻳﻪ ﺍﺳﺖ ‪.‬‬
‫* ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻧﻬﺎ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ‬
‫؛ﻳﻌﻨﻰ ﻃﺮﺯ ﺭﻭﺍﺑﻂ ﺍﺗﻮﻣﻬﺎ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﺷﺎﻥ ﺍﺯﻫﻢ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ ‪ ،‬ﺍﻳﺰﻭﻣﻴﺮ )‪ (Isomers‬ﻫﻢ ﺩﻳﮕﺮ‬
‫ﮔﻔﺘﻪ ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫ﺗﻤﺮﻳﻦ ﻭﺳﺆﺍﻻﺕ ﻓﺼﻞ ﺩﻭﻡ‬
‫ﺳﺆﺍﻻﺕ ﭼﻬﺎﺭ ﺟﻮﺍﺑﻪ‬
‫‪ - 1‬ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﺍﺳﺎﺱ ‪......‬ﻛﻴﻤﻴﺎﻭﻯ ﺗﻌﻴﻴﻦ ﻧﻤﻮﺩ ‪.‬‬
‫ﺍﻟﻒ ‪ -‬ﺗﻌﺎﻣﻼﺕ ﻛﻴﻤﻴﺎﻭﻯ ﺏ ﺳﻨﺘﻴﺰ ﻛﻴﻤﻴﺎﻭﻯ ﺝ ‪ -‬ﺗﺠﺰﻳﻪ ﺩ – ﻫﻴﭽﻜﺪﺍﻡ‬
‫‪ - 2‬ﺑﺮﺍﻯ ﺩﺍﻧﺴﺘﻦ ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺳﺎﺩﻩ ﻭﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺒﺎﺕ ‪،‬ﻻﺯﻡ ﺍﺳﺖ ﺗﺎ ﺗﺤﻠﻴﻞ‪ .......‬ﻣﺮﻛﺐ ﺩﺍﻧﺴﺘﻪ ﺷﻮﺩ ‪:‬‬
‫ﺩ – ﻫﻴﭽﻜﺪﺍﻡ‬ ‫ﺏ ‪ -‬ﻣﻘﺪﺍﺭﻯ ﺝ ‪ -‬ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭ‬ ‫ﺍﻟﻒ ‪ -‬ﺗﻮﺻﻴﻔﻰ‬
‫‪ - 3‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻋﻼﻭﻩ ﺍﺯ ﻧﻮﻉ ‪ ،‬ﺗﻌﺪﺍﺩ ﺍﺗﻮﻣﻬﺎﻯ ﻫﺮ ﻋﻨﺼﺮ‪....... ،‬ﺍﺗﻮﻡ ﻫﺎ ‪......‬ﺭﺍ ﺑﺎﻳﻚ ﺩﻳﮕﺮ ﻧﻴﺰ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ‬
‫ﺍﻟﻒ ‪ -‬ﺷﻴﻮﺓ ﺍﺗﺼﺎﻝ ﺏ‪ -‬ﻃﺮﺯ ﺭﻭﺍﺑﻂ ﺝ ‪ -‬ﺗﻌﺪﺍﺩ ﻣﺎﻟﻴﻜﻮﻟﻬﺎ ﺩ ‪ -‬ﺍﻟﻒ ﻭﺏ ﺩﺭﺳﺖ ﺍﺳﺖ ‪.‬‬
‫‪34‬‬
‫‪ - 4‬ﺳﺎﺧﺘﻤﺎﻥ ﺧﺎﺻﻰ ﺍﺯ ﺍﺗﻮﻡ ﻫﺎ ﻛﻪ ﺑﺎﻋﺚ ﻣﻴﺸﻮﺩ ﺗﺎ ﺑﻴﻦ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﻫﺎﻯ ﺭﺍﺑﻄﻪ ﻳﻰ ﻭﻏﻴﺮ ﺭﺍﺑﻄﻪ ﻳﻰ‬
‫ﻣﺎﻟﻴﻜﻮﻟﻬﺎ ﻛﻤﺘﺮﻳﻦ ﺩﻓﻌﻪ ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ‪ .......‬ﻳﺎﺩ ﻣﻴﺸﻮﺩ‬
‫ﺍﻟﻒ ‪ -‬ﻣﺪﺍﺭ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺏ – ﻗﺸﺮ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺝ‪ -‬ﻗﺸﺮ ﻓﺮﻋﻰ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺩ ‪ -‬ﺳﺎﺣﺔ ﺍﻟﻜﺘﺮﻭﻧﻰ‬
‫‪ - 5‬ﺍﺷﻜﺎﻝ ﻫﻨﺪﺳﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﻋﺎﻣﻞ ﺑﺴﻴﺎﺭ ﻣﻬﻤﻰ ﺩﺭ ﺗﻌﻴﻴﻦ ‪ .....‬ﺁﻧﻬﺎ ﺍﺳﺖ‬
‫ﺍﻟﻒ ‪ -‬ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺏ – ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ ﺝ ‪ -‬ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭ ﺩ ‪ -‬ﻫﻴﭻ ﻛﺪﺍﻡ‬
‫‪ - 6‬ﺩﺭ ﺳﺎﺧﺘﻤﺎﻥ ﭼﻬﺎﺭ ﻭﺟﻬﻰ ﺟﻮﺭﻩ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺑﺎﻳﻚ ﺩﻳﮕﺮ ﺯﺍﻭﻳﺔ ‪ ...‬ﺍﺳﺖ ‪.‬‬
‫‪180‬‬ ‫ﺍﻟﻒ ‪ 120 o -‬ﺏ ‪ 109.5 o -‬ﺝ ‪ 309.5 o -‬ﺩ ‪-‬‬
‫‪o‬‬
‫‪H H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫| |‬ ‫|‬ ‫|‬
‫‪ H − C − C − O − H‬ﻋﺒﺎﺭﺕ ﺍﺳﺖ ﺍﺯ ‪:‬‬ ‫ﻭ‬ ‫‪H − C− O − C− H‬‬ ‫‪ - 7‬ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺒﺎﺕ‬
‫| |‬ ‫|‬ ‫|‬
‫‪H H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﺏ ‪ C 2 H 6 O -‬ﺝ ‪ C 3 H 5O -‬ﺩ – ﻫﻴﭽﻜﺪﺍﻡ‬ ‫‪..‬‬
‫ﺍﻟﻒ ‪C H O -‬‬
‫‪4 14‬‬
‫‪ - 8‬ﺷﻜﻞ ﻣﺎﻟﻴﻜﻮﻝ ‪ H : N.. : H‬ﺑﻪ ﻧﺎﻡ ﺳﺎﺧﺘﻤﺎﻥ ﻛﺪﺍﻡ ﻋﺎﻟﻢ ﺯﻳﺮ ﻳﺎﺩ ﻣﻴﺸﻮﺩ ؟‬
‫ﺍﻟﻒ – ﺍﻭﮔﺪﺭﻭ ‪H‬ﺏ ‪ -‬ﻭﺍﻧﺪﺭ ﻭﺍﻟﺲ ﺝ – ﻣﺎﻛﺴﻴﺒﻮﻳﻞ ﺩ ‪ -‬ﻟﻴﻮﻳﺲ‬
‫‪ – 9‬ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻧﻬﺎ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ‪،‬‬
‫‪. ....‬ﻫﻢ ﺩﻳﮕﺮ ﮔﻔﺘﻪ ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫ﺏ ‪ (Isomers) -‬ﺝ ‪ -‬ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭ ﺩ – ﻫﻴﭽﻜﺪﺍﻡ‬ ‫ﺍﻟﻒ ‪ -‬ﺍﻳﺰﻭﻣﻴﺮ‬
‫ﺳﺆﺍﻻﺕ ﺗﺸﺮﻳﺤﻰ‬
‫‪ –1‬ﻓﺮﻕ ﺑﻴﻦ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﻩ ﻭﻣﺎﻟﻴﻜﻮﻟﻰ ﭼﻴﺴﺖ ﺁﻥ ﺭﺍ ﺗﻮﺳﻂ ﻣﺜﺎﻝ ﻭﺍﺿﺢ ﺳﺎﺯﻳﺪ‬
‫‪ – 2‬ﺑﻪ ﻣﻘﺪﺍﺭ ‪ 0.3‬ﮔﺮﺍﻡ ﻳﻚ ﻣﺎﺩﺓ ﻋﻀﻮﻯ ﺩﺍﺭﺍﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ‪ ،‬ﻛﺎﺭﺑﻦ ﻭﺁﻛﺴﻴﺠﻦ ﺍﺳﺖ ‪ ،‬ﻣﻘﺪﺍﺭ ﻛﺎﺭﺑﻦ‬
‫ﺩﺭﺍﻳﻦ ﻣﻘﺪﺍﺭ ﻣﺎﺩﺓ ﻋﻀﻮﻯ ‪0.12‬ﮔﺮﺍﻡ ﻭﻣﻘﺪﺍﺭ ﻫﺎﻳﺪﺭﻭﺟﻦ ‪0.02‬ﮔﺮﺍﻡ ﺍﺳﺖ ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﺗﺠﺮﺑﻰ ﺍﻳﻦ ﻣﺮﻛﺐ‬
‫ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻛﻨﻴﺪ‪ ).‬ﻛﺘﻠﺔ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ‪ ، 12‬ﻫﺎﻳﺪﺭﻭﺟﻦ ‪ 1‬ﻭ ﺁﻛﺴﻴﺠﻦ ‪ 16‬ﺍﺳﺖ (‬
‫‪ - 3‬ﻓﻮﺭﻣﻮﻝ ﺳﺎﺩﺓ ﻳﻚ ﻣﺮﻛﺐ ‪ CH 2O‬ﺑﻮﺩﻩ ﻭﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺐ ﻣﺬﻛﻮﺭ ‪ 180g/mo l‬ﺍﺳﺖ‬
‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻥ ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻛﻨﻴﺪ ‪.‬‬
‫‪ – 4‬ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺮﻛﺐ ﻋﻀﻮﻯ ‪ 180g/mo l‬ﺍﺳﺖ ‪ ،‬ﺩﺭ ﺗﺮﻛﻴﺐ ﻣﺮﻛﺐ ﻣﺬﻛﻮﺭ ‪ 55%‬ﻛﺎﺭﺑﻦ ‪36% ،‬‬
‫ﺁﻛﺴﻴﺠﻦ ﻭ ‪ 9%‬ﻫﺎﻳﺪﺭﻭﺟﻦ ﺷﺎﻣﻞ ﺍﺳﺖ ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻥ ﺭﺍ ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻭﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪.‬‬
‫‪ – 5‬ﺩﺭ ﺗﺮﻛﻴﺐ ﻳﻚ ﻣﺮﻛﺐ ﻋﻀﻮﻯ ﺻﺮﻑ ﻛﺎﺭﺑﻦ ﻭﻫﺎﻳﺪﺭﻭﺟﻦ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ‪ 1.5‬ﮔﺮﺍﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ﻭ‪ 9‬ﮔﺮﺍﻡ ﻛﺎﺭﺑﻦ ﺍﺯ ﺍﻧﺎﻟﻴﺰ ﺁﻥ ﺑﻪ ﺩﺳﺖ ﺁﻣﺪﻩ ﺍﺳﺖ ‪ ،‬ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻥ ‪ 210‬ﺑﻮﺩﻩ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻥ‬
‫ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪ – 6‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻭ ﺍﺳﻜﻠﻴﺘﻰ ﻣﺮﻛﺒﺎﺕ ﺯﻳﺮ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪:‬‬
‫ﺍﻟﻒ – ‪ di chloro-1-butene 1,1-‬ﺏ – ‪ dibromoethene – 1,2‬ﺝ ‪hexene 3- -‬‬
‫‪ - 7‬ﻣﺮﻛﺒﻰ ﺩﺍﺭﺍﻯ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ‪ C H‬ﺩﺍﺭﺍﻯ ﻛﺪﺍﻡ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎ ﺍﺳﺖ؟ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻥ ﺗﻤﺎﻣﻰ‬
‫‪6‬‬ ‫‪14‬‬
‫ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﺁﻥ ﺭﺍ ﺗﺤﺮﻳﺮﺩﺍﺭﻳﺪ ‪.‬‬
‫‪ – 8‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﻨﺪﺳﻰ ﭼﻪ ﻧﻮﻉ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺍﺳﺖ؟ ﺩﺭ ﺑﺎﺭﻩ ﻣﻌﻠﻮﻣﺎﺕ ﺩﻫﻴﺪ ‪.‬‬
‫‪ - 9‬ﺗﻤﺎﻣﻰ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﻣﻤﻜﻨﺔ ﻣﺮﻛﺐ ‪ C 4 H 8O‬ﺭﺍ ﺑﺎ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻭﺍﺳﻜﻠﻴﺘﻰ ﺷﺎﻥ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪.‬‬
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 ‫ﻓﺼـﻞ ﺳـﻮﻡ‬
‫ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ‬
‫ﺍﺳﺎﺱ ﺑﻴﻮﻟﻮژﻯ ‪ ،‬ﻃﺐ ﻭﺻﻨﻌﺖ ﺍﻣﺮﻭﺯﻯ ﺭﺍ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺗﺸﻜﻴﻞ ﺩﺍﺩﻩ ﺍﺳﺖ‪ .‬ﺟﺰء ﺍﺳﺎﺳﻰ‬
‫ﺳﺎﺧﺘﻤﺎﻥ ﻣﻮﺟﻮﺩﺍﺕ ﺯﻧﺪﻩ ﻋﻼﻭﻩ ﺍﺯ ﺁﺏ‪ ،‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺍﺳﺖ ؛ ﭼﻮﻥ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ‬
‫ﻋﺒﺎﺭﺕ ﺍﺯ ﻣﺮﻛﺒﺎﺕ ﻛﺎﺭﺑﻦ ﺑﻮﺩﻩ؛ ﺑﻨﺎﺑﺮ ﺍﻳﻦ ﮔﻔﺘﻪ ﻣﻴﺘﻮﺍﻧﻴﻢ ﻛﻪ ﻣﺎ ﺩﺭ ﻋﻨﺼﺮ ﻛﺎﺭﺑﻦ ﺯﻧﺪﻩ ﮔﻰ‬
‫ﻣﻴﻨﻤﺎﻳﻢ‪.‬‬
‫ﭼﺮﺍ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﻰ ﻧﻤﺎﻳﻨﺪ؟ ﺁﻳﺎ ﺁﻣﻮﺧﺘﻦ ﺧﻮﺍﺹ ﻫﺮ ﻣﺮﻛﺐ ﺑﻪ ﻃﻮﺭ‬
‫ﺟﺪﺍﮔﺎﻧﻪ ﻛﺎﺭ ﺳﺎﺩﻩ ﺧﻮﺍﻫﺪﺑﻮﺩ ؟ ﺳﻠﺴﻠﻪ ﻫﻮﻣﻮﻟﻮگ ﭼﻴﺴﺖ؟ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﭼﻴﺴﺖ؟‬
‫ﭼﻮﻥ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺑﻪ ﭘﻴﻤﺎﻧﺔ ﺯﻳﺎﺩ ﺩﺭ ﻃﺒﻴﻌﺖ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻣﻄﺎﻟﻌﻪ ﻫﺮﻳﻚ ﺁﻧﻬﺎ ﺑﻪ ﻃﻮﺭ‬
‫ﺟﺪﺍﮔﺎﻧﻪ ﻛﺎﺭ ﻣﺸﻜﻞ ﺧﻮﺍﻫﺪ ﺑﻮﺩ؛ ﺍﺯ ﺍﻳﻦ ﺳﺒﺐ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﺑﻪ ﻃﺒﻘﺎﺕ ﻣﺨﺘﻠﻒ ﺗﻘﺴﻴﻢ‬
‫ﻧﻤﻮﺩﻩ ﺍﻧﺪ ﻛﻪ ﺍﻳﻦ ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﺩﺭ ﺯﻳﺮ ﻣﻄﺎﻟﻌﻪ ﻣﻰ ﻧﻤﺎﻳﻴﻢ‪.‬‬
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 ‫‪ :1 – 3‬ﻣﻌﻠﻮﻣﺎﺕ ﻋﻤﻮﻣﻰ‬
‫ﻣﺮﻛﺒﺎﺗﻰ ﻋﻀﻮﻯ ﻛﻪ ﺗﻌﺪﺍﺩ ﺁﻧﻬﺎ ﺑﻴﺶ ﺍﺯ ﺑﻴﺴﺖ ﻣﻠﻴﻮﻥ ﻣﻰ ﺑﺎﺷﺪ‪ ،‬ﺑﻪ ﺍﺳﺎﺱ ﺳﺎﺧﺘﻤﺎﻥ ﺯﻧﺠﻴﺮ ﻛﺎﺭﺑﻨﻰ‬
‫)ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ( ﻭ ﻳﺎ ﺑﻪ ﺍﺳﺎﺱ ﻣﻮﺟﻮﺩﻳﺖ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﻴﮕﺮﺩﻧﺪ‪ ،‬ﻧﻮﻉ ﺭﻭﺍﺑﻂ ﺍﺗﻮﻡ‬
‫ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺑﺎ ﻫﻢ ﺩﻳﮕﺮ ﻧﻴﺰ ﺩﺭ ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﻭﻝ ﺍﺳﺎﺳﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ‪.‬‬
‫ﻧﻈﺮ ﺑﻪ ﺳﺎﺧﺘﻤﺎﻥ ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ‪ ،‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﺑﻪ ﺩﻭ ﺩﺳﺘﻪ ﺗﻘﺴﻴﻢ ﻧﻤﻮﺩﻩ ﺍﻧﺪ ﻛﻪ ﻋﺒﺎﺭﺕ ﺍﺯ‬
‫ﺍﺳﻜﻠﻴﺖ ﺯﻧﺠﻴﺮﻯ )‪ ( Acyclic‬ﻭ ﺣﻠﻘﻪ ﻳﻰ )‪ (Cyclic‬ﻣﻴﺒﺎﺷﺪ‪.‬‬
‫ﻣﺮﻛﺒﺎﺕ ﺯﻧﺠﻴﺮﻯ ﻧﻮﻉ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺩﺍﺭﺍﻯ ﺯﻧﺠﻴﺮ ﺑﺎﺯ ﺑﻮﺩﻩ ﻭ ﺍﺳﺎﺱ ﺁﻧﻬﺎ ﺭﺍ ﺳﺎﺧﺘﻤﺎﻥ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ‬
‫ﻫﺎﻯ ﺍﻟﻴﻔﺎﺗﻴﻚ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ‪.‬‬
‫‪ - 1‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﺍﻟﻴﻔﺎﺗﻴﻚ‪ :‬ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺗﻨﻬﺎﺍﺯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻭ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺗﺸﻜﻴﻞ‬
‫ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪ ،‬ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﻣﻴﺘﻮﺍﻧﻨﺪ ﻣﺸﺒﻮﻉ؛ ﻣﺎﻧﻨﺪ ‪:‬ﺍﻟﻜﺎﻥ ﻫﺎ )‪ ( Alkanes‬ﻭ ﻳﺎ ﻏﻴﺮ ﻣﺸﺒﻮﻉ ﺩﺍﺭﺍﻯ ﺭﺍﺑﻄﺔ‬
‫ﺩﻭﮔﺎﻧﻪ )‪ ( Alkenenes‬ﻭ ﺳﻪ ﮔﺎﻧﻪ ﻛﺎﺭﺑﻨﻰ )‪ ( Alkynes‬ﻭﺍﻟﻜﺎﺩﺍﻳﻦ ﻫﺎ )‪ ( Alka di enes‬ﺑﺎﺷﺪ‪.‬‬
‫‪ - 2‬ﻣﺮﻛﺒﺎﺕ ﺣﻠﻘﻪ ﻳﻰ) ‪ :( Cyclo Compounds‬ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﺧﻮﺩ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ‬
‫ﺯﻧﺠﻴﺮ ﺑﺴﺘﻪ ﺑﻪ ﺷﻜﻞ ﺣﻠﻘﻪ ﺑﻮﺩﻩ ﻭ ﻧﻈﺮ ﺑﻪ ﻧﻮﻋﻴﺖ ﺍﺗﻮﻡ ﻫﺎﻯ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﺓ ﺣﻠﻘﻪ ﺑﻪ ﻛﺎﺭﺑﻮﺳﻜﻠﻴﻚ‬
‫)‪ (Carbocycli c‬ﻭ ﻫﺘﺮﻭﺳﻜﻠﻴﻚ )‪ ( Hetrocyclic‬ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﮔﺮﺩﻳﺪﻩ ﺍﻧﺪ‪.‬‬
‫‪- 3‬ﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﻫﺎ )‪ : (Carbocyclic‬ﺩﺭ ﺍﻳﻦ ﻧﻮﻉ ﻣﺮﻛﺒﺎﺕ ﺣﻠﻘﻪ ﺗﻨﻬﺎ ﺍﺯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺗﺸﻜﻴﻞ‬
‫ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ﻭ ﻧﻈﺮ ﺑﻪ ﺗﻔﺎﻭﺕ ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺷﺎﻥ ﺑﻪ ﺩﻭ ﮔﺮﻭپ ﺗﻘﺴﻴﻢ ﮔﺮﺩﻳﺪﻩ ﺍﻧﺪ ﻛﻪ ﻋﺒﺎﺭﺕ ﺍﺯ‬
‫ﺍﻟﻴﺴﻜﻠﻴﻚ )‪ ( Alicyclhc‬ﻭ ﺍﺭﻭﻣﺎﺗﻴﻚ )‪ ( Aromatic‬ﺍﺳﺖ‪.‬‬
‫ﺍﺳﺎﺱ ﻣﺮﻛﺒﺎﺕ ﺍﺭﻭﻣﺎﺗﻴﻚ ﺭﺍ ﻣﺮﻛﺒﺎﺕ ﺑﻨﺰﻳﻦ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ ﻭ ﻋﺒﺎﺭﺕ ﺍﻧﺪ ﺍﺯ ﺑﻨﺰﻳﻦ‪ ،‬ﻧﻔﺘﺎﻟﻴﻦ‪ ،‬ﺍﻧﺘﺮﺍﺳﻴﻦ ﻭ‬
‫ﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ‪.‬‬
‫ﻣﺮﻛﺒﺎﺕ ﺍﻟﻴﺴﻜﻠﻴﻚ ﻫﺎﺑﻪ ﻣﺮﻛﺒﺎﺕ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ ) ‪ (Cyclo alcanes‬ﻭ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫) ‪ (Cyclo alkenes‬ﻣﻨﻘﺴﻢ ﻣﻴﮕﺮﺩﻧﺪ‪.‬‬
‫ﺍﻭﻟﻴﻦ ﻣﺮﻛﺐ ﺧﺎﻧﺪﺍﻥ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻥ ﻫﺎ ﺳﺎﻳﻜﻠﻮ ﭘﺮﻭﭘﺎﻥ ﺑﻮﺩﻩ ﻭ ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻥ ﻫﺎ ‪CnH 2 n‬‬
‫ﺍﺳﺖ ﻛﻪ ﺑﺎ ﺍﻟﻜﻴﻦ ﻫﺎ ﺍﻳﺰﻭﻣﻴﺮ ﺍﻧﺪ‪.‬‬
‫ﺳﻜﻠﻴﻚ ﻫﺎﻯ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﺗﻌﺪﺍﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭ ﺁﻧﻬﺎ ﺑﻴﺸﺘﺮ ﺍﺯ ‪ 30‬ﺍﺗﻮﻡ ﺍﺳﺖ‪.‬‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﺍﺭﻭﻣﺎﺗﻴﻚ )‪( Arenes‬‬
‫ﺍﻳﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﺩﺭ ﺗﺮﻛﻴﺐ ﺧﻮﺩﺩﺍﺭﺍﻯ ﺣﻠﻘﺔ ﺑﻨﺰﻳﻦ ﺑﻮﺩﻩ ‪ ،‬ﻧﻔﺘﺎﻟﻴﻦ‪ ،‬ﺍﻧﺘﺮﺍﺳﻴﻦ ﻭ ﻓﻴﻨﺎﻧﺘﻴﻦ ﺍﺯ ﺟﻤﻠﺔ ﺍﻳﻦ‬
‫ﻣﺮﻛﺒﺎﺕ ﻣﻴﺒﺎﺷﻨﺪ ﻛﻪ ﺍﺯ ﺗﺮﺍﻛﻢ ﭼﻨﺪﻳﻦ ﺣﻠﻘﺔ ﺑﻨﺰﻳﻦ ﺣﺎﺻﻞ ﺷﺪﻩ ﺍﻧﺪ‪.‬‬
‫ﻫﺘﺮﻭﺳﻜﻠﻴﻚ )‪(Hetrocyclic‬‬
‫ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﻋﻼﻭﻩ ﺍﺯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ‪ ،‬ﺩﺭ ﺣﻠﻘﻪ ﺧﻮﺩ ﺩﺍﺭﺍﻯ ﻳﻚ ﻭ ﻳﺎ ﭼﻨﺪﻳﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺩﻳﮕﺮ‬
‫ﺑﻮﺩﻩ ﻛﻪ ﻋﻤﺪﺗﺎً ﺍﻳﻦ ﻋﻨﺎﺻﺮ ﻋﺒﺎﺭﺕ ﺍﺯ ﺍﻛﺴﻴﺠﻦ‪ ،‬ﻧﺎﻳﺘﺮﻭﺟﻦ‪ ،‬ﺳﻠﻔﺮ ﻭ ﻏﻴﺮﻩ ﺍﺳﺖ‪ .‬ﻣﺮﻛﺒﺎﺕ ﻫﺘﺮﻭﺳﻜﻠﻴﻚ‬
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 ‫ﻣﻴﺘﻮﺍﻧﻨﺪ ﻣﺸﺒﻮﻉ‪ ،‬ﻏﻴﺮ ﻣﺸﺒﻮﻉ ﻭ ﻳﺎ ﺍﺭﻭﻣﺎﺗﻴﻚ ﺑﻮﺩﻩ ﺑﺎﺷﻨﺪ‪.‬‬
‫ﺗﻤﺎﻡ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﻣﻰ ﺗﻮﺍﻥ ﻣﺸﺘﻖ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻓﻮﻕ ﺍﻟﺬﻛﺮ ﭘﻨﺪﺍﺷﺖ ؛ ﺯﻳﺮﺍ ﺍﻳﻦ ﻣﺸﺘﻘﺎﺕ‬
‫ﻋﻀﻮﻯ ﺍﺯ ﺗﻌﻮﻳﺾ ﻳﻚ ﻭ ﻳﺎ ﭼﻨﺪﻳﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺗﻮﺳﻂ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ‬
‫ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﻧﺪ‪ .‬ﺷﻴﻤﺎﻯ ﺫﻳﻞ ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﺑﻪ ﺷﻜﻞ ﻓﺸﺮﺩﻩ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ‪:‬‬
‫ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ‬
‫ﺍﻟﻴﻔﺎﺗﻴﻚ )ﺗﻴﻞ ﺳﺎﺯ (‬
‫ﺍﺭﻭﻣﺎﺗﻴﻚ‬
‫ﻏﻴﺮ ﻣﺸﺒﻮﻉ‬ ‫ﻣﺸﺒﻮﻉ‬
‫ﺗﻴﻮﻓﺎﻥ‬
‫ﺍﻟﻜﺎﻳﻦ‬ ‫ﺍﻟﻜﻴﻦ‬
‫ﺑﻨﺰﻳﻦ‬
‫‪ : 2- 3‬ﺻﻨﻒ ﺑﻨﺪﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺍﺯ ﺗﺮﻛﻴﺐ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻭ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺗﺸﻜﻴﻞ ﮔﺮﺩﻳﺪﻩ ﺍﻧﺪ‪ .‬ﺩﺭ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻫﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﭼﻬﺎﺭ ﺭﺍﺑﻄﻪ ﺍﺷﺘﺮﺍﻛﻰ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻛﻪ ﺍﻳﻦ ﺭﻭﺍﺑﻂ ﺑﺎ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻭ‬
‫ﺍﺗﻮﻡ ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺩﻳﮕﺮ ﺑﺮ ﻗﺮﺍﺭ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪.‬‬
‫ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺩﺭ ﻗﺪﻡ ﺍﻭﻝ ﺑﻪ ﺍﺳﺎﺱ ﻣﻮﺟﻮﺩﻳﺖ ﻭ ﻋﺪﻡ ﻣﻮﺟﻮﺩﻳﺖ ﺣﻠﻘﺔ ﺷﺶ ﻛﺎﺭﺑﻦ‬
‫ﻳﻌﻨﻰ ﺑﻨﺰﻳﻦ ﺩﺭ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺻﻮﺭﺕ ﻣﻴﮕﻴﺮﺩ ﻭ ﺍﻳﻦ ﺣﻠﻘﻪ ﺑﻪ ﺣﻴﺚ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺑﻪ ﺷﻤﺎﺭ ﻣﻴﺮﻭﺩ‪.‬‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻛﻪ ﺩﺍﺭﺍﻯ ﺣﻠﻘﻪ ﺑﻨﺰﻳﻦ ﺑﺎﺷﻨﺪ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺍﺭﻭﻣﺎﺕ ﻫﺎ ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ ﻭ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻛﻪ‬
‫ﺩﺍﺭﺍﻯ ﺣﻠﻘﻪ ﺑﻨﺰﻳﻦ ﻧﺒﺎﺷﻨﺪ ﺑﻪ ﻧﺎﻡ ﺍﻟﻴﻔﺎﺗﻴﻚ )ﺗﻴﻞ ﺳﺎﺯ( ﻳﺎﺩ ﻣﻴﮕﺮﺩﻧﺪ‪ .‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﺍﻟﻴﻔﺎﺗﻴﻚ ﻧﻈﺮ ﺑﻪ‬
‫ﻧﻮﻋﻴﺖ ﺭﺍﺑﻄﺔ ﺍﺗـــــــــــﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ – ﻛﺎﺭﺑﻦ ﺑﻪ ﻣﺸﺒﻮﻉ ﻭ ﻏﻴﺮ ﻣﺸﺒﻮﻉ ﺗﻘﺴﻴﻢ ﺷﺪﻩ ﺍﻧﺪ ‪ ،‬ﺍﻟﻴﻔﺎﺗﻴﻚ ﻫﺎﻯ‬
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‫ﻣﺸﺒﻮﻉ ﺑﻪ ﺍﻟﻜﺎﻥ ﻫﺎ )‪ ( Alkanes‬ﻭ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻥ ﻫﺎ ﺗﻘﺴﻴﻢ ﺷﺪﻩ ﺍﻧﺪ ‪ ،‬ﺍﻟﻴﻔﺎﺗﻴﻚ ﻫﺎﻯ ﻏﻴﺮ ﻣﺸﺒﻮﻉ ﺑﻪ ﺍﻟﻜﻴﻦ‬
‫ﻫﺎ )‪ ( Alkens‬ﻭ ﺍﻟﻜﺎﻳﻦ ﻫﺎ )‪ ( Alkynes‬ﺗﻘﺴﻴﻢ ﺷﺪﻩ ﺍﻧﺪ ‪.‬‬
‫ﺍﻟﻜﺎﻥ ﻫﺎ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺗﻤﺎﻡ ﻭﻻﻧﺲ ﻫﺎﻯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺗﻮﺳﻂ ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻣﺸﺒﻮﻉ‬
‫ﮔﺮﺩﻳﺪﻩ ﻭ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭ ﺁﻧﻬﺎ ﺩﺍﺭﺍﻯ ﺭﻭﺍﺑﻂ ﻳﮕﺎﻧﻪ ﻣﻴﺒﺎﺷﻨﺪ‪.‬‬
‫ﺍﻟﻜﻴﻦ ﻫﺎ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﺁﻧﻬﺎ ﺭﺍﺑﻄﻪ ﺩﻭﮔﺎﻧﻪ ﺑﺮ ﻗﺮﺍﺭ ﮔﺮﺩﻳﺪﻩ‪ ،‬ﻏﻴﺮ ﻣﺸﺒﻮﻉ‬
‫ﻣﻴﺒﺎﺷﻨﺪ‪ .‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻏﻴﺮ ﻣﺸﺒﻮﻉ ﺩﻳﮕﺮ ﺍﻟﻜﺎﻳﻦ ﻫﺎ ﺑﻮﺩﻩ‪ ،‬ﺩﺭ ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ‬
‫ﺳﻪ ﮔﺎﻧﻪ ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ﻭ ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﺎﻥ ﻫﺎ ﭼﻬﺎﺭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﻴﻦ ﻫﺎ ﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ﻛﻤﺘﺮ ﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺷﺎﮔﺮﺩﺍﻥ ﺑﻪ ﮔﺮﻭپ ﻫﺎﻯ ﻣﻨﺎﺳﺐ ﺗﻘﺴﻴﻢ ﮔﺮﺩﺩ‪ ،‬ﻫﺮ ﮔﺮﻭپ ﺗﻌﺪﺍﺩ ﺯﻳﺎﺩ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﻟﺴﺖ‬
‫ﻧﻤﻮﺩﻩ ﻭ ﺑﺎ ﺍ ﺭﺍﺋﻪ ﺩﻻﻳﻞ ﻣﻘﻨﻊ ﺁﻧﻬﺎ ﺭﺍ ﮔﺮﻭپ ﺑﻨﺪﻯ ﻧﻤﺎﻳﻨﺪ ﻭ ﺩﺭ ﻃﺒﻘﻪ ﺑﻨﺪﻯ ﻣﺮﻛﺒﺎﺕ ﺍﺯ ﺷﻴﻤﺎﻯ ﻓﻮﻕ‬
‫ﺍﺳﺘﻔﺎﺩﻩ ﻧﻤﺎﻳﻨﺪ‪.‬‬
‫‪ : 3- 3‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺩﺭ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ‬
‫ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺩﺭ ﺍﻧﻮﺍﻉ ﻣﺨﺘﻠﻒ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﻣﺮﻛﺒﺎﺕ ﻣﺨﺘﻠﻒ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ‬
‫ﻫﺎ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ‪ ،‬ﺍﻳﻦ ﮔﺮﻭپ ﻧﻈﺮ ﺑﻪ ﻃﺮﺯ ﺭﻭﺍﺑﻂ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ – ﻛﺎﺭﺑﻦ ﺑﻪ ﻣﻴﺎﻥ ﺁﻣﺪﻩ ﺍﻧﺪ ﻛﻪ ﺩﺭ‬
‫ﺟﺪﻭﻝ ﺫﻳﻞ ﺩﺭﺝ ﺷﺪﻩ ﺍﻧﺪ‪:‬‬
‫ﺟﺪﻭﻝ )‪ (1 - 3‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ‬
‫ﮔﺮﻭپ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ‬
‫‪Alkanes‬‬ ‫‪CH 3 − CH 3‬‬ ‫ﺍﻳﺘﺎﻥ‬ ‫‪-‬‬
‫‪Alkenes‬‬ ‫‪CH 2 = CH 2‬‬ ‫ﺍﻳﺘﻠﻴﻦ ﻳﺎ ﺍﻳﺘﻴﻠﻴﻦ‬ ‫ﺑﻘﻴﺔ ﺍﻟﻜﺘﺮﻭﻓﻴﻠﻴﻚ‬
‫‪Alkynes‬‬ ‫‪CH ≡ CH‬‬ ‫ﺍﻳﺘﺎﻳﻦ ﻳﺎ ﺍﺳﺘﻴﻠﻴﻦ‬ ‫ﺑﻘﻴﺔ ﺍﻟﻜﺘﺮﻭﻓﻴﻠﻴﻚ‬
‫‪Alkadienes‬‬ ‫‪CH 2 = CHCH = CH 2‬‬ ‫‪ - 1،3‬ﺑﻴﻮﺗﺎﺩﺍﻳﻦ‬ ‫ﺑﻘﻴﺔ ﺍﻟﻜﺘﺮﻭﻓﻴﻠﻴﻚ‬
‫‪Arenes‬‬ ‫ﺑﻨﺰﻳﻦ‬ ‫ﺍﺭﻭﻣﺎﺗﻴﻚ‬ ‫ﺗﻌﻮﻳﺾ‬
‫ﺍﻟﻜﺘﺮﻭﻓﻴﻠﻴﻚ‬
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 ‫‪ : 4- 3‬ﺳﻠﺴﻠﻪ ﻫﻮﻣﻮﻟﻮگ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺑﻪ ﺍﻧﺪﺍﺯﺓ ﻳﻚ ﮔﺮﻭپ ﻣﺘﻠﻴﻦ ) ‪ ( −CH −‬ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ ﺑﻪ ﻧﺎﻡ ﻫﻮﻣﻮﻟﻮگ )‪(Homologe‬‬
‫‪2‬‬
‫ﻳﻚ ﺩﻳﮕﺮ ﻳﺎﺩ ﻣﻰ ﺷﻮﻧﺪ‪ .‬ﺳﻠﺴﻠﻪ ﻫﻮﻣﻮﻟﻮگ ﺩﺭ ﺍﻟﻜﺎﻥ ﻫﺎ‪ ،‬ﺍﻟﻜﻴﻦ ﻫﺎ‪ ،‬ﻭ ﺍﻟﻜﺎﻳﻦ ﻫﺎ ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ‪ ،‬ﻃﻮﺭﻯ ﻛﻪ‬
‫ﺩﺭ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺍﻟﻜﺎﻥ ﻫﺎ ﻣﺸﺎﻫﺪﻩ ﻣﻴﺸﻮﺩ‪ ،‬ﻣﺮﻛﺐ ﺍﻳﺘﺎﻥ ﺍﺯ ﻣﺮﻛﺐ ﻗﺒﻠﻰ ﺧﻮﺩ ﻣﻴﺘﺎﻥ ﺑﻪ ﺍﻧﺪﺍﺯﺓ ﻳﻚ‬
‫) ‪ ( −CH 2 −‬ﻓﺮﻕ ﺩﺍﺭﺩ‪ ،‬ﺑﻪ ﻫﻤﻴﻦ ﺗﺮﺗﻴﺐ ﭘﺮﻭﭘﺎﻥ ﻧﺴﺒﺖ ﺑﻪ ﺍﻳﺘﺎﻥ ﻭ ﺑﻴﻮﺗﺎﻥ ﻧﺴﺒﺖ ﺑﻪ ﭘﺮﻭﭘﺎﻥ ﺑﻪ ﺍﻧﺪﺍﺯﺓ ﻳﻚ ﮔﺮﻭپ‬
‫ﻣﺘﻠﻴﻦ ) ‪ ( −CH 2 −‬ﺑﺰﺭگ ﺍﺳﺖ‪ .‬ﺍﻳﻦ ﺳﻠﺴﻠﻪ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮگ‪ (Homologe‬ﻳﺎﺩ ﻣﻰ ﻧﻤﺎﻳﻨﺪ‪.‬‬
‫ﺟﺪﻭﻝ )‪ ( 2 - 3‬ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮگ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﻧﺎﻡ ﻣﺮﻛﺐ‬ ‫ﻓﻮﺭﻭﻣﻮﻝ ﻣﺮﻛﺐ‬
‫‪Methane‬‬ ‫‪CH 4‬‬
‫‪Ethane‬‬ ‫‪CH3 − CH3‬‬
‫‪Propane‬‬ ‫‪CH3 − CH 2 − CH3‬‬
‫‪Butane‬‬ ‫‪CH3 − CH 2 − CH 2 − CH3‬‬
‫‪Pentane‬‬ ‫‪CH3 − CH 2 − CH 2 − CH 2 − CH3‬‬
‫‪Hexane‬‬ ‫‪CH3 − CH 2 − CH 2 − CH 2 − CH 2 − CH3‬‬
‫‪Heptane‬‬ ‫‪CH3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH3‬‬
‫‪Octane‬‬ ‫‪CH3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH3‬‬
‫‪Nonane‬‬ ‫‪CH3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 3‬‬
‫‪Decane‬‬ ‫‪CH 3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 3‬‬
‫‪Undecane‬‬ ‫‪CH 3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 3‬‬
‫‪Dodecane‬‬ ‫‪CH 3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 3‬‬
‫‪Tridecane‬‬ ‫‪CH 3 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 2 − CH 3‬‬
‫ﻋﻼﻭﻩ ﺍﺯ ﺍﺻﻄﻼﺡ ﻫﻮﻣﻮﻟﻮگ‪ ،‬ﺍﺻﻄﻼﺡ ﺍﻳﺰﻭﻟﻮگ ﻧﻴﺰ ﺩﺭ ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﺑﻪ ﻛﺎﺭﺑﺮﺩﻩ ﻣﻴﺸﻮﺩ ‪ ،‬ﻣﻔﻬﻮﻡ ﺍﻳﻦ‬
‫ﺍﺻﻄﻼﺡ ﻣﻴﺮﺳﺎﻧﺪ ‪ :‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻛﻪ ﺩﺍﺭﺍﻯ ﻋﻴﻦ ﺗﻌﺪﺍﺩﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺑﺎﺷﻨﺪ ﺑﻪ ﻧﺎﻡ‬
‫ﺍﻳﺰﻭﻟﻮگ ﻳﻚ ﺩﻳﮕﺮ ﻳﺎﺩ ﻣﻰ ﺷﻮﻧﺪ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺷﺎﮔﺮﺩﺍﻥ ﺑﻪ ﭼﻨﺪ ﮔﺮﻭپ ﻣﻨﺎﺳﺐ ﺗﻘﺴﻴﻢ ﮔﺮﺩﻧﺪ ﺗﺎ ﻫﺮ ﮔﺮﻭپ ﺑﻪ ﻃﻮﺭ ﺟﺪﺍﮔﺎﻧﻪ ﺭﺍﺟﻊ ﺑﻪ ﺍﺻﻄﻼﺡ‬
‫ﻫﻮﻣﻮﻟﻮگ ﺩﺭ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻣﺒﺎﺣﺜﻪ ﻧﻤﺎﻳﻨﺪ ﻭ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺍﻳﺘﻠﻴﻦ ﺍﻟﻰ ﻫﮕﺰﻳﻦ ﻭ ﺍﺳﺘﻠﻴﻦ ﺍﻟﻰ‬
‫ﺍﻭﻛﺘﺎﻳﻦ ﺭﺍ ﺗﺤﺮﻳﺮ ﻧﻤﻮﺩﻩ ﻭ ﺍﺷﻜﺎﻝ ﻫﻮﻣﻮﻟﻮﮔﻰ ﺭﺍ ﺩﺭ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﻣﺬﻛﻮﺭ ﺗﻮﺿﺢ ﻭ ﺗﺸﺮﻳﺢ ﻧﻤﺎﻳﻨﺪ‬
‫ﻭ ﻧﻤﺎﻳﻨﺪﺓ ﻫﺮ ﮔﺮﻭپ ﻛﺎﺭ ﻫﺮ ﮔﺮﻭپ ﺭﺍ ﺍﺭﺍﺋﻪ ﺑﺪﺍﺭﺩ‪.‬‬
‫‪40‬‬
 ‫‪ : 5 – 3‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻭ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ )ﻣﺸﺘﻘﺎﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ(‬
‫ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﻋﺒﺎﺭﺕ ﺍﺯ ﻛﻴﻤﻴﺎﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻭ ﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﻣﻰ ﺑﺎﺷﺪ‬
‫ﺍﮔﺮ ﻳﻚ ﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺍﺗﻮﻣﻬﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﺑﻪ ﮔﺮﻭﭘﻬﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ)‪(Functional groups‬‬
‫ﻣﺸﺨﺺ ﺗﻌﻮﻳﺾ ﮔﺮﺩﺩ‪ ،‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ﻛﻪ ﺑﻪ ﻧﺎﻡ ﻣﺸﺘﻘﺎﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻳﺎﺩ ﻣﻰ ﺷﻮﻧﺪ‪.‬‬
‫ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ)‪ (Functional groups‬ﻋﺒﺎﺭﺕ ﺍﺯ ﺍﺗﻮﻣﻬﺎﻭ ﻳﺎ ﮔﺮﻭﭘﻰ ﺍﺯ ﺍﺗﻮﻣﻬﺎ ﺩﺭﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﺑﻮﺩﻩ ﻛﻪ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﻣﻌﻴﻦ ﻭ ﻣﺸﺨﺺ ﻣﻴﺒﺎﺷﻨﺪ ﻭ ﺑﺎﻋﺚ ﺗﺒﺎﺭﺯ ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﻓﺰﻳﻜﻰ‬
‫ﻣﺸﺨﺺ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻣﻴﮕﺮﺩﻧﺪ‪ .‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﺩﺍﺭﻧﺪﻩ ﻋﻴﻦ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺩﺍﺭﺍﻯ ﺧﻮﺍﺹ‬
‫ﻛﻴﻤﻴﺎﻭﻯ ﻳﻜﺴﺎﻥ ﺍﻧﺪ‪:‬‬
‫ﺟﺪﻭﻝ )‪ (3 - 3‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ‬
‫ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ‬ ‫ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﻣﺮﻛﺐ ﻧﺎﻡ ﮔﺮﻭپ ﻭﻇﻴﻔﻮﻯ‬ ‫ﻣﺮﻛﺐ‬ ‫ﻧﺎﻡ ﻣﺮﻛﺐ‬
‫‪CH 3 − X‬‬
‫) ‪(− F − Cl − Br − I‬‬
‫ﻫﻼﻳﺪﻫﺎ‬ ‫‪R− X‬‬ ‫‪Methyl halide‬‬
‫) ‪(Halyds‬‬
‫‪− OH‬‬ ‫‪Hydroxyl‬‬ ‫‪R − OH‬‬ ‫‪CH 3 − CH 2 − OH‬‬ ‫‪Ethano‬‬
‫‪O‬‬ ‫‪Carbonyl‬‬ ‫‪Aldihydes‬‬ ‫‪O‬‬ ‫‪Pr opanal‬‬
‫‪//‬‬
‫‪//‬‬ ‫‪O‬‬ ‫‪CH − CH − C − H‬‬
‫‪− C −‬‬ ‫‪//‬‬
‫‪3‬‬ ‫‪2‬‬
‫‪R − C− H‬‬ ‫‪O‬‬
‫‪O‬‬
‫‪//‬‬ ‫‪//‬‬ ‫‪Pr opanon‬‬
‫‪R − C− R‬‬ ‫‪CH 3 − C −CH 3‬‬
‫‪Ketones‬‬
‫‪− COOH‬‬ ‫‪Carboxyl‬‬ ‫‪R − COOHacide‬‬ ‫‪CH 3 − COOH‬‬ ‫‪aceticacid‬‬
‫‪Oxy‬‬ ‫‪Oxy‬‬ ‫‪R −O − R‬‬ ‫‪CH3 − O − CH3 Eteres‬‬ ‫‪Dimethyleter‬‬
‫‪EsterGroup‬‬ ‫‪O‬‬ ‫‪O‬‬ ‫‪Dimethylester‬‬
‫‪//‬‬ ‫‪//‬‬
‫‪O‬‬ ‫‪R − C − O − R Ester‬‬ ‫‪H − C − O − CH‬‬
‫‪3‬‬ ‫‪3‬‬
‫‪//‬‬
‫‪− C −O −‬‬
‫‪− NH 2‬‬ ‫‪R − NH Amines‬‬
‫‪2‬‬
‫‪R − NH Amines‬‬
‫‪2‬‬ ‫‪C H3 − N H2‬‬ ‫‪Methylamin es‬‬
‫‪O‬‬ ‫‪AmidesGroup‬‬ ‫‪O‬‬ ‫‪O‬‬ ‫‪Methylamide‬‬
‫‪//‬‬ ‫‪//‬‬ ‫‪//‬‬
‫‪− C − N H2‬‬ ‫‪R − C − N H2‬‬ ‫‪C H3 − C − N H2‬‬
‫‪−S −H‬‬ ‫‪MarcaptanGroup‬‬ ‫‪R−S −H‬‬ ‫‪C H3 − C H2 − S − H‬‬ ‫‪Marcaptan e‬‬
‫‪−S −‬‬ ‫‪Thioether‬‬ ‫‪− S − R Thioether‬‬ ‫‪C H3 − S − C H3‬‬ ‫‪Dimethylthioether‬‬
‫‪− SO3 H‬‬ ‫‪SulphoGroup‬‬ ‫‪Sulphocomp‬‬ ‫‪ound‬‬
‫‪C H − SO H‬‬ ‫‪BenzSulphonic−‬‬
‫‪6 5‬‬ ‫‪3‬‬
‫‪R − SO‬‬
‫‪3‬‬ ‫‪− acid‬‬
‫ﻧﻈﺮ ﺑﻪ ﻧﻮﻋﻴﺖ ﻫﺘﺮﻭﺍﺗﻮﻡ ﻫﺎﻯ ﻛﻪ ﺩﺭ ﺗﺮﻛﻴﺐ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺷﺎﻣﻞ ﺍﻧﺪ‪ ،‬ﺁﻧﻬﺎﺭﺍ ﺑﻪ ﮔﺮﻭپ ﻫﺎﻯ ﺫﻳﻞ‬
‫ﺗﻘﺴﻴﻢ ﻧﻤﻮﺩﻩ ﺍﻧﺪ‪:‬‬
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 ‫‪ :1 –5-3‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﻛﺴﻴﺠﻦ ﺩﺍﺭ‪ :‬ﺩﺭ ﺗﺮﻛﻴﺐ ﺍﻳﻦ ﮔﺮﻭپ ﻫﺎ ﺍﻛﺴﻴﺠﻦ ﺑﻪ ﺣﻴﺚ ﻫﺘﺮﻭ ﺍﺗﻮﻡ‬
‫‪O‬‬ ‫‪O‬‬
‫‪ //‬ﻭ ﻏﻴﺮﻩ ﺍﺭﺍﺋﻪ ﻛﺮﺩ‪.‬‬ ‫‪//‬‬ ‫ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﻣﺜﺎﻝ ﺁﻥ ﺭﺍ ﻣﻴﺘﻮﺍﻥ‬
‫‪− C − O − , − O − , − C − OH‬‬
‫‪ :2-5-3‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺩﺍﺭ‪ :‬ﺩﺭ ﺗﺮﻛﻴﺐ ﺍﻳﻦ ﮔﺮﻭپ ﻫﺎ‪ ،‬ﺍﺗﻮﻡ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺑﻪ ﺣﻴﺚ ﻫﺘﺮﻭ ﺍﺗﻮﻡ‬
‫‪O‬‬
‫ﻫﺎ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﻣﺜﺎﻝ ﺁﻥ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ‪ − NO , − C− NH ,−NH‬ﻭ ﻏﻴﺮﻩ ﺍﺭﺍﺋﻪ ﻛﺮﺩ‪.‬‬
‫‪//‬‬
‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬
‫‪ : 3-5-3‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺳﻠﻔﺮ ﺩﺍﺭ‪ :‬ﺩﺭ ﺗﺮﻛﻴﺐ ﺍﻳﻦ ﮔﺮﻭپ ﻫﺎ‪ ،‬ﺍﺗﻮﻡ ﺳﻠﻔﺮ ﺑﻪ ﺣﻴﺚ ﻫﺘﺮﻭ ﺍﺗﻮﻡ ﺩﺭ‬
‫ﺗﺮﻛﻴﺐﮔﺮﻭپﻣﺬﻛﻮﺭﻣﻮﺟﻮﺩﺍﺳﺖﻛﻪﻣﺜﺎﻝﺁﻥﺭﺍﻣﻰﺗﻮﺍﻥ‪ − SO 3 H , − S − , − S − H‬ﻭﻏﻴﺮﻩﺍﺭﺍﺋﻪﻛﺮﺩ‪.‬‬
‫‪ : 4-5-3‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﻓﺎﺳﻔﻮﺭ ﺩﺍﺭ‪ :‬ﺩﺭ ﺗﺮﻛﻴﺐ ﺍﻳﻦ ﮔﺮﻭپ ﻫﺎ‪ ،‬ﺍﺗﻮﻡ ﻓﺎﺳﻔﻮﺭ ﺑﻪ ﺣﻴﺚ ﻫﺘﺮﻭ ﺍﺗﻮﻡ‬
‫ﺩﺭﮔﺮﻭﭘﻬﺎﻯ ﻣﺬﻛﻮﺭ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﻣﺜﺎﻝ ﺁﻥ ﺭﺍ ﻣﻰ ﺗﻮﺍﻥ ‪ − H PO , − PH‬ﻭ ﻏﻴﺮﻩ ﺍﺭﺍﺋﻪ ﻛﺮﺩ‪.‬‬
‫‪2‬‬ ‫‪3‬‬ ‫‪2‬‬
‫ﺗﻌﺪﺍﺩ ﻣﻌﻠﻮﻡ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺩﺭ ﺍﻳﻦ ﻋﺼﺮ ﻓﻮﻕ ﺍﻟﻌﺎﺩﻩ ﺯﻳﺎﺩ ﺍﺳﺖ ﻛﻪ ﺣﺘﻰ ﺩﺭﻛﺘﺎﺏ ﻫﺎﻯ ﺑﺰﺭگ ﻭ‬
‫ﺣﺠﻴﻢ ﻛﻴﻤﻴﺎﻯ ﻋﻀﻮﻯ ﻳﻚ ﺗﻌﺪﺍﺩ ﻛﻢ ﺁﻥ ﻣﻮﺭﺩ ﺑﺮﺭﺳﻰ ﻗﺮﺍﺭ ﻣﻴﮕﻴﺮﺩ‪.‬‬
‫ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻣﻴﺘﻮﺍﻧﺪ ﭼﻨﺪﻳﻦ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻭﺟﻮﺩ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ‪ ،‬ﺩﺭ ﺻﻮﺭﺗﻰ ﻛﻪ‬
‫ﺍﻳﻦ ﮔﺮﻭپ ﻫﺎ ﻫﻢ ﻧﻮﻉ ﺑﺎﺷﺪ )ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪ :‬ﺩﻭ ﮔﺮﻭپ ﻫﻠﻮﺟﻦ ﻭ ﻳﺎ ﺩﻭ ﮔﺮﻭپ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ ﻭ ﻏﻴﺮﻩ( ﺍﻳﻦ‬
‫ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﭼﻨﺪﻳﻦ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﻳﺎﺩ ﻣﻴﻨﻤﺎﻳﻨﺪ‪ .‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻛﻪ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺁﻧﻬﺎ‬
‫ﭼﻨﺪﻳﻦ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ )‪ (Polyfunct ional groups‬ﻣﺨﺘﻠﻒ ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ‪،‬ﺑﻪ ﻧﺎﻡ ﻣــــــﺮﻛﺒﺎﺗﻰ ﺩﺍﺭﺍﻯ‬
‫ﮔــــــﺮﻭپ ﻫﺎﻯ ﻣﺨﺘﻠﻒ ﺗﺮﻛﻴﺐ )‪ (Hetro Functional groups‬ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ‪.‬‬
‫ﺩﺭ ﺫﻳﻞ ﻣﺜﺎﻝ ﻫﺎﻯ ﻣﺮﻛﺒﺎﺕ ﻣﻮﻧﻮ‪ ،‬ﭘﻮﻟﻰ‪ ،‬ﻭ ﻫﺘﺮﻭ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ‪:‬‬
‫ﻣﺮﻛﺐ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ ﻣﻮﻧﻮ ﻓﻮﻧﮕﺸﻨﺎﻝ ﮔﺮﻭپ ‪CH 3 − CH 2 − OH‬‬
‫ﻣﺮﻛﺐ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ ﭘﻮﻟﻰ ﻓﻮﻧﮕﺸﻨﺎﻝ ﮔﺮﻭپ ‪HOCH 2 − CH (OH ) − CH 2 OH‬‬
‫ﻣﺮﻛﺐ ﻫﺘﺮﻭﻓﻮﻧﮕﺸﻨﺎﻝ ﮔﺮﻭپ )ﺍﻣﻴﻨﻮ ﺍﺳﻴﺪ( ‪H 2 N − CH 2 − CH 2 − COOH‬‬
‫ﻣﺮﻛﺐ ﻫﺘﺮﻭﻓﻮﻧﮕﺸﻨﺎﻝ ﮔﺮﻭپ )ﺳﻴﺘﻮ ﺍﺳﻴﺪ( ‪CH 3 − CO − CH 2 − COOH‬‬
‫‪ :6-3‬ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺑﺎ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ‬
‫‪ :1-6-3‬ﻣﺸﺨﺼﺎﺕ ﺑﻌﻀﻰ ﺍﺯ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ‬
‫‪ -1‬ﮔﺮﻭپ ﻫﻼﻳﺪ ﻫﺎ‪ :‬ﺍﮔﺮ ﺭﺍﺑﻄﺔ ﺍﺗﻮﻡ ﻫﺎﻯ ﻣﺎﻟﻴﻜﻮﻝ ﻋﻨﺎﺻﺮ ﻫﻠﻮﺟﻦ ﻫﺎ ﺑﻪ ﺷﻜﻞ ﻫﻮﻣﻮﻟﻴﺘﻴﻜﻰ ﻗﻄﻊ‬
‫ﮔﺮﺩﺩ‪ ،‬ﺭﺍﺩﻳﻜﺎﻝ ﻫﺎﻯ ﺁﻥ ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ ﻛﻪ ﺑﻪ ﺷﻜﻞ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺭﺍ ﺗﻌﻮﻳﺾ ﻣﻰ ﻧﻤﺎﻳﻨﺪ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪:‬‬
‫‪Cl‬‬ ‫→‬ ‫• ‪Cl • + Cl‬‬
‫‪2‬‬
‫ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻫﻼﻳﺪ ﻫﺎ ﺩﺍﺭﺍﻯ ﺍﻟﻜﺘﺮﻭﻥ ﻃﺎﻗﻪ ﺑﻮﺩﻩ ﻭ ﻓﻌﺎﻝ ﻣﻰ ﺑﺎﺷﺪ؛ ﺍﺯ ﺍﻳﻦ ﺳﺒﺐ ﺑﻪ ﺁﺳﺎﻧﻰ ﺗﻌﺎﻣﻞ‬
‫ﻧﻤﻮﺩﻩ ﻭ ﻣﺸﺘﻘﺎﺕ ﻫﻠﻮﺟﻨﻰ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎﺭﺍﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ‪:‬‬
‫‪R − H + Cl‬‬ ‫→‬ ‫‪R − Cl + HCl‬‬
‫‪2‬‬
‫‪42‬‬
 ‫‪H‬‬ ‫‪H‬‬
‫‪Cl‬‬ ‫‪Cl‬‬
‫‪H‬‬ ‫‪H‬‬
‫‪Br‬‬ ‫‪Br‬‬
‫ﺷﻜﻞ )‪ ( 1 – 3‬ﻣﻮﺩﻝ ﺑﺮﻭﻣﻮ ﻛﻠﻮﺭﻭ ﻣﻴﺘﺎﻥ‬
‫ﺫﺭﺍﺗﻰ ﻛﻪ ﺩﺍﺭﺍﻯ ﺍﻟﻜﺘﺮﻭﻥ ﻫﺎ ﻃﺎﻗﻪ ﺑﻮﺩﻩ ﺑﺎﺷﻨﺪ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺭﺍﺩﻳﻜﺎﻝ ﻫﺎ )‪ (Radicals‬ﻳﺎﺩ ﻣﻴﺸﻮﺩ‪.‬‬
‫‪-2‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ‬
‫ﮔﺮﻭپ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ ﻣﺘﺸﻜﻞ ﺍﺯ ﻳﻚ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﻳﻚ ﺍﺗﻮﻡ ﺍﻛﺴﻴﺠﻦ ﺑﻮﺩﻩ ﻛﻪ ﺍﺗﻮﻡ ﺍﻛﺴﻴﺠﻦ‬
‫ﺩﺭ ﺁﻥ ﺩﺍﺭﺍﻯ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻃﺎﻗﻪ ﻣﻰ ﺑﺎﺷﺪ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻥ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ‪:‬‬
‫‪−‬‬
‫‪− O− H‬‬
‫‪−‬‬
‫ﺷﻜﻞ )‪ ( 2 - 3‬ﻣﻮﺩﻝ ﮔﺮﻭپ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ‬
‫ﻣﺮﻛﺒﺎﺕ ﺩﺍﺭﻧﺪﺓ ﮔﺮﻭپ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﻮﻟﻬﺎ )‪ (A lcoholes‬ﻳﺎﺩ ﻣﻴﺸﻮﻧﺪ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺍﻟﻜﻮﻝ ﻫﺎ‬
‫‪ R − O − H‬ﺑﻮﺩﻩ ﻛﻪ ﺩﺭ ﺍﻳﻦ ﻓﻮﺭﻣﻮﻝ ‪R‬ﺭﺍﺩﻳﻜﺎﻝ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺭﺍ ﺍﻓﺎﺩﻩ ﻣﻴﻨﻤﺎﻳﺪ‪.‬‬
‫ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻛﻪ ﺑﻪ ﺁﻥ ﮔﺮﻭپ ﻭﻇﻴﻔﻮﻯ ﺍﻟﻜﻮﻝ ﻫﺎ ) ‪ (−OH‬ﻭﺻﻞ ﺍﺳﺖ ﺑﺎ ﺍﻳﻦ ﮔﺮﻭپ ﺟﻤﻌﺎً ﺑﻪ ﻧﺎﻡ ﻛﺎﺭﺑﻴﻨﻮﻝ‬
‫‪OH‬‬
‫‪ (Carbinol) − C| −‬ﻳﺎﺩ ﻣﻴﺸﻮﺩ‪.‬‬
‫ﻧﻈﺮ ﺑﻪ ﺭﺍﺑﻄﺔ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﮔﺮﻭپ ﻛﺎﺭﺑﻴﻨﻮﻝ‪ ،‬ﺍﻟﻜﻮﻝ ﻫﺎ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﻮﻝ ﻫﺎﻯ ﺍﻭﻟﻰ‪ ،‬ﺩﻭﻣﻰ ﻭ ﺳﻮﻣﻰ ﻳﺎﺩ ﻣﻰ ﻧﻤﺎﻳﻨﺪ‪.‬‬
‫ﺍﮔﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﮔﺮﻭپ ﻛﺎﺭﺑﻴﻨﻮﻝ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺧﻮﺩ ﺭﺍ ﺑﺎ ﻳﻚ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻏﺮﺽ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ‬
‫ﺑﻪ ﻣﺼﺮﻑ ﺭﺳﺎﻧﻴﺪﻩ ﺑﺎﺷﺪ‪ ،‬ﺍﻟﻜﻮﻝ ﻣﺬﻛﻮﺭ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﻮﻝ ﺍﻭﻟﻰ ﻳﺎﺩ ﻣﻰ ﻧﻤﺎﻳﻨﺪ‪ ،‬ﺩﺭ ﺻﻮﺭﺗﻰ ﻛﻪ ﺑﺎ ﺩﻭ ﻛﺎﺭﺑﻦ‬
‫‪43‬‬
‫ﺭﺍﺑﻄﻪ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﻮﻝ ﺩﻭﻣﻰ ﻳﺎﺩ ﻣﻴﮕﺮﺩﻧﺪ‪ .‬ﺍﮔﺮ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﮔﺮﻭپ ﻛﺎﺭﺑﻴﻨﻮﻝ ﺳﻪ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ‬
‫ﺧﻮﺩ ﺭﺍ ﺑﺎ ﺳﻪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﻳﮕﺮ ﻏﺮﺽ ﺗﺸﻜﻴﻞ ﺭﻭﺍﺑﻂ ﺑﻪ ﻣﺼﺮﻑ ﺭﺳﺎﻧﻴﺪﻩ ﺑﺎﺷﺪ‪ ،‬ﺍﻳﻦ ﻧﻮﻉ ﺍﻟﻜﻮﻝ ﺭﺍ ﺑﻪ ﻧﺎﻡ‬
‫ﺍﻟﻜﻮﻝ ﺳﻮﻣﻰ ﻳﺎﺩ ﻣﻰ ﻧﻤﺎﻳﻨﺪ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺑﻪ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺫﻳﻞ ﺩﻗﻴﻖ ﺷﺪﻩ‪ ،‬ﻧﻮﻉ ﺍﻟﻜﻮﻝ ﺍﻭﻟﻰ‪ ،‬ﺩﻭﻣﻰ ﻭ ﺳﻮﻣﻰ ﺭﺍ ﺩﺭ ﺁﻧﻬﺎ ﺗﺸﺨﻴﺺ ﻧﻤﻮﺩﻩ ﻭ‬
‫ﻫﻢ ﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﺪ ﻛﻪ ﺍﻟﻜﻮﻝ ﭼﻬﺎﺭﻣﻰ ﻭ ﺑﺎﻻﺗﺮ ﺍﺯ ﺁﻥ ﻧﻴﺰ ﻣﻮﺟﻮﺩ ﺧﻮﺍﻫﺪ ﺑﻮﺩ ﻭ ﻳﺎ ﺧﻴﺮ؟‬
‫‪CH‬‬ ‫‪− CH‬‬ ‫‪− OH, CH‬‬ ‫‪− C(CH‬‬ ‫‪) − OH, CH(CH ) − OH, CH − OH‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪3 2‬‬ ‫‪3 2‬‬ ‫‪3‬‬
‫‪ - 3‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎ ﻭ ﻛﻴﺘﻮﻥ ﻫﺎ )ﻛﺎﺭﺑﻮﻧﻴﻞ(‬
‫ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻧﻴﻞ ﻣﺘﺸﻜﻞ ﺍﺯ ﻳﻚ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭ ﻳﻚ ﺍﺗﻮﻡ ﺍﻛﺴﻴﺠﻦ ﺍﺳﺖ ﻛﻪ ﺑﻴﻦ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭ ﺍﻛﺴﻴﺠﻦ‬
‫ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺑﺮ ﻗﺮﺍﺭ ﻣﻰ ﺑﺎﺷﺪ‪..‬‬
‫ﺭﺍﺑﻄﺔ ﺑﻴﻦ ﺍﺗﻮﻡ ﺍﻛﺴﻴﺠﻦ – ﻛﺎﺭﺑﻦ ﺩﺭ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻧﻴﻞ ﺩﻭﮔﺎﻧﻪ ﺑﻮﺩﻩ ﻛﻪ ﻳﻚ ﺭﺍﺑﻄﺔ ﺁﻥ ﺳﮕﻤﺎ ) ‪ (D‬ﻭ ﺩ‬
‫ﻳﮕﺮ ﺁﻥ ﭘﺎﻯ) ‪ (P‬ﺍﺳﺖ‪ .‬ﺯﺍﻭﻳﺔ ﺭﻭﺍﺑﻂ ﺑﻴﻦ ﺁﻧﻬﺎ ‪120‬ﻣﻰ ﺑﺎﺷﺪ‪ .‬ﻃﻮﻝ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ‪ 1.24 A‬ﺍﺳﺖ‪ .‬ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ‬
‫‪o‬‬
‫‪o‬‬
‫ﺢ ﺍﺳﺖ ﻛﻪ ﺍﺷﻜﺎﻝ ﺫﻳﻞ ﺍﻳﻦ ﺳﺎﺧﺘﻤﺎﻥ ﺭﺍ‬ ‫ﺩﺭ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻧﻴﻞ ﺩﺍﺭﺍﻯ ﻫﻴﺒﺮﻳﺪ ‪ SP‬ﺑﻮﺩﻩ ﻭ ﺳﺎﺧﺘﻤﺎﻥ ﺁﻥ ﻣﺴﻄﺢ‬
‫‪2‬‬
‫ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ‪:‬‬
‫ﺷﻜﻞ )‪ (2 - 3‬ﻓﻮﺭﻣﻮﻝ ﻭﻣﻮﺩﻝ ﺳﺎﺧﺘﻤﺎﻥ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻧﻴﻞ‬
‫ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ‪ C = O‬ﺑﺮ ﺧﻼﻑ ‪ C = C‬ﺑﻨﺎﺑﺮ ﻣﻮﺟﻮﺩﻳﺖ ﻋﻨﺼﺮ ﺍﻟﻜﺘﺮﻭﻧﻴﮕﺎﺗﻴﻒ ﺍﻛﺴﻴﺠﻦ ﻛﻪ ﻛﺜﺎﻓﺖ ﺍﻟﻜﺘﺮﻭﻧﻰ‬
‫ﺭﺍﺑﻄﺔ ‪ P‬ﺭﺍ ﺑﻪ ﻃﺮﻑ ﺧﻮﺩ ﻛﺶ ﻣﻰ ﻧﻤﺎﻳﻴﺪ‪ ،‬ﻓﻮﻕ ﺍﻟﻌﺎﺩﻩ ﻗﻄﺒﻰ ﻣﻰ ﺑﺎﺷﺪ‪ ،‬ﺍﻳﻦ ﻗﻄﺒﻴﺖ ﺑﺎﻻﻯ ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ‬
‫ﻭﻛﻴﻤﻴﺎﻭﻯ ﻣﺮﻛﺒﺎﺕ ﻛﺎﺭﺑﻮﻧﻴﻞ )ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎ ﻭ ﻛﻴﺘﻮﻥ ﻫﺎ( ﺗﺎﺛﻴﺮ ﻭﺍﺭﺩ ﻣﻰ ﻧﻤﺎﻳﻴﺪ ﻭ ﺍﻛﺜﺮ ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎﻭ ﻛﻴﺘﻮﻥ‬
‫ﻫﺎ ﺩﺭ ﺁﺏ ﺑﻪ ﺧﻮﺑﻰ ﺣﻞ ﻣﻴﮕﺮﺩﻧﺪ‪.‬‬
‫‪ - 4‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﻭ ﻣﺮﻛﺒﺎﺕ ﺁﻥ )‪(Carboxylic Group‬‬
‫ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﺍﺳﻴﺪ ﻫﺎ ﺑﻪ ﻧﺎﻡ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﻳﺎﺩ ﻣﻰ ﺷﻮﺩ ﻛﻪ ﻓﻮﺭﻣﻮﻝ ﺁﻥ ‪ − COOH‬ﻣﻴﺒﺎﺷﺪ‪.‬‬
‫ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻥ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ‪:‬‬
‫‪O‬‬
‫‪//‬‬
‫‪− C −O − H‬‬
‫ﺷﻜﻞ ) ‪ ( 3 – 3‬ﻣﻮﺩﻝ ﻣﺎﻟﻴﻜﻮﻝ ﺍﺳﻴﺘﻴﻚ ﺍﺳﻴﺪ ﺣﺎﻭﻯ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ‬
‫‪44‬‬
‫ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﻣﺘﺸﻜﻞ ﺍﺯ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻧﻴﻞ ﻭ ﻳﻚ ﮔﺮﻭپ ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ ﺑﻮﺩﻩ ﻛﻪ ﺍﻛﺜﺮﺍ ً ﺑﻪ‬
‫ﺷﻜﻞ ‪ − COOH‬ﺗﺤﺮﻳﺮﻣﻴﮕﺮﺩﺩ ؛ ﺍﻣﺎﺭﺍﺑــﻄﻪ ﺑﻴﻦ ‪ O − O‬ﻫﺮﮔﺰﻣﻮﺟﻮﺩ ﻧﻤﻴـــﺒﺎﺷﺪ‪ .‬ﺍﻳﻦ ﮔﺮﻭپ ﻣﻴــﺘﻮﺍﻧﺪ‬
‫) ‪ (Proton − Donator‬ﭘﺮﻭﺗﻮﻥ ﺩﻫﻨﺪﻩ ﻋﻤﻞ ﻧﻤﺎﻳﻨﺪ ﻭ ﺑﻪ ﺁﻳﻮﻥ ‪ − C O O‬ﺑﻪ ﻧﺎﻡ ﻛﺎﺭﺑﻮﻛﺴﻼﺕ ﻣﺒﺪﻝ ﮔﺮﺩﺩ‪.‬‬
‫‪−‬‬
‫ﺩﺭ ﺍﻳﻦ ﺁﻳﻮﻥ ﻫﺮ ﺩﻭ ﺍﺗﻮﻡ ﺍﻛﺴﻴﺠﻦ ﻋﻴﻦ ﺍﺭﺯﺵ ﺭﺍﺩﺍﺭﺍ ﺍﻧﺪ‪ ،‬ﺯﻳﺮﺍ ﺍﻟﻜﺘﺮﻭﻥ ﺩﺭ ﺁﻥ ﺩﺭ ﺣﺎﻟﺖ ﺭﻳﺰﻭﻧﺎﻧﺲ‬
‫ﻣﻴﺒﺎﺷﺪ‪:‬‬
‫ﺗﻤﺎﻡ ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺩﺍﺭﺍﻯ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﺩﺭ ﺗﺮﻛﻴﺐ ﻣﺎﻟﻴﻜــــــﻮﻟﻰ ﺧﻮﺩ ﺑﺎﺷﻨـــــﺪ‪،‬ﺑﻪ ﻧﺎﻡ ﻣﺮﻛﺒﺎﺕ‬
‫ﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﺍﺳﻴﺪ ﻳﺎﺩ ﻣﻴﺸﻮﻧﺪ‪.‬‬
‫ﻼ ﺗﺤﺮﻳﺮ ﻣﻴﮕﺮﺩﺩ‪ .‬ﻣﻮﺟﻮﺩﻳﺖ ﺍﺗﻮﻡ ﻫﺎﻯ‬ ‫ﻣﺸﺨﺼﺎﺕ ﺭﺍﺑﻄﻪ ﻳﻰ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﺍﺳﻴﺪﻫﺎ ﻛﻪ ﺫﻳ ً‬
‫ﺍﻛﺴﻴﺠﻦ ‪ ،‬ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﻛﺎﺭﺑﻦ ﺑﺎﺍﻟﻜﺘﺮﻭﻧﻴﮕﺎﺗﻴﻮﺗﻰ ﻣﺨﺘﻠﻒ ﻣﺎﻟﻴﻜﻮﻝ ﺁﻥ ﺭﺍ ﻗﻄﺒﻰ ﻣﻴﺴﺎﺯﺩ‪:‬‬
‫ﺟﺪﻭﻝ )‪ ( 4 - 3‬ﻣﺸﺨﺼﺎﺕ ﺗﻴﺰﺍﺏ ﻫﺎ‬
‫ﻑﻭﺭﻣﻮﻝ‬ ‫ﻧﺎﻡ ﻣﺮﻭﺟﻪ‬ ‫‪Pka1‬‬ ‫‪Pka 2‬‬ ‫ﻧﻘﻄﻪ ﺫﻭﺑﺎﻥ‬ ‫ﻧﻘﻄﻪ ﻏﻠﻴﺎﻥ‬
‫‪H − COOH‬‬ ‫‪ 3.75‬ﻓﺎﺭﻣﻴﻚ ﺍﺳﻴﺪ‬ ‫‪8o C‬‬ ‫‪101C o‬‬
‫‪CH‬‬
‫‪3‬‬
‫‪− COOH‬‬ ‫‪ 4.75‬ﺍﺳﻴﺘﻴﻚ ﺍﺳﻴﺪ‬ ‫‪17o C‬‬ ‫‪118C o‬‬
‫‪CH Cl − COOH‬‬
‫‪2‬‬ ‫‪ 2.86‬ﻛﻠﻮﺭﻭﺍﺳﻴﺘﻴﻚ ﺍﺳﻴﺪ‬ ‫‪63o C‬‬ ‫‪189C o‬‬
‫‪CH Cl − COOH‬‬
‫‪2‬‬
‫‪ 4.87‬ﭘﺮﻭﭘﺎﻧﻮﺋﻴﻚ ﺍﺳﻴﺪ‬ ‫‪− 2 1o C‬‬ ‫‪1 4 1o C‬‬
‫‪C H COOH‬‬
‫‪6 5‬‬ ‫‪ 4.20‬ﺑﻨﺰﻭﺋﻴﻚ ﺍﺳﻴﺪ‬ ‫‪122o C‬‬ ‫‪2 4 9o C‬‬
‫‪HOOC − COOH‬‬ ‫‪ 1.23‬ﺍﻛﺰﺍﻟﻴﻚ ﺍﺳﻴﺪ‬ ‫ﺗﺨﺮﻳﺐ ) ‪4.28 190 o C ( d‬‬
‫‪HOOC − CH‬‬
‫‪2‬‬
‫‪− COOH‬‬ ‫‪ 2.83‬ﻣﺎﻟﻮﺗﻴﻚ ﺍﺳﻴﺪ‬ ‫ﺗﺨﺮﻳﺐ ) ‪5.69 136 o C ( d‬‬
‫‪ - 5‬ﮔﺮﻭپ ﺍﻳﺘﺮ )‪(−O −‬‬
‫ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺩﺭ ﺁﻧﻬﺎ ﺍﺗﻮﻡ ﺍﻛﺴﻴﺠﻦ ﺑﺎ ﺩﻭ ﺑﻘﻴﻪ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻣﺮﺗﺒﻂ ﺑﺎﺷﺪ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺍﻳﺘﺮ ﻳﺎﺩ ﺷﺪﻩ ﻭ ﺍﻳﻦ‬
‫ﮔﺮﻭپ ﺳﺎﺧﺘﻤﺎﻥ )‪ (−O −‬ﺩﺍﺭﺍ ﺍﺳﺖ‪ .‬ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺍﻳﺘﺮ ﻫﺎ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ‪:‬‬
‫)‪ (R − − O − R‬ﻳﺎ )‪(R − O − R‬‬
‫ﺍﮔﺮ ﻓﺮﺽ ﻧﻤﺎﻳﻴﻢ ﻛﻪ ﺍﻟﻜﻮﻝ ﻫﺎ ﻣﺸﺘﻖ ﺍﺯ ﻣﺎﻟﻴﻜﻮﻝ ﺁﺏ ﺑﻮﺩﻩ‪ ،‬ﻃﻮﺭﻯ ﻛﻪ ﻳﻚ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺁﺏ ﺑﻪ ﺑﻘﻴﺔ‬
‫ﻋﻀﻮﻯ ﺗﻌﻮﻳﺾ ﻭ ﺍﻟﻜﻮﻝ ﺣﺎﺻﻞ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪ ،‬ﺩﺭ ﺻﻮﺭﺗﻰ ﻛﻪ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺩﻳﮕﺮ ﺁﻥ ﻧﻴﺰ ﺗﻌﻮﻳﺾ ﮔﺮﺩﻳﺪﻩ‬
‫ﺑﺎﺷﺪ‪ ،‬ﺍﻳﺘﺮ ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪:‬‬
‫‪45‬‬
 ‫‪H −O−H‬‬ ‫‪CH3 − CH2 − O − H‬‬ ‫‪CH 3 − CH 2 − O − CH 2 − CH 3‬‬
‫ﺁﺏ‬ ‫ﺍﻳﺘﺎﻧﻮﻝ‬ ‫ﺩﺍﻯ ﺍﻳﺘﺎﻳﻞ ﺍﻳﺘﺮ‬
‫ﺷﻜﻞ ) ‪ ( 4 - 3‬ﻣﻮﺩﻝ ﻣﺎﻟﻴﻜﻮﻝ ﺩﺍﻯ ﺍﻳﺘﺎﻳﻞ ﺍﻳﺘﺮ‬
‫‪ - 6‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﻣﻴﻦ ﻫﺎ ) ‪( −NH‬‬
‫‪2‬‬
‫ﮔﺮﻭپ ﺍﻣﻴﻦ ) ‪ (−NH‬ﻣﺘﺸﻜﻞ ﺍﺯ ﺩﻭﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﻳﻚ ﺍﺗﻮﻡ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺑﻮﺩﻩ ﻛﻪ ﺩﺭ ﺣﻘﻴﻘﺖ ﻳﻚ ﺍﺗﻮﻡ‬ ‫‪2‬‬
‫ﻫﺎﻳﺪﺭﻭﺟﻦ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻣﻮﻧﻴﺎ ﺍﺯ ﺍﻳﻦ ﻣﺎﻟﻴﻜﻮﻝ ﺑﻪ ﺷﻜﻞ ﻫﻮﻣﻮﻟﻴﺘﻴﻜﻰ ﺗﺠﺰﻳﻪ ﮔﺮﺩﻳﺪﻩ ﻭ ﺩﺭ ﻧﺘﻴﺠﻪ ﺍﻳﻦ ﮔﺮﻭپ‬
‫ﺣﺎﺻﻞ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪ .‬ﺩﺭ ﺻﻮﺭﺗﻰ ﻛﻪ ﺭﺍﺑﻄﺔ ﺍﻳﻦ ﮔﺮﻭپ ﺑﺎ ﺭﺍﺩﻳﻜﺎﻝ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﺑﺮ ﻗﺮﺍﺭ ﮔﺮﺩﺩ‪،‬‬
‫ﻣﺮﻛﺒﺎﺕ ﺍﻣﻴﻦ ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ‪ .‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﻋﻤﻮﻣﻰ ﺍﻣﻴﻦ ﻫﺎ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ‪:‬‬
‫‪H−N−H‬‬ ‫‪R−N−H‬‬ ‫‪R−N−R‬‬ ‫‪R−N−R‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪R‬‬
‫ﺍﻣﻮﻧﻴﺎ‬ ‫ﺍﻣﻴﻦ ﺍﻭﻟﻰ‬ ‫ﺍﻣﻴﻦ ﺩﻭﻣﻰ‬ ‫ﺍﻣﻴﻦ ﺳﻮﻣﻰ‬
‫ﺩﺭ ﺗﻤﺎﻡ ﺣﺎﻻﺕ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻣﻴﻦ ﻫﺎ ﺳﺎﺧﺘﻤﺎﻥ ﻫﺮﻣﻰ ﺑﺎ ﻗﺎﻋﺪﻩ ﻣﺜﻠﺜﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﺳﺖ ﻛﻪ ﻳﻚ ﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ‬
‫ﻏﻴـــــﺮ ﺭﺍﺑﻄﻪ ﻳﻰ ﺁﺯﺍﺩ ﺍﺯ ﻫﺎﻳﭙﺮﻳﺪ ‪ SP‬ﺍﻭﺭﺑﻴﺘﺎﻝ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺍﺳﺖ ﻛﻪ ﺑﺎ ﺯﺍﻭﻳﻪ ﻫﺎﻯ ﺁﻥ ﺍﺧﺘﻼﻑ ﺩﺍﺭﺩ‪ .‬ﺍﻛﺜﺮﺍ ً‬
‫‪3‬‬
‫ﺍﻣﻴﻦ ﻫﺎﺩﺭ ﻣﻮﺍﺩ ﻃﺒﻴﻌﻰ ﻭ ﻳﺎ ﻣﺤﺼﻮﻻﺕ ﺗﺮﻛﻴﺒﻰ ﻳﺎﻓﺖ ﺷﺪﻩ ﻭ ﺯﻳﺎﺩ ﺗﺮ ﻣﺮﻛﺒﺎﺕ ﺁﻥ ﺑﻮﻯ ﻧﺎ ﻣﻄﺒﻮﻉ ﺭﺍ ﺩﺍﺭﺍ‬
‫ﺍﻧﺪ‪ ،‬ﺩﺭ ﺗﺮﻛﻴﺐ ﭘﺮﻭﺗﻴﻦ ﻫﺎﻯ ﻣﻮﺍﺩ ﻋﻀﻮﻯ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺷﺎﻣﻞ ﺑﻮﺩﻩ ﻭ ﺍﻣﻴﻦ ﻫﺎ ﻧﻴﺰ ﺑﻌﺪ ﺍﺯ ﺗﺠﺰﻳﻪ ﻭ ﺗﺨﺮﻳﺐ ﻣﻮﺍﺩ‬
‫ﺯﻧﺪﻩ ﺑﺎ ﻣﺮﻛﺒﺎﺕ ﺳﻠﻔﺮ ﺩﺍﺭ ﺑﻮﻯ ﻣﺘﻌﻔﻦ ﺭﺍ ﺍﻳﺠﺎﺩ ﻣﻴﻨﻤﺎﻳﻨﺪ‪ .‬ﻧﺎﻡ ﺩﻭ ﻧﻮﻉ ﻣﺮﻛﺐ ﺩﺍﻯ ﺍﻣﻴﻦ } ‪{NH (CH ) NH‬‬
‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﭘﻴﻮﺗﺮﺳﻴﻦ ) ‪ Putrescine‬ﺑﻪ ﻣﻌﻨﻰ ﺗﻌﻔﻦ( ﻭ ‪ NH (CH ) NH‬ﻛﺪﺍﻭﻳﺮﻳﻦ ) ‪ Cadaverine‬ﺑﻪ ﻣﻌﻨﻰ ﺗﻌﻔﻦ‬
‫‪2‬‬ ‫‪2‬‬ ‫‪5‬‬ ‫‪2‬‬
‫ﺟﺴﺪ( ﺩﻗﻴﻘﺎً ﺍﺯ ﺗﻌﻔﻦ ﺍﺟﺴﺎﺩ ﻣﺮﺩﻩ ﮔﺮﻓﺘﻪ ﺷﺪﻩ ﺍﺳﺖ‪.‬‬
‫ﺷﻜﻞ )‪ : ( 5 - 3‬ﺳﺎﺧﺘﻤﺎﻥ ﻭ ﻣﻮﺩﻝ ﺍﻣﻴﻦ ﻫﺎ ) ‪ - a‬ﺍﻣﻮﻧﻴﺎ ‪ – b‬ﻣﻴﺘﺎﻳﻞ ﺍﻣﻴﻦ ‪ – c‬ﺩﺍﻯ ﻣﻴﺘﺎﻳﻞ ﺍﻣﻴﻦ ‪ – d‬ﺗﺮﺍﻯ ﻣﻴﺘﺎﻳﻞ ﺍﻣﻴﻦ(‬
‫‪46‬‬
 ‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺷﺎﮔﺮﺩﺍﻥ ﺭﺍ ﺑﻪ ﮔﺮﻭپ ﻫﺎﻯ ﻣﻨﺎﺳﺐ ﺗﻘﺴــــﻴﻢ ﻧﻤﻮﺩﻩ‪ ،‬ﻫﺮ ﮔﺮﻭپ ﺧﻤﻴﺮﺓ ﻛﺎﻏﺬ‪ ،‬ﺳﺮﺵ ﻛﺎﻫﻰ ﺭﺍ ﺑﺎ‬ ‫ﮔ‬
‫ﺩﻳﮕﺮ ﻣﻮﺍﺩ ﻣﻮﺭﺩ ﺿﺮﻭﺭﺕ ﺗﻬﻴﻪ ﻧﻤﻮﺩﻩ ﻭ ﺍﺯ ﺁﻧﻬﺎ ﻣﻮﺩﻝ ﻫﺎﻯ ﺍﻳﺘﺮ ﻫﺎ‪ ،‬ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎ‪ ،‬ﻛﻴﺘﻮﻥ ﻫﺎ ﻭ ﺍﻣﻴﻦ ﻫﺎ‬
‫ﺭﺍ ﺁﻣﺎﺩﻩ ﺳﺎﺧﺘﻪ ﻭ ﺩﺭ ﺑﺎﺭﺓ ﺁﻥ ﻧﻤﺎﻳﻨﺪﺓ ﻫﺮ ﮔﺮﻭپ ﺩﺭ ﺻﻨﻒ ﺗﻮﺿﻴﺤﺎﺕ ﺍﺭﺍﺋﻪ ﻧﻤﺎﻳﺪ‪.‬‬
‫‪ - 7‬ﮔﺮﻭپ ﺗﻴﻮﻝ‪ ،‬ﺳﻠﻔﺎﻳﺪ ﻫﺎ‬
‫ﮔﺮﻭپ ﺗﻴﻮﻝ )‪ ( −S − H‬ﻣﺘﺸﻜﻞ ﺍﺯ ﻳﻚ ﺍﺗﻮﻡ ﺳﻠﻔﺮ ﻭ ﻳﻚ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺑﻮﺩﻩ ﻛﻪ ﻣﺸﺘﻘﺎﺕ ﺳﻠﻔﺮ ﺩﺍﺭ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ‪ .‬ﺍﻳﻦ ﮔـــــــﺮﻭپ ﺩﺭ ﻧﺘﻴﺠﺔ ﻗﻄـــــــﻊ ﺭﺍﺑﻄـــﺔ ﻳﻚ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺳﻠﻔﺎﻳﺪ ) ‪ (H − S − H‬ﺑﻪ ﺷﻜﻞ ﻫﻮﻣﻮﻟﻴﺘﻴﻜﻰ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ‪ .‬ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺍﻳﻦ‬
‫ﻣﺮﻛﺒﺎﺕ )‪ (R − S − H‬ﺑﻮﺩﻩ ﻭ ﻣﺸﺎﺑﻪ ﺑﻪ ﺍﻟﻜﻮﻝ ﻫﺎ ﻣﻴﺒﺎﺷﺪ‪.‬‬
‫ﺍﮔﺮ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺩﻭﻣﻰ ﮔﺮﻭپ ﺗﻴـــــﻮﻝ ﻧﻴﺰ ﺑﻪ ﺑﻘﻴﺔ ﻋﻀﻮﻯ ﺗﻌﻮﻳﺾ ﮔـــــﺮﺩﺩ‪ ،‬ﺳﻠﻔﺎﻳﺪ ﻫﺎ ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ‬
‫ﻛﻪ ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺁﻧﻬﺎ ‪ R − S − R‬ﺍﺳﺖ‪ .‬ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﻣﺸﺎﺑﻪ ﺍﻳﺘﺮ ﻫﺎ ﻣﻴﺒﺎﺷﻨﺪ ﻭ ﻓﺮﻕ ﺁﻥ ﺑﺎ ﺍﻳﺘﺮ ﻫﺎ ﺍﻳﻦ ﺍﺳﺖ‬
‫ﻛﻪ ﺩﺭ ﺍﻳﺘﺮ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﻛﺴﻴﺠﻦ ﺩﺍﺭ ﺷﺎﻣﻞ ﺑﻮﺩﻩ ؛ﺍﻣﺎ ﺩﺭ ﺗﻴﻮ ﺍﻳﺘﺮ ﻫﺎ‪ ،‬ﺳﻠﻔﺮ ﺷﺎﻣﻞ ﻣﻴﺒﺎﺷﺪ‪ .‬ﺍﻳﻦ ﮔﺮﻭپ‬
‫ﻭﻇﻴﻔﻪ ﻳﻰ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﻣﺮﻛﭙﺘﻮ ﮔﺮﻭپ )‪ (MercaptoGroup‬ﻧﻴﺰ ﻳﺎﺩ ﻣﻰ ﻧﻤﺎﻳﻨﺪ‪ .‬ﻣﺜﺎﻟﻬﺎﻯ ﺳﺎﺩﺓ ﻣﺮﻛﺒﺎﺕ ﺗﻴﻮﻝ ﻭ‬
‫ﺗﻴﻮ ﺍﻳﺘﺮ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ‪:‬‬
‫‪−S−H‬‬ ‫‪−S−H‬‬ ‫‪CH − S − H‬‬ ‫‪, −S−H‬‬
‫‪3‬‬
‫‪Methyl‬‬‫‪thiol‬‬
‫‪(CH‬‬ ‫‪− CH‬‬ ‫‪− S − CH‬‬ ‫)‬
‫‪Cyclo hexanthiol‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪3‬‬
‫‪Cyclo hexenthiol‬‬
‫‪Methylethy lether‬‬
‫‪ - 8‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﻳﺴﺘﺮ ﻩ‬
‫‪O‬‬
‫ﺑﻮﺩﻩ ﻛﻪ ﺩﺭ ﺍﻳﻦ ﮔﺮﻭپ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺁﺯﺍﺩ ﺍﺗﻮﻡ ﺍﻛﺴﻴﺠﻦ‬ ‫ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﻳﺴﺘﺮ ﻫﺎ‬
‫‪//‬‬
‫‪− C −O−‬‬
‫ﻭ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻃﺎﻗﻪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﺁﺯﺍﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍﺩﻳﻜﺎﻝ ﻋﻀﻮﻯ ﺭﺍﺑﻄﻪ ﺑﺮ ﻗﺮﺍﺭ‬
‫ﻧﻤﻮﺩﻩ ﻭ ﻣﺮﻛﺒﺎﺗﻰ ﺑﻪ ﻧﺎﻡ ﺍﻳﺴﺘﺮ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻰ ﺩﻫﺪ‪ .‬ﺩﺭ ﺣﻘﻴﻘﺖ ﺍﮔﺮ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﺑﻪ‬
‫ﺑﻘﻴﻪ ﻫﺎﻯ ﻋﻀﻮﻯ ﺗﻌﻮﻳﺾ ﮔﺮﺩﺩ ‪ ،‬ﺍﻳﺴﺘﺮ ﻫﺎ ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ‪ ،‬ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺍﺳﻴﺘﺮ ﻫﺎ ﻋﺒﺎﺭﺕ ﺍﻧﺪ ﺍﺯ‪:‬‬
‫‪O‬‬ ‫‪O‬‬
‫‪//‬‬ ‫‪ R − C// − O − R‬ﻳﺎ‬
‫‪R − C − O − R−‬‬
‫ﻛﻞ )‪ (7 - 3‬ﻣﻮﺩﻝ ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻳﻞ ﺍﻳﺘﺎﻳﻞ ﺍﻳﺴﺘﺮ‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺷﺎﮔﺮﺩﺍﻥ ﺭﺍ ﺑﻪ ﮔﺮﻭپ ﻫﺎﻯ ﻣﻨﺎﺳﺐ ﺗﻘﺴﻴﻢ ﻧﻤﻮﺩﻩ‪ ،‬ﻫﺮ ﮔﺮﻭپ ﻣﻮﺩﻝ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺴﺘﺮ ﺭﺍ ﺍﺯ ﭼﻮﺏ‪ ،‬ﮔﻞ‬
‫ﺭﺋﺲ ﻭ ﻳﺎ ﻛﺎﻏﺬ ﻋﻴﺎﺭ ﺳﺎﺧﺘﻪ ﻭ ﺭﺍﺟﻊ ﺑﻪ ﻋﻤﻞ ﻛﺮﺩ ﺷﺎﻥ ﻧﻤﺎﻳﻨﺪﺓ ﮔﺮﻭپ ﺗﻮﺿﻴﺤﺎﺕ ﻻﺯﻣﻪ ﺑﺪﻫﻨﺪ‪.‬‬
‫‪47‬‬
 ‫ﺧﻼﺻﻪ ﻓﺼﻞ ﺳﻮﻡ‬
‫* ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﻋﺒﺎﺭﺕ ﺍﺯ ﻣﺮﻛﺒﺎﺕ ﻛﺎﺭﺑﻦ ﻭ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻭ ﻣﺸﺘﻘﺎﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﻣﻰ ﺑﺎﺷﺪ‪.‬‬
‫* ﺑﻪ ﺻﻮﺭﺕ ﻋﻤﻮﻡ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﻧﻈﺮ ﺑﻪ ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ ﻭ ﻣﻮﺟﻮﺩﻳﺖ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ‬
‫ﺗﻘﺴﻴﻢ ﻧﻤﻮﺩﻩ ﺍﻧﺪ‪.‬‬
‫* ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺭﺍ ﺑﻪ ﺩﻭ ﺩﺳﺘﻪ ﺍﻟﻴﺴﻴﻜﻠﻴﻚ ﻭ ﻛﺎﺭﺑﻮ ﺳﻜﻠﻴﻚ ﺗﻘﺴﻴﻢ ﻧﻤﻮﺩﻩ ﺍﻧﺪ‪.‬‬
‫* ﺍﻟﻴﺴﻴﻜﻠﻴﻚ ﻫﺎ ﻣﺮﻛﺒﺎﺕ ﺯﻧﺠﻴﺮﻯ ﺑﻮﺩﻩ ﻛﻪ ﺯﻧﺠﻴﺮ ﺁﻧﻬﺎ ﻣﻰ ﺗﻮﺍﻧﻨﺪ ﻧﺎﺭﻣﻞ ﻭ ﻳﺎ ﻣﻨﺸﻌﺐ ﺑﻮﺩﻩ ﺑﺎﺷﺪ‪.‬‬
‫* ﺳﻜﻠﻴﻚ ﻫﺎ ﺑﻪ ﺩﻭ ﮔﺮﻭپ ﻛﺎﺭﺑﻮﺳﻜﻠﻴﻚ ﻭ ﻫﺘﺮﻭ ﺳﻜﻠﻴﻚ ﺗﻘﺴﻴﻢ ﺷﺪﻩ ﺍﻧﺪ‪.‬‬
‫* ﻛﺎﺭﺑﻮﺳﺎﻳﻜﻠﻴﻚ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪﻛﻪ ﺩﺍﺭﺍﻯ ﺯﻧﺠﻴﺮ ﺑﺴﺘﻪ )ﺣﻠﻘﻪ( ﻣﻴﺒﺎﺷﻨﺪ ﻭ ﺑﻪ ﺳﻜﻠﻴﻚ ﻫﺎﻭ ﺍﺭﻭﻣﺎﺕ ﻫﺎ ﻣﻨﻘﺴﻢ‬
‫ﻣﻴﮕﺮﺩﻧﺪ ‪ ،‬ﺍﻟﻴﺴﻜﻠﻴﻚ ﻫﺎ ﻧﻴﺰ ﺑﻪ ﻧﻮﺑﺔ ﺧﻮﺩ ﺑﻪ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻥ ﻭ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﻴﻦ ﺗﻘﺴﻴﻢ ﮔﺮﺩﻳﺪﻩ ﺍﻧﺪ‪.‬‬
‫* ﺍﮔﺮ ﻳﻚ ﻭ ﻳﺎ ﭼﻨﺪﻳﻦ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺗﻮﺳﻂ ﮔﺮﻭﭘﻬﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺗﻌﻮﻳﺾ ﮔﺮﺩﺩ‪،‬‬
‫ﻣﺮﻛﺒﺎﺗﻰ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ﻛﻪ ﺑﻨﺎﻡ ﻣﺸﺘﻘﺎﺕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻳﺎﺩ ﻣﻴﮕﺮﺩﻧﺪ ﻭ ﻋﺒﺎﺭﺕ ﺍﺯ ﻣﺸﺘﻘﺎﺕ ﻫﻠﻮﺟﻨﻰ‪،‬‬
‫ﺍﻛﺴﻴﺠﻨﻰ‪ ،‬ﻧﺎﻳﺘﺮﻭﺟﻨﻰ‪ ،‬ﺳﻠﻔﺮﻯ‪ ،‬ﻓﺎﺳﻔﻮﺭﻯ ﻭ ﻏﻴﺮﻩ ﻣﻰ ﺑﺎﺷﻨﺪ‪.‬‬
‫* ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﻫﻠﻮﺟﻦ ﻫﺎ ﻋﺒﺎﺭﺕ ﺍﺯ ‪ R − X‬ﺍﺳﺖ‪.‬‬
‫* ﻣﺮﻛﺒﺎﺗﻰ ﺩﺍﺭﺍﻯ ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺍﻛﺴﻴﺠﻦ ﺩﺍﺭ ﻋﺒﺎﺭﺕ ﺍﺯ ﺍﻟﻜﻮﻟﻬﺎ‪ ،‬ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎ‪ ،‬ﻛﻴﺘﻮﻧﻬﺎ‪ ،‬ﺗﻴﺰﺍﺑﻬﺎ‪،‬‬
‫‪O‬‬
‫‪،‬‬ ‫‪//‬‬ ‫‪،‬‬ ‫‪//‬‬
‫‪O‬‬ ‫‪،‬‬ ‫‪R‬‬ ‫‪−‬‬ ‫‪OH‬‬ ‫ﺍﻳﺘﺮ ﻫﺎ‪ ،‬ﺍﻳﺴﺘﺮ ﻫﺎ‪ ،‬ﻭ ﻏﻴﺮﻩ ﺍﺳﺖ ﻛﻪ ﺑﺘﺮﺗﻴﺐ ﺩﺍﺭﺍﻯ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ‬
‫‪R − C − R R − C− H‬‬
‫ﻣﻰ ﺑﺎﺷﻨﺪ‪.‬‬ ‫‪،‬‬
‫‪O‬‬
‫‪R − C − O − R R − O − R, R − COOH‬‬
‫‪//‬‬
‫* ﻣﺮﻛﺒﺎﺗﻰ ﺩﺍﺭﺍﻯ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻧﺎﻳﺘﺮﻭﺟﻦ ﺩﺍﺭ‪ ،‬ﺍﻣﻴﻦ ﻫﺎ ﻭ ﺍﻣﺎﻳﺪ ﻫﺎ ﻭ ﻏﻴﺮﻩ ﺑﻮﺩﻩ ﻛﻪ ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺁﻧﻬﺎ‬
‫ﺍﺳﺖ‬ ‫ﺑﻴﺘﺮﺗﻴﺐ‪، R − NH .‬‬
‫‪O‬‬
‫‪//‬‬
‫‪R − C − NH‬‬ ‫‪2‬‬
‫‪2‬‬
‫* ﻣﺮﻛﺒﺎﺗﻰ ﺩﺍﺭﺍﻯ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺳﻠﻔﺮ ﺩﺍﺭﻋﺒﺎﺭﺕ ﺍﺯ ‪ R − S − R, R − S − H‬ﻭ ﻏﻴﺮﻩ ﺍﺳﺖ‪.‬‬
‫ﺳﺆﺍﻻﺕ ﻓﺼﻞ ﺳﻮﻡ‬
‫ﺳﺆﺍﻻﺕ ﭼﻬﺎﺭ ﺟﻮﺍﺑﻪ‪ :‬ﺳﺆﺍﻻﺕ ﺫﻳﻞ ﺩﺍﺭﺍﻯ ﭼﻬﺎﺭ ﺟﻮﺍﺏ ﺑﻮﺩﻩ ﻛﻪ ﺍﺯ ﺟﻤﻠﻪ ﻳﻜﻰ ﺁﻥ ﺩﺭﺳﺖ ﺍﺳﺖ‪ ،‬ﺷﻤﺎ‬
‫ﺟﻮﺍﺏ ﺩﺭﺳﺖ ﺁﻥ ﺭﺍ ﺩﺭ ﻳﺎﻓﺖ ﻭ ﺍﻧﺘﺨﺎﺏ ﻧﻤﺎﻳﺪ‪.‬‬
‫‪ - 1‬ﻣﻮﺟﻮﺩﻳﺖ ﻛﺪﺍﻡ ﻳﻜﻰ ﺍ ﺯ ﺟﻮﺭﻩ ﻋﻨﺎﺻﺮ ﺫﻳﻞ ﺩﺭ ﺗﺮﻛﻴﺐ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺣﺘﻤﻰ ﺍﺳﺖ؟‬
‫ﺏ‪ -‬ﺳﻠﻔﺮ ﻭ ﻫﺎﻳﺪﺭﻭﺟﻦ‬ ‫ﺍﻟﻒ‪ -‬ﻛﺎﺭﺑﻦ ﻭ ﺳﻠﻔﺮ‬
‫ﺩ‪ -‬ﻛﺎﺭﺑﻦ ﻭ ﻫﺎﻳﺪﺭﻭﺟﻦ‬ ‫ﺝ‪ -‬ﻛﺎﺭﺑﻦ ﻭ ﻓﺎﺳﻔﻮﺭﺱ‬
‫‪ - 2‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻛﻪ ﺑﻪ ﺍﻧﺪﺍﺯﺓ ﻳﻚ ﮔﺮﻭپ ﻣﺘﻠﻴﻦ ) ‪ (−CH‬ﺍﺯ ﻫﻢ ﺩﻳﮕﺮ ﻓﺮﻕ ﺩﺍﺭﻧﺪ ﺑﻪ ﻧﺎﻡ‪-------‬‬
‫‪2‬‬
‫ﻳﺎﺩ ﻣﻴﺸﻮﻧﺪ‪.‬‬
‫ﺝ‪ -‬ﻫﻮﻣﻮﻟﻮگ ﺩ‪ -‬ﻏﻴﺮ ﻣﺸﺒﻮﻉ‬ ‫ﺍﻟﻒ‪ -‬ﺍﻳﺰﻭﻟﻮگ ﺏ‪ -‬ﺍﻳﺰﻭﻣﻴﺮ‬
‫‪ - 3‬ﻛﺪﺍﻡ ﻳﻜﻰ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺫﻳﻞ ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺍﻳﺘﺮ ﻫﺎ ﻣﻰ ﺑﺎﺷﺪ؟‬
‫‪O‬‬
‫||‬
‫ﺩ‪ -‬ﺍﻟﻒ ﻭ ﺝ ﻫﺮ ﺩﻭ‬ ‫ﺝ‪R − S − H -‬‬ ‫ﺏ‪R − C − H -‬‬ ‫ﺍﻟﻒ‪R − O − R -‬‬
‫‪ - 4‬ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺗﻴﻮﻝ ﻫﺎﻋﺒﺎﺭﺕ ﺍﺯ ‪ ------‬ﺍﺳﺖ‪.‬‬
‫‪48‬‬
 ‫ﺩ‪R − S − R -‬‬ ‫ﺍﻟﻒ‪ R − OH -‬ﺏ‪ R − NH -‬ﺝ‪R − S − H -‬‬
‫‪2‬‬
‫‪ - 5‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﺩﺭ ﻣﺮﻛﺒﺎﺕ ﺗﻴﺰﺍﺑﻰ ﻋﺒﺎﺭﺕ ﺍﺯ ‪ -------‬ﺍﺳﺖ‪.‬‬
‫‪O‬‬
‫‪ R − C‬ﺏ‪ R − C// − OH -‬ﺝ‪ R − C// − O − R -‬ﺩ‪R − O H -‬‬ ‫ﺍﻟﻒ‪-‬‬
‫‪O‬‬ ‫‪O‬‬
‫‪//‬‬
‫‪−H‬‬
‫‪ - 6‬ﻣﺮﻛﺒﺎﺕ ﺳﺎﺩﺓ ﻛﻪ ﻋﻼﻭﻩ ﺍﺯ ﻛﺎﺭﺑﻦ‪ ،‬ﻫﺎﻳﺪﺭﻭﺟﻦ ﻧﻴﺰ ﺩﺭ ﺗﺮﻛﻴﺐ ﺷﺎﻥ ﻣﻮﺟﻮﺩﺍﺳﺖ‪ ،‬ﺑﻪ ﻧﺎﻡ ‪---‬ﻳﺎﺩ‬
‫ﻣﻴﺸﻮﻧﺪ‪.‬‬
‫ﺍﻟﻒ‪ -‬ﺍﻟﻜﺎﻥ ﺏ – ﺍﻟﻜﻴﻦ ﺝ‪ -‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﺩ‪ -‬ﻣﺸﺘﻘﺎﺕ ﺍﻟﻜﺎﻧﻬﺎ‬
‫‪ - 7‬ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺍﻟﻜﺎﻳﻞ ﻫﻼﻳﺪ ﻫﺎ ﻋﺒﺎﺭﺕ ﺍﺯ ‪ ---‬ﺍﺳﺖ‪.‬‬
‫ﺩ‪R − S − R -‬‬ ‫ﺍﻟﻒ ‪ R − OH -‬ﺏ‪ R − X -‬ﺝ‪R − S − H -‬‬
‫‪ - 8‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﻋﺒﺎﺭﺕ ﺍﺯ ﺍﺗﻮﻡ ﻭ ﻳﺎ ﮔﺮﻭﭘﻰ ﺍﺯ ﺍﺗﻮﻡ ﻫﺎﻯ ﻣﺮﺗﺒﻂ ﺷﺪﻩ ﺍﻧﺪ ﻛﻪ ﺩﺭ ﻳﻚ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﻣﺮﻛﺐ ﺷﺎﻣﻞ ﺑﻮﺩﻩ ﻭ ‪ ----‬ﺭﺍ ﻣﺸﺨﺺ ﻣﻰ ﺳﺎﺯﺩ‪.‬‬
‫ﺍﻟﻒ ‪ -‬ﺻﻨﻒ ﻣﺮﻛﺐ ﺏ‪ -‬ﺗﺮﻛﻴﺐ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺝ ‪ -‬ﻣﺸﺘﻘﺎﺕ ﻣﺮﻛﺐ ﺩ – ﺍﻟﻒ ﻭ ﺝ ﻫﺮﺩﻭ‬
‫‪ R − O H - 9‬ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ‪ -----‬ﺍﺳﺖ‪.‬‬
‫ﺩ‪ -‬ﺍﻟﺪﻳﻬﺎﻳﺪ‬ ‫ﺍﻟﻒ ‪ -‬ﺗﻴﺰﺍﺏ ﺏ‪ -‬ﺍﻟﻘﻠﻰ ﺝ ‪ -‬ﺍﻟﻜﻮﻝ‬
‫( ﺗﻘﺴﻴﻢ ﮔﺮﺩﻳﺪﻩ ﺍﻧﺪ‪.‬‬ ‫‪ - 10‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﺑﻪ ﺻﻮﺭﺕ ﻋﻤﻮﻡ ﺑﻪ )‬
‫ﺩ ‪ -‬ﭘﻨﺞ‬ ‫ﺍﻟﻒ ‪ -‬ﺩﻭ ﺏ – ﺳﻪ ﺝ – ﭼﻬﺎﺭ‬
‫‪ - 11‬ﻫﺘﺮﻭ ﺳﻜﻠﻴﻚ ﻫﺎ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺩﺭ ﺗﺮﻛﻴﺐ ﺣﻠﻘﺔ ﺁﻧﻬﺎ ﻋﻨﺎﺻﺮ ﺑﻴﮕﺎﻧﻪ ‪ ----‬ﺷﺎﻣﻞ ﺍﻧﺪ‪.‬‬
‫ﺍﻟﻒ ‪-‬ﺳﻠﻔﺮ‪ ،‬ﺍﻛﺴﻴﺠﻦ ﺏ‪ -‬ﻧﺎﻳﺘﺮﻭﺟﻦ‪ ،‬ﻓﺎﺳﻔﻮﺭ ﻭ ﻏﻴﺮﻩ ﺝ – ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭ ﺩ – ﻫﻴﭽﻜﺪﺍﻡ‬
‫‪ - 12‬ﺗﻴﻮ ﺍﻳﺘﺮ ﻫﺎ ﻣﺸﺎﺑﻪ ﺑﻪ ﺍﻟﻜﻮﻝ ﻫﺎ ﺑﻮﺩﻩ؛ ﺍﻣﺎ ﻓﺮﻕ ﺷﺎﻥ ﺑﺎﺍﻳﺘﺮ ﻫﺎ ﺩﺭ ﺍﻳﻦ ﺍﺳﺖ ﻛﻪ ﺩﺭ ﺍﻳﺘﺮ ﻫﺎ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ‬
‫ﻳﻰ ﺍﻛﺴﻴﺠﻨﻰ ﺷﺎﻣﻞ ﺑﻮﺩﻩ ؛ ﻻﻛﻦ ﺩﺭ ﺗﻴﻮ ﺍﻳﺘﺮ ‪ ---‬ﺷﺎﻣﻞ ﻣﻰ ﺑﺎﺷﺪ‪.‬‬
‫ﺍﻟﻒ‪ -‬ﻧﺎﻳﺘﺮﻭﺟﻦ ﺏ‪ -‬ﻓﺎﺳﻔﻮﺭﺱ ﺝ‪ -‬ﺳﻠﻔﺮ ﺩ ‪ -‬ﻧﺎﻳﺘﺮﻭﺟﻦ‬
‫‪- 13‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻛﻴﺘﻮﻥ ﻫﺎ ﻋﺒﺎﺭﺕ ﺍﺯ ﮔﺮﻭپ ‪-----‬ﺍﺳﺖ‪.‬‬
‫ﺍﻟﻒ‪ -‬ﻛﺎﺭﺑﻮﻧﻴﻞ ﺏ‪ -‬ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﺝ‪ -‬ﻫﺎﻳﺪﺭﻭﻛﺴﻴﻞ ﺩ‪ -‬ﻫﻴﭽﻜﺪﺍﻡ‬
‫‪ - 14‬ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻛﻪ ﺩﺍﺭﺍﻯ ﺯﻧﺠﻴﺮ ﺑﺴﺘﻪ ﺑﺎﺷﺪ‪ ،‬ﺑﻪ ﻧﺎﻡ ‪ - ---‬ﻳﺎﺩ ﻣﻰ ﺷﻮﻧﺪ‪:‬‬
‫ﺍﻟﻒ ‪ -‬ﺳﻜﻠﻴﻚ ﻫﺎ ﺏ‪ -‬ﺍﻟﻴﺴﻜﻠﻴﻚ ﻫﺎ ﺝ‪ -‬ﺍﺭﻭﻣﺎﺗﻬﺎ ﺩ ‪ -‬ﺗﻤﺎﻣﺎ"‬
‫ﺳﺆﺍﻻﺕ ﺗﺸﺮﻳﺤﻰ‬
‫‪ - 1‬ﺩﺭ ﻣﻮﺭﺩ ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮگ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﻣﻌﻠﻮﻣﺎﺕ ﻣﺨﺘﺼﺮ ﺍﺭﺍﺋﻪ ﺑﺪﺍﺭﻳﺪ‪.‬‬
‫‪ - 2‬ﮔﺮﻭپ ﻫﺎﻯ ﻭﻇﻴﻔﻪ ﻳﻰ ﺭﺍ ﻣﺨﺘﺼﺮﺍ ً ﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﺪ‪.‬‬
‫‪ - 3‬ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﻋﻤﻮﻣﻰ ﺫﻳﻞ ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﻮﺩﻩ ﻭ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ﻛﻪ ﺑﻪ ﻛﺪﺍﻡ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺗﻌﻠﻖ ﺩﺍﺭﻧﺪ؟‬
‫‪O‬‬ ‫‪O‬‬
‫‪O‬‬
‫‪//‬‬ ‫‪//‬‬ ‫‪//‬‬
‫‪R −O−R‬‬ ‫‪R − OH‬‬ ‫‪R − C − NH 2‬‬ ‫‪R − C − OH‬‬ ‫‪R − C −O−R‬‬
‫‪ - 4‬ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻛﺎﺭﺑﻮﻧﻴﻞ ﺭﺍ ﻣﺨﺘﺼﺮﺍ ً ﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﺪ‪.‬‬
‫‪ - 5‬ﺩﺭﺑﺎﺭﺓ ﮔﺮﻭپ ﻭﻇﻴﻔﻪ ﻳﻰ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﻣﻌﻠﻮﻣﺎﺕ ﻻﺯﻣﻪ ﺍﺭﺍﺋﻪ ﺑﺪﺍﺭﻳﺪ‪.‬‬
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 ‫ﻓﺼﻞ ﭼﻬﺎﺭﻡ‬
‫ﺍﻟﻜﺎﻧﻬﺎ ﻭﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﻣﺮﻛﺒﺎﺗﻰ ﻛﻪ ﺩﺭ ﺁﻧﻬﺎ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺑﻪ ﺷﻜﻞ ﺯﻧﺠﻴﺮ ﻳﺎ ﺣﻠﻘﻪ ﺑﺎﻫﻢ ﺍﺭﺗﺒﺎﻁ ﺩﺍﺭﻧﺪ ﻭ ﺗﻤﺎﻡ ﺍﺗﻮﻡ ﻫﺎﻯ‬
‫ﻛﺎﺭﺑﻦ ﺁﻧﻬﺎ ﺩﺍﺭﺍﻯ ﺭﺍﺑﻄﺔ ﻳﮕﺎﻧﺔ ﺳﮕﻤﺎ ) ‪ (D‬ﺍﻧﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﺎﻧﻬﺎ ﻳﺎ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ ﻳﺎﺩﺷﺪﻩ ﺍﻧﺪ ‪ .‬ﺩﺭﺍﻳﻦ‬
‫‪3‬‬
‫ﻣﺮﻛﺒﺎﺕ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﻫﺎﻳﺒﺮﻳﺪ ‪ sp‬ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻭﺑﻴﻦ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ ﻳﮕﺎﻧﻪ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪،‬‬
‫ﺍﻟﻜﺎﻧﻬﺎ ﺩﺍﺭﺍﻯ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﺯﻧﺠﻴﺮ ﻛﺎﺭﺑﻨﻰ ﺑﻮﺩﻩ ﻭﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺩﺍﺭﺍﻯ ﺯﻧﺠﻴﺮ ﺑﺴﺘﻪ ﻭﺣﻠﻘﻪ ﻣﻴﺒﺎﺷﻨﺪ ‪.‬‬
‫ﺩﺭﺍﻳﻦ ﻓﺼﻞ ﺩﺍﻧﺴﺘﻪ ﺧﻮﺍﻫﺪ ﺷﺪ ﻛﻪ ﺍﻟﻜﺎﻧﻬﺎ ﻭﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﻛﺪﺍﻡ ﻧﻮﻉ ﻣﺮﻛﺒﺎﺕ ﺍﻧﺪ ؟ ﻣﻨﺎﺑﻊ ﻃﺒﻴﻌﻰ‬
‫ﺁﻧﻬﺎ ﻛﺪﺍﻡ ﻫﺎ ﺍﻧﺪ ؟ ﺩﺍﺭﺍﻯ ﻛﺪﺍﻡ ﺧﻮﺍﺹ ﺑﺨﺼﻮﺹ ﻣﻴﺒﺎﺷﻨﺪ ؟ ﺩﺭﻛﺪﺍﻡ ﻋﺮﺻﻪ ﻫﺎ ﺑﻪ ﻛﺎﺭﻣﻴﺮﻭﻧﺪ ؟‬
‫ﻓﺮﻕ ﺑﻴﻦ ﺍﻟﻜﺎﻧﻬﺎ ﻭﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﻛﺪﺍﻡ ﻓﻜﺘﻮﺭ ﺍﺳﺖ ؟ ﺩﺭﺍﻳﻦ ﻓﺼﻞ ﺍﺑﺘﺪﺍ ﺍﻟﻜﺎﻧﻬﺎ ﺭﺍ ﺗﻮﺿﻴﺢ ﻧﻤﻮﺩﻩ‬
‫ﻭﺑﻌﺪﺍ" ﺑﻪ ﻣﻄﺎﻟﻌﺔ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﻣﻰ ﭘﺮﺩﺍﺯﻳﻢ ‪.‬‬
‫‪50‬‬
 ‫‪ : 1- 4‬ﺍﻟﻜﺎﻥ ﻫﺎ )‪( Alkanes‬‬
‫ﺍﻟﻜﺎﻥ ﻫﺎ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺑﻴﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺁﻧﻬﺎ ﺭﺍﺑﻄﺔ ﺳﺎﺩﻩ ) ﻳﮕﺎﻧﻪ ( ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ﻭ ﻭﻻﻧﺲ ﻫﺎﻯ ﻣﺘﺒﺎﻗﻰ‬
‫ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺗﻮﺳﻂ ﺍﺗﻮﻣﻬﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻣﺸﺒﻮﻉ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪ .‬ﻣﺮﻛﺒﺎﺕ ﺳﺎﺩﺓ ﺁﻧﻬﺎ ﻣﻴﺘﺎﻥ ‪CH 4‬‬
‫ﻭﺍﻳﺘﺎﻥ ‪ C2 H 6‬ﺍﺳﺖ‪ .‬ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻥ ﺩﺍﺭﺍﻯ ﺳﺎﺧﺘﻤﺎﻥ ﻫﻨﺪ ﺳﻰ ﭼﻬﺎﺭﻭﺟﻬﻰ ﺑﻮﺩﻩ ﻭ ﺭﺍﺑﻄﺔ ‪ C-H‬ﺩﺭﺁﻧﻬﺎ‬
‫ﺩﺭ ﻧﺘﻴﺠﺔ ﺗﺪﺍﺧﻞ ﻣﺴﺘﻘﻴﻢ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp 3‬ﻫﺎ ﻳﺒﺮﻳﺪ ﻛﺎﺭﺑﻦ ﻭ‪ s‬ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺑﺮﻗﺮﺍﺭ ﮔﺮﺩﻳﺪﻩ ﻭ ﻧﻮﻉ‬
‫ﺭﺍﺑﻄﻪ ﻣﺴﺘﺤﻜﻢ ‪ S‬ﻣﻴﺒﺎﺷﺪ ‪.‬‬
‫ﺩﺭﺷﻜﻞ ) ‪ ( 1 - 4‬ﺯﺍﻭﻳﻪ‪ ،‬ﻃﻮﻝ ﺭﺍﺑﻄﻪ ﻭﻫﻢ ﺳﺎﺧﺘﻤﺎﻥ ﭼﻬﺎﺭ ﻭﺟﻬﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻥ ﺍﺭﺍﺋﻪ ﻛﺮﺩﻳﺪﻩ ﺍﺳﺖ ‪.‬‬
‫ﻃﻮﻝ ﺭﺍﺑﻄﻪ ﺑﻪ ﻭﺍﺣﺪ ﭘﻴﻜﺎﻣﺘﺮ ‪ (10 −12 m) pm‬ﺍﺭﺍﺋﻪ ﺷﺪﻩ ﺍﺳﺖ ‪.‬‬
‫ﻗﺮﺍﺭﺩﺍﺩ ﺑﻴﻦ ﺍﻟﻤﻠﻠﻰ ﺑﺮﺍﻯ ﻧﻤﺎﻳﺶ ﺳﺎﺧﺘﻤﺎﻥ ﺭﻭﺍﺑﻂ ﺩﺭﻳﻚ ﻣﺎﻟﻴﻜﻮﻝ ﻣﻄﺎﺑﻖ ﺑﻪ ﺷﻜﻞ ) ‪ ( 2 - 4‬ﺑﻮﺩﻩ ‪ ،‬ﻃﻮﺭﻯ‬
‫( ﺭﺍﺑﻄﺔ‬ ‫ﻛﻪ ﺧﻄﻮﻁ ﺑﺎﺭﻳﻚ ‪ − C −‬ﻧﻤﺎﻳﺎﻧﮕﺮﺭﻭﺍﺑﻄﻰ ﺍﻧﺪ ﻛﻪ ﺩﺭﺳﻄﺢ ﻗﺮﺍﺭﺩﺍﺷﺘﻪ‪ ،‬ﻋﻼﻣﺔ ﻣﺜﻠﺜﻰ)‬
‫( ﺭﺍﺑﻄﻪ ﻋﻘﺐ ﺳﻄﺢ ﺭﺍ ﺍﻓﺎﺩﻩ ﻣﻴﻜﻨﻨﺪ ‪.‬‬ ‫ﭘﻴﺸﺮﻭﻯ ﺻﺤﻔﻪ ﻭ ﻋﻼﻣﻪ ﻣﺜﻠﺜﻰ)‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻥ ‪.‬‬
‫ﻜﻮ‬
‫ﺍﺭﺍﺋﺔ ﻣﺎﻟﻴﻜ‬
‫ﻣﺨﺘﻠﻒ ﺍﺍﺭﺍﺋﺔ‬
‫ﺩﻭﻃﺮﻳﻘﻪ ﻣﺨﺘﻠﻒ‬
‫ﺷﻜﻞ ) ‪ ( 1 - 4‬ﺩﻭﻃﻃﺮﻳﻘﻪ‬
‫ﺷﻜﻞ‬
‫ﺷﻜﻞ ) ‪ ( 2 - 4‬ﻗﺮﺍﺭﺩﺍﺩ ﺑﻴﻦ ﺍﻟﻤﻠﻠﻰ ﺑﺮﺍﻯ ﻧﻤﺎﻳﺶ ﺭﺍﺑﻄﻪ ﻫﺎ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻥ ﻭﺍﻳﺘﺎﻥ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﺎﻥ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﻣﺘﺸﻜﻞ ﺍﺯﺍﺭﺗﺒﺎﻁ ﺩﻭ ﺑﻘﻴﻪ ﻣﻴﺘﺎﻳﻞ ‪ − C H3‬ﺑﺎﻳﻚ ﺩﻳﮕﺮ ﺗﺼﻮﺭﻛﺮﺩ ‪ .‬ﺩﺭﮔﺮﻭپ ﻣﻴﺘﺎﻳﻞ‬
‫) ‪ (−CH 3‬ﻫﺮﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻳﻚ ﺍﻭﺭﺑﻴﺘﺎﻝ ‪ sp3‬ﻫﺎﻳﺒﺮﻳﺪ ﺁﺯﺍﺩ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻭ ﺩﺭﻣﻮﻗﻊ ﺍﺗﺼﺎﻝ ﺑﺎ ﻫﻤﺪﻳﮕﺮ‬
‫ﺗﺪﺍﺧﻞ ﻣﺴﺘﻘﻴﻢ ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ‪ − sp3‬ﻫﺎﻳﺒﺮﻳﺪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ ‪ C-C‬ﺭﺍ ﺑﺮﻗﺮﺍﺭ ﻧﻤﻮﺩﻩ ﻛﻪ ﺩﺭﺷﻜﻞ ) ‪( 3 - 4‬‬
‫ﻧﻤﺎﻳﺶ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ ‪:‬‬
‫ﺷﻜﻞ )‪ ( 3 – 4‬ﻧﻤﺎﻳﺶ ﻓﻀﺎﻯ ﻣﺎﻟﻴﻜﻮﻝ ‪ Ethane‬ﺑﻪ ﻭﺳﻴﻠﻪ ﻣﻮﺩﻝ ﭼﻮﺑﻰ‬
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‫ﺍﻟﻜﺎﻥ ﻫﺎ ﺩﺍﺭﺍﻯ ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ) ‪ (C n H 2n + 2‬ﺑﻮﺩﻩ ﻭ ﺳﺮ ﺩ ﺳﺘﺔ ﺁﻥ ﻫﺎ ﻣﻴﺘﺎﻥ ﻭ ﺩﻭﻣﻰ ﺁﻥ ﺍﻳﺘﺎﻥ ﻭﻏﻴﺮﻩ ﺍﺳﺖ‬
‫ﻛﻪ ﺑﻪ ﺷﻜﻞ ﻫﻮﻣﻮﻟﻮﻙ ﺑﻪ ﺍﻧﺪﺍﺯﻩ ﻳﻚ ﮔﺮﻭپ ﻣﺘﻠﻴﻦ ‪ − CH −‬ﺍﺯ ﻫﻢ ﺩ ﻳﮕﺮ ﻓﺮﻕ ﺩﺍﺭﻧﺪ ‪.‬‬
‫‪2‬‬
‫ﺩﺭﺟﺪﻭﻝ )‪ ( 1 - 4‬ﻧﺎﻡ ﻫﺎ ﻭ ﺩﺭﺟﻪ ﻏﻠﻴﺎﻥ ﻋﺪﺓ ﺍﺯﻣﺮﻛﺒﺎﺕ ﺍﻳﻦ ﺧﺎﻧﺪﺍﻥ ﺑﺎﺭﺍﺩﻳﻜﺎﻝ ﻫﺎﻯ ﻳﻚ ﻭﻻﻧﺴﻪ‬
‫ﺷﺎﻥ ﺍﺭﺍﺋﻪ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪ .‬ﻗﺎﺑﻞ ﻳﺎﺩﺁﻭﺭﻯ ﺍﺳﺖ ﺍﻳﻦ ﻛﻪ ‪ :‬ﭘﺴﻮﻧﺪ‪ ane‬ﻧﺎﻡ ﺍﻟﻜﺎﻥ )‪ (Alkane‬ﻣﺮﺑﻮﻃﻪ ﺩﺭ‬
‫ﺭﺍﺩﻳﻜﺎﻝ ﺁﻥ ﺑﻪ ‪ (Alkyl )yl‬ﺗﻌﻮﻳﺾ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫ﺟﺪﻭﻝ )‪ ( 1- .4‬ﻧﺎﻡ ﺍﻟﻜﺎﻥ ﻫﺎ ﻭﺭﺍﺩﻳﻜﺎﻝ ﻣﺮﺑﻮﻃﺔ ﺁﻧﻬﺎ ‪:‬‬
‫ﻧﺎﻡ‬ ‫ﻓﻮﺭﻣﻮﻝ‬ ‫ﻧﻘﻄﻪ ﻏﻠﻴﺎﻥ‬ ‫ﻧﺎﻡ ﺭﺍﺩﻳﻜﺎﻝ‬ ‫ﻓﻮﺭﻣﻮﻝ‬
‫‪Alkane‬‬ ‫‪Cn H 2 n+ 2‬‬ ‫‪-‬‬ ‫‪Alkyl‬‬
‫‪−C H‬‬
‫‪n 2n + 1‬‬
‫‪Methane‬‬ ‫‪CH 4‬‬ ‫‪− 1610 C‬‬ ‫‪Methyl‬‬ ‫‪− CH3‬‬
‫‪Ethane‬‬ ‫‪CH3 − CH3‬‬ ‫‪− 890 C‬‬ ‫‪Ethyl‬‬ ‫‪CH 2 CH 2‬‬
‫‪Propane‬‬ ‫‪C H‬‬
‫‪3 8‬‬ ‫‪− 40 0 C‬‬ ‫‪Propyl‬‬ ‫‪C3 H 7 −‬‬
‫‪Butane‬‬ ‫‪C H‬‬ ‫‪− 0.50 C‬‬ ‫‪Butyl‬‬ ‫‪C H −‬‬
‫‪4 10‬‬ ‫‪4 9‬‬
‫‪Pentane‬‬ ‫‪C5 H 12‬‬ ‫‪36 0 C‬‬ ‫‪Pentyl‬‬ ‫‪C5 H 11 −‬‬
‫‪Hexane‬‬ ‫‪C6 H 14‬‬ ‫‪680 C‬‬ ‫‪Hexyl‬‬ ‫‪C6 H 13 −‬‬
‫‪Heptane‬‬ ‫‪C7 H 16‬‬ ‫‪88 0 C‬‬ ‫‪Heptyl‬‬ ‫‪C7 H 15 −‬‬
‫‪Octane‬‬ ‫‪C8 H 18‬‬ ‫‪126 0 C‬‬ ‫‪Octyl‬‬ ‫‪C8 H 17 −‬‬
‫‪Nonane‬‬ ‫‪C9 H 20‬‬ ‫‪1510 C‬‬ ‫‪Nonyl‬‬ ‫‪C9 H 19 −‬‬
‫‪Decane‬‬ ‫‪C10 H 22‬‬ ‫‪174 0 C‬‬ ‫‪Decyl‬‬ ‫‪C10 H 21 −‬‬
‫‪ : 1- 1- 4‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﺍﻟﻜﺎﻥ ﻫﺎ‬
‫ﺍﻳﺰﻭﻣﻴﺮﻯ ﺩﺭ ﺍﻟﻜﺎﻧﻬﺎ ﺍﺯ ﻣﺮﻛﺐ ﺑﻴﻮﺗﺎﻥ ﺁﻏﺎﺯ ﻣﻴﮕﺮﺩﺩ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪ :‬ﺑﻴﻮﺗﺎﻥ ﺩﺍﺭﺍﻯ ﺩﻭ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺑﻮﺩﻩ‬
‫ﻛﻪ ﻓﻮﺭﻣﻮﻟﻬﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺁﻥ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ ‪:‬‬
‫‪H H H H‬‬ ‫‪H H H‬‬
‫| | | |‬ ‫|‬ ‫|‬ ‫|‬
‫‪H − C− C− C− C− H‬‬ ‫‪, H − C− C − C− H‬‬
‫| | | |‬ ‫|‬ ‫|‬ ‫|‬
‫‪H H H H‬‬ ‫‪H C H3 H‬‬
‫‪N − b u tan e‬‬ ‫‪Isob u tan‬‬
‫‪52‬‬
 ‫ﺷﻜﻞ ) ‪ (4 - 4‬ﻣﻮﺩﻝ ﻣﺎﻟﻴﻜﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻧﺎﺭﻣﻞ ﺑﻴﻮﺗﺎﻥ ﻭﺍﻳﺰﻭﺑﻴﻮﺗﺎﻥ‬
‫ﻗﺎﺑﻞ ﻳﺎﺩ ﺁﻭﺭﻯ ﺍﺳﺖ ﻛﻪ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻣﺮﻛﺒﺎﺕ ﺩﺍﺭﺍﻯ ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ ﻣﺨﺘﻠﻒ ﺍﻧﺪ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪ :‬ﻧﻘﻄﺔ‬
‫ﻏﻠﻴﺎﻥ ﻧﺎﺭﻣﻞ ﺑﻴﻮﺗﺎﻥ ‪ − 0.5o C‬ﻭﻛﺜﺎﻓﺖ ﺁﻥ ‪ 0.106g/cm 3‬ﺑﻮﺩﻩ ﻭﺩﺭﺣﺎﻟﻰ ﻛﻪ ﻧﻘﻄﺔ ﻏﻠﻴﺎﻥ ﺍﻳﺰﻭﺑﻴﻮﺗﺎﻥ ‪− 11.6 C‬‬
‫‪o‬‬
‫ﻭﻛﺜﺎﻓﺖ ﺁﻥ ‪ 0.549g/cm 3‬ﺍﺳﺖ ‪.‬‬
‫ﺩﺭ ﺍﻟﻜﺎﻥ ﻫﺎﻯ ﺯﻧﺠﻴﺮﻯ ﺑﺎﺍﺯﺩﻳﺎﺩ ﺗﻌﺪﺍﺩ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ)‪ (n‬ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺁﻧﻬﺎ ‪ ،‬ﺗﻌﺪﺍﺩ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎ ﺗﺰﺍﻳﺪ‬
‫ﻣﻴﻨﻤﺎﻳﺪ ‪ ،‬ﺟﺪﻭﻝ ﺫﻳﻞ ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫ﺟﺪﻭﻝ )‪ ( 2 - 4‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﺑﻌﻀﻰ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺗﻌﺪﺍﺩ ﺍﻳﺰﻭﻣﻴﺮﻯ‬ ‫ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ‬ ‫ﺗﻌﺪﺍﺩ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ )‪(n‬‬
‫‪3‬‬ ‫‪C H‬‬
‫‪4 10‬‬
‫‪n=4‬‬
‫‪5‬‬ ‫‪C H‬‬
‫‪6 14‬‬
‫‪n=6‬‬
‫‪18‬‬ ‫‪C H‬‬
‫‪8 18‬‬
‫‪n=8‬‬
‫‪75‬‬ ‫‪C H‬‬
‫‪10 22‬‬
‫‪n=10‬‬
‫ﺗﻘﺮﺑﺎ"‪ 366‬ﻫﺰﺍﺭ‬ ‫‪C‬‬
‫‪20‬‬
‫‪H‬‬
‫‪42‬‬
‫‪n=20‬‬
‫‪13‬‬ ‫‪n=40‬‬
‫ﺩﺭﺣﺪﻭﺩ ‪6.0 ⋅ 10‬‬
‫‪C‬‬ ‫‪H‬‬
‫‪40‬‬ ‫‪82‬‬
‫‪ : 2- 1 – 4‬ﻧﺎ ﻣﮕﺬﺍﺭﻯ ﺍﻟﻜﺎﻥ ﻫﺎ ﺑﻪ ﺍﺳﺎﺱ ﻗﻮﺍﻋﺪ ) ‪( IUPAC‬‬
‫ﻧﺎﻣﮕﺬﺍﺭﻯ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺍﺯ ﺍﻫﻤﻴﺖ ﻭﻳﮋﻩ ﺑﺮﺧﻮﺭﺩﺍﺭﺍﺳﺖ؛ ﺯﻳﺮﺍ ﺑﺎ ﺗﻮﺟﻪ ﺑﻪ ﻓﺮﺍﻭﺍﻧﻰ ) ﺑﻴﺶ ﺍﺯ ﺑﻴﺴﺖ‬
‫ﻣﻠﻴﻮﻥ ( ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﻭ ﺍﻓﺰﺍﻳﺶ ﺭﻭﺯﺍﻧﺔ ﺁﻧﻬﺎ ﻧﻤﻴﺘﻮﺍﻥ ﺁﻧﻬﺎ ﺭﺍ ﺧﺎﺭﺝ ﺍﺯ ﻗﻮﺍﻋﺪ ﻧﺎﻣﮕﺬﺍﺭﻯ ﻧﻤﻮﺩ ‪ .‬ﺍﺗﺤﺎﺩﻳﻪ ﺑﻴﻦ‬
‫ﺍﻟﻤﻠﻠﻰ ﻛﻴﻤﻴﺎﻯ ﺗﺠـــﺮﺑﻰ ﻭ ﺧﺎﻟـﺺ )‪(International Union of Pure and Applied Chemistery) (IUPAC‬‬
‫ﻃﺮﻳﻘﻪ ﻫﺎﻯ ﺭﺍ ﺑﺮﺍﻯ ﻧﺎﻣﮕﺬﺍﺭﻯ ﺩﺭﻧﻈﺮﮔﺮﻓﺘﻪ ﻛﻪ ﺑﻪ ﺍﺳﺎﺱ ﺁﻥ ﻣﻴﺘﻮﺍﻥ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻯ ﺭﺍ ﭼﻨﻴﻦ ﻧﺎﻣﮕﺬﺍﺭﻯ ﻛﺮﺩ ‪:‬‬
‫ﺑﺎ ﺍﺭﻗﺎﻡ ‪ .... ، Metha ، Etha ، propa ، Buta ، penta‬ﻭﻏﻴﺮﻩ ﺁﺷﻨـــــﺎﻳﻰ ﺩﺍﺭﻳﺪ ﻭ ﻫﻢ‬
‫‪ Methane ، Ethane ، propane ، Butane‬ﻛﻪ ﻣﺮﻛﺒﺎﺕ ﺍﻭﻟﻰ ﺍﻟﻜﺎﻥ ﻫﺎ ﺍﺳﺖ ‪ ،‬ﺁﺷﻨﺎ ﻫﺴﺘﻴﺪ ‪،‬‬
‫ﻃﻮﺭﻯ ﻛﻪ ﺩﻳﺪﻩ ﻣﻴﺸﻮﺩ ‪ ،‬ﭘﺴﻮﻧﺪ ) ‪ ( ane‬ﺩﺭ ﺃﺧﻴﺮ ﻧﺎﻡ ﺍﺭﻗﺎﻡ ﻣﺬﻛﻮﺭﺗﺤﺮﻳﺮ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ﻛﻪ ﻣﺸﺨﺺ ﻛﻨﻨﺪﺓ‬
‫‪53‬‬
‫ﻧﻮﻉ ﻣﺮﻛﺐ ﺑﻮﺩﻩ ﻭ ﺍﻳﻦ ﺍﺭﻗﺎﻡ ﻣﺸﺨﺺ ﻛﻨﻨﺪﻩ ﺗﻌﺪﺍﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭ ﻣﺮﻛﺐ ﻣﻄﻠﻮﺏ ﻣﻰ ﺑﺎﺷﻨﺪ ‪ ،‬ﺟﺪﻭﻝ‬
‫)‪ (1 - 4‬ﻧﺎﻡ ﺑﻌﻀﻰ ﺍﺯ ﺍﻟﻜﺎﻥ ﻫﺎ ﺭﺍ ﻧﺸﺎﻥ ﻣﻴﺪﻫﺪ ‪ .‬ﺍﻟﻜﺎﻧﻬﺎﻯ ﺩﺍﺭﻧﺪﺓ ﺯﻧﺠﻴﺮ ﻣﺴﺘﻘﻴﻢ ﺭﺍ ﺍﻟﻜﺎﻧﻬﺎﻯ ﻧﺎﺭﻣﻞ ﻣﻰ‬
‫ﻧﺎﻣﻨﺪ ﻭ ﺑﻪ ) ‪ ( n‬ﻣﺸﺨﺺ ﺷﺪﻩ ﺍﻧﺪ ‪.‬‬
‫ﺍﮔﺮ ﻳﻚ ﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻟﻜﺎﻧﻬﺎ ﺣﺬﻑ ﻭ ﺍﺯ ﻣﺎﻟﻴﻜﻮﻝ ﺫﺭﺍﺗﻰ ﺩﺍﺭﺍﻯ ﺍﻟﻜﺘﺮﻭﻥ‬
‫ﻫﺎﻯ ﻃﺎﻗﻪ ﺗﺸﻜﻴﻞ ﮔﺮﺩﻳﺪﻩ ﺑﺎﺷﺪ ‪ ،‬ﭼﻨﻴﻦ ﺫﺭﺍﺕ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺭﺍﺩﻳﻜﺎﻝ ) ‪ ( Radical‬ﻳﺎ ﺑﻘﻴﻪ ﻋﻀﻮﻯ ﻓﻌﺎﻝ ﻳﺎﺩ‬
‫ﻣﻴﻜﻨﻨﺪ ‪ ،‬ﺩﺭﺻﻮﺭﺗﻰ ﻛﻪ ﻣﺮﻛﺒﺎﺕ ﻣﻄﻠﻮﺏ ﺍﻟﻜﺎﻥ ﺑﻮﺩﻩ ﺑﺎﺷﺪ ﻭﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﺁﻥ ﺑﺪﻭﻥ ﺟﻮﺭﻩ ﺷﺪﻥ ﺑﺎﻗﻰ ﻣﺎﻧﺪﻩ ﺑﺎﺷﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﺎﻳﻞ ) ‪ ( Alkyl‬ﻳﺎﺩ ﻣﻴﺸﻮﻧﺪ ‪ ،‬ﺩﺭﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﭘﺴﻮﻧﺪ ‪ane‬‬
‫ﻧﺎﻡ ﺁﻧﻬﺎ ﺩﺭ ﺣﺎﻟﺖ ﺩﺍﺷﺘﻦ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻃﺎﻗﻪ ﺑﻪ ‪ yl‬ﺗﻌﻮﻳﺾ ﻭﻧﺎﻡ ﺭﺍﺩ ﻳﻜﺎﻝ ﺁﻥ ﺑﻪ ﺩﺳﺖ ﻣﻰ ﺁﻳﺪ ‪.‬‬
‫ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ ‪:‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫‪2‬‬
‫‪، C H 3 − CH‬‬ ‫‪−‬‬ ‫‪, C H 3 − C H − C| H − C H − C H 2‬‬
‫‪3‬‬ ‫‪1‬‬
‫‪CH −‬‬ ‫‪CH 2 − C H −‬‬ ‫‪2‬‬
‫‪3‬‬ ‫‪2‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪Ethyyl‬‬
‫‪1 − propyl‬‬
‫‪M ethyl‬‬ ‫‪Isobutyl‬‬
‫ﻧﺎﻣﮕﺬﺍﺭﻯ ﺍﻟﻜﺎﻥ ﻫﺎﻯ ﺩﺍﺭﺍﻯ ﺯﻧﺠﻴﺮﻣﻨﺸﻌﺐ ﻃﻮﺭﻯ ﺍﺳﺖ ﻛﻪ ﺍﻭﻻً ﺯﻧﺠﻴﺮ ﻃﻮﻳﻞ ﺭﺍ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻟﻜﺎﻥ‬
‫ﻫﺎ ﺩﺭﻳﺎﻓﺖ ﻭ ﻧﻤﺒﺮﮔﺬﺍﺭﻯ ﻣﻰ ﻧﻤﺎﻳﻨﺪ ‪ ،‬ﻧﻤﺒﺮﮔﺬﺍﺭﻯ ﺭﺍ ﺍﺯ ﻫﻤﺎﻥ ﺍﻧﺠﺎﻡ ﺯﻧﺠﻴﺮ ﺁﻏﺎﺯ ﻣﻰ ﻧﻤﺎﻳﻨﺪ ﻛﻪ ﺍﻧﺸﻌﺎﺏ‬
‫ﺑﻪ ﺁﻥ ﻧﺰﺩﻳﻚ ﺑﺎﺷﺪ ‪ ،‬ﺩﺭﻳﻦ ﺻﻮﺭﺕ ﺍﻭﻻً ﻧﻤﺒﺮ ﻛﺎﺭﺑﻦ ﻛﻪ ﺩﺭ ﺁﻧﻬﺎ ﺑﻘﻴﻪ ﻧﺼﺐ ﺍﺳﺖ ﺑﻪ ‪...... 1 , 2 , 3‬‬
‫ﻭﻏﻴﺮﻩ ﺗﺤﺮﻳﺮ ﻭ ﺑﻘﻴﻪ ﻫﺎ ﺭﺍ ﻛﻪ ﺑﻪ ﺁﻥ ﻭﺻﻞ ﺍﺳﺖ ﺑﻌﺪ ﺍﺯ ﻧﻤﺒﺮ ﻛﺎﺭﺑﻦ ﺗﺤﺮﻳﺮ ﻣﻴﻨﻤﺎﻳﻨﺪ ﻭ ﺩﺭﺑﻴﻦ ﺑﻘﻴﻪ ﻭﻧﻤﺒﺮ‬
‫ﻛﺎﺭﺑﻦ ﻣﺮﺑﻮﻁ ﺁﻥ ﻋﻼﻣـﻪ ) ــ ( ﺭﺍ ﻗﺮﺍﺭ ﻣﻴﺪﻫﻨﺪ‪ .‬ﺫﻛﺮ ﺑﻘﻴﻪ ﻫﺎ ﺑﻪ ﺍﺳﺎﺱ ﺑﺰﺭﮔﻰ ﻭ ﻛﻮﭼﻜﻰ ﻭ ﻳﺎ ﺑﻪ ﺍﺳﺎﺱ‬
‫ﺗﻘ ُﺪ ﻡ ﺣﺮﻑ ﺍﻭﻝ ﻧﺎﻡ ﺁﻥ ﺑﻪ ﺍﻟﻔﺒﺎﻯ ﺍﻧﮕﻠﻴﺴﻰ ﻋﻤﻠﻰ ﻣﻴﮕﺮﺩﺩ ﻭ ﺩﺭﺍﺧﻴﺮ ﻧﺎﻡ ﺍﻟﻜﺎﻥ ﻫﺎﻯ ﺩﺍﺭﺍﻯ ﺯﻧﺠــﻴﺮ ﻃﻮﻳﻞ‬
‫ﺩﺭﻣﺮﻛﺐ ﺗﺤﺮﻳﺮ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﺩﺭﺻــــﻮﺭﺗﻰ ﻛﻪ ﺑﻘﻴﻪ ﻫﺎﻯ ﻣﺸﺎﺑﻪ ﺩﺭﺯﻧﺠﻴﺮ ﻃﻮﻳﻞ ﻧﺼﺐ ﮔﺮﺩﻳﺪﻩ ﺑﺎﺷﺪ ‪ ،‬ﺗﻌﺪﺍﺩ‬
‫ﺁﻧﻬﺎ ﺭﺍ ﺑﻪ ‪ Di ، Tri ، Tetra‬ﻭﻏﻴﺮﻩ ﻣﺸﺨﺺ ﻣﻴﺴﺎﺯﻧﺪ ؛ ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ ‪:‬‬
‫‪CH 3‬‬ ‫‪CH 3‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪CH‬‬
‫‪C H − CH − C H‬‬ ‫‪3‬‬ ‫‪1‬‬ ‫|‬ ‫‪3‬‬ ‫|‬ ‫‪5‬‬
‫‪3‬‬ ‫|‬ ‫‪3‬‬ ‫|‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫‪5‬‬ ‫‪C H − 2C − C H − 4C − C H‬‬
‫‪CH‬‬
‫‪3‬‬ ‫‪CH − C − CH − CH − CH‬‬ ‫‪3‬‬ ‫|‬ ‫‪2‬‬ ‫|‬ ‫‪3‬‬
‫‪3‬‬ ‫|‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪CH 3‬‬ ‫‪CH 3‬‬
‫‪2 −methyl propane‬‬ ‫‪CH‬‬
‫‪3‬‬
‫‪2,2,4,4 − tetramethyl pentane‬‬
‫‪2,2−dimethylpentane‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫‪5‬‬
‫‪C H 3 − C H − C H − CH2 −‬‬
‫|‬
‫‪CH‬‬
‫|‬
‫‪− CH2 − CH3‬‬
‫‪CH‬‬ ‫‪6‬‬
‫‪3‬‬ ‫‪CH‬‬
‫‪2‬‬
‫|‬
‫‪8‬‬ ‫‪7‬‬
‫‪CH CH‬‬
‫‪3‬‬ ‫‪2‬‬
‫‪3 − methyl− 5 − ethyloctane‬‬
‫‪ : 3- 1- 4‬ﻧﺎﻡ ﮔﺬﺍﺭﻯ ﺍﺷﺘﻘﺎ ﻗﻰ ﺍﻟﻜﺎﻥ ﻫﺎﻯ ﻣﻨﺸﻌﺐ‬
‫ﺩﺭﺍﻳﻦ ﻧﻮﻉ ﻧﺎﻣﮕﺬﺍﺭﻯ ﺍﻧﻮﺍﻉ ﻛﺎﺭﺑﻦ ﻫﺎ ﺑﺎﻳﺪ ﺍﺑﺘﺪﺍ ﻣﺸﺨﺺ ﮔﺮﺩﺩ ﻛﻪ ﻋﺒﺎﺭﺕ ﺍﺯ ﻛﺎﺭﺑﻦ ﺍﻭﻟﻰ ‪ ،‬ﺩﻭﻣﻰ ‪ ،‬ﺳﻮﻣﻰ‬
‫ﻭ ﭼﻬﺎﺭﻣﻰ ﻣﻴﺒﺎﺷﺪ ‪ .‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻛﻪ ﺩﺭﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺒﺎﺕ ﻋﻀــــﻮﻯ ﻳﻚ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺧﻮﺩﺭﺍ ﺑﺎ‬
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‫ﺍﺗﻮﻡ ﺩﻳﮕﺮ ﻛﺎﺭﺑﻦ ﻏﺮﺽ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺑﻪ ﻣﺼﺮﻑ ﺭﺳﺎﻧﻴﺪﻩ ﺑﺎﺷﺪ ‪ ،‬ﺑﻨﺎﻡ ﻛﺎﺭﺑﻦ ﺍﻭﻟﻰ)‪( primary carbon‬‬
‫ﻳﺎﺩ ﻣﻴﺸﻮﺩ ‪ ،‬ﺩﺭﺻﻮﺭﺗﻰ ﻛﻪ ﺩﻭﺍﻟﻜﺘﺮﻭﻥ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎ ﺩﻭ ﺍﺗﻮﻡ ﺩﻳﮕﺮ ﻛﺎﺭﺑﻦ ﻏﺮﺽ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺑﻪ ﻣﺼﺮﻑ‬
‫ﺭﺳﻴﺪﻩ ﺑﺎﺷﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﻛﺎﺭﺑﻦ ﺩﻭﻣﻰ) ‪ (secondary carbon‬ﻳﺎﺩ ﺷﺪﻩ ﻭ ﺍﮔﺮ ﺳﻪ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﻛﺎﺭﺑﻦ‬
‫ﺑﺎ ﺳﻪ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﻳﮕﺮ ﻏﺮﺽ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺑﻪ ﻣﺼﺮﻑ ﺭﺳﻴﺪﻩ ﺑﺎﺷﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﻛﺎﺭﺑﻦ ﺳﻮﻣﻰ) ‪Teritiary‬‬
‫‪ (carbon‬ﻭﺍﮔﺮ ﻫﺮﭼﻬﺎﺭ ﺍﻟﻜﺘﺮﻭﻥ ﻭﻻﻧﺴﻰ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎ ﭼﻬﺎﺭﺍﺗﻮﻡ ﺩﻳﮕﺮﻏﺮﺽ ﺗﺸﻜﻴﻞ ﺭﺍﺑﻄﻪ ﺑﻪ ﻣﺼﺮﻑ‬
‫ﺭﺳﻴﺪﻩ ﺑﺎﺷﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﻛﺎﺭﺑﻦ ﭼﻬﺎﺭﻣﻰ)‪ ( quaternary carbon‬ﻳﺎﺩ ﻣﻴﺸﻮﺩ ؛ ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ ‪:‬‬
‫‪p‬‬
‫‪C H3‬‬ ‫ﺍﻭﻟﻰ = ‪p‬‬
‫‪p‬‬ ‫‪t‬‬ ‫|‬ ‫‪s‬‬ ‫‪p‬‬ ‫ﺩﻭﻣﻰ=‪S‬‬
‫‪C H 3 − C H −qC− CH 2 − C H 3‬‬
‫‪pCH‬‬
‫|‬ ‫|‬ ‫ﺳﻮﻣﻰ = ‪T‬‬
‫‪3‬‬
‫‪sCH 2 −C H 3‬‬
‫‪p‬‬
‫ﭼﻬﺎﺭﻣﻰ = ‪q‬‬
‫ﺩﺭﻧﺎﻣﮕﺬﺍﺭﻯ ﺍﺷﺘﻘﺎﻗﻰ ﻛﺎﺭﺑﻨﻰ ﻛﻪ ﺑﺎ ﺑﻴﺸﺘﺮﻳﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﺩﻳﮕﺮ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﻪ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ‪ ،‬ﺑﻪ ﺣﻴﺚ ﻣﺮﻛﺰ‬
‫ﻗﺒﻮﻝ ﺷﺪﻩ ﻭ ﺁﻥ ﺭﺍ ﺑﻪ ﻧﺎﻡ ‪ Methane‬ﻳﺎﺩ ﻧﻤﻮﺩﻩ ﻭ ﺑﻘﻴﻪ ﻫﺎﻯ ﻛﻪ ﺑﻪ ﺍﻳﻦ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﻪ ﺩﺍﺭﻧﺪ‪ ،‬ﺑﻪ ﺣﻴﺚ‬
‫ﺭﺍﺩﻳــــــــــﻜﺎﻝ ﻫﺎ ) ﺍﻟﻜﺎﻳﻞ ﻫﺎ ( ﻗﺒﻮﻝ ﺷﺪﻩ‪ ،‬ﺩﺭﺍﻳﻦ ﺻﻮﺭﺕ ﺍﻭﻻً ﻧﺎﻡ ﺑﻘﻴﻪ ﻫﺎﻯ ﻛﻮﭼﻚ ﺩﺭﻧﺎﻣﮕﺬﺍﺭﻯ ﺫﻛﺮ‬
‫ﮔﺮﺩﻳﺪﻩ ﻭ ﺑﻌﺪﺍ ً ﻣﺘﻮﺳﻂ ﻭ ﺩﺭﺍﺧﻴﺮ ﺑﻘﻴﻪ ﻫﺎﻯ ﺑﺰﺭگ ﻭ ﺑﺎﻻﺧﺮﻩ ﻛﻠﻤﺔ )‪ ( Methane‬ﺗﺤﺮﻳﺮﻣﻴﮕﺮﺩﺩ‪.‬‬
‫‪CH 3‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫‪5‬‬
‫‪1‬‬ ‫‪4‬‬ ‫‪5‬‬ ‫‪C H 3 − C H 2 − C H − CH 2 − C H 3‬‬ ‫‪1‬‬ ‫‪2‬‬ ‫‪|3‬‬ ‫‪4‬‬ ‫‪5‬‬
‫‪C H 3 − C H − C − CH 2 − C H 3‬‬
‫‪C H 3 − CH 2 − C H 3‬‬
‫|‬
‫‪CH‬‬ ‫|‬ ‫|‬
‫‪3‬‬ ‫‪CH 3 CH 3‬‬
‫‪Dimethyl methane‬‬ ‫‪Dimethyl ethylisopropylmethan e‬‬
‫‪Methyldiethylmethane‬‬
‫‪ : 4- 1-4‬ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺩﺭ ﺟﺪﻭﻝ ﺫﻳﻞ ﺑﻌﻀﻰ ﺍﺯ ﺧﻮﺍﺹ ﻫﺎﻯ ﻓﺰﻳﻜﻰ ﺍﻟﻜﺎﻧﻬﺎﺩﺭﺝ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ‪:‬‬
‫ﺟﺪﻭﻝ)‪ ( 3 - 4‬ﺑﻌﻀﻰ ﺍﺯ ﺧﻮﺍﺹ ﻫﺎﻯ ﻓﺰﻳﻜﻰ‬
‫ﻛﺜﺎﻓﺖ ﻣﺨﺼﻮﺻﻪ‬ ‫ﻧﻘﻄﺔﻏﻠﻴﺎﻥ‬ ‫ﻧﻘﻄﺔﺫﻭﺑﺎﻥ ‪C‬‬ ‫ﻓﻮﺭﻣﻮﻝ‬ ‫ﻧﺎﻡ‬
‫‪0‬‬
‫‪0.424‬‬ ‫‪-161.5‬‬ ‫‪-182.5‬‬ ‫‪CH 4‬‬ ‫‪Methane‬‬
‫‪0.546‬‬ ‫‪-88.6‬‬ ‫‪-183.7‬‬ ‫‪C2 H 6‬‬ ‫‪Ethane‬‬
‫‪0.585‬‬ ‫‪-42.2‬‬ ‫‪-187.6‬‬ ‫‪C3 H 8‬‬ ‫‪Propane‬‬
‫‪0.579‬‬ ‫‪-0.5‬‬ ‫‪-138.3‬‬ ‫‪C4 H 10‬‬ ‫‪Buhane‬‬
‫‪0.626‬‬ ‫‪+36.1‬‬ ‫‪-129.7‬‬ ‫‪C5 H 12‬‬ ‫‪Penhane‬‬
‫‪0.659‬‬ ‫‪68.8‬‬ ‫‪-95.3‬‬ ‫‪C6 H 14‬‬ ‫‪Hexane‬‬
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 ‫‪0.684‬‬ ‫‪98.4‬‬ ‫‪90.6‬‬ ‫‪C7 H 16‬‬ ‫‪Hephane‬‬
‫‪0.730‬‬ ‫‪173.0‬‬ ‫‪-30.0‬‬ ‫‪C10 H 22‬‬ ‫‪Decane‬‬
‫‪0.764‬‬ ‫‪253.0‬‬ ‫‪+5.5‬‬ ‫‪C13 H 28‬‬ ‫‪Tetradecane‬‬
‫‪0.769‬‬ ‫‪270.5‬‬ ‫‪10.0‬‬ ‫‪C15 H 32‬‬ ‫‪Pentadecane‬‬
‫‪0.775‬‬ ‫‪287.5‬‬ ‫‪18.1‬‬ ‫‪C16 H 34‬‬ ‫‪Hexadecane‬‬
‫‪0.778‬‬ ‫‪344.0‬‬ ‫‪36.5‬‬ ‫‪C20 H 42‬‬ ‫‪Eicosane‬‬
‫‪0.942‬‬ ‫‪421.0‬‬ ‫‪93.0‬‬ ‫‪C50 H 102‬‬ ‫‪pentacontane‬‬
‫‪-‬‬ ‫‪-‬‬ ‫‪115.5‬‬ ‫‪C100 H 202‬‬ ‫‪Hectane‬‬
‫ﻃﻮﺭﻳﻜﻪ ﺩﺭ ﺟﺪﻭﻝ ﺩﻳﺪﻩ ﻣﻴﺸﻮﺩ ‪ ،‬ﭼﻬﺎﺭ ﻣﺮﻛﺐ ﺍﻭﻝ ﻫﻮﻣﻮﻟﻮگ ﺍﻳﻦ ﺧﺎﻧﺪﺍﻥ ﺩﺭ ﺷﺮﺍﻳﻂ ﺳﺘﻨﺪﺭﺩ ﺑﻪ ﺣﺎﻟﺖ‬
‫ﮔﺎﺯﻳﺎﻓﺖ ﺷﺪﻩ ﻭﺩﺍﺭﻧﺪﺓ ‪ 5‬ﺍﻟﻰ‪ 16‬ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﻪ ﺣﺎﻟﺖ ﻣﺎﻳﻊ ﻭﺑﺎﻻﺗﺮ ﺍﺯ ﺁﻥ ﺑﻪ ﺣﺎﻟﺖ ﺟﺎﻣﺪ ﻳﺎﻓﺖ ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫ﺩﺭ ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮﮔﻰ ﺍﻟﻜﺎﻧﻬﺎ ﺩﺭﺟﺔ ﻏﻠﻴﺎﻥ ‪ ،‬ﺫﻭﺑﺎﻥ ﻭﻛﺜﺎﻓﺖ ﻣﺨﺼﻮﺻﺔ ﺁﻧﻬﺎ ﺑﻪ ﺗﺪﺭﻳﺞ ﺍﺯﺩﻳﺎﺩ ﻣﻰ ﻳﺎﺑﺪ ‪.‬‬
‫ﺩﺭ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺍﻟﻜﺎﻧﻬﺎ ﻧﻴﺰ ﺩﺭﺟﺔ ﻏﻠﻴﺎﻥ ﻓﺮﻕ ﺩﺍﺭﺩ ؛ ﻃﻮﺭﻯ ﻛﻪ ﺍﻳﺰﻭﻣﻴﺮﻫﺎﻯ ﻧﺎﺭﻣﻞ ﺩﺍﺭﺍﻯ ﻧﻘﻄﺔ ﻏﻠﻴﺎﻥ ﺑﻠﻨﺪ‬
‫ﻭﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﺩﺍﺭﺍﻯ ﺍﻧﺸﻌﺎﺑﺎﺕ ﺑﻴﺸﺘﺮﺩﺍﺭﺍﻯ ﻧﻘﻄﺔ ﻏﻠﻴﺎﻥ ﭘﺎﻳﻴﻦ ﺍﻧﺪ ؛ ﺯﻳﺮﺍ ﺩﺭﺍﻟﻜﺎﻧﻬﺎﻯ ﻣﻨﺸﻌﺐ ﻗﻮﺍﻯ ﻭﺍﻧﺪﺭ ﻭﺍﻟﺲ‬
‫ﻛﻤﺘﺮ ﺑﻮﺩﻩ ﻭﻗﻮﺓ ﺟﺬﺏ ﺑﻴﻦ ﺫﺭﺍﺕ ﻛﻤﺘﺮ ﻣﻴﺒﺎﺷﺪ ‪،‬ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺑﺎ ﺣﺮﺍﺭﺕ ﻛﻢ ﻏﻠﻴﺎﻥ ﻣﻰ ﻧﻤﺎﻳﻨﺪ ‪.‬‬
‫ﻓﻜﺮ ﻛﻨﻴﺪ‬
‫ﻛﺪﺍﻡ ﻳﻜﻰ ﺍﺯ ﺍﻟﻜﺎﻧﻬﺎﻯ ﻧﺎﺭﻣﻞ ﺯﻧﺠﻴﺮﻯ ﻣﺮﻛﺒﺎﺗﻰ ﺩﺍﺭﺍﻯ ﻓﻮﺭﻣﻮﻝ ﺟﻤﻌﻰ ﺫﻳﻞ ﺑﻪ ﺯﻭﺩﻯ ﺫﻭﺏ ﻣﻴﮕﺮﺩﺩ؟‬
‫‪ 45 92‬ﻭ ‪32 66‬‬
‫‪C H‬‬ ‫‪C H‬‬
‫ﻟﺰﻭﺟﻴﺖ ﺍﻟﻜﺎﻧﻬﺎﻯ ﻣﺎﻳﻊ ﺑﺎ ﺍﺯﺩﻳﺎﺩ ﺗﻌﺪﺍﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺁﻧﻬﺎ )ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻧﺴﺒﺘﻰ( ﺯﻳﺎﺩﺗﺮ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ‪ :‬ﺣﻞ ﻛﻨﻴﺪ‪.‬‬
‫ﺍﺷﻜﺎﻝ ﺫﻳﻞ ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﻮﺩﻩ ‪ ،‬ﺑﮕﻮﻳﻴﺪ ﻛﻪ ﻛﺪﺍﻡ ﺍﻟﻜﺎﻥ ﺳﺮﻳﻊ ﺗﺮ ﺍﺯ ﺩﻳﻜﺮ ﺑﻪ ﻛﺘﺎﻟﻰ ﻣﻴﺮﻳﺰﻧﺪ؟‬
‫ﺷﻜﻞ ) ‪ ( 5 – 4‬ﺍﻟﻒ – ﺳﺮﻋﺖ ﺣﺮﻛﺖ ﺏ – ﺳﺮﻋﺖ ﺣﺮﻛﺖ‬
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 ‫‪ : 5- 1- 4‬ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﻓﻌﺎﻟﻴﺖ ﻛﻴﻤﻴﺎﻭﻯ ﺍﻟﻜﺎﻧﻬﺎ ﻛﻤﺘﺮ ﺑﻮﺩﻩ ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺁﻧﻬﺎﺭﺍ ﺑﻪ ﻧﺎﻡ ﭘﺎﺭﺍﻓﻴﻦ )‪(Paraffins‬؛ﻳﻌﻨﻰ ﻛﻢ ﻣﻴﻞ ﻳﺎﺩ‬
‫ﻣﻴﻨﻤﺎﻳﻨﺪ ‪ .‬ﭼﻮﻥ ﺗﻤﺎﻣﻰ ﺭﻭﺍﺑﻂ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﺍﻟﻜﺎﻧﻬﺎ ﻳﮕﺎﻧﻪ ﻭﻧﻮﻉ ﺳﮕﻤﺎ ﺍﻧﺪ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺗﻨﻬﺎ ﺗﻌﺎﻣﻼﺕ‬
‫ﺗﻌﻮﻳﻀﻰ ﺭﺍ ﺍﻧﺠﺎﻡ ﻣﻴﺪﻫﻨﺪ ‪.‬‬
‫ﺍﻟﻜﺎﻧﻬﺎ ﺑﺎ ﺁﻛﺴﻴﺠﻦ ﺗﻌﺎﻣﻞ ﻧﻤﻮﺩﻩ ﻣﺮﻛﺒﺎﺕ ﺁﻛﺴﻴﺠﻦ ﺩﺍﺭ ﻋﻀﻮﻯ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ‪ .‬ﺩﺭ ﺯﻳﺮ ﺑﻌﻀﻰ ﺗﻌﺎﻣﻼﺕ‬
‫ﺍﻟﻜﺎﻧﻬﺎ ﺭﺍ ﻣﻄﺎﻟﻌﻪ ﻣﻴﻨﻤﺎﻳﻢ ‪:‬‬
‫‪ : 1- 5- 1- 4‬ﺍﻛﺴﻴﺪ ﻳﺸﻦ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﺷﺮﺍﻳﻂ ﻋﺎﺩﻯ ﺩﺭ ﻣﻘﺎﺑﻞ ﺁﻛﺴﻴﺠﻦ ﻫﻮﺍ ﻭ ﺍﻛﺴﻴﺪﺍﻧﺘﻬﺎ ﻣﻘﺎﻭﻡ ﺑﻮﺩﻩ‪ ،‬ﺩﺭﺻﻮﺭﺗﻰ ﻛﻪ ﭘﺎﺭﺍﻓﻴﻨﻬﺎ ﺩﺭﻫﻮﺍ‬
‫ﻣﺤﺘﺮﻕ ﮔﺮﺩﻧﺪ ‪ ،‬ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺑﺎ ﺷﻌﻠﺔ ﺁﺑﻰ ﺳﻮﺧﺘﻪ ‪،‬ﺑﻪ ﻛﺎﺭﺑﻦ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ ‪،‬ﺁﺏ ﻭﺍﻧﺮژﻯ ﺗﻮﻟﻴﺪ ﻣﻴﮕﺮﺩﺩ‪:‬‬
‫→ ‪C H + 5O‬‬ ‫‪3CO‬‬ ‫‪+ 4H O + E‬‬
‫‪3 8‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺍﻟﻜﺎﻧﻬﺎ ﻣﻮﺍﺩ ﺧﻮﺏ ﺳﻮﺧﺘﻰ ﺑﻮﺩﻩ ﻭﺍﺯ ﺍﺣﺘﺮﺍﻕ ﺁﻧﻬﺎ ﺍﻧﺮژﻯ ﺯﻳﺎﺩ ﺗﻮﻟﻴﺪ ﻣﻴﮕﺮﺩﺩ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪:‬‬
‫→ ‪CH + 2O‬‬ ‫‪CO‬‬ ‫‪+ 2 H O + 891 kjoul/mol‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺍﺯ ﺍﺣﺘﺮﺍﻕ ﻳﻚ ﻛﻴﻠﻮﮔﺮﺍﻡ ﻣﻴﺘﺎﻥ ‪ 57000‬ﻛﻴﻠﻮ ِژﻭﻝ ﺍﻧﺮژﻯ ﺁﺯﺍﺩ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﺍﺣﺘﺮﺍﻕ ﻳﻜﻰ ﺍﺯ ﻋﻤﺪﻩ ﺗﺮﻳﻦ‬
‫ﺗﻌﺎﻣﻼﺕ ﭘﺎﺭﺍﻓﻴﻦ ﻣﻴﺒﺎﺷﺪ ﻛﻪ ﺩﺭ ﻋﻤﻞ ﺍﺯﺁﻥ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﺸﻮﺩ ‪.‬‬
‫ﮔﺎﺯ ﻃﺒﻴﻌﻰ ﻣﺨﻠﻮﻁ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﺑﻮﺩﻩ ‪ 90‬ﻓﻴﺼﺪ ﺁﻥ ﺭﺍ ﻣﻴﺘﺎﻥ ﺗﺸﻜﻴﻞ ﻧﻤﻮﺩﻩ ﺍﺳﺖ‬
‫ﺍﺯ ﺍﻛﺴﻴﺪﻳﺸﻦ ﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﺷﺮﺍﻳﻂ ﻣﻨﺎﺳﺐ ﻣﻴﺘﻮﺍﻥ ﺍﻟﻜﻮﻟﻬﺎ‪ ،‬ﺍﻟﺪﻳﻬﺎﻳﺪ ﻫﺎ ﻭﺗﻴﺰﺍﺑﻬﺎ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ﻛﻪ‬
‫ﺩﺭﻣﻮﺭﺩ ﺍﺳﺘﺤﺼﺎﻝ ﻣﺮﻛﺒﺎﺕ ﻓﻮﻕ ﻣﻌﻠﻮﻣﺎﺕ ﺩﺍﺩﻩ‬
‫ﺧﻮﺍﻫﺪ ﺷﺪ ‪ ،‬ﺩﺭﺍﻳﻦ ﻣﺒﺤﺚ ﺍﺣﺘﺮﺍﻕ ﺑﻌﻀﻰ ﺍﺯ‬
‫ﻣﺮﻛﺒﺎﺕ ﻛﻴﻤﻴﺎﻭﻯ ﺭﺍ ﻣﻄﺎﻟﻌﻪ ﻣﻴﻨﻤﺎﻳﻢ ‪.‬‬
‫ﺍﮔﺮ ﻣﻴﺘﺎﻥ ﺗﻮﺳﻂ ﺁﻛﺴﻴﺠﻦ ﻫﻮﺍ ﺩﺭ ﻣﻮﺟﻮﺩﻳﺖ‬
‫ﻛﺘﻠﺴﺖ ﺍﻛﺴﻴﺪﻳﺸﻦ ﮔﺮﺩﺩ‪ ،‬ﻣﻴﺘﺎﻧﻮﻝ ‪،‬ﻓﺎﺭﻡ ﺍﻟﺪﻳﻬﺎﻳﺪ‬
‫ﻭﻓﺎﺭﻣﻴﻚ ﺍﺳﻴﺪ ﺗﻮﻟﻴﺪ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫‪Ni‬‬
‫‪2CH‬‬ ‫‪+O‬‬ ‫⎯‬
‫‪⎯→ 2CH OH‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪3‬‬
‫‪O‬‬
‫‪Ni‬‬ ‫‪//‬‬
‫⎯ ‪CH + O‬‬‫‪⎯→ H − C − H + H O‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺷﻜﻞ )‪ (6 - 4‬ﺳﻮﺧﺘﻦ ﮔﺎﺯ ﻃﺒﻴﻌﻰ‬ ‫‪O‬‬
‫‪Ni‬‬ ‫‪//‬‬
‫‪2CH + 3O‬‬ ‫⎯‬
‫‪⎯→ 2H −‬‬
‫‪C− O − H + 2H O‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪2‬‬
‫‪ : 2- 5- 1- 4‬ﺗﻌﺎﻣﻞ ﻛﺮﻛﻨﮓ ))‪Cracking‬‬
‫ﻫﺮﮔﺎﻩ ﺍﻟﻜﺎﻧﻬﺎ ﺗﺎ‪ 600 - 400‬ﺩﺭﺟﻪ ﺣﺮﺍﺭﺕ ﺩﺍﺩﻩ ﺷﻮﺩ ‪ ،‬ﺩﺭﺍﻳﻦ ﺻﻮﺭﺕ ﻗﻄﻊ ﻣﺘﺠﺎﻧﺲ ﺭﺍﺑﻄﺔ ﻛﺎﺭﺑﻦ –‬
‫ﻛﺎﺭﺑﻦ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﺍﻟﻜﺎﻧﻬﺎ ﺻﻮﺭﺕ ﮔﺮﻓﺘﻪ ﻛﻪ ﺍﻳﻦ ﻋﻤﻠﻴﻪ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻧﺸﻘﺎﻕ ) ‪ ( Cracking‬ﻳﺎﺩ ﻣﻴﻨﻤﺎﻳﻨﺪ ‪.‬‬
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‫‪ Cracking‬ﻛﻠﻤﺔ ﺍﻧﮕﻠﻴﺴﻰ ﺑﻮﺩﻩ ﻛﻪ ﺑﻪ ﻣﻌﻨﻰ ﭼﺎﻙ ﻛﺮﺩﻥ ﺍﺳﺖ ‪ ،‬ﺩﺭﺍﻳﻦ ﺟﺎ ﻧﻴﺰ ﺑﻪ ﻫﻤﻴﻦ ﻣﻔﻬﻮﻡ ﺑﻪ ﻛﺎﺭﺭﻓﺘﻪ‬
‫ﻭﻋﺒﺎﺭﺕ ﺍﺯ ﺍﻧﺸﻘﺎﻕ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎﻯ ﺑﺰﺭگ ﺑﻪ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎﻯ ﻛﻮﭼﻚ ﻣﺸﺒﻮﻉ ﻭﻏﻴﺮ ﻣﺸﺒﻮﻉ ﺍﺳﺖ ‪:‬‬
‫‪Δ‬‬
‫‪CH − CH − CH − CH‬‬ ‫⎯‬
‫‪⎯→ CH − CH + CH = CH‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪3‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺗﻌﺎﻣﻞ ﺍﻧﺸﻘﺎﻕ ﺩﺭ ﺻﻨﻌﺖ ﺭﻭﻝ ﺍﺳﺎﺳﻰ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻛﻪ ﺑﻪ ﻛﻤﻚ ﺁﻥ ﻧﻔﺖ ﺧﺎﻡ ﺭﺍ ﺑﻪ ﺩﺭﺟﻪ ﻫﺎﻯ ﺑﻠﻨﺪ ﺣﺮﺍﺭﺕ‬
‫ﺑﻪ ﺍﺟﺰﺍﻯ ﻛﻮﭼﻚ ﻗﻴﻤﺘﻰ ﺍﺯ ﻗﺒﻴﻞ ﭘﺘﺮﻭﻝ ‪ ،‬ﺩﻳﺰﻝ ‪ ،‬ﺗﻴﻞ ﺧﺎﻙ ﻭﻏﻴﺮﻩ ﻣﺒﺪﻝ ﻣﻴﺴﺎﺯﻧﺪ‪.‬‬
‫‪ : 3- 5- 1- 4‬ﻫﻠﻮﺟﻨﻴﺸﻦ‬
‫ﻫﻠﻮﺟﻨﻴﺸﻦ ﺍﺯ ﺟﻤﻠﺔ ﻣﻬﻢ ﺗﺮﻳﻦ ﺗﻌﺎﻣﻼﺕ ﺍﻟﻜﺎﻧﻬﺎ ﻣﻴﺒﺎﺷﺪ ‪ ،‬ﺩﺭ ﻋﻤﻠﻴﺔ ﻫﻠﻮﺟﻨﻴﺸﻦ ﻋﻼﻭﻩ ﺍﺯ ﻛﻠﻮﺭﻳﻦ ‪ ،‬ﻓﻠﻮﺭﻳﻦ‬
‫ﻧﻴﺰ ﻣﻮﺭﺩ ﺍﺳﺘﻔﺎﺩﻩ ﻗﺮﺍﺭ ﻣﻴﮕﻴﺮﺩ ‪ ،‬ﺁﻳﻮﺩﻳﻦ ﻗﺎﺩﺭ ﺑﻪ ﺗﻌﻮﻳﺾ ﻣﺴﺘﻘﻴﻢ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺍﻟﻜﺎﻧﻬﺎ ﻧﻤﻴﺒﺎﺷﺪ؛ ﺍﻣﺎ ﻓﻠﻮﺭﻳﻦ ﺑﻪ‬
‫ﺷﺪﺕ ﻋﻤﻞ ﻣﻴﻨﻤﺎﻳﺪ ﻛﻪ ﺑﺎﻳﺪ ﺩﺭ ﻋﻤﻠﻴﺔ ﻓﻠﻮﺭﻳﻨﻴﺸﻦ ﺍﺣﺘﻴﺎﻁ ﺷﻮﺩ‪ .‬ﻛﻠﻮﺭﻳﻨﻴﺸﻦ ﺍﻟﻜﺎﻧﻬﺎ ﺑﻪ ﺣﺮﺍﺭﺕ ‪ 300‬ﺩﺭﺟﺔ‬
‫ﺳﺎﻧﺘﻰ ﮔﺮﺍﺩ ﺻﻮﺭﺕ ﻣﻴﮕﻴﺮﺩ ‪ .‬ﺟﺮﻳﺎﻥ ﻛﻠﻮﺭﻳﻨﻴﺸﻦ ﻣﻴﺘﺎﻥ ﺭﺍ ﺑﺎ ﻣﺮﺍﺣﻞ ﺁﻥ ﻣﻴﺘﻮﺍﻥ ﻗﺮﺍﺭﺫﻳﻞ ﻣﻼﺣﻈﻪ ﻛﺮﺩ‪:‬‬
‫ﻧﻮﺭ‬
‫‪CH + Cl‬‬ ‫‪⎯⎯→ CH Cl + HCl‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪3‬‬
‫ﻧﻮﺭ‬
‫⎯⎯ ‪CH Cl + Cl‬‬
‫‪⎯→ CH Cl + HCl‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪2 2‬‬
‫ﻧﻮﺭ‬
‫⎯ ‪CH Cl + Cl‬‬‫‪⎯→ CHCl + HCl‬‬
‫‪2 2‬‬ ‫‪2‬‬ ‫‪3‬‬
‫ﻧﻮﺭ‬
‫⎯ ‪CHCl + Cl‬‬‫‪⎯→ CCl + HCl‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪4‬‬
‫‪ : 6-1-4‬ﺍﺳﺘﺤﺼﺎﻝ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺍﻟﻜﺎﻥ ﻫﺎ ﺩﺭ ﻧﻔﺖ ﺑﻪ ﻣﻘﺪﺍﺭ ﺯﻳﺎﺩ ﺑﻪ ﺷﻜﻞ ﻣﺨﻠﻮﻁ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﻣﻴﺘﻮﺍﻥ ﺁﻧﻬﺎﺭﺍ ﺍﺯ ﻧﻔﺖ ﺟﺪﺍﻛﺮﺩ ‪ ،‬ﻫﻤﭽﻨﺎﻥ‬
‫ﮔﺎﺯ ﻃﺒﻴﻌﻰ ﻣﺨﻠﻮﻁ ﺍﻟﻜﺎﻧﻬﺎﻯ ﮔﺎﺯﻯ ﻣﻴﺒﺎﺷﺪ ؛ ﻻﻛﻦ ﺍﻟﻜﺎﻥ ﻫﺎ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﻃﺮﻳﻘﻪ ﻫﺎﻯ ﺫﻳﻞ ﻧﻴﺰ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ‪:‬‬
‫‪ - 1‬ﺑﻪ ﻃﺮﻳﻘﺔ ﺳﻨﺘﻴﺰ ﻭﺭﺗﺲ ‪ :‬ﻳﻜﻰ ﺍﺯ ﻃﺮﻳﻘﻪ ﻫﺎﻯ ﻣﻬﻢ ﺍﺳﺘﺤﺼﺎﻝ ﺍﻟﻜﺎﻧﻬﺎ ﻃﺮﻳﻘﺔ ﻭﺭﺗﺲ ﺍﺳﺖ؛ ﺩﺭ ﺍﻳﻦ‬
‫ﻃﺮﻳﻘﻪ ﻫﻼﻳﺪ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺭﺍ ﺑﺎ ﺳﻮﺩﻳﻢ ﻓﻠﺰﻯ ﺗﻌﺎﻣﻞ ﺩﺍﺩﻩ ‪ ،‬ﺩﺭ ﻧﺘﻴﺠﻪ ﺍﻟﻜﺎﻥ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫→ ‪2R − X + 2Na‬‬ ‫‪R − R + 2NaX‬‬
‫‪Alkylhalid e‬‬ ‫‪Alkane‬‬
‫‪2CH‬‬ ‫→ ‪− Cl + 2Na‬‬ ‫‪CH‬‬ ‫‪− CH‬‬ ‫‪+ 2NaCl‬‬
‫‪3‬‬ ‫‪3‬‬ ‫‪3‬‬
‫‪Methylchlo ride‬‬ ‫‪Ethane‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﻛﺪﺍﻡ ﻫﻼﻳﺪ ﺍﻟﻜﺎﻥ ﺑﺎ ﺳﻮﺩﻳﻢ ﺗﻌﺎﻣﻞ ﺩﺍﺩﻩ ﺷﻮﺩ ﺗﺎ ﻫﮕﺰﺍﻥ ﺗﺸﻜﻴﻞ ﮔﺮﺩﺩ ؟ ﺍﮔﺮ ‪ iodo butane - 2‬ﺑﺎ‬
‫ﺳﻮﺩﻳﻢ ﺗﻌﺎﻣﻞ ﺩﺍﺩﻩ ﺷﻮﺩ ‪ ،‬ﻛﺪﺍﻡ ﺍﻟﻜﺎﻥ ﺣﺎﺻﻞ ﺧﻮﺍﻫﺪ ﺷﺪ؟ ﻣﻌﺎﺩﻟﺔ ﺗﻌﺎﻣﻞ ﺁﻥ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ‬
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‫‪ - 2‬ﺩﺭ ﺳﺎﻝ‪ 1901‬ﻋﺎﻟﻤﻲ ﺑﻪ ﻧﺎﻡ ﮔﺮﻳﻨﺎﺭﺩ )‪ (Victor Grignard‬ﻳﻚ ﻣﺮﻛﺐ ﻋﻀﻮﻯ ﻫﻼﻳﺪ‬
‫ﻣﮕﻨﻴﺰﻳﻢ ﺭﺍ ﻗﺮﺍﺭ ﻣﻌﺎﺩﻟﺔ ﺯﻳﺮ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩﻩ ‪ ،‬ﺁﻥ ﺭﺍ ﻫﺎﻳﺪﺭﻭﻟﻴﺰ ﻧﻤﻮﺩ ﻛﻪ ﺩﺭ ﻧﺘﻴﺠﻪ ﺍﻟﻜﺎﻧﻬﺎ ﻭﺩﻳﮕﺮ ﻣﺮﻛﺒﺎﺕ‬
‫ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ‪:‬‬
‫→ ‪R − X + Mg‬‬ ‫‪R − Mg − X‬‬
‫⎯ ‪R − Mg − X + HOH‬‬
‫‪⎯→ R − H + Mg(OH)X‬‬
‫‪HOH‬‬
‫⎯ ‪C H − Br + Mg‬‬
‫⎯ ⎯⎯ ‪⎯→ C H − Mg − Br‬‬
‫‪⎯→ C H + Mg(OH)Br‬‬
‫‪2 5‬‬ ‫‪2 5‬‬ ‫‪2 6‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺑﻪ ﺍﺳﺎﺱ ﺗﻌﺎﻣﻞ ﮔﺮﻳﻨﺎﺭﺩ ﻣﺮﻛﺒﺎﺕ ﺯﻳﺮ ﺭﺍ ﺍﺳﺘﺤﺼﺎﻝ ﻭﻣﻌﺎﺩﻟﻪ ﻛﻴﻤﻴﺎﻭﻯ ﺁﻧﻬﺎ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪.‬‬
‫‪a) C 3 H 8‬‬ ‫)‪, b‬‬ ‫‪CH 3 − CH − CH 3‬‬
‫|‬
‫‪CH‬‬
‫‪3‬‬
‫‪ - 3‬ﺍﺯ ﺍﺭﺟﺎﻉ ﻧﻤﻮﺩﻥ ﺍﻟﻜﺎﻳﻞ ﻫﻼﻳﺪ ﻫﺎ ﻧﻴﺰ ﻣﻴﺘﻮﺍﻥ ﺍﻟﻜﺎﻧﻬﺎ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ؛ ﻃﻮﺭﻯ ﻛﻪ ﺍﻟﻜﺎﻳﻞ‬
‫ﻫﻼﻳﺪﻫﺎ ﺭﺍ ﺑﺎ ﺟﺴﺖ ﻓﻠﺰﻯ ﺗﻌﺎﻣﻞ ﺩﺍﺩﻩ ‪ ،‬ﺩﺭﻧﺘﻴﺠﻪ ﺍﻟﻜﺎﻥ ﻭ ﻫﻼﻳﺪ ﺟﺴﺖ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫‪2 R − X + Zn + 2 H ⎯⎯→ 2 R − H + ZnX 2‬‬
‫‪CH CH 3‬‬
‫‪3‬‬
‫|‬ ‫|‬
‫→ ‪2CH − CH − CH + Zn‬‬ ‫‪CH − CH − CH − CH − CH + ZnBr‬‬
‫‪3‬‬ ‫|‬ ‫‪3‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪2‬‬
‫‪Br‬‬
‫‪ - 4‬ﺍﺯ ﺣﺮﺍﺭﺕ ﺩﺍﺩﻥ ﻧﻤﻚ ﻓﻠﺰﻯ ﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﺍﺳﻴﺪﻫﺎ ﺑﺎ ﺳﻮﺩﺍﻻﻳﻢ )ﻣﺨﻠﻮﻁ ﺳﻮﺩﻳﻢ ﻫﺎﻳﺪﺭﻭﻛﺴﺎﻳﺪﭼﻮﻧﻪ(‬
‫‪R − COONa + NaOH‬‬
‫‪(⋅CaO)Δ‬‬
‫⎯ ⎯⎯‬
‫‪⎯→ R − H + Na‬‬ ‫‪CO‬‬
‫ﻣﻴﺘﻮﺍﻥ ﺍﻟﻜﺎﻧﻬﺎ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ‪:‬‬
‫‪2‬‬ ‫‪3‬‬
‫‪(⋅CaO) Δ‬‬
‫‪C H − COONa + NaOH‬‬ ‫⎯ ⎯⎯‬
‫‪⎯→ C H − H + Na CO‬‬
‫‪2 5‬‬ ‫‪2 5‬‬ ‫‪2‬‬ ‫‪3‬‬
‫‪ - 5‬ﺍﺯ ﻫﺎﻳﺪﺭﻭﺟﻨﻴﺸﻦ ﺍﻟﻜﻴﻨﻬﺎ ﻭﺍﻟﻜﺎﻳﻦ ﻫﺎ ﺩﺭ ﻣﻮﺟﻮﺩﻳﺖ ﻛﺘﻠﺴﺖ ﻧﻜﻞ ‪ ،‬ﭘﻼﺗﻴﻦ ﻭﻏﻴﺮﻩ ﺍﻟﻜﺎﻧﻬﺎﻯ ﺍﻳﺰﻭﻟﻮگ‬
‫ﺷﺎﻥ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫| |‬
‫\‬ ‫‪/‬‬ ‫‪Ni‬‬
‫⎯ ‪C=C +H‬‬‫→⎯‬ ‫‪− C− C−‬‬
‫‪/‬‬ ‫\‬ ‫‪2‬‬ ‫| |‬
‫‪H H‬‬
‫‪H H‬‬
‫‪CH3‬‬ ‫| |‬
‫\‬ ‫‪/H‬‬ ‫‪Ni‬‬
‫‪C=C‬‬ ‫⎯ ‪+H‬‬‫→⎯‬ ‫‪CH − C − C − H‬‬
‫‪H/‬‬ ‫‪\H‬‬‫‪2‬‬ ‫| | ‪3‬‬
‫‪H H‬‬
‫‪59‬‬
 ‫‪ :7- 1- 4‬ﻣﻴﺘﺎﻥ )‪( Methane‬‬
‫ﺳﺎﺩﻩ ﺗﺮﻳﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎﻯ ﭘﺎﺭﺍﻓﻴﻦ ‪ ،‬ﻣﻴﺘﺎﻥ ﺑﻮﺩﻩ ﻛﻪ ﺑﻪ ﻧﺎﻡ ﻫﺎﻯ ﻣﺨﺘﻠﻒ ﻳﺎﺩ ﺷﺪﻩ ﻭ ﺍﻳﻦ ﻧﺎﻡ ﻫﺎﻱ ﺁﻥ‬
‫ﻣﺮﻳﻮﻁ ﺑﻪ ﭼﮕﻮﻧﻪ ﮔﻰ ﺣﺎﻟﺖ ﻫﺎﻯ ﻣﺨﺘﻠﻒ ﭘﻴﺪﺍﻳﺶ ﺁﻥ ﻣﻴﭙﺎﺷﺪ ‪ ،‬ﭼﻮﻥ ﺍﻳﻦ ﮔﺎﺯ ﺍﺯ ﮔﻨﺪﻩ ﺷﺪﻥ ﻣﻮﺍﺩ ﻋﻀﻮﻯ‬
‫ﺩﺭﺧﻨﺪﻕ ﻫﺎ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪ ،‬ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺑﻪ ﻧﺎﻡ ﮔﺎﺯ ﺧﻨﺪﻕ ﻳﺎﺩ ﻣﻴﺸﻮﺩ ‪ ،‬ﺑﻪ ﻫﻤﻴﻦ ﺗﺮﺗﻴﺐ ﺍﻳﻦ ﮔﺎﺯ ﺩﺭ ﻣﻌﺎﺩﻥ‬
‫ﻧﻴﺰ ﻳﺎﻓﺖ ﺷﺪﻩ ؛ﺑﻨﺎﺑﺮﺁﻥ ﺑﻪ ﻧﺎﻡ ﮔﺎﺯ ﻣﻌﺎﺩﻥ ﻧﻴﺰ ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ‪ .‬ﺗﺮﺍﻛﻢ ﮔﺎﺯ ﻣﻴﺘﺎﻥ ﺩﺭ ﻣﻌﺎﺩﻥ ﺳﺒﺐ ﺍﻧﻔﺠـــــــﺎﺭﺍﺕ‬
‫ﻣﻬﻠﻚ ﻭ ﺧﻄﺮﻧﺎﻙ ﺷﺪﻩ ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺑﻪ ﻧﺎﻡ )‪ ( Firedamp‬ﻳﻌﻨﻰ ﺑﺨﺎﺭ ﺁﺗﺸﺰﺍ ﻧﻴﺰ ﻳﺎﺩ ﻣﻴﺸﻮﺩ ‪.‬‬
‫ﺍﺗﻤﻮﺳﻔﻴﺮ ﺳﻴﺎﺭﻩ ﻫﺎﻯ ﺑﺰﺭگ ) ﺯﺣﻞ ﻭﻣﺸﺘﺮﻯ ( ﺩﺍﺭﺍﻯ ﻣﻴﺘﺎﻥ ﺍﺳﺖ ‪ .‬ﺍﻳﻦ ﺍﻣﺮ ﺩﻻﻟﺖ ﺑﺮ ﺁﻥ ﻣﻴﻨﻤﺎﻳﺪ ﻛﻪ‬
‫ﻣﻴﺘﺎﻥ ﺩﺭ ﺷﺮﺍﻳﻂ ﻃﺒﻴﻌﻰ ﺩﺭ ﻋﺪﻡ ﻣﻮﺟﻮﺩﻳﺖ ﻗﻮﺓ ﺣﻴﺎﺗﻰ ﻧﻴﺰ ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫ﺩﺭ ﺩﺍﺧﻞ ﺯﻣﻴﻦ ﻣﻘﺪﺍﺭ ﺯﻳﺎﺩ ﺫﺧﺎﻳﺮ ﮔﺎﺯﺍﺕ ﻣﺤﺘﺮﻗﻪ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﺁﻧﻬﺎ ﺑﻪ ﺣﺎﻟﺖ ﺁﺯﺍﺩ ﺑﻪ ﺷﻜﻞ ﮔﺎﺯ ﻃﺒﻴﻌﻰ‬
‫)ﺫﺧﺎﻳﺮ ﺩﺭ ﺩﺍﺧﻞ ﻗﺸﺮﺿﺨﻴﻢ ﺯﻣﻴﻦ ( ﻭﺑﻪ ﺣﺎﻟﺖ ﻣﺤﻠﻮﻝ ﺩﺭ ﻧﻔﺖ ﻭﻳﺎ ﺁﺑﻬﺎﻯ ﺗﺤﺖ ﺍﻻﺭﺿﻰ ﺑﻪ ﺣﻴﺚ ﮔﺎﺯﺍﺕ‬
‫ﺿﻤﻴﻤﺔ ﻧﻔﺖ ﻳﺎﻓﺖ ﻣﻴﺸﻮﻧﺪ ‪ .‬ﺩﺭﮔﺎﺯ ﻃﺒﻴﻌﻰ ‪ 98%‬ﻣﻴﺘﺎﻥ ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ‪ ،‬ﻭﺑﻪ ﺷﻜﻞ ﻣﺨﻠﻮﻁ ﺍﻳﺘﺎﻥ ‪،‬ﭘﺮﻭﭘﺎﻥ‬
‫ﻭﻏﻴﺮﻩ ﻧﻴﺰ ﻣﻮﺟﻮﺩ ﻣﻴﺒﺎﺷﺪ ‪ .‬ﮔﺎﺯﻫﺎﻯ ﺿﻤﻴﻤﺔ ﺗﻴﻞ ﺩﺍﺭﺍﻯ ﻛﻤﺘﺮﻳﻦ ﻣﻘﺪﺍﺭ ﻣﻴﺘﺎﻥ ﺍﺳﺖ ﻛﻪ ‪ 30‬ﺍﻟﻰ ‪80%‬‬
‫ﺍﺳﺖ ؛ ﺍﻣﺎ ﻣﺮﻛﺒﺎﺕ ﻫﻮﻣﻮﻟﻮگ ﺁﻥ ﻳﻌﻨﻰ ﺍﻳﺘﺎﻥ ‪ 4‬ﺍﻟﻰ ‪ 20‬ﻓﻴﺼﺪ ‪ ،‬ﭘﺮﻭﭘﺎﻥ ‪ 5‬ﺍﻟﻰ ‪ 22‬ﻓﻴﺼﺪ ‪ ،‬ﺑﻴﻮﺗﺎﻥ ‪5‬‬
‫ﺍﻟﻲ ‪ 20‬ﻓﻴﺼﺪ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪ ،‬ﺩﻳﮕﺮ ﮔﺎﺯﺍﺕ ﻧﻴﺰ ﺩﺭﺍﻳﻦ ﮔﺎﺯ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪ .‬ﺍﻟﻜﺎﻥ ﻫﺎﻯ ﻋﺎﻟﻰ ﺩﺭ ﺗﺮﻛﻴﺐ‬
‫ﻧﻔﺖ ﺷﺎﻣﻞ ﺍﺳﺖ ‪.‬‬
‫ﺑﻪ ﻃﻮﺭ ﺍﻭﺳﻂ ﺍﺯ ﻳﻚ ﻣﺘﺮ ﻣﻜﻌﺐ ﮔﺎﺯ ﻃﺒﻴﻌﻰ ‪ 46000‬ﻛﻴﻠﻮ ژﻭﻝ ﺣﺮﺍﺭﺕ ﺗﻮﻟﻴﺪ ﻣﻴﺸﻮﺩ ﻛﻪ ﺑﺮﺍﻯ ﺫﻭﺏ‬
‫‪ 30‬ﻛﻴﻠﻮﮔﺮﺍﻡ ﭼﺪﻥ ﻛﺎﻓﻰ ﻣﻴﺒﺎﺷﺪ ‪.‬‬
‫‪ : 1 – 7- 1- 4‬ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ ﻣﻴﺘﺎﻥ‬
‫ﻣﻴﺘﺎﻥ ﮔﺎﺯ ﺑﻰ ﺑﻮ ‪ ،‬ﺑﻰ ﺫﺍﻳﻘﻪ ﻭ ﺑﻰ ﺭﻧﮓ ﺑﻮﺩﻩ ﻭﻧﺴـــــﺒﺖ ﺑﻪ ﻫﻮﺍﺳﺒﻚ ﻣﻴﺒﺎﺷﺪ ‪ .‬ﺳﻨﮕﻴﻨﻰ ﺁﻥ ﻧﺴﺒﺖ ﺑﻪ‬
‫ﻫﻮﺍ ‪ d = M = 16‬ﺍﺳﺖ ‪ .‬ﻣﺎﻟﻴﻜﻮﻝ ﻣﻴﺘﺎﻥ ﻏﻴﺮ ﻗﻄﺒﻰ ﺑﻮﺩﻩ ﻭ ﻗﻮﺓ ﺟﺎﺫﺑﻪ ﺑﻴﻦ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﻯ ﻣﻴﺘﺎﻥ ﻗﻮﺓ ﻭﺍﻧﺪﺭ‬
‫‪29 29‬‬
‫ﻭﺍﻟﺲ ﻭﻟﻨﺪﻥ ﺍﺳﺖ ‪ .‬ﺍﻳﻦ ﻗﻮﻩ ﻧﺴﺒﺖ ﻛﻮﭼﻜﻰ ﻣﺎﻟﻴﻜﻮﻟﻬﺎﻯ ﻣﻴﺘﺎﻥ ﺑﺴﻴﺎﺭ ﺿﻌﻴﻒ ﺑﻮﺩﻩ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﻧﻘﻄﺔ ﻏﻠﻴﺎﻥ‬
‫ﻭﺫﻭﺑﺎﻥ ﺁﻥ ﺑﺴﻴﺎﺭ ﭘﺎﻳﻴﻦ ﺍﺳﺖ ‪ .‬ﻣﻴﺘﺎﻥ ﺩﺭ ﺁﺏ ﺣﻞ ﻧﻤﻰ ﺷﻮﺩ‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫‪ - 1‬ﻛﺜﺎﻓﺖ ﻣﺨﺼﻮﺻﺔ ﻳﻚ ﺍﻟﻜﺎﻥ ‪1.52‬ﺍﺳﺖ ‪ ،‬ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻭ ﻓﻮﺭﻣﻮﻝ ﻣﺎﻟﻴﻜﻮﻟﻰ ﺁﻥ ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪ - 2‬ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻳﻚ ﺍﻟﻜﺎﻥ ‪ 62‬ﺍﺳﺖ ‪ ،‬ﻛﺜﺎﻓﺖ ﻣﺨﺼﻮﺻﺔ ﺁﻥ ﺭﺍ ﺩﺭﻳﺎﻓﺖ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪ : 2 – 6- 1- 4‬ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻱ ﻣﻴﺘﺎﻥ‬
‫ﮔﺎﺯﻃﺒﻴﻌﻰ ﻛﻪ ‪ 98%‬ﺁﻥ ﺭﺍ ﻣﻴﺘﺎﻥ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ ‪ ،‬ﺁﻥ ﺭﺍ ﺑﻪ ﺣﻴﺚ ﻣﺎﺩﺓ ﺧﺎﻡ ﻛﻴﻤﻴﺎﻭﻯ ﺑﺮﺍﻯ ﺍﺳﺘﺤﺼﺎﻝ‬
‫ﻣﻮﺍﺩ ﺫﻳﻞ ﺑﻪ ﻛﺎﺭ ﻣﻴﺮﻭﺩ ‪:‬‬
‫‪60‬‬
 ‫‪ – 1‬ﺍﺳﺘﺤﺼﺎﻝ ﺩﻭﺩﻩ )‪ (soot‬ﻭ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺑﻪ ﻃﺮﻳﻘﺔ ﭘﺎﻳﺮﻭﻟﻴﺰ )‪(Pyrolysis‬‬
‫‪1000 0 C‬‬
‫‪CH‬‬ ‫⎯ ⎯⎯‬
‫‪⎯→ 2H‬‬ ‫‪+C‬‬
‫‪4‬‬ ‫‪2‬‬
‫ﺩﻭﺩﻩ ﺑﻪ ﺣﻴﺚ ﻣﺎﺩﺓ ﺍﺿﺎﻓﻰ ﺩﺭ ﻣﻮﺍﺩ ﺧﺎﻡ ﺭﺍﺑﺮ ﺑﻪ ﻛﺎﺭﺑﺮﺩﻩ ﻣﻴﺸﻮﺩ ﻭﻫﻢ ﺍﺯ ﺁﻥ ﺩﺭ ﺩﺑﺎﻏﻰ ﺑﻪ ﺣﻴﺚ ﺭﻧﮓ ﺍﺳﺘﻔﺎﺩﻩ‬
‫ﺑﻪ ﻋﻤﻞ ﻣﻰ ﺁﻳﺪ‪.‬‬
‫‪ – 2‬ﺑﺮﺍﻯ ﺍﺳﺘﺤﺼﺎﻝ ﺍﺳﻴﺘﻴﻠﻴﻦ ﺍﺯ ﻣﻴﺘﺎﻥ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﻜﻨﻨﺪ ‪:‬‬
‫‪1500 0 C‬‬
‫‪2CH‬‬ ‫⎯ ⎯⎯‬
‫‪⎯→ C‬‬ ‫‪H‬‬ ‫‪+ 3H‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬
‫‪ – 3‬ﻣﻴﺘﺎﻥ ﺭﺍ ﺑﺎ ﺑﺨﺎﺭﺍﺕ ﺁﺏ ﺗﻌﺎﻣﻞ ﺩﺍﺩﻩ ﮔﺎﺯ ﻛﺎﺭﺑﻦ ﻣﻮﻧﻮﺍﻛﺴﻴﺎﻳﺪ ﻭﻫﺎﻳﺪﺭﻭﺟﻦ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﻣﻴﺂﻭﺭﻧﺪ ‪:‬‬
‫‪800 0 C‬‬
‫‪CH‬‬ ‫‪+ H O ⎯⎯⎯→ 3H + CO‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺑﻪ ﺍﻳﻦ ﺍﺳﺎﺱ ﺍﺯ ﻣﺤﺼﻮﻻﺕ ﻓﻮﻕ ﻣﻴﺘﺎﻳﻞ ﺍﻟﻜﻮﻝ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﻣﻴﺂﻭﺭﻧﺪ ‪.‬‬
‫‪ – 4‬ﺍﺯ ﺗﻌﺎﻣﻞ ﺍﻛﺴﻴﺪﻳﺸﻦ ﻣﻴﺘﺎﻥ ‪ ،‬ﻣﻴﺘﺎﻳﻞ ﺍﻟﻜﻮﻝ ‪ ،‬ﻓﺎﺭﻡ ﺍﻟﺪﻳﻬﺎﻳﺪ ﻭ ﻓﺎﺭﻣﻴﻚ ﺍﺳﻴﺪ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﻣﻰ ﺁﻭﺭﻧﺪ ‪:‬‬
‫→ ‪2CH + O‬‬ ‫‪2CH − OH‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪3‬‬
‫‪O‬‬
‫‪//‬‬
‫⎯ ‪CH 4 + O 2‬‬‫‪⎯→ H − C − H + H 2O‬‬
‫‪O‬‬
‫‪//‬‬
‫⎯ ‪2CH 4 + 2O 2‬‬
‫‪⎯→ 2H − C −O − H + 2H 2O‬‬
‫‪ – 5‬ﺍﺯ ﭘﺎﻳﺮﻭﻟﻴﺰ ﻣﻴﺘﺎﻥ ﻭ ﺍﻣﻮﻧﻴﺎ ﺩﺭﻣﻮﺟﻮﻳﺖ ﺁﻛﺴﻴﺠﻦ ‪ ،‬ﻫﺎﻳﺪﺭﻭﺟﻦ ﺳﻴﺎﻧﺎﻳﺪ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫‪10000 C‬‬
‫‪2CH + 2 NH + 3O‬‬ ‫⎯ ⎯⎯‬
‫‪⎯→ 2HCN + 6 H 2 O‬‬
‫‪4‬‬ ‫‪3‬‬ ‫‪2‬‬
‫‪ - 6‬ﺍﺯ ﻛﻠﻮﺭﻳﻨﻴﺸﻦ ﻣﻴﺘﺎﻥ ‪ ،‬ﻣﻴﺘﺎﻳﻞ ﻛﻠﻮﺭﺍﻳﺪ ‪ ،‬ﻛﻠﻮﺭﻭﻓﺎﺭﻡ ﻭ ﻛﺎﺭﺑﻦ ﺗﺘﺮﺍﻛﻠﻮﺭﺍﻳﺪ ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ ‪:‬‬
‫ﻧﻮﺭ‬
‫‪CH + Cl‬‬ ‫⎯‬
‫‪⎯→ CH Cl + HCl‬‬
‫‪4‬‬ ‫‪2‬‬ ‫‪3‬‬
‫ﻧﻮﺭ‬
‫‪CH Cl + Cl ⎯⎯→ CH Cl + HCl‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪2 2‬‬
‫ﻧﻮﺭ‬
‫‪CH Cl + Cl ⎯⎯→ CH Cl + HCl‬‬
‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪2‬‬
‫ﻧﻮﺭ‬
‫‪CH Cl + Cl ⎯⎯→ CCl + HCl‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪4‬‬
‫ﻣﻴﺘﺎﻥ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﻗﺮﺍﺭ ﻃﺮﻳﻘﻪ ﻫﺎﻯ ﻋﻤﻮﻣﻰ ﺍﻟﻜﺎﻧﻬﺎ ﺍﺳﺘﺤﺼﺎﻝ ﻧﻤﻮﺩ ‪:‬‬
‫‪61‬‬
 ‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺍﺳﺘﺤﺼﺎﻝ ﻣﻴﺘﺎﻥ‬
‫ﻣﻮﺍﺩ ﻣﻮﺭﺩ ﺿﺮﻭﺭﺕ ‪ :‬ﺗﺴﺖ ﺗﻴﻮﺏ ﺩﻭﻋﺪﺩ ‪ ،‬ﺳﺘﻴﻨﺪ ﻫﻤﺮﺍﻩ ﮔﻴﺮﺍ ﺩﻭﻋﺪﺩ ‪ ،‬ﻧﻞ ﺯﺍﻧﻮﺧﻢ ‪ ،‬ﻛﺎﺭﻙ‬
‫ﺳﻮﺭﺍﺥ ﺩﺍﺭ ‪ ،‬ﺗﺸﺖ ﭘﺮ ﺍﺯ ﺁﺏ‪،‬ﻣﻨﺒﻊ ﺣﺮﺍﺭﺕ ‪ ،‬ﺳﻮﺩﺍ‪ -‬ﻻﻳﻢ ) ﻣﺨﻠﻮﻁ ﺳﻮﺩﻳﻢ ﻫﺎﻳﺪﺭﻭﻛﺴﺎﻳﺪ ﻭ ﻛﻠﺴﻴﻢ‬
‫ﺍﻛﺴﺎﻳﺪ ( ‪ ،‬ﺳﻮﺩﻳﻢ ﺍﺳﻴﺘﺎﺕ‪.‬‬
‫ﻃﺮﺯﺍﻟﻌﻤﻞ ‪ :‬ﻗﺮﺍﺭ ﺷﻜﻞ )‪( 7 - 4‬ﻣﻘﺪﺍﺭ ﺳﻮﺩﻳﻢ ﺍﺳﻴﺘﺎﺕ ﺭﺍ ﺑﺎ ﺳﻮﺩﺍ‪ -‬ﻻﻳﻢ ﺩﺭ ﻳﻚ ﺗﺴﺖ ﺗﻴﻮﺏ‬
‫ﺍﻧﺪﺍﺧﺘﻪ ﺩﻫﻦ ﺗﺴﺖ ﺗﻴﻮﺏ ﺭﺍ ﺑﺎﻛﺎﺭﻙ ﺳﻮﺭﺍﺥ ﺩﺍﺭ ﺑﺴﺘﻪ ﻧﻤﺎﻳﻴﺪ ‪ ،‬ﺍﺯ ﺳﻮﺭﺍﺥ ﻛﺎﺭﻙ ﻳﻚ ﻧﻞ ﺯﺍﻧﻮﺧﻢ ﺭﺍ‬
‫ﺑﻪ ﺗﺴﺖ ﺗﻴﻮﺏ ﺩﻳﮕﺮ ﻛﻪ ﺩﺭ ﺗﺸﺖ ﭘﺮ ﺍﺯ ﺁﺏ ﺳﺮﭼﭙﻪ ﻗﺮﺍﺭ ﺩﺍﺭﺩ ‪ ،‬ﺩﺍﺧﻞ ﻧﻤﺎﻳﻴﺪ ؛ ﺳﭙﺲ ﻣﺤﺘﻮﻳﺎﺕ ﺩﺍﺧﻞ‬
‫ﺗﺴﺖ ﺗﻴﻮﺏ ﺭﺍ ﺣﺮﺍﺭﺕ ﺩﻫﻴﺪ ‪ ،‬ﺗﻐﻴﻴﺮﺍﺕ ﻭﺗﻌﺎﻣﻼﺗﻰ ﺭﺍ ﻛﻪ ﻣﺸﺎﻫﺪﻩ ﻣﻴﻜﻨﻴﺪ ‪ ،‬ﺗﺤﺮﻳﺮ ﺩﺍﺷﺘﻪ ‪ ،‬ﻣﻌﺎﺩﻟﺔ ﺗﻌﺎﻣﻞ‬
‫ﻣﺤﺘﻮﻳﺎﺕ ﺗﺴﺖ ﺗﻴﻮﺏ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺷﺘﻪ ﻭ ﺑﮕﻮﻳﺪ ﻛﻪ ﮔﺎﺯ ﺟﻤﻊ ﺷﺪﻩ ﺩﺭ ﺗﺴﺘﻴﻮﺏ ﺳﺮﭼﭙﻪ ﺩﺭ ﺗﺸﺖ ﭘﺮ ﺍﺯ‬
‫ﺁﺏ ﻛﺪﺍﻡ ﮔﺎﺯ ﺧﻮﺍﻫﺪ ﺑﻮﺩ؟‬
‫ﺷﻜﻞ )‪ (7 - 4‬ﺩﺳﺘﮕﺎﻩ ﺍﺳﺘﺤﺼﺎﻝ ﻣﻴﺘﺎﻥ‬
‫‪ : 2- 4‬ﻣﺮﻛﺒﺎﺕ ﺣﻠﻘﻮﻱ )ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻥ ﻫﺎ (‬
‫ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮگ ﺳﺎﻳﻜﻠﻮ ﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ‪ Cn H 2 n‬ﻳﺎ ‪ (CH2 )n‬ﺍﺳﺖ ﻛﻪ ﺑﻪ ﺍﻳﻦ ﺗﺮﺗﻴﺐ ﻣﺎﻟﻴﻜﻮﻝ‬
‫ﺳﺎﻳﻜﻠﻮﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﺎﻥ ﺍﻳﺰﻭﻟﻮگ ﺷﺎﻥ ﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻛﻤﺘﺮﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ‪.‬‬
‫ﺩﺭﻳﻚ ﺳﻠﺴﻠﻪ ﺍﺯﻣﺮﻛﺒﺎﺕ ﻣﺸﺒﻮﻉ ﺩﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻣﻴﺘﻮﺍﻧﻨﺪ ﺑﻴﻦ ﺧﻮﺩ ﺭﺍﺑﻄﻪ ﺍﺷﺘﺮﺍﻛﻰ ﻳﮕﺎﻧـــــــــﻪ ) ﻛﺎﻣ ً‬
‫ﻼ‬
‫ﻣﺸﺎﺑﻪ ﺑﻪ ﺭﺍﺑﻄﻪ ﻫﺎﻯ ‪ sp 3 − hybrid‬ﺩﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭﺳﻄﻰ ﻛﻪ ﺑﻴﺸﺘﺮﺍﺯﻳﻚ ﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺑﻘﻴﻪ ‪− CH 2‬‬
‫ﺑﻴﻦ ﺁﻧﻬﺎ ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ( ﺩﺭﺣﻠﻘﻪ ﺑﺮﻗﺮﺍﺭﻧﻤﺎﻳﻨﺪ ‪ ،‬ﺍﻳﻦ ﻧﻮﻉ ﻣﺮﻛﺒﺎﺕ ﺑﻪ ﻧﺎﻡ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ )‪(Cycloalkanes‬‬
‫ﻳﺎﺩ ﻣﻴﺸﻮﻧﺪ ﻛﻪ ﺍﻭﻟﻴﻦ ﻣﺮﻛﺐ ﺁﻧﻬﺎ ‪ C3 H 6‬ﺑﺎ ﻓﻮﺭﻣﻮﻝ ﻣﺸﺮﺡ ﺫﻳﻞ ﻣﻴﺒﺎﺷﺪ ‪:‬‬
‫ ‪&+‬‬
‫ ‪&+‬‬ ‫ ‪&+‬‬
‫‪Cyclopropane‬‬
‫‪62‬‬
‫ﻣﺮﻛﺒﺎﺕ ﺩﻳﮕﺮﺁﻥ ﻋﺒﺎﺭﺕ ﺍﺯ‪ Cyclobutane ، Cycopentane ، Cyclohexane .‬ﻭﻏﻴﺮﻩ ﺍﺳﺖ‪.‬‬
‫ﺳﺎﻳﻜﻠﻮﻫﻜﺰﺍﻥ ﺩﺍﺭﺍﻯ ﻓﻮﺭﻣﻮﻝ ﺟﻤﻌﻰ ‪ C6 H 12‬ﻭﻃﺒﻖ ﻗﺎﻧﻮﻥ ﻟﻴﻮﻳﺲ ﺑﻪ ﺷﻜﻞ ﺷﺶ ﺿﻠﻌﻰ ﺳﺎﺩﻩ ﺩﺭﻳﻚ‬
‫ﺳﻄﺢ ﺗﺤﺮﻳﺮ ﻣﻴﮕﺮﺩﺩ ؛ﺍﻣﺎ ﺩﺭﺣﻘﻴﻘﺖ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺑﺎ ﺳﺎﺧﺘﻤﺎﻥ ﭼﻬﺎﺭﻭﺟﻬﻰ ﺑﻮﺩﻩ ‪ ،‬ﻣﺴﻄﺢ ﻧﻤﻴﺒﺎﺷﺪ ‪.‬‬
‫ﺩﺭﺷﺮﺍﻳﻂ ﻋﺎﺩﻯ ﻓﻮﺭﻣﻮﻟﻰ ﻛﻪ ﻧﺸﺎﻥ ﺩﻫﻨﺪﺓ ﭘﺎﻳﺪﺍﺭﺗﺮﻳﻦ ﺣﺎﻟﺖ ﻣﺎﻟﻴﻜﻮﻝ ﺳﺎﻳﻜﻠﻮﻫﻜﺰﺍﻥ ﺍﺳﺖ ‪ ،‬ﺑﻪ ﺷﻜﻞ‬
‫ﭼﻮﻛﻰ ﺑﻮﺩﻩ‪ ) .‬ﻣﺎﻧﻨﺪ ﭼﻮﻛﻴﻬﺎﻯ ﻛﻪ ﺩﺭﻛﻨﺎﺭﺩﺭﻳﺎ ﺍﺯ ﺁﻥ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﮕﺮﺩﺩ( ﺩﺭﺷــــــﻜﻞ )‪ ( 4 - 8‬ﺳﺎﺧﺘﻤﺎﻥ‬
‫ﻧﻤﺎﻳﺶ ﺩﺍﺩﻩ ﺷﺪﻩ ﺍﺳﺖ ‪:‬‬
‫ﻰ ﺶ‬ ‫ﻞ ﭼﻮﻛﻰ‬‫ﻓﻀﺎﻳﻰ ﺳﺎﻳﻜﻠﻮ ﻫﻜﺰﺍﻥ ﺑﻪ ﺷﻜﻞ‬
‫ﺩﺭﺷــــــﻜﻞ )‪ ( 4 - 8‬ﺳﺎﺧﺘﻤﺎﻥ ﻓﻀﺎﻳﻰ ﺳﺎﻳﻜﻠﻮ ﻫﻜﺰﺍﻥ ﺑﻪ ﺷﻜﻞ ﭼﻮﻛﻰ‬
‫‪ : 1 – 2- 4‬ﭘﻴﺪﺍﻳﺶ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ ﺑﻪ ﻣﻘﺪﺍﺭ ﺯﻳﺎﺩ ﺩﺭﻃﺒﻴﻌﺖ ﻣﻨﺘﺸﺮ ﺑﻮﺩﻩ ﻭﻣﺮﻛﺒﺎﺕ ﻣﺬﻛﻮﺭ ﻳﻜﻰ ﺍﺯ ﺍﺟﺰﺍﻯ ﻣﺮﻛﺒﺔ ﻋﻤﺪﺓ ﺑﻌﻀﻰ‬
‫ﺍﺯ ﻧﻔﺖ ﺍﺳﺖ ‪).‬ﺩﺭﻧﻔﺖ ﺑﺎﻛﻮ ﻭﺍﻛﺮﺍﻳﻦ ﺯﻳﺎﺩ ﻳﺎﻓﺖ ﻣﻴﺸﻮﺩ ( ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ ﺭﺍ ﺑﺮﺍﻯ ﺍﻭﻟﻴﻦ ﺑﺎﺭ ﺩﺭﻧﻔﺖ ﻋﺎﻟﻢ‬
‫ﺭﻭﺳﻰ ﺑﻪ ﻧﺎﻡ ﻣﺎﺭﻛﻮﻓﻨﻴﻜﻮﻑ )‪ (Markovnikov‬ﻛﺸﻒ ﻛﺮﺩ ‪ ،‬ﻋﺎﻟﻢ ﻣﺬﻛﻮﺭ ﺍﻳﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ﺭﺍ ﺑﻪ‬
‫ﻧﺎﻡ ﻧﻔﺘﻴﻦ )‪ (Naphthenes‬ﻳﺎﺩ ﻛﺮﺩ ‪ .‬ﻣﻮﺻﻮﻑ ﺩﺭﻳﺎﻓﺖ ﻧﻤﻮﺩﻛﻪ ﺩﺭ ﻃﺒﻴﻌﺖ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﭘﻨﺞ ﺿﻠﻌﻰ‬
‫ﻭﺷﺶ ﺿﻠﻌﻰ ؛ﻳﻌﻨﻰ ﺳﺎﻳﻜﻠﻮﭘﻨﺘﺎﻥ ‪ ،‬ﺳﺎﻳﻜﻠﻮﻫﻜﺰﺍﻥ ﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﺑﻴﺸﺘﺮ ﻣﻨﺘﺸﺮ ﻣﻴﺒﺎﺷﺪ ‪.‬‬
‫ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﺭﻭﻏﻨﻬﺎﻯ ﺍﻳـــﺘﺮﻯ ﻧﺒـﺎﺗﻰ ﻳﺎﻓﺖ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ ﻫﻮﻣﻮﻟﻮگ ﺳﺎﻳﻜﻠﻮﻫﮕﺰﺍﻥ‬
‫)‪ (1-methyl-4- isopropyl cyclohexane‬ﺍﺳﺎﺱ ﺑﺴﻴﺎﺭﻯ ﺍﺯ ﺗﺮﭘﻴﻦ ﻫﺎ )‪ (Terpenes‬ﺭﺍ ﺗﺸﻜﻴﻞ‬
‫ﻣﻴﺪﻫﺪ ﻛﻪ ﺍﺯ ﺟﻤﻠﺔ ﻣﺮﻛﺒﺎﺕ ﻋﻤﺪﺓ ﻃﺒﻴﻌﻰ ﺍﺳﺖ ‪.‬‬
‫ﺑﻴﺸﺘﺮ ﺑﻴﺎﻣﻮﺯﻳﺪ‬
‫ﺗﺮﭘﻴﻦ ﻫﺎ )‪ (Terpenes‬ﻋﺒﺎﺭﺕ ﺍﺯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎﻯ ﻣﻔﺮ ﻭﻣﻌﻄﺮ ﺑﺎ ﻓﻮﺭﻣﻮﻝ ﺑﺴﻴﻂ ‪ C10 H 16‬ﺍﺳﺖ ‪.‬‬
‫ﺗﺮﭘﻴﻦ ﻫﺎ ﺍﺯ ﺍﻫﻤﻴﺖ ﻋﻠﻤﻰ ﻭﺻﻨﻌﺘﻰ ﺯﻳﺎﺩ ﺗﺮ ﺑﺮﺧﻮﺭﺩﺍﺭ ﺍﻧﺪ ﻭﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﺓ ﺍﺳﺎﺳﻰ ﺍﻛﺜﺮ ﻧﺒﺎﺗﺎﺕ ﺍﻧﺪ ‪ .‬ﺗﺮﭘﺒﻦ ﻫﺎ‬
‫ﺍﺟﺰﺍﻯ ﻣﻮﺍﺩ ﺧﺸﺒﻮﻯ ﺑﻮﺩﻩ ﻭﺩﺭ ﻋﻄﺮ ﺳﺎﺯﻯ ﺑﻪ ﻛﺎﺭﻣﻴﺮﻭﺩ ‪ .‬ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺍﺯ ﻧﺒﺎﺗﺎﺕ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ‪.‬‬
‫‪ : 1 – 1 – 2- 4‬ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ‬
‫ﺣﺮﺍﺭﺕ ﺫﻭﺑﺎﻥ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﺎﻧﻬﺎﻯ ﺍﻳﺰﻭﻟﻮگ ﺁﻧﻬﺎ ﺑﻠﻨﺪ ﻣﻰ ﺑﺎﺷﺪ ؛ ﺟﺪﻭﻝ ﺫﻳﻞ ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫‪63‬‬
 ‫ﺟﺪﻭﻝ )‪ ( 3 – 4‬ﻣﻘﺎﻳﺴﺔ ﺩﺭﺟﺔ ﺫﻭﺑﺎﻥ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺑﺎ ﺍﻟﻜﺎﻧﻬﺎﻯ ﺍﻳﺰﻭﻟﻮگ ﺁﻧﻬﺎ‬
‫ﺩﺭﺟﺔ ﻏﻠﻴﺎﻥ‬ ‫ﺩﺭﺟﺔ ﺫﻭﺑﺎﻥ‬ ‫ﻓﻮﺭﻣﻮﻝ‬ ‫ﻭ‬ ‫ﻧﺎﺭﻣﻞ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ‬
‫‪-42‬‬ ‫‪-187‬‬ ‫‪CH 3 − CH 2 − CH 3‬‬ ‫ﭘﺮﻭﭘﺎﻥ‬
‫ﺳﺎﻳﻜﻠﻮ ﭘﺮﻭﭘﺎﻥ‬
‫‪-33‬‬ ‫‪-127‬‬
‫‪-0.5‬‬ ‫‪-135‬‬ ‫‪CH 3 − (CH 2 ) 2 − CH 3‬‬ ‫ﺑﻴﻮﺗﺎﻥ‬
‫ﺳﺎﻳﻜﻠﻮﺑﻴﻮﺗﺎﻥ‬
‫‪13‬‬ ‫‪-90‬‬
‫‪36‬‬ ‫‪-130‬‬ ‫‪CH 3 − (CH 2 ) 3 − CH 3‬‬ ‫ﭘﻨﺘﺎﻥ‬
‫‪49‬‬ ‫‪-94‬‬ ‫ﺳﺎﻳﻜﻠﻮ ﭘﻨﺘﺎﻥ‬
‫‪69‬‬ ‫‪-95‬‬ ‫‪CH 3 − (CH 2 ) 4 − CH 3‬‬ ‫ﻫﮕﺰﺍﻥ‬
‫‪81‬‬ ‫‪7‬‬ ‫ﺳﺎﻳﻜﻠﻮﻫﮕﺰﺍﻥ‬
‫ﺳﺎﻳﻜﻠﻮ ﭘﺮﻭﭘﺎﻥ ﻭ ﺳﺎﻳﻜﻠﻮ ﺑﻴﻮﺗﺎﻥ ﺑﻪ ﺣﺎﻟﺖ ﮔﺎﺯﻳﺎﻓﺖ ﺷﺪﻩ ﻭ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎﻯ ﺩﺍﺭﻧﺪﺓ ﺗﻌﺪﺍﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ‬
‫ﺑﺎﻻﺗﺮﺍﺯ ﺳﻪ ﺑﻪ ﺣﺎﻟﺖ ﺟﺎﻣﺪ ﻳﺎﻓﺖ ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫‪ : 2 - 1 – 2- 4‬ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻥ ﻫﺎﻯ ﺩﺍﺭﺍﻯ ﺣﻠﻘﺔ ﻛﻮﭼﻜﺘﺮ ﺗﻤﺎﻳﻞ ﺑﻪ ﺗﻌﺎﻣﻼﺕ ﺟﻤﻌﻰ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻛﻪ ﺣﻠﻘﺔ ﺁﻧﻬﺎ ﺑﺎﺯ‬
‫ﮔﺮﺩﻳﺪﻩ ‪ ،‬ﺍﻟﻜﺎﻧﻬﺎﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ﻭﺧﺎﺻﻴﺖ ﺍﻟﻜﻴﻨﻬﺎ ﺭﺍ ﺍﺯ ﺧﻮﺩ ﻧﺸﺎﻥ ﻣﻴﺪﻫﻨﺪ ‪ .‬ﺣﻠﻘﻪ ﻫﺎﻯ‬
‫ﺩﺍﺭﻧﺪﺓ‪ 7 – 5‬ﻛﺎﺭﺑﻦ ﺩﺍﺭﺍﻯ ﺛﺒﺎﺕ ﺯﻳﺎﺩ ﺑﻮﺩﻩ ؛ ﻣﺎﻧﻨﺪ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻣﺸﺒﻮﻉ ﺗﻌﺎﻣﻼﺕ ﺗﻌﻮﻳﻀﻰ ﺭﺍ ﺍﻧﺠﺎﻡ ﻣﻴﺪﻫﻨﺪ ‪:‬‬
‫‪ - 1‬ﻋﻤﻞ ﻫﻠﻮﺟﻨﻬﺎ ﺑﺎﻻﻯ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎﻯ ﺩﺍﺭﻧﺪﺓ ﺣﻠﻘﺔﻛﻮﭼﻚ ﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﺑﺎ ﺑﺮﻭﻣﻴﻦ ﺑﻪ ﺁﺳﺎﻧﻰ ﺗﻌﺎﻣﻞ ﻧﻤﻮﺩﻩ ‪ ،‬ﺩﺭﻧﺘﻴﺠﻪ ﺣﻠﻘﺔ‬
‫ﺁﻧﻬﺎ ﺑﺎﺯ ﻭﻣﺸﺘﻘﺎﺕ ﺑﺮﻭﻣﻴﻨﻰ ﺍﻟﻜﺎﻧﻬﺎ ‪1,3 − dibromo alkanes‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ‪:‬‬
‫ ‪&+‬‬
‫⎯ ‪+ Br2‬‬
‫‪⎯→ Br − CH 2 − CH 2 − CH 2 − Br‬‬
‫ ‪&+‬‬ ‫ ‪&+‬‬
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‫ﺗﻌﺎﻣﻞ ﻓﻮﻕ ﻧﺴﺒﺖ ﺑﻪ ﺑﺮﻭﻣﻴﻨﻴﺸﻦ ﭘﺮﻭﭘﻠﻴﻦ ﺑﻄﻰ ﺍﺳﺖ ﻭﺗﻌﺎﻣﻞ ﺑﺮﻭﻣﻴﻨﻴﺸﻦ ﺳﺎﻳﻜﻠﻮﺑﻴﻮﺗﺎﻥ ﺑﻪ ﺣﺮﺍﺭﺕ ﺑﻠﻨﺪ‬
‫ﺻﻮﺭﺕ ﮔﺮﻓﺘﻪ ﻭﺑﻄﻰ ﻣﻴﺒﺎﺷﺪ ﻭﻣﺮﻛﺐ ﻣﺬﻛﻮﺭ ﺑﻪ ﺣﺮﺍﺭﺕ ﺑﻠﻨﺪ ﺑﺮﻭﻣﻴﻦ ﺭﺍ ﺁﻫﺴﺘﻪ ﺗﺮ ﺩﺭ ﺧﻮﺩ ﻧﺼﺐ ﻧﻤﻮﺩﻩ‬
‫ﻭﻣﺮﻛﺐ ‪1,4 − dibromo bu tan e‬ﺭﺍ ﺗﻮﻟﻴﺪ ﻣﻴﻜﻨﺪ‪:‬‬
‫ ‪&+  − &+‬‬
‫‪Δ‬‬
‫ ‪&+  − &+‬‬ ‫‪+ Br ⎯⎯→ Br − CH − CH − CH − CH − Br‬‬
‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺩﺭﺍﺛﺮﻋﻤﻞ ﻫﻠﻮﺟﻨﻬﺎ ﺣﻠﻘﺔ ﺳﺎﻳﻜﻠﻮﭘﻨﺘﺎﻥ ﻭﺳﺎﻳﻜﻠﻮ ﻫﮕﺰﺍﻥ ﺑﺎﺯ ﻧﻪ ﮔﺮﺩﻳﺪﻩ ؛ ﺑﻠﻜﻪ ﺗﻌﻮﻳﺾ ﺍﺗﻮﻣﻬﺎ ﻫﺎﻳﺪﺭﻭﺟﻦ‬
‫ &‬
‫‪&+‬‬ ‫ &‬
‫‪&+‬‬ ‫ﺁﻧﻬﺎ ﺑﻪ ﻫﻠﻮﺟﻨﻬﺎ ﺻﻮﺭﺕ ﻣﻴﮕﻴﺮﺩ ‪:‬‬
‫& ‪+‬‬ ‫‪&+‬‬
‫&‬ ‫⎯ ‪+ %U‬‬
‫‪⎯→ +%U +‬‬
‫⎯‬
‫& ‪+‬‬ ‫ ‪&+‬‬
‫& ‪+‬‬ ‫‪&+‬‬ ‫& ‪+‬‬ ‫‪&+%U‬‬
‫‪&+‬‬ ‫&‬
‫‪&+‬‬
‫‬ ‫‬
‫‪ - 2‬ﺍﻛﺴﻴﺪﻳﺸﻦ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ‪:‬‬
‫ﺳﺎﻳﻜﻠﻮﭘﺮﻭﭘﺎﻥ ﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﺑﻪ ﺣﺮﺍﺭﺕ ﻋﺎﺩﻯ ﺗﻮﺳﻂ ﻣﺤﻠﻮﻝ ﭘﻮﺗﺎﺷﻴﻢ ﭘﺮﻣﻨﮕﻨﺎﺕ ﺩﺭﻣﺤﻴﻂ ﺧﻨﺜﻰ ﻭﻳﺎ‬
‫ﺍﻟﻘﻠﻰ ﺑﻪ ﺁﻫﺴﺘﻪ ﮔﻰ ﺍﻛﺴﻴﺪﻯ ﮔﺮﺩﻳﺪﻩ ﻭ ﺑﻪ ﻭﺍﺳﻄﺔ ﺍﻛﺴﻴﺪﺍﻧﺖ ﻫﺎﻯ ﻗﻮﻯ ﻭﺣﺮﺍﺭﺕ ﺯﻳﺎﺩ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎﻯ‬
‫ﺩﻳﮕﺮ ﻧﻴﺰ ﺍﻛﺴﻴﺪﻯ ﻣﻴﮕﺮﺩﻧﺪ‪ ،‬ﺩﺭﺍﻳﻦ ﺻﻮﺭﺕ ﺣﻠﻘﻪ ﻗﻄﻊ ﻭﺍﺳﻴﺪﻫﺎﻯ ﺩﻭﻗﻴﻤﺘﻪ ﺑﺎ ﻋﻴﻦ ﺗﻌﺪﺍﺩ ﻛﺎﺭﺑﻦ ﺣﺎﺻﻞ‬
‫ﻣﻴﮕﺮﺩﻧﺪ‪:‬‬
‫‪CH − COO H‬‬
‫&‪+‬‬ ‫&‬
‫‪&+‬‬ ‫‪2‬‬
‫‬ ‫‬
‫& ‪+‬‬ ‫ ‪&+‬‬ ‫⎯ ‪+ 2O‬‬‫→⎯‬
‫⎯‬ ‫‪CH‬‬
‫‪2‬‬ ‫‪2‬‬
‫ ‪&+‬‬
‫&‬ ‫‪CH − COO H‬‬
‫‪2‬‬
‫‪Glutaric acide‬‬
‫‪&+‬‬
‫& ‪+‬‬ ‫‪&+‬‬ ‫‪CH − CH − COOH‬‬
‫‪2‬‬ ‫‪2‬‬
‫& ‪+‬‬ ‫‪&+‬‬ ‫⎯ ‪+ 2O‬‬
‫‪2‬‬ ‫‪⎯→ CH −CH − COOH‬‬
‫⎯‬ ‫‪2‬‬ ‫‪2‬‬
‫‪&+‬‬ ‫‪Adipicacid e‬‬
‫‪ : 2 – 2- 4‬ﺳﺎﺧﺘﻤﺎﻥ ﻭ ﻧﺎﻣﮕﺬﺍﺭﻯ ﻣﺮﻛﺒﺎﺕ ﺣﻠﻘﻪ ﻳﻰ‬
‫ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺒﺎﺕ ﺣﻠﻘﻪ ﻳﻰ ﻣﺎﻧﻨﺪ ﺍﻟﻜﺎﻧﻬﺎ ﺗﻮﺳﻂ ﺭﺍﺑﻄﺔ ﻳﮕﺎﻧﻪ ﺑﺎﻫﻢ ﻭﺻﻞ ﮔﺮﺩﻳﺪﻩ‬
‫ﻛﻪ ﺑﻪ ﻧﺎﻡ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﻳﺎﺩﺷﺪﻩ ﺍﺳﺖ ﻭ ﺍﺗﻮﻣﻬﺎﻯ ﻛﺎﺭﺑﻦ ﻫﺎﻳﺒﻴﺮﻳﺪ ‪ sp3‬ﺭﺍﺩﺍﺭﺍ ﺍﻧﺪ ‪.‬‬
‫ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮگ ﺳﺎﻳﻜﻠﻮ ﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ‪ C H‬ﻳﺎ ‪ (CH2 )n‬ﺍﺳﺖ ؛ ﺑﻪ ﺍﻳﻦ ﺗﺮﺗﻴﺐ‬
‫‪n‬‬ ‫‪2n‬‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﺳﺎﻳﻜﻠﻮﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﺎﻥ ﺍﻳﺰﻭﻟﻮگ ﺷﺎﻥ ﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻛﻤﺘﺮﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ‪.‬‬
‫ﻧﺎﻣﮕﺬﺍﺭﻯ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺑﺎ ﻋﻼﻭﻩ ﻧﻤﻮﺩﻥ ﭘﻴﺸﻮﻧﺪ )‪ ( prefix‬ﺳﺎﻳﻜﻠﻮ )‪ (Cyclo‬ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﺎﻥ‬
‫ﺍﻳﺰﻭﻟﻮگ ﺁﻧﻬﺎ ﺻﻮﺭﺕ ﻣﻴﮕﻴﺮﺩ ‪.‬‬
‫ﺑﺮﺍﻯ ﺗﺤﺮﻳﺮ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺷﺮﻃﻰ ﺁﻧﻬﺎ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﻨﻤﺎﻳﻨﺪ ﻛﻪ ﺩﺭ ﺁﻧﻬﺎ ﺳﻤﺒﻮﻝ‬
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 ‫ﻫﺎﻯ ﻋﻨﺎﺻﺮ ﺗﺤﺮﻳﺮ ﻧﻤﻴﮕﺮﺩﺩ ؛ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ ‪:‬‬
‫ ‪&+‬‬
‫& ‪&+  −‬‬
‫&‬ ‫ ‪&+‬‬
‫ ‪&+‬‬ ‫ ‪&+‬‬
‫&‬
‫ ‪&+  − &+‬‬
‫‪Cyclbutane‬‬ ‫‪Cyclopropane‬‬
‫& ‪+‬‬ ‫&‬
‫‪&+‬‬ ‫‪&+‬‬
‫&‬
‫‬ ‫‬
‫& ‪+‬‬ ‫ ‪&+‬‬ ‫& ‪+‬‬ ‫ &‬
‫‪&+‬‬
‫ &‬
‫‪&+‬‬ ‫& ‪+‬‬ ‫‪&+‬‬
‫‪&+‬‬
‫‪Cyclohexane‬‬ ‫‪Cyclopentane‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﺩﺭ ﺫﻳﻞ ﻓﻮﺭﻣﻮﻝ ﻫﺎﻯ ﺷﺮﻃﻰ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺗﺤﺮﻳﺮﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ‪ ،‬ﺷﻤﺎ ﻓﻮﺭﻣﻮﻝ ﻣﺸﺮﺡ ﺁﻧﻬﺎ ﺭﺍ ﺗﺤﺮﻳﺮ‬
‫ﻭﻧﺎﻣﮕﺬﺍﺭﻯ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫‪ : 3 – 2- 4‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺍﻳﺰﻭﻣﻴﺮﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﻣﺮﺑﻮﻁ ﺑﻪ ﺟﺴﺎﻣﺖ ﺣﻠﻘﻪ ‪ ،‬ﺳﺎﺧﺘﻤﺎﻥ ﺯﻧﺠﻴﺮﺟﺎﻧﺒﻰ ﻭﻣﻮﻗﻌﻴﺖ ﺯﻧﺠﻴﺮ‬
‫ﺁﻧﻬﺎ ﺍﺳﺖ ‪ ،‬ﺩﺭ ﺫﻳﻞ ﻓﻮﺭﻣﻮﻝ ﭘﻨﺞ ﺍﻳﺰﻭﻣﺮ ﻣﺮﻛﺐ ﺑﺎ ﻧﺎﻡ ﻫﺎﻯ ﺁﻧﻬﺎ ﺗﺤﺮﻳﺮ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ ﻛﻪ ﻣﻄﻠﺐ ﻓﻮﻕ ﺭﺍ‬
‫ﺗﻮﺿﻴﺢ ﻣﻴﻨﻤﺎﻳﺪ ‪:‬‬
‫‪− &+‬‬ ‫‪− C2 H 5‬‬
‫‪Ethylcyclo propane‬‬
‫‪Methylcyclobutane‬‬ ‫‪Cyclopentan‬‬
‫‪C H3‬‬
‫‪CH3‬‬ ‫‪− CH3‬‬
‫‪1,1- Dimethyl cyclopro‬‬
‫‪cycloprop‬‬
‫‪cyclopropane‬‬ ‫‪Methyl cyclopropane‬‬
‫ﺳﺎﻳﻜﻠﻮﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ﺩﺍﺭﺍﻯ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﻓﻀﺎﻯ ﻧﻴﺰ ﺑﻮﺩﻩ ﻭﺍﻳﻦ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻭﻗﺘﻰ ﺑﻪ ﻣﻼﺣﻈﻪ ﻣﻴﺮﺳﺪ ﻛﻪ ﻣﻮﺍﺩ‬
‫ﺩﺍﺭﺍﻯ ﻳﻚ ﻧﻮﻉ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﺑﻮﺩﻩ ؛ﻻﻛﻦ ﻣﻮﻗﻌﻴﺖ ﻓﻀﺎﻳﻰ ﺍﺗﻮﻣﻬﺎ ﺍﺯ ﻳﻚ ﺩﻳﮕﺮ ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ‪.‬‬
‫ﺍﻳﺰﻭﻣﻴﺮﻯ ﻓﻀﺎﻳﻰ ﺩﺭ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﻣﺮﺑﻮﻁ ﺑﻪ ﻣﻮﻗﻌﻴﺖ ﻓﻀﺎﻳﻰ ﺯﻧﺠﻴﺮﺟﺎﻧﺒﻰ ﻧﻈﺮ ﺑﻪ ﺣﻠﻘﻪ ﻣﻴﺒﺎﺷﺪ ‪ ،‬ﺍﻳﻦ‬
‫ﻧﻮﻉ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﻨﺪﺳﻰ )‪ (Geometric isomerism‬ﻳﺎ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺗﺮﺍﻧﺲ ﻭﺳﻴﺲ‬
‫)‪ (Trans, cis isomerism‬ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﺍﮔﺮ ﺑﻘﻴﻪ ﻫﺎﻱ ﻣﻮﺟﻮﺩ ﺩﺭ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺑﻪ ﻳﻚ ﺳﻄﺢ ﺣﻠﻘﻪ‬
‫ﻫﺎ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ ‪ ،‬ﺍﻳﻦ ﻧﻮﻉ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺳﻴﺲ )‪(Cis‬ﻳﺎﺩ ﻣﻴﻨﻤﺎﻧﺪ ‪ ،‬ﺩﺭﺻﻮﺭﺗﻰ ﻛﻪ ﺑﻘﻴﻪ ﻫﺎ ﺩﺭ ﺳﻄﻮﺡ‬
‫ﻣﺨﺘﻠﻒ ﺣﻠﻘﻪ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ ‪ ،‬ﺑﻪ ﻧﺎﻡ ﺗﺮﺍﻧﺲ )‪ (Trans‬ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ ؛ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ‪:‬‬
‫‪66‬‬
 ‫‪− CH 3‬‬
‫‪CH3 −‬‬
‫‪− CH3‬‬
‫‪− CH 3‬‬
‫‪Transdi methylcyclopropane‬‬
‫‪Cis di methyl cyclopropane‬‬
‫ﺍﻳﺰﻭﻣﻴﺮﻱ ﺳﻴﺲ ﻭ ﺗﺮﻧﺲ ﺩﺍﺭﺍﻯ ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﻭ ﻓﺰﻳﻜﻰ ﻣﺨﺘﻠﻒ ﺍﻧﺪ ‪.‬‬
‫ﻓﻌﺎﻟﻴﺖ‬
‫ﻓﻮﺭﻣﻮﻝ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻭﻓﻀﺎﻳﻰ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎﻯ ﺫﻳﻞ ﺭﺍ ﺗﺤﺮﻳﺮ ﻭﻧﺎﻡ ﮔﺬﺍﺭﻯ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫‪Di ethylcyclopentane , Dichlorocyclo butane, trimethyl cyclo hexane‬‬
‫‪ : 4 – 2-4‬ﺍﺳﺘﺤﺼﺎﻝ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ‬
‫ﻃﺮﻳﻘﺔ ﻋﻤﻮﻣﻰ ﺍﺳﺘﺤﺼﺎﻝ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﻋﺒﺎﺭﺕ ﺍﺯ ﻋﻤﻞ ﻓﻠﺰﺍﺕ ﺑﺎﻻﻯ ﻣﺸﺘﻘﺎﺕ ﺩﺍﻯ ﻫﻼﻳﺪ ﻫﺎﻯ ﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺍﺳﺖ ؛ ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ ‪ :‬ﺍﮔﺮ ‪ 1,3 − diboromopr opane‬ﺑﺎ ﻓﻠﺰ ﺟﺴﺖ ﺗﻌﺎﻣﻞ ﺩﺍﺩﻩ ﺷﻮﺩ ‪ ،‬ﺳﺎﻳﻜﻠﻮ‬
‫‪CH 2 − Br‬‬ ‫ﭘﺮﻭﭘﺎﻥ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪:‬‬
‫‪&+‬‬ ‫‬
‫‪/‬‬
‫‪CH 2‬‬ ‫⎯ ‪+ Zn‬‬
‫‪⎯→ ZnBr +‬‬ ‫ ‪&+‬‬ ‫ ‪&+‬‬
‫‪2‬‬
‫\‬
‫‪CH 2 − BU‬‬
‫ﺍﺯ ﻣﺮﻛﺐ ‪ 1,4 − diboromobutan e‬ﻣﻴﺘﻮﺍﻥ ﺳﺎﻳﻜﻠﻮﺑﻴﻮﺗﺎﻥ ﺭﺍ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ‪:‬‬
‫‪CH 2 − CH 2 − Br‬‬ ‫‪CH 2 − CH 2‬‬
‫⎯ ‪CH 2 − CH 2 − Br + Zn‬‬
‫‪⎯→ CH 2 − CH 2 + ZnBr2‬‬
‫‪1 ,4-dibromobutane‬‬ ‫‪cyclobutane‬‬
‫‪ : 5 – 2- 4‬ﻣﺮﻛﺒﺎﺕ ﻣﻬﻢ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ‬
‫ﺳﺎﻳﻜﻠﻮ ﭘﻨﺘﺎﻥ ﺩﺭ ﻧﻔﺖ ﻳﺎﻓﺖ ﺷﺪﻩ ﻭﺁﻥ ﺭﺍ ﺩﺭﻣﺎﺩﺓ ﻣﻬﻢ ﺍﺣﺘﺮﺍﻗﻰ ﻣﻮﺗﻮﺭﻫﺎ ﻏﺮﺽ ﺑﻠﻨﺪ ﺑﺮﺩﻥ ﻛﻴﻔﻴﺖ ﺁﻥ ﻋﻼﻭﻩ‬
‫ﻣﻴﻨﻤﺎﻳﻨﺪ؛ ﻫﻤﭽﻨﺎﻥ ﻣﺮﻛﺒﺎﺕ ﻣﺬﻛﻮﺭ ﺭﺍ ﺩﺭﺳﻨﺘﻴﺰ ﻫﺎﻯ ﻣﺨﺘﻠﻒ ﺍﺳﺘﻌﻤﺎﻝ ﻣﻴﻜﻨﻨﺪ ‪.‬‬
‫ﻧﻔﺖ ﺩﺍﺭﺍﻯ ﻣﺸﺘﻘﺎﺕ ﻛﺎﺭﺑﻮﻛﺴﻴﻞ ﺩﺍﺭ ﺳﺎﻳﻜﻠﻮﭘﻨﺘﺎﻥ ﻳﻌﻨﻰ ﺳﺎﻳﻜﻠﻮ ﭘﻨﺘﺎﻥ ﻛﺎﺭﺑﻮﻛﺴﻠﻴﻚ ﺍﺳﻴﺪ ﻭ ﻫﻮﻣﻮﻟﻮگ‬
‫ﻫﺎﻯ ﺁﻥ ﻛﻪ ﺑﻪ ﻧﺎﻡ ﻧﻔﺘﻴﻨﻚ ﺍﺳﻴﺪ )‪ ( Naphthnec acide‬ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ ‪ ،‬ﻧﻴﺰ ﻣﻮﺟﻮﺩ ﺍﺳﺖ‪.‬‬
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 ‫ﺧﻼﺻﺔ ﻓﺼﻞ ﭼﻬﺎﺭﻡ‬
‫* ﺍﻟﻜﺎﻥ ﻫﺎ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺑﻴﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺁﻧﻬﺎ ﺭﺍﺑﻄﺔ ﺳﺎﺩﻩ ) ﻳﮕﺎﻧﻪ ( ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ﻭ ﻭﻻﻧﺲ ﻫﺎﻯ‬
‫ﻣﺘﺒﺎﻗﻰ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺗﻮﺳﻂ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻣﺸﺒﻮﻉ ﮔﺮﺩﻳﺪﻩ ﺍﺳﺖ‪.‬‬
‫* ﭼﻬﺎﺭ ﻣﺮﻛﺐ ﺍﻭﻝ ﻫﻮﻣﻮﻟﻮگ ﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﺷﺮﺍﻳﻂ ﺳﺘﻨﺪﺭﺩ ﺑﻪ ﺣﺎﻟﺖ ﮔﺎﺯﻳﺎﻓﺖ ﺷﺪﻩ ﻭﺩﺍﺭﻧﺪﺓ ‪ 5‬ﺍﻟﻰ ‪16‬‬
‫ﻛﺎﺭﺑﻦ ﺑﻪ ﺣﺎﻟﺖ ﻣﺎﻳﻊ ﻭﺑﺎﻻﺗﺮ ﺍﺯ ﺁﻥ ﺑﻪ ﺣﺎﻟﺖ ﺟﺎﻣﺪ ﻳﺎﻓﺖ ﻣﻴﺸﻮﻧﺪ ‪.‬‬
‫* ﻓﻌﺎﻟﻴﺖ ﻛﻴﻤﻴﺎﻭﻯ ﺍﻟﻜﺎﻧﻬﺎ ﻛﻤﺘﺮ ﺑﻮﺩﻩ ؛ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺁﻧﻬﺎﺭﺍ ﺑﻪ ﻧﺎﻡ ﭘﺎﺭﺍﻓﻴﻦ )‪ (Paraffins‬ﻳﻌﻨﻰ ﻛﻢ ﻣﻴﻞ ﻳﺎﺩ ﻣﻴﻨﻤﺎﻳﻨﺪ ‪.‬‬
‫* ﺩﺭﻳﻚ ﺳﻠﺴﻠﻪ ﺍﺯﻣﺮﻛﺒﺎﺕ ﻣﺸﺒﻮﻉ ﺩﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻣﻴﺘﻮﺍﻧﻨﺪ ﺑﻴﻦ ﺧﻮﺩ ﺭﺍﺑﻄﻪ ﺍﺷﺘﺮﺍﻛﻰ ﻳﮕﺎﻧـــــــــﻪ ) ﻛﺎﻣ ً‬
‫ﻼ‬
‫ﻣﺸﺎﺑﻪ ﺑﻪ ﺭﺍﺑﻄﻪ ﻫﺎﻯ ‪ sp 3 − hybrid‬ﺩﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻭﺳﻄﻰ ﻛﻪ ﺑﻴﺸﺘﺮﺍﺯﻳﻚ ﻭﻳﺎ ﭼﻨﺪﻳﻦ ﺑﻘﻴﻪ ‪ CH 2‬ﺑﻴﻦ‬
‫ﺁﻧﻬﺎ ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ( ﺑﻪ ﺷﻜﻞ ﺣﻠﻘﻪ ﺑﺮﻗﺮﺍﺭﻧﻤﺎﻳﻨﺪ ‪ ،‬ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺑﻨﺎﻡ ﺳﺎﻳﻜﻮﺍﻟﻜﺎﻧﻬﺎ )‪ (Cycloalkanes‬ﻳﺎﺩ‬
‫ﻣﻴﺸﻮﻧﺪ ﻛﻪ ﺍﻭﻟﻴﻦ ﻣﺮﻛﺐ ﺁﻧﻬﺎ ﺳﺎﻳﻜﻠﻮ ﭘﺮﻭﭘﺎﻥ ﺍﺳﺖ ‪:‬‬
‫* ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺩﺭ ﺭﻭﻏﻨﻬﺎﻯ ﺍﻳﺘﺮﻯ ﻧﺒﺎﺗﻰ ﻳﺎﻓﺖ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ ﻫﻮﻣﻮﻟﻮگ ﺳﺎﻳﻜﻠﻮﻫﮕﺰﺍﻥ‬
‫)‪ (1-methyl4 - isopropyl cyclohexane‬ﺍﺳﺎﺱ ﺑﺴﻴﺎﺭﻯ ﺍﺯ ﺗﺮﭘﻴﻦ ﻫﺎ )‪ (Terpenes‬ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ‪.‬‬
‫* ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮگ ﺳﺎﻳﻜﻠﻮ ﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ‪ Cn H 2 n‬ﻳﺎ ‪ (CH2 )n‬ﺍﺳﺖ ﻛﻪ ﺑﻪ ﺍﻳﻦ ﺗﺮﺗﻴﺐ‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﺳﺎﻳﻜﻠﻮﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﺎﻥ ﺍﻳﺰﻭﻟﻮگ ﺷﺎﻥ ﺩﻭ ﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﻛﻤﺘﺮﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ‪.‬‬
‫* ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻥ ﻫﺎﻯ ﺩﺍﺭﺍﻯ ﺣﻠﻘﺔ ﻛﻮﭼﻜﺘﺮ ﺗﻤﺎﻳﻞ ﺑﻪ ﺗﻌﺎﻣﻼﺕ ﺟﻤﻌﻰ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻛﻪ ﺣﻠﻘﺔ ﺁﻧﻬﺎ ﺑﺎﺯ‬
‫ﮔﺮﺩﻳﺪﻩ ‪ ،‬ﺍﻟﻜﺎﻧﻬﺎﻭﻣﺸﺘﻘﺎﺕ ﺁﻧﻬﺎ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ﻛﻪ ﺧﺎﺻﻴﺖ ﺍﻟﻜﻴﻨﻬﺎ ﺭﺍ ﻧﺸﺎﻥ ﻣﻴﺪﻫﻨﺪ ‪.‬‬
‫* ﺣﻠﻘﻪ ﻫﺎﻯ ﺩﺍﺭﻧﺪﺓ ‪ 7 – 5‬ﻛﺎﺭﺑﻦ ﺩﺍﺭﺍﻯ ﺛﺒﺎﺕ ﺯﻳﺎﺩ ﺑﻮﺩﻩ ‪ ،‬ﻣﺎﻧﻨﺪ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻣﺸﺒﻮﻉ ﺗﻌﺎﻣﻼﺕ‬
‫ﺗﻌﻮﻳﻀﻰ ﺭﺍ ﺍﻧﺠﺎﻡ ﻣﻴﺪﻫﻨﺪ ‪:‬‬
‫ﺳﺆﺍﻻﺕ ﻓﺼﻞ ﭼﻬﺎﺭﻡ‬
‫ﺳﺆﺍﻻﺕ ﭼﻬﺎﺭ ﺟﻮﺍﺑﻪ‬
‫‪ - 1‬ﺍﻟﻜﺎﻥ ﻫﺎ ﻣﺮﻛﺒﺎﺗﻰ ﺍﻧﺪ ﻛﻪ ﺑﻴﻦ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺁﻧﻬﺎ ﺭﺍﺑﻄﺔ ‪ ---‬ﻣﻮﺟﻮﺩ‬
‫ﺍﻟﻒ ‪ -‬ﺳﺎﺩﻩ ﺏ ‪ -‬ﻳﮕﺎﻧﻪ ﺝ – ﺩﻭﮔﺎﻧﻪ ﺩ – ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭ ﺩﺭﺳﺖ ﺍﺳﺖ‬
‫‪ - 2‬ﺍﻟﻜﺎﻥ ﻫﺎ ﺩﺍﺭﺍﻯ ﻛﺪﺍﻡ ﻳﻚ ﺍﺯ ﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺫﻳﻞ ﺍﻧﺪ ؟‬
‫‪C H‬‬
‫ﺍﻟﻒ ‪ n 2n -‬ﺏ ‪ Cn H 2n + 2 -‬ﺝ ‪ n 2n − 2 -‬ﺩ ‪n 2n + 1 -‬‬
‫‪C H‬‬ ‫‪C H‬‬
‫‪ - 3‬ﻧﺎﻡ ﻣﺮﻛﺐ ‪ CH − CCHH − CCHH − C H − CH‬ﻋﺒﺎﺭﺕ ﺍﺳﺖ ﺍﺯ ‪:‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫‪5‬‬
‫‪3‬‬ ‫|‬ ‫|‬ ‫‪2‬‬ ‫‪3‬‬
‫ﺍﻟﻒ ‪ ، 2,3 − diemthyl pen tan e -‬ﺏ‪، 3,3 dim ethyl pen tan e -‬ﺝ ‪4,3 dinethyl pen tan e -‬‬
‫‪3‬‬ ‫‪3‬‬
‫ﺩ ‪I ,3 dim ethyl pen tan e -‬‬
‫‪ - 4‬ﭘﺴﻮﻧﺪ‪ ane‬ﻧﺎﻡ ﺍﻟﻜﺎﻥ )‪ (Alkane‬ﻣﺮﺑﻮﻁ ﺩﺭ ﺭﺍﺩﻳﻜﺎﻝ ﺁﻥ ﺑﻪ ﻛﺪﺍﻡ ﭘﺴﻮﻧﺪ ﺗﻌﻮﻳﺾ ﻣﻴﮕﺮﺩﺩ ؟‬
‫ﺍﻟﻒ – ‪ ene‬ﺏ – ‪ yne‬ﺝ‪ yl -‬ﺩ ‪yne -‬‬
‫‪ – 5‬ﺍﻟﻜﺎﻧﻬﺎﻯ ﺩﺍﺭﻧﺪﺓ ‪ 5‬ﺍﻟﻰ ‪ 16‬ﺑﻪ ﻛﺪﺍﻡ ﺣﺎﻟﺖ ﻳﺎﻓﺖ ﻣﻴﺸﻮﻧﺪ ؟‬
‫ﺍﻟﻒ – ﺟﺎﻣﺪ ﺏ – ﮔﺎﺯ ﺝ – ﻣﺎﻳﻊ ﺩ – ﭘﻼﺯﻣﺎ‬
‫‪ - 6‬ﻓﻌﺎﻟﻴﺖ ﻛﻴﻤﻴﺎﻭﻯ ﺍﻟﻜﺎﻧﻬﺎ ﻛﻤﺘﺮ ﺑﻮﺩﻩ ؛ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺁﻧﻬﺎﺭﺍ ﺑﻪ ﻧﺎﻡ‪ ------‬ﻳﺎﺩ ﻣﻴﻨﻤﺎﻳﻨﺪ ‪.‬‬
‫‪68‬‬
 ‫ﺏ ‪ Paraffins -‬ﺝ‪ -‬ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭﺩﺭﺳﺖ ﺍﺳﺖ ﺩ – ﻫﻴﭽﻜﺪﺍﻡ‬ ‫ﺍﻟﻒ – ﭘﺎﺭﺍﻓﻴﻦ‬
‫‪ - 7‬ﺍﺯ ﺍﺣﺘﺮﺍﻕ ﻳﻚ ﻛﻴﻠﻮﮔﺮﺍﻡ ﻣﻴﺘﺎﻥ ‪ ----‬ﺍﻧﺮژﻯ ﺁﺯﺍﺩ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫ﺍﻟﻒ ‪ 57000 -‬ﻛﻴﻠﻮ ِژﻭﻝ ﺏ ‪ِ 57000 -‬ژﻭﻝ ﺝ ‪ 57000 -‬ﻣﻴﮕﺎ ِژﻭﻝ ﺩ ﻫﻴﭽﻜﺪﺍﻡ‬
‫‪ - 8‬ﻧﺎﻣﮕﺬﺍﺭﻯ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﺑﺎ ﻋﻼﻭﻩ ﻧﻤﻮﺩﻥ ﭘﻴﺸﻮﻧﺪ )‪ ---) prefix‬ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﺎﻥ ﺍﻳﺰﻭﻟﻮگ ﺁﻧﻬﺎ ﺻﻮﺭﺕ ﻣﻴﮕﻴﺮﺩ ‪.‬‬
‫ﺍﻟﻒ – ﺳﺎﻳﻜﻠﻮ ﺏ ‪ Cyclo -‬ﺝ – ﺍﻟﻜﺎﻳﻞ ﺩ ‪ -‬ﺍﻟﻒ ﻭﺏ ﻫﺮﺩﻭ ﺩﺭﺳﺖ ﺍﺳﺖ ‪.‬‬
‫‪ - 9‬ﺳﺎﻳﻜﻠﻮ ﺍﻟﻜﺎﻧﻬﺎ ﺭﺍ ﺑﺮﺍﻯ ﺍﻭﻟﻴﻦ ﺑﺎﺭ ﺩﺭﻧﻔﺖ ﻋﺎﻟﻢ ﺭﻭﺳﻰ ﺑﻪ ﻧﺎﻡ ‪ ---‬ﻛﺸﻒ ﻛﺮﺩ ‪،‬‬
‫ﺍﻟﻒ – ﻣﺎﺭﻛﻮﻓﻨﻴﻜﻮﻑ ﺏ ‪ Markovnikov -‬ﺝ ‪ -‬ﺍﻟﻒ ﻭﺏ ﺩ‪ -‬ﺯﺍﻳﺘﺴﻒ‬
‫‪ - 10‬ﺩﺭﺗﻤﺎﻡ ﺍﻟﻜﺎﻥ ﻫﺎ ﭼﺮﺧﺶ ﺁﺯﺍﺩﺍﻧﻪ ﺑﻪ ﺩﻭﺭ ﻣﺤﻮﺭ ﺭﺍﺑﻄﺔ‪ C– C‬ﻣﻮﺟﻮﺩ ﺑﻮﺩﻩ ﺗﺎ ﺯﻭﺍﻳﺎﻯ ﺭﻭﺍﺑﻂ ﺁﻧﻬﺎ ﺑﻪ ‪ ----‬ﺑﺎﻟﻎ ﮔﺮﺩﺩ ‪.‬‬
‫ﺍﻟﻒ ‪ 109 -‬ﺩﺭﺟﻪ ﻭ ‪ 28‬ﺩﻗﻴﻘﻪ ﺏ ‪ 90 -‬ﺩﺭﺟﻪ ‪ 30‬ﺩﻗﻴﻘﻪ ﺝ – ‪ 60‬ﺩﺭﺟﻪ ﺩ – ‪ 65‬ﺩﺭﺟﻪ‬
‫ﺳﺆﺍﻻﺕ ﺗﺸﺮﻳﺤﻰ‬
‫‪ – 1‬ﻣﻔﺎﻫﻴﻢ ﺫﻳﻞ ﺭﺍ ﺗﻌﺮﻳﻒ ﻭﺗﻮﺿﻴﺢ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫ﺍﻟﻒ – ﭘﺎﺭﺍﻓﻴﻦ ﺏ – ﻫﻮﻣﻮﻟﻮگ ﺝ ‪ -‬ﺍﻳﺰﻭﻣﻴﺮ ﺩ‪ -‬ﺍﻳﺰﻭﻟﻮگ‬
‫‪ – 2‬ﺩﺭ ﺳﻠﺴﻠﺔ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻣﺸﺒﻮﻉ ﺑﺎ ﺍﺯﺩﻳﺎﺩ ﺗﻌﺪﺍﺩ ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﻛﺪﺍﻡ ﺗﻐﻴﻴﺮﺍﺕ ﺩﺭ ﺧﻮﺍﺹ‬
‫ﻓﺰﻳﻜﻰ ﺭﻭﻧﻤﺎ ﻣﻴﮕﺮﺩﺩ ؟‬
‫‪ - 3‬ﻛﺪﺍﻡ ﻳﻜﻰ ﺍﺯ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎ ﺯﻳﺮ ﻧﻮﻉ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻣﺸﺒﻮﻉ ﺍﺳﺖ ؟‬
‫‪C H‬‬
‫‪24 50‬‬
‫‪ C H‬ﺩ‪-‬‬ ‫ﺍﻟﻒ ‪ C7 H14 -‬ﺏ ‪ C12 H 26 -‬ﺝ ‪-‬‬
‫‪10 20‬‬
‫‪ - 4‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎ ﺭﺍ ﺩﺭ ﻣﺮﻛﺒﺎﺕ ﺯﻳﺮ ﻣﺸﺨﺺ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪CH3‬‬
‫‪CH − CH − CH‬‬
‫‪3‬‬ ‫|‬ ‫‪3‬‬ ‫‪، CH − CH − CH − CH − CH CH3 − CH| − CH3 ، CH3 −‬‬ ‫|‬
‫‪C − CH‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫|‬ ‫‪3‬‬
‫‪CH 3‬‬ ‫‪CH3‬‬
‫‪CH3‬‬
‫‪ - 5‬ﻓﻮﺭﻣﻮﻝ ﻣﺮﻛﺒﺎﺕ ﺫﻳﻞ ﺭﺍ ﺗﺤﺮﻳﺮﺩﺍﺭﻳﺪ ‪.‬‬
‫ﺍﻟﻒ‪ − 1,2 − dichloropropane -‬ﺏ ‪1 − ethyl − 2 − Iaopropylbutane -‬‬
‫ﺝ ‪ 1,3 − diethyl nonatane -‬ﺩ ‪1 − bromo 3 − chloro decane -‬‬
‫‪ - 6‬ﻛﺜﺎﻓﺖ ﻳﻚ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻣﺸﺒﻮﻉ ‪ 2.59‬ﮔﺮﺍﻡ ﻓﻰ ﻟﻴﺘﺮ ﺍﺳﺖ ﻛﺘﻠﺔ ﻣﺎﻟﻴﻜﻮﻟﻰ ﻣﺎﺩﺓ ﻣﺬﻛﻮﺭ ﺭﺍ ﺑﺎ‬
‫ﻓﻮﺭﻣﻮﻝ ﺁﻥ ﺩﺭ ﻳﺎﻓﺖ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪ – 7‬ﻓﻮﺭﻣﻮﻝ ﻣﻴﺘﺎﻳﻞ ﺳﺎﻳﻜﻠﻮﭘﺮﻭﭘﺎﻥ ﺭﺍ ﺗﺤﺮﻳﺮ ﻭ ﺍﻧﻮﺍﻉ ﻛﺎﺭﺑﻦ ﻫﺎﻯ ﺁﻧﺮﺍ ﻣﺸﺨﺺ ﺳﺎﺧﺘﻪ ‪ ،‬ﻧﺎﻣﮕﺬﺍﺭﻯ ﻧﻤﺎﻳﻴﺪ ‪.‬‬
‫‪ – 8‬ﻧﺎﻡ ﺁﻳﻮﭘﻚ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻫﺎﻯ ﺫﻳﻞ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ‪:‬‬
‫‪CH 2‬‬
‫& ‪+‬‬ ‫ ‪&+‬‬
‫&‬
‫‪HC‬‬ ‫‪CH 2‬‬
‫‪C‬‬
‫& ‪+‬‬ ‫ ‪&+ − &+  − &+‬‬ ‫‪2‬‬
‫‪H 2C‬‬ ‫‪CH − CH 3‬‬
‫ ‪&+‬‬ ‫‪CH − CH 2 − CH 3‬‬
‫‪ - 9‬ﺳﺎﺧﺘﻤﺎﻥ ﻓﻀﺎﻳﻰ ﺳﺎﻳﻜﻠﻮﺍﻟﻜﺎﻧﻬﺎ ﻯ ﺫﻳﻞ ﺭﺍ ﺗﺤﺮﻳﺮ ﺩﺍﺭﻳﺪ ‪.‬‬
‫ﺍﻟﻒ‪ Cis − 1,2 − dichlorocyclopropane-‬ﺏ ‪Trans − 1 − ethyl − 2 − Isopropylcyclobutane -‬‬
‫ﺝ ‪ Cis − 1,3 − diethyl lcyclobutane -‬ﺩ ‪Trans − 1 − bromo3 − chlorocyclopentane -‬‬
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 ‫ﻓﺼﻞ ﭘﻨﺠﻢ‬
‫ﺍﻟﻜﻴـﻨﻬﺎ ﻭﺍﻟﻜﺎﻳﻨـﻬﺎ‬
‫ﻳﻜﻰ ﺍﺯ ﺻﻨﻒ ﻫﺎﻯ ﻣﻬﻢ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻨﻬﺎ ‪ ،‬ﻣﺮﻛﺒﺎﺕ ﻏﻴﺮ ﻣﺸﺒﻮﻉ ﻓﺎﻣﻴﻞ ﺍﻟﻜﻴﻨﻬﺎ ﻭﺍﻟﻜﺎﻳﻨﻬﺎ ﺑﻮﺩﻩ ﻛﻪ‬
‫ﺩﺭﺣﻴﺎﺕ ﺭﻭﺯﻣﺮﺓ ﻣﺎ ﺭﻭﻝ ﺍﺳﺎﺳﻰ ﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ‪ ،‬ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺩﺭ ﻣﺎﻟﻴﻜﻮﻝ ﺧﻮﺩ ﺩﺍﺭﺍﻯ ﺭﺍﺑﻄﺔ ﺩﻭ ﮔﺎﻧﻪ‬
‫ﻭﺳﻪ ﮔﺎﻧﻪ ﺑﻮﺩﻩ ؛ ﻃﻮﺭﻳﻜﻪ ﺩﺭ ﺍﻟﻜﻴﻦ ﻫﺎ ﺑﻴﻦ ﺩﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ ﺍﺷﺘﺮﺍﻛﻲ ﺩﻭﮔﺎﻧﻪ ﻭﺩﺭ ﺍﻟﻜﺎﻳﻦ ﻫﺎ ﺑﻴﻦ‬
‫ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﺔ ﺳﻪ ﮔﺎﻧﻪ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪.‬‬
‫ﺩﺭﺍﻳﻦ ﻓﺼﻞ ﺭﺍﺟﻊ ﺑﻪ ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﻣﻌﻠﻮﻣﺎﺕ ﺍﺭﺍﺋﻪ ﻣﻴﮕﺮﺩﺩ ‪ .‬ﺑﺎ ﻣﻄﺎﻟﻌﺔ ﺍﻳﻦ ﻓﺼﻞ ﺧﻮﺍﻫﻴﺪ ﺁﻣﻮﺧﺖ‬
‫ﻛﻪ ﺍﻟﻜﻴﻦ ﻫﺎ ﻭﺍﻟﻜﺎﻳﻦ ﻫﺎ ﭼﻰ ﻧﻮﻉ ﻣﺮﻛﺒﺎﺕ ﺍﻧﺪ ؟ ﻃﺮﺯ ﺭﻭﺍﺑﻂ ﺩﺭ ﺍﻟﻜﻴﻨﻬﺎ ﻭﺍﻟﻜﺎﻳﻨﻬﺎ ﭼﻄﻮﺭ ﺍﺳﺖ ؟‬
‫ﺩﺭ ﻛﺪﺍﻡ ﻋﺮﺻﻪ ﻫﺎﻯ ﺣﻴﺎﺗﻰ ﺑﻪ ﻛﺎﺭﻣﻴﺮﻭﻧﺪ ؟ ﭼﻄﻮﺭ ﻭﺍﺯ ﻛﺪﺍﻡ ﻣﻨﺎﺑﻊ ﺁﻧﻬﺎ ﺭﺍ ﻣﻴﺘﻮﺍﻥ ﺑﻪ ﺩﺳﺖ ﺁﻭﺭﺩ ؟‬
‫ﺍﻧﺘﺸﺎﺭ ﺷﺎﻥ ﺩﺭ ﻃﺒﻴﻌﺖ ﺑﻪ ﻛﺪﺍﻡ ﺷﻜﻞ ﺍﺳﺖ ؟ ﺑﺎ ﻣﻄﺎﻟﻌﺔ ﺍﻳﻦ ﻓﺼﻞ ﺑﻪ ﺳﺆﺍﻟﻬﺎﻯ ﻓﻮﻕ ﻭﻣﺎﻧﻨﺪ ﺁﻥ ﺟﻮﺍﺏ‬
‫ﺧﻮﺍﻫﻴﻢ ﺩﺍﺩ ‪.‬‬
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 ‫‪ : 1 – 5‬ﺍﻟﻜـﻴـﻦ ﻫﺎ‬
‫ﺳﺎﺩﻩ ﺗﺮﻳﻦ ﻫﺎﻳﺪﺭﻭﻛﺎﺭﺑﻦ ﻏﻴﺮﻣﺸﺒﻮﻉ ﻓﺎﻣﻴﻞ ﺍﻟﻜﻴﻦ ﻋﺒﺎﺭﺕ ﺍﺯ ﺍﻳﺘﻠﻴﻦ ﺑﻮﺩﻩ ﻛﻪ ﻓﻮﺭﻣﻮﻝ ﺁﻥ ‪ CH = CH‬ﻣﻴﺒﺎﺷﺪ ‪،‬‬
‫‪2‬‬ ‫‪2‬‬
‫ﺩﺭﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﻠﻴﻦ ﺑﻴﻦ ﺩﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺭﺍﺑﻄﻪ ﺍﺷﺘﺮﻛﻲ ﺩﻭﮔﺎﻧﻪ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ﻛﻪ ﻳﻚ ﺭﺍﺑﻄﻪ ﺁﻥ ﺳﮕﻤﺎ ) ‪(D‬‬
‫ﻭﻳﻚ ﺭﺍﺑﻄﻪ ﺩﻳﮕﺮ ﺁﻥ ‪ P‬ﺍﺳﺖ ‪ ).‬ﻣﺸﺨﺼﺎﺕ ﺭﺍﺑﻄﺔ ﺍﻳﺘﻠﻴﻦ ( ﺯﺍﻭﻳﻪ ﻭﻃﻮﻝ ﺭﺍﺑﻄﻪ ﺩﺭﻣﺒﺤﺚ ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﻴﻦ‬
‫ﻫﺎ ﺍﺭﺍﺋﻪ ﺷﺪﻩ ﺍﺳﺖ( ‪ ،‬ﺳﻠﺴﻠﺔ ﻫﻮﻣﻮﻟﻮگ ﻣﺮﻛﺒﺎﺕ ﺍﻟﻜﻴﻦ ﺑﻪ ﺍﻧﺪﺍﺯﻩ ﻳﻚ ﮔﺮﻭپ ﻣﺘﻠﻴﻦ )‪ ( −CH −‬ﺍﺯﻫﻤﺪ ﻳﮕﺮ‬
‫‪2‬‬
‫ﻓﺮﻕ ﺩﺍﺷﺘﻪ ﻭﻓﻮﺭﻣﻮﻝ ﻋﻤﻮﻣﻰ ﺁﻧﻬﺎ ‪ C H n‬ﺍﺳﺖ ﻛﻪ ﺩﺭﺍﻳﻦ ﻓﻮﺭﻣﻮﻝ ‪ n‬ﻣﺴﺎﻭﻯ ﺑﻪ ‪ 2‬ﻭﺑﺎ ﻻﺗﺮﺍﺯ ﺁﻥ ﻗﻴﻤﺖ‬
‫‪2‬‬ ‫‪2‬‬
‫ﻫﺎﻯ ﺗﺎﻡ ﺭﺍ ﺑﻪ ﺧﻮﺩ ﺍﺧﺘﻴﺎﺭ ﻛﺮﺩﻩ ﻣﻴﺘﻮﺍﻧﺪ ‪ .‬ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺍﻳﺘﻠﻴﻦ ﺩﺭ ﻳﻚ ﺳﻄﺢ ﻭﺍﻗﻊ ﺷﺪﻩ ﺍﺳﺖ‪ .‬ﻣﺮﻛﺐ ﺩﻭﻣﻰ‬
‫ﺁﻥ ‪ (CH = CH − CH ) ) propene‬ﻣﻴﺒﺎﺷﺪ ‪ .‬ﻣﻮﺟﻮﺩﻳﺖ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻓﻌﺎﻟﻴﺖ ﻣﺮﻛﺒﺎﺕ ﺍﻟﻜﻴﻦ ﻫﺎ ﺭﺍ‬
‫‪2‬‬ ‫‪3‬‬
‫ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﺎﻥ ﻫﺎ ﺑﻴﺸﺘﺮ ﺳﺎﺧﺘﻪ ﺍﺳﺖ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﻣﻮﺟﻮﺩﻳﺖ ﺁﻧﻬﺎ ﺩﺭﻣﻮﺍﺩ ﻧﻔﺘﻰ ﻛﻤﺘﺮﺍﺳﺖ ‪.‬‬
‫ﺍﻟﻜﻴﻦ ﻫﺎ ﺩﺭ ﭘﺘﺮﻭﺷﻴﻤﻰ ﺍﺯ ﺍﻫﻤﻴﺖ ﺧﺎﺻﻰ ﺑﺮﺧﻮﺭﺩﺍﺭ ﺑﻮﺩﻩ ﻭ ﺩﺭ ﺍﻭﻟﻴﻦ ﻣﺮﺣﻠﺔ ﺗﺒﺪﻻﺕ ﻛﻴﻤﻴﺎﻭﻯ‬
‫ﻣﺤﺼﻮﻻﺕ ﻧﻔﺘﻰ ) ﺍﻟﻜﺎﻥ ﻫﺎ ( ﺣﺎﺻﻞ ﺷﺪﻩ ﻣﻴﺘﻮﺍﻧﺪ ‪ ،‬ﻃﻮﺭﻯ ﻛﻪ ﺍﺯ ﺍﻟﻜﺎﻥ ﻫﺎ ﺩﻭﺍﺗﻮﻡ ﻫﺎﻳﺪﺭﻭﺟﻦ ﺗﺠﺮﻳﺪ‬
‫ﺳﺎﺧﺘﻪ ﺷﺪﻩ ﺍﻟﻜﻴﻦ ﺍﻳﺰﻭﻟﻮﻙ ﺁﻥ ﺑﻪ ﺩﺳﺖ ﻣﻴﺎﻳﺪ‪:‬‬
‫‪500 o C C r2O 3‬‬
‫‪CH − CH‬‬ ‫⎯ ⎯ ⎯ ⎯⎯‬ ‫‪⎯→ CH = CH + H‬‬
‫‪3‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬
‫ﺍﮔﺮ ﺍﻟﻜﺎﻳﻞ ﺑﺮﻭﻣﺎﻳﺪ ﻫﺎ ﺑﺎ ﺍﻟﻘﻠﻰ ﻫﺎ ﺩﺭﺣﺮﺍﺭﺕ ‪ 550 C‬ﺗﻌﺎﻣﻞ ﺩﺍﺩﻩ ﺷﻮﺩ‪ ،‬ﺍﻟﻜﻴﻦ ﻫﺎ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ‪:‬‬
‫‪55o C‬‬
‫‪CH − CH− CH + NaOH ⎯⎯⎯→ CH − CH = CH + NaBr + H O‬‬
‫‪3‬‬ ‫|‬ ‫‪3‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬
‫‪Br‬‬
‫ﺍﻟﻜﻴﻦ ﻫﺎ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻭﻟﻔﻴﻦ ﻫﺎ )‪ (Olefines‬ﺑﻪ ﻣﻌﻨﻰ ﺗﻴﻞ ﺳﺎﺯ ﻧﻴﺰ ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪ ؛ ﺯﻳﺮﺍ ﺩﺭ ﻣﺮﻛﺒﺎﺕ ﺗﻴﻞ ﻧﻴﺰ‬
‫ﻣﻮﺟﻮﺩ ﻣﻴﺒﺎﺷﻨﺪ ‪.‬‬
‫‪ : 1 – 1 - 5‬ﺳﺎﺧﺘﻤﺎﻥ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫ﻳﻜﻰ ﺍﺯ ﺧﺼﻮﺻﻴﺎﺕ ﺳﺎﺩﺓ ﺍﻟﻜﻴﻨﻬﺎ ﻣﻮﺟﻮﺩﻳﺖ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺑﻴﻦ ﺩﻭ ﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺩﺭ ﺗﺮﻛﻴﺐ ﻣﺎﻟﻴﻜﻮﻝ ﺁﻧﻬﺎ‬
‫ﺍﺳﺖ ‪ ،‬ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺑﻪ ﻛﻤﻚ ﺩﻭﺟﻮﺭﻩ ﺍﺯ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﻣﺸﺘﺮﻙ )ﺭﺍﺑﻄﺔ ﭼﻬﺎﺭ ﺍﻟﻜﺘﺮﻭﻧﻰ ( ﺗﺸﻜﻴﻞ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻨﻰ ﻛﻪ ﺑﻴﻦ ﻫﻢ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ‪ ،‬ﺑﻪ ﺣﺎﻟﺖ ‪ sp 2‬ﻫﺎﻳﺒﺮﻳﺪﻳﺰﻳﺸﻦ ﻗﺮﺍﺭﺩﺍﺷﺘﻪ ﻭﻫﺮﻳﻚ‬
‫ﺍﺯﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻣﺬﻛﻮﺭ ﺳﻪ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﺭﺍ ﻛﻪ ﺩﺭ ﻳﻚ ﺳﻄﺢ ﺗﺤﺖ ﺯﺍﻭﻳﺔ ‪ 120‬ﺩﺭﺟﻪ ﻗﺮﺍﺭ ﺩﺍﺭﻧﺪ ‪ ،‬ﺑﺮﻗﺮﺍﺭ‬
‫ﻣﻰ ﻧﻤﺎﻳﻨﺪ ‪ .‬ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻏﻴﺮ ﻫﺎﻳﺒﺮﻳﺪ ﺷﺪﻩ ﺑﺎﻻﻯ ﺳﻄﺢ ﺳﮕﻤﺎ ﻋﻤﻮﺩ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﻭﻣﻮﺍﺯﻯ ﺑﺎ ﻳﻚ ﺩﻳﮕﺮ‬
‫ﻣﻴﺒﺎﺷﻨﺪ ﻛﻪ ﺩﺭﻧﺘﻴﺠﻪ ﺑﺎﻫﻢ ﺗﺪﺍﺧﻞ ﺟﺎﻧﺒﻰ ﺭﺍ ﻋﻤﻠﻰ ﻧﻤﻮﺩﻩ ﻭ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ) ﺭﺍﺑﻄﺔ ﺩﻭﻣﻰ ( ﺭﺍ ﺑﺮ ﻗﺮﺍﺭ ﻣﻴﻨﻤﺎﻳﺪ‬
‫‪.‬ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺗﺸﻜﻴﻞ ﺩﻫﻨﺪﺓ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﭘﺎﻯ)‪ (π − elctrons‬ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪ ‪ .‬ﺍﺑﺮﺍﻟﻜﺘﺮﻭﻧﻰ ﭘﺎﻯ‬
‫ﺩﺭ ﻗﺴﻤﺖ ﺑﺎﻻ ﻭﭘﺎﻳﻴﻦ ﺳﻄﺢ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﻭ ﺑﻪ ﺍﻳﻦ ﺍﺳﺎﺱ ﺩﻭﺟﻮﺭﻩ ﺍﻟﻜﺘﺮﻭﻥ ﺭﺍﺑﻄﺔ ﺟﻔﺘﺔ ) ﻳﻚ‬
‫ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﻭﻳﻚ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ( ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ‪ .‬ﺭﺍﺑﻄﺔ ﺟﻔﺘﻪ ﻋﺒﺎﺭﺕ ﺍﺯ ﻣﺠﻤﻮﻋﺔ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﻭﺭﺍﺑﻄﺔ‬
‫ﭘﺎﻯ ) ‪ (S + π − bond‬ﺍﺳﺖ ‪ .‬ﭘﻮﺷﺶ ﻭ ﺗﺪﺍﺧﻞ ﺟﺎﻧﺒﻰ ﺍﺑﺮ ﻫﺎﻯ ﺍﻟﻜﺘﺮﻭﻧﻰ ‪ – p‬ﺍﻭﺭﺑﻴﺘﺎﻝ ﻫﺎﻯ ﻏﻴﺮ ﻫﺎﻳﺒﺮﻳﺪ‬
‫ﺷﺪﻩ ﻛﻪ ﺭﺍﺑﻄﺔ ‪ P‬ﺭﺍ ﺑﻪ ﻭﺟﻮﺩ ﻣﻴﺂﻭﺭﻧﺪ ‪ ،‬ﺍﺗﻮﻡ ﻫﺎﻯ ﻛﺎﺭﺑﻦ ﺭﺍ ﺑﺎﻫﻢ ﻧﺰﺩﻳﻚ ﻣﻴﺴﺎﺯﺩ ﻭ ﻓﺎﺻﻠﻪ ﺑﻴﻦ ﺁﻧﻬﺎ ﺭﺍ ﻛﻮﺗﺎﻩ‬
‫‪71‬‬
‫ﻣﻴﺴﺎﺯﺩ ؛ ﻳﻌﻨﻰ ﻃﻮﻝ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ‪ C = C‬ﺑﻪ ﺍﻧﺪﺍﺯﺓ ‪ 0.33‬ﻧﺎﻧﻮﻣﺘﺮ ﺗﻘﺮﺏ ﻧﻤﻮﺩﻩ ‪ ،‬ﺩﺭ ﺣﺎﻟﻰ ﻛﻪ ﻃﻮﻝ ﺭﺍﺑﻄﺔ‬
‫ﺳﺎﺩﻩ ‪ 0.154 ، C − C‬ﻧﺎﻧﻮﻣﺘﺮ ﺍﺳﺖ ‪ .‬ﺷﻜﻞ )‪ (1 - 5‬ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫ﻳﻚ ﺭﺍﺑﻄﺔ ‪[one P bond ]P‬‬
‫‪134 pm‬‬
‫‪p‬‬ ‫‪H‬‬
‫‪H‬‬
‫‪120 °‬‬
‫‪pm‬‬
‫‪110‬‬

‫‪120 °‬‬ ‫‪C‬‬ ‫‪C‬‬

‫‪120 °‬‬
‫‪H‬‬
‫)ﺏ(‬ ‫)ﺍﻟﻒ(‬
‫ﺷﻜﻞ )‪ (1 – 5‬ﻧﻤﺎﻯ ﺭﺍﺑﻄﻪ ﺩﺭﺍﻳﺘﻴﻠﻴﻦ ‪ ،‬ﺯﺍﻭﻳﻪ ﻭ ﻃﻮﻝ ﺭﻭﺍﺑﻂ ﺁﻥ‬
‫‪ : 2 -1 – 5‬ﻧﺎﻣﮕﺬﺍﺭﻯ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫ﺩﺭﻧﺎﻣﮕﺬﺍﺭﻯ ﺍﻟﻜﻴﻦ ﻫﺎ ﭘﺴﻮﻧﺪ ‪ ene‬ﺭﺍ ﺑﻪ ﻋﻮﺽ ﭘﺴﻮﻧﺪ‪ ane‬ﻧﺎﻡ ﺍﻟﻜﺎﻥ ﺍﻳﺰﻭﻟﻮﻙ ﺁﻥ ﻋﻼﻭﻩ ﻣﻴﻨﻤﺎﻳﻨﺪ ‪.‬‬
‫ﺩﺭﻣﺮﻛﺒﺎﺕ ﺍﻟﻜﻴﻦ ﻫﺎ ﻧﻴﺰ ﻃﻮﻳﻞ ﺗﺮﻳﻦ ﺯﻧﺠﻴﺮ ﺭﺍ ﻣﺸﺨﺺ ﻣﻴﺴﺎﺯﻧﺪ ‪ ،‬ﺩﺭﻳﻦ ﺻﻮﺭﺕ ﺍﻭﻻً ﻧﻤﺒﺮ ﻛﺎﺭﺑﻦ ﻫﺎﻯ ﻛﻪ‬
‫ﺑﻘﻴﻪ ﻭﻳﺎ ﺍﻧﺸﻌﺎﺑﺎﺕ ﺩﺭ ﺁﻥ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪ ،‬ﺑﻪ ﺍﺭﻗﺎﻡ ‪ 3 ، 2 ، 1‬ﻭ ﻏﻴﺮﻩ ﺗﺤﺮﻳﺮ ﻭ ﺑﻌﺪ ﺍﺯ ﻋﻼﻣﺔ ــــ ﻧﺎﻡ ﺑﻘﻴﻪ ﻫﺎ‬
‫ﺭﺍ ﺑﻪ ﺍﺳﺎﺱ ﺣﺮﻑ ﺍﻭﻝ ﻧﺎﻡ ﺁﻧﻬﺎ ﺑﺎ ﺩﺭ ﻧﻈﺮﺩﺍﺷﺖ ﺗﻘﺪ ﻡ ﺁﻥ ﺣﺮﻑ ﺩﺭﺣﺮﻭﻑ ﺍﻟﻔﺒﺎﻯ ﺍﻧﮕﻠﻴﺴﻰ ﺗﺤﺮﻳﺮ ﻭ ﺳﭙﺲ‬
‫ﻧﺎﻡ ﺯﻧﺠﻴﺮ ﻃﻮﻳﻞ ﺭﺍ ﺑﺎ ﭘﺴﻮﻧﺪ ‪ ene‬ﺗﺤﺮﻳﺮ ﻭ ﻧﻤﺒﺮ ﻛﺎﺭﺑﻦ ﺭﺍ ﻛﻪ ﺭﺍﺑﻄﺔ ﺟﻔﺘﻪ ﺩﺭﺁﻥ ﻣﻮﺟﻮﺩ ﺍﺳﺖ ‪ ،‬ﻧﻴﺰﺩﺭ‬
‫ﺍﺑﺘﺪﺍﻯ ﻧﺎﻡ ﺯﻧﺠﻴﺮﻯ ﻃﻮﻝ ﺗﺤﺮﻳﺮ ﻣﻴﻨﻤﺎﻳﻨﺪ‪ .‬ﻧﺎﮔﻔﺘﻪ ﻧﺒﺎﻳﺪ ﮔﺬﺍﺷﺖ ﺍﻳﻨﻜﻪ ﻧﻤﺒﺮﮔﺬﺍﺭﻯ ﺯﻧﺠﻴﺰ ﻃﻮﻳﻞ ﺍﺯﺁﻥ ﺍﻧﺠﺎﻡ‬
‫ﺯﻧﺠﻴﺮﻯ ﺁﻏﺎﺯ ﻣﻴﮕﻴﺮﺩ ﻛﻪ ﺭﺍﺑﻄﺔ ﺟﻔﺘﻪ ﺑﻪ ﺁﻥ ﻧﺰﺩﻳﻚ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ ؛ ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ‪:‬‬
‫‪4‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪1‬‬ ‫‪CH‬‬
‫‪CH 3 − CH = CH − CH 3‬‬ ‫‪3‬‬
‫|‬
‫‪2 − butene‬‬
‫‪1 CH − 2 CH = 3 CH − 4 C H − 5 CH − 6 CH − 7 CH‬‬
‫‪4‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪1‬‬
‫‪CH 3 − CH 2 − CH = CH 2‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬
‫‪4 −methyl − 2 −heptene‬‬
‫‪1−butene‬‬
‫ﺩﺭﺻﻮﺭﺗﻰ ﻛﻪ ﭼﻨﺪﻳﻦ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺩﺭﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ ‪ ،‬ﻗﺒﻞ ﺍﺯ ﭘﺴﻮﻧﺪ‪ ، ene‬ﺍﺭﻗﺎﻡ ‪di ، Tri‬‬
‫ﻭﻏﻴﺮﻩ ﺫﻛﺮ ﻣﻴﮕﺮﺩﺩ ﻛﻪ ﺍﻳﻦ ﺍﺭﻗﺎﻡ ﺗﻌﺪﺍﺩ ﺭﻭﺍﺑﻂ ﺟﻔﺘﻪ ﺭﺍ ﺍﻓﺎﺩﻩ ﻣﻴﻜﻨﻨﺪ ؛ ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ ‪:‬‬
‫‪4‬‬ ‫‪5‬‬ ‫‪6‬‬
‫‪1 CH − 2 CH = 3 CH − C H = CH‬‬ ‫‪− CH‬‬
‫‪3‬‬ ‫‪3‬‬
‫‪2,4 −hexadiene‬‬
‫‪: 3- 1 – 5‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫ﺍﻟــﻒ ‪ :‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻭ ﻣﻮﻗﻌﻴﺖ ﺭﺍﺑﻂ ﺩﻭﮔﺎﻧﻪ‬
‫‪4‬‬ ‫ﻣﺮﻛﺒﺎﺕ ﺫﻳﻞ ﺭﺍ ﺩﺭﻧﻈـﺮ ﺑﮕﻴﺮﻳﺪ ‪:‬‬
‫‪1 CH = 2 CH− 3 CH − C H‬‬
‫‪2‬‬ ‫‪3‬‬
‫‪2‬‬
‫‪1−butene‬‬
‫‪4‬‬
‫‪1‬‬
‫‪CH3 − 2 CH= 3 CH−C H 3‬‬
‫‪2 − butene‬‬
‫‪72‬‬
‫ﻓﻮﺭﻣﻮﻝ ﺟﻤﻌﻰ ﻫﺮﺩﻭ ﻣﺮﻛﺐ ﻓﻮﻕ ‪ C H‬ﺑﻮﺩﻩ ؛ ﺍﻣﺎ ﻓﻮﺭﻣﻮﻝ ﺳﺎﺧﺘﻤﺎﻧﻰ ﻫﺮﺩﻭ ﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ ﺍﺯﻫﻢ‬
‫‪4‬‬ ‫‪8‬‬
‫ﻣﺘﻔﺎﻭﺕ ﺑﻮﺩﻩ ‪ ،‬ﻣﻮﻗﻌﻴﺖ ﺭﺍﺑﻂ ﺩﻭﮔﺎﻧﻪ ﺩﺭﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ﺍﺯ ﻫﻢ ﻓﺮﻕ ﺩﺍﺭﺩ ‪،‬ﺍﻳﻦ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻳﺰﻭﻣﻴﺮﻯ‬
‫ﺳﺎﺧﺘﻤﺎﻧﻰ ﺍﺯﻟﺤﺎﻅ ﻣﻮﻗﻌﻴﺖ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﻳﺎﺩ ﻣﻴﻜﻨﻨﺪ ‪.‬‬
‫ﺏ – ﺍﻳﺰﻭﻣﻴﺮﻯ ﻓﻀﺎﻳﻰ ) ‪( Stereo isomeris‬‬
‫‪ Stereo‬ﻛﻠﻤﻪ ﻳﻮﻧﺎﻧﻰ ﺑﻮﺩﻩ ﻛﻪ ﺑﻪ ﻣﻌﻨﻰ ﺟﺎﻣﺪ ﻭﺍﺟﺴﺎﻡ ﺳﺨﺖ ﻣﻴﺒﺎﺷﺪ ؛ ﺑﻨﺎﺑﺮﺍﻳﻦ ‪Stereo isomeris‬‬
‫ﻣﺮﺑﻮﻁ ﺑﻪ ﻣﺮﻛﺒﺎﺗﻰ ﺍﺳﺖ ﻛﻪ ﺳﺎﺧﺘﻤﺎﻥ ﻓﻀﺎﻳﻰ ﻣﺴﺘﺤﻜﻢ ﺭﺍ ﺩﺍﺭﺍ ﺑﻮﺩﻩ ﻭ ﺷﻜﻞ ﻫﻨﺪﺳﻰ ﺁﻥ ﺩﺭﻓﻀﺎ ﺗﻐﻴﻴﺮ‬
‫ﻧﻤـــــﻴﻜﻨﺪ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ‪ :‬ﻣﺮﻛﺐ ‪ 2-Butene‬ﺭﺍ ﺩﺭﻧﻈﺮﻣﻴﮕﻴﺮﻳﻢ ﻭ ﺑﻪ ﻭﺍﺳﻄﺔ ﻣﻮﺩﻝ ﻫﺎﻯ ﭼﻮﺑﻰ ﺍﺷﻜﺎﻝ‬
‫ﻣﻤﻜﻨﻪ ﺁﻥ ﺭﺍ ﻋﻴﺎﺭ ﻣﻴﺴﺎﺯﻳﻢ ‪ ،‬ﺍﻳﻦ ﻣﺮﻛﺐ ﻗﺮﺍﺭ ﺷﻜﻞ )‪ (2 - 5‬ﺩﻭﺣﺎﻟﺖ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺭﺍ ﺧﻮﺍﻫﺪ ﺩﺍﺷﺖ؛ ﻃﻮﺭﻯ‬
‫ﻼ ﻣﺨﺘﻠﻒ‬ ‫ﻛﻪ ﻣﻼﺣﻈﻪ ﻣﻴﮕﺮﺩﺩ ‪ ،‬ﻣﺤﻞ ﺍﺳﺘﻘﺮﺍﺭ ﮔﺮﻭپ ﻫﺎﻯ ﻣﻴﺘﺎﻳﻞ ﺩﺭﻣﺎﻟﻴﻜﻮﻝ ﻣﺮﻛﺐ‪ 2-Butene‬ﻛﺎﻣ ً‬
‫ﺑﻮﺩﻩ ﻭ ﺩﺭ ﺣﺮﺍﺭﺕ ﻋﺎﺩﻯ ﺍﻧﺮژﻯ ﺣﺮﻛﻰ ﻣﺎﻟﻴﻜﻮﻝ ﻫﺎ ﻗﺎﺩﺭ ﺑﻪ ﺗﻌﻮﻳﺾ ﻭ ﭼﺮﺧﺶ ﺭﺍﺩﻳﻜﺎﻝ ﻫﺎﻯ ﻣﻴﺘﺎﻳﻞ ﺩﺭﺁﻥ‬
‫ﻧﻤﻴﺒﺎﺷﺪ؛ ﺯﻳﺮﺍ ﺍﻧﺮژﻯ ﺭﺍﺑﻄﻪ ‪ P‬ﻣﺎﻧﻊ ﺩﺭﻣﻘﺎﺑﻞ ﺗﻌﻮﻳﺾ ﻭﭼﺮﺧﺶ ﺭﺍﺩﻳﻜﺎﻝ ﻫﺎﻯ ﻣﺬﻛﻮﺭ ﻣﻴﮕﺮﺩﺩ ﻭ ﻏﺮﺽ ﺍﺯﺑﻴﻦ‬
‫ﺑﺮﺩﻥ ﺍﻳﻦ ﻣﺎﻧﻊ ﺍﻧﺮژﻳﻜﻰ ﺑﺎﻳﺪ ﺍﻧﺮژﻯ ﻓﻌﺎﻝ ﺳﺎﺯﻯ )‪ ( activation Energy‬ﻣﻮﺟﻮﺩ ﺑﺎﺷﺪ ؛ ﺑﻨﺎﺑﺮﺍﻳﻦ ﺩﺭﺣﺮﺍﺭﺕ‬
‫ﻋﺎﺩﻯ ﻣﻴﺘﻮﺍﻥ ﺍﻳﻦ ﺩﻭﻧﻮﻉ ﺍﻳﺰﻭﻣﻴﺮ ﺭﺍ ﺍﺯ ﻫﻢ ﺩﻳﮕﺮ ﺟﺪﺍ ﺳﺎﺧﺖ؛ ﺯﻳﺮﺍ ﻧﻘﻄﻪ ﻏﻠﻴﺎﻥ ﺁﻧﻬﺎ ﺍﺯﻫﻤﺪﻳﮕﺮﻓﺮﻕ ﺩﺍﺭﺩ ‪.‬‬
‫ﺷﻜﻞ )‪ ( 2 – 5‬ﺩﻭ ﺳﺎ ﺧﺘﻤﺎﻥ ﻓﻀﺎﻳﻰ ﻣﺎﻟﻴﻜﻮﻝ ‪ - 2‬ﺑﻴﻮﺗﻴﻦ ‪:‬‬
‫‪ - 1‬ﺑﻪ ﻃﺮﻳﻘﺔ ﻗﺪ ﻳﻤﻰ ﻧﺎﻡ ﮔﺬﺍﺭﻯ ‪ Cis‬ﻭ ‪ Trams‬ﻛﻪ ﺗﻨﻬﺎ ﺩﺭﻣﻮﺭﺩ ﺍﻳﻦ ﺣﺎﻟﺖ ﺧﺎﺹ؛ ﻳﻌﻨﻰ ‪2-Butene‬‬
‫ﻭﺍﺷﻜﺎﻝ ﻣﺸﺎﺑﻪ ﻫﻨﺪ ﺳﻰ ﺁﻥ ﺻﺪﻕ ﻧﻤﻮﺩﻩ ﻛﻪ ﻳﻚ ﺧﻂ ﻣﺴﺘﻘﻴﻢ ﺭﺍ ﺍﺯ ﻣﺮﻛﺰ ﺩﻭﺍﺗﻮﻡ ﻛﺎﺭﺑﻦ ﺑﺎ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ‬
‫ﺁﻧﻬﺎ ﺭﺳﻢ ﻣﻰ ﻧﻤﺎﻳﻨﺪ ‪ ،‬ﺍﮔﺮ ﻫﺮﺩﻭﮔﺮﻭپ ﻣﻴﺘﺎﻳﻞ ﺑﻪ ﻳﻚ ﻃﺮﻑ ﺧﻂ ﻣﺴﺘﻘﻴﻢ ﻳﻌﻨﻰ ﺩﺭﻳﻚ ﻣﺴﺘﻮﻯ ﻗﺮﺍﺭ ﮔﻴﺮﻧﺪ ‪ ،‬ﺍﻳﻦ‬
‫ﺳﺎﺧﺘﻤﺎﻥ ﺭﺍ ﺑﻨﺎﻡ ‪ Cis‬ﻳﺎﺩ ﻧﻤﻮﺩﻩ ﻭ ﺍﮔﺮ ﻳﻜﻰ ﺁﻥ ﺩﺭ ﺑﺎﻻ ﻭﺩﻳﮕﺮ ﺁﻥ ﺩﺭﭘﺎﻳﻴﻦ ﺧﻂ ﻣﺴﺘﻘﻴﻢ ﻳﻌﻨﻰ ﺩﺭﺩﻭ ﻣﺴﺘﻮﻯ‬
‫ﻣﺨﺘﻠﻒ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﺑﺎﺷﻨﺪ ﺑﻪ ﻧﺎﻡ ﺍﻳﺰﻭﻣﻴﺮﻯ ‪ Trans‬ﻳﺎﺩ ﻣﻴﮕﺮﺩﺩ‪.‬‬
‫‪ - 2‬ﺭﻭﺵ ﺟﺪﻳﺪﻯ ﻛﻪ ﺑﺮﺍﻯ ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﻓﻀﺎﻳﻰ ﺑﻪ ﻛﺎﺭ ﺑﺮﺩﻩ ﻣﻴﺸﻮﺩ ‪ ،‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﻫﺎﻯ ﻣﺬﻛﻮﺭ ﺭﺍ ﺑﻪ‬
‫ﺣﺮﻭﻑ ‪ Z‬ﻭ ‪ E‬ﻣﺸﺨﺺ ﻣﻴﺴﺎﺯﻧﺪ ‪ ،‬ﺍﻳﻦ ﺭﻭﺵ ﺍﻳﺰﻭﻣﻴﺮﻯ ﺭﺍ ﻛﻪ ﻫﺮ ﺩﻭﮔﺮﻭپ ﻣﻴﺘﺎﻳﻞ ﺁﻥ ﺩﺭ ﻳﻚ ﻃﺮﻑ ﺧﻂ‬
‫ﻣﺴﺘﻘﻴﻢ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ ‪ ،‬ﺍﻳﻦ ﺳﺎﺧﺘﻤﺎﻥ ﺭﺍ ‪ Z‬ﮔﻮﻳﻨﺪ ) ‪ Z‬ﻛﻠﻤﻪ ﺁﻟﻤﺎﻧﻰ ‪ Zusammen‬ﺑﻮﺩﻩ ﻛﻪ ﻣﻌﻨﻰ‬
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‫ﺑﺎﻫﻢ ﺍﺳﺖ ( ﺍﻳﺰﻭﻣﻴﺮﻯ ﻛﻪ ﺩﻭﮔﺮﻭپ ﻣﻴﺘﺎﻳﻞ ﺑﻪ ﺩﻭﺳﻤﺖ ﻣﺨﺘﻠﻒ ﺧﻂ ﻳﻌﻨﻰ ﺩﺭﺳﻄﻮﺡ ﻣﺨﺘﻠﻒ ﻭ ﺑﺎ ﺟﻬﺖ‬
‫ﻣﺨﺘﻠﻒ ﺑﺎﻫﻢ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ ﺑﺎﺷﺪ ﺑﻪ ‪ E‬ﻣﺸﺨﺺ ﻣﻴﮕﺮﺩﺩ‪ E ) .‬ﺍﺯﻛﻠﻤﻪ ﺁﻟﻤﺎﻧﻰ‪ Entgegen‬ﮔﺮﻓﺘﻪ ﺷﺪﻩ ﻛﻪ‬
‫ﻣﻌﻨﻰ ﻣﺨﺎﻟﻒ ﺑﺎﻫﻢ ﺩﻳﮕﺮ ﺭﺍ ﺩﺍﺭﺩ ( ؛ ﺑﻪ ﻃﻮﺭﻣﺜﺎﻝ ‪:‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪CH 3‬‬
‫‪CH 2‬‬ ‫‪CH 2‬‬ ‫‪CH 3‬‬ ‫‪H‬‬
‫ﺳﺎﺧﺘﻤﺎﻥ ‪( Z ( Cls‬‬ ‫ﺳﺎﺧﺘﻤﺎﻥ ‪ ) E‬ﺗﺮﺍﻧﺲ (‬
‫) ‪( E) 2-butane‬‬ ‫‪2- butane ( Z‬‬
‫‪R‬‬ ‫‪R/‬‬ ‫‪H‬‬ ‫‪R/‬‬
‫‪C=C‬‬ ‫‪C=C‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪R‬‬ ‫‪H‬‬
‫‪Cis Isomery‬‬ ‫) ‪(Z‬‬ ‫‪) E( Trans Isomer‬‬
‫‪ : 4 - 1 – 5‬ﺧﻮﺍﺹ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫‪ :1 – 4 – 1- 5‬ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ ﺍﻟﻜﻴﻨﻬﺎ ﺑﻪ ﺧﻮﺍﺹ ﻓﺰﻳﻜﻰ ﺍﻟﻜﺎﻧﻬﺎﻯ ﺍﻳﺰﻭﻟﻮگ ﺷﺎﻥ ﻣﺸﺎﺑﻬﺖ ﺩﺍﺭﺩ ؛ ﺍﻣﺎ ﺩﺭﺟﺔ ﻏﻠﻴﺎﻥ‬
‫ﺍﻟﻜﻴﻦ ﻫﺎ ﻧﻈﺮ ﺑﻪ ﺍﻟﻜﺎﻥ ﻫﺎﻯ ﺍﻳﺰﻭﻟﻮگ ﺷﺎﻥ ﭘﺎﻳﻴﻦ ﺗﺮ ﻭ ﻛﺜﺎﻓﺖ ﺷﺎﻥ ﺑﻴﺸﺘﺮ ﺍﺳﺖ ‪.‬‬
‫ﺳﻪ ﻋﻀﻮﺍﻭﻝ ﺍﻳﻦ ﻣﺮﻛﺒﺎﺕ ) ‪ (C 2 − C 4‬ﺑﻪ ﺣﺎﻟﺖ ﮔﺎﺯ‪ ،‬ﺍﻟﻜﻴﻨﻬﺎﻯ ﺩﺍﺭﻧﺪﺓ ) ‪ (C5 − C18‬ﺣﺎﻟﺖ ﻣﺎﻳﻊ ﻭ‬
‫ﺑﺎﻻﺗﺮ ﺍﺯ ﺁﻥ ﺣﺎﻟﺖ ﻣﻮﻡ ﻳﺎ ﺟﺎﻣﺪ ﺭﺍ ﺩﺍﺭﺍ ﺍﻧﺪ ‪ .‬ﺍﻳﺰﻭﻣﻴﺮﻯ ﺳﺎﺧﺘﻤﺎﻧﻰ ‪ ،‬ﺍﺳﻜﻠﻴﺖ ﻛﺎﺭﺑﻨﻰ ﻭ ﻓﻀﺎﻳﻰ ﺩﺭ ﺧﻮﺍﺹ‬
‫ﻓﺰﻳﻜﻰ ﺍﻟﻜﻴﻨﻬﺎ ﺗﺄﺛﻴﺮ ﺩﺍﺭﺩ ‪ .‬ﺟﺪﻭﻝ ﺫﻳﻞ ﺭﺍ ﻣﻼﺣﻈﻪ ﻧﻤﺎﻳﻴﺪ ‪:‬‬
‫ﺟﺪﻭﻝ ) ‪ ( 2 - 5‬ﻣﺸﺨﺼﺎﺕ ﻓﺰﻳﻜﻰ ﺍﻟﻜﻴﻨﻬﺎ‬
‫ﻛﺜﺎﻓﺖ ﻣﺨﺼﻮﺻﻪ‬ ‫‪0‬‬
‫ﺩﺭﺟﺔ ﻏﻠﻴﺎﻥ ﺑﻪ ‪C‬‬ ‫‪0‬‬
‫ﺩﺭﺟﺔ ﺫﻭﺑﺎﻥ ﺑﻪ ‪C‬‬ ‫ﻓﻮﺭﻣﻮﻝ‬ ‫ﻧﺎﻡ‬
‫‪0.570‬‬ ‫‪-105‬‬ ‫‪-169‬‬ ‫‪CH 2 = CH 2‬‬ ‫‪Ethylene‬‬
‫‪0.610‬‬ ‫‪-47.8‬‬ ‫‪-185.2‬‬ ‫‪CH 2 = CH − CH 3‬‬ ‫‪propene 1-‬‬
‫‪0.595‬‬ ‫‪-6.3‬‬ ‫‪-130.0‬‬ ‫‪CH2 = CH − CH2 − CH3‬‬ ‫‪butene- 1‬‬
‫‪0.621‬‬ ‫‪+3.5‬‬ ‫‪cis138.9‬‬ ‫‪CH3 − CH = CH − CH3‬‬ ‫‪butene- 2‬‬
‫‪0.604‬‬ ‫‪0.9‬‬ ‫)‪trans(-105.5‬‬
‫‪0.594‬‬ ‫‪-6.9‬‬ ‫‪-140‬‬ ‫‪CH = C − CH‬‬ ‫‪Iosbutene‬‬
‫‪2‬‬ ‫|‬ ‫‪3‬‬
‫‪CH 3‬‬
‫ﻛﺜﺎﻓﺖ ﻣﺨﺼﻮﺻﺔ ﺗﻤﺎﻡ ﺍﻭﻟﻔﻴﻦ ﻫﺎ ﻛﻤﺘﺮ ﺍﺯ ﻳﻚ ﺑﻮﺩﻩ ﻭﺩﺍﺭﺍﻯ ﺑﻮﻯ ﻣﺸﺨﺺ ﻣﻴﺒﺎﺷﺪ ‪ .‬ﺩﺭﺁﺏ ﺑﻪ ﺧﻮﺑﻰ‬
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 ‫ﺣﻞ ﻧﻪ ﺷﺪﻩ؛ ﻭﻟﻰ ﺍﻧﺤﻼﻟﻴﺖ ﺷﺎﻥ ﻧﺴﺒﺖ ﺑﻪ ﺍﻟﻜﺎﻧﻬﺎ ﻯ ﺍﻳﺰﻭﻟﻮگ ﺷﺎﻥ ﺑﻴﺸﺘﺮ ﺍﺳﺖ ‪.‬‬
‫‪ : 2 – 3 – 1- 5‬ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫ﺧﻮﺍﺹ ﻛﻴﻤﻴﺎﻭﻯ ﺍﻟﻜﻴﻨﻬﺎ ﺭﺍ ﺭﺍﺑﻄﺔ ﺟﻔﺘﻪ ﻭﻣﻮﻗﻌﻴﺖ ﻓﻀﺎﻳﻰ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﻭ ﭘﺎﻯ ﺗﻌﻴﻴﻦ ﻣﻰ ﻧﻤﺎﻳﺪ ‪ ،‬ﻛﺜﺎﻓﺖ‬
‫ﺍﺑﺮ ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍﺑﻄﺔ ﺳﮕﻤﺎ ﺩﺭ ﺑﺎﻻﻯ ﺧﻄﻰ ﻛﻪ ﻫﺴﺘﺔ ﺩﻭﺍﺗﻮﻡ ﺭﺍ ﻭﺻﻞ ﻣﻴﺴﺎﺯﺩ ‪ ،‬ﻣﺘﻤﺮﻛﺰ ﺷﺪﻩ ﻭ ﻛﺜﺎﻓﺖ ﺍﺑﺮ‬
‫ﺍﻟﻜﺘﺮﻭﻧﻰ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ﺍﺯﺍﻳﻦ ﺣﺪﻭﺩ ﺧﺎﺭﺝ ﮔﺮﺩﻳﺪﻩ ﻭﺳﺎﺣﺔ ﻭﺳﻴﻊ ﭼﺎﺭﺝ ﻣﻨﻔﻰ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﺪ ‪ .‬ﺗﺤﺮﻳﻚ‬
‫ﺍﺯ ﺧﺼﻮﺻﻴﺎﺕ ﺍﺳﺎﺳﻰ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ﺑﻮﺩﻩ ﻭ ﺭﺍﺑﻄﺔ ﺍﻳﻦ ﺍﻟﻜﺘﺮﻭﻧﻬﺎ ﺑﺎ ﻫﺴﺘﻪ ﻧﺴﺒﺖ ﺑﻪ ﺭﺍﺑﻄﺔ ﺍﻟﻜﺘﺮﻭﻧﻬﺎﻯ ﺳﮕﻤﺎ‬
‫ﺿﻌﻴﻒ ﺍﺳﺖ ؛ ﺍﺯﺍﻳﻦ ﺳﺒﺐ ﺑﻪ ﺁﺳﺎﻧﻰ ﻗﻄﺒﻰ ﺷﺪﻩ ﻭ ﺯﻣﻴﻨﺔ ﺣﻤﻠﻪ ﺑﻪ ﺫﺭﺍﺕ ﺍﻟﻜﺘﺮﻭﻥ ﺩﻭﺳﺖ )‪(Electrophilic‬‬
‫ﻣﻴﺴﺮ ﺷﺪﻩ ‪ ،‬ﺑﻪ ﺍﻳﻦ ﺍﺳﺎﺱ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ﺑﻪ ﺷﻜﻞ ﻫﺘﺮﻭﻟﻴﺘﻴﻜﻰ ﻗﻄﻊ ﻭ ﺗﻌﺎﻣﻼﺕ ﺟﻤﻌﻰ ﺻﻮﺭﺕ ﻣﻴﮕﻴﺮﺩ ‪ .‬ﻓﺮﻕ ﺑﻴﻦ‬
‫ﺍﻧﺮژﻯ ﺭﺍﺑﻄﺔ ﭘﺎﻯ ﻭﺳﮕﻤﺎ‪ 270kj/mol‬ﺍﺳﺖ ‪ .‬ﺑﻌﻀﻰ ﺍﺯ ﺗﻌﺎﻣﻼﺕ ﺍﻟﻜﻴﻨﻬﺎ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ ‪:‬‬
‫‪ - 1‬ﻫﺎﻳﺪﺭﻭﺟﻨﻴﺸﻦ ﺍﻟﻜﻴﻦ‬
‫ﺍﮔﺮ ﺍﻳﺘﻠﻴﻦ ﺩﺭ ﻣﻮﺟﻮﺩﻳﺖ ﻧﻜﻞ ﺑﻪ ﺣﻴﺚ ﻛﺘﻠﺴﺖ ﻫﺎﻳﺪﺭﻭﺟﻨﺸﻦ ﮔﺮﺩﺩ ‪ ،‬ﺍﻳﺘﺎﻥ ﺣﺎﺻﻞ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫)‪Ni(500 0 C‬‬
‫⎯ ⎯ ⎯ ⎯⎯ ‪CH 2 = CH 2 + H 2‬‬ ‫‪⎯→ CH 3 − CH 3‬‬
‫ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﻠﻴﻦ ﺩﺭﻳﻚ ﺳﻄﺢ ﻗﺮﺍﺭ ﺩﺍﺷﺘﻪ‪ ،‬ﺩﺭﺣﺎﻟﻴﻜﻪ ﻣﺎﻟﻴﻜﻮﻝ ﺍﻳﺘﺎﻥ ﭼﻬﺎﺭﺳﻄﺤﻰ ﺍﺳﺖ ‪.‬‬
‫‪ - 2‬ﻫﻠﻮﺟﻨﻴﺸﻦ ﺍﻟﻜﻴﻨﻬﺎ‬
‫ﺍﻭﻟﻔﻴﻦ ﻫﺎ ﺩﺭ ﺷﺮﺍﻳﻂ ﻋﺎﺩﻯ ﻫﻠﻮﺟﻨﻬﺎ ﺑﺨﺼﻮﺹ ﻛﻠﻮﺭﻳﻦ ﻭﺑﺮﻭﻣﻴﻦ ﺭﺍ ﺑﺎﻻﻯ ﺧﻮﺩ ﻧﺼﺐ ﻧﻤﻮﺩﻩ ﻭﺩﺍﻯ‬
‫ﻫﻼﻳﺪ ﻫﺎﻯ ﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ﺭﺍ ﺗﺸﻜﻴﻞ ﻣﻴﺪﻫﻨﺪ ؛ ﺑﻪ ﻃﻮﺭ ﻣﺜﺎﻝ ‪ :‬ﺗﻌﺎﻣﻞ ﺍﻳﺘﻠﻴﻦ ﺭﺍ ﺑﺎ ﻛﻠﻮﺭﻳﻦ ﻭ ﺑﺮﻭﻣﻴﻦ ﻣﺸﺎﻫﺪﻩ‬
‫ﻣﻴﻨﻤﺎﻳﻴﻢ ﻛﻪ ﺗﻌﺎﻣﻞ ﺍﻛﺰﻭﺗﺮﻣﻴﻚ ﺑﻮﺩﻩ ‪ ،‬ﺗﻌﺎﻣﻞ ﺁﻧﻬﺎ ﻗﺮﺍﺭ ﺫﻳﻞ ﺍﺳﺖ ‪:‬‬
‫‪H H‬‬ ‫‪Cl Cl‬‬ ‫‪Br Br‬‬
‫‪H H‬‬
‫\‬ ‫‪/‬‬ ‫|‬ ‫|‬
‫‪C = C + Cl‬‬ ‫⎯‬
‫‪Δ‬‬
‫‪⎯→ H − C − C − H‬‬ ‫‪،‬‬ ‫\‬ ‫‪/‬‬
‫‪C = C + Br‬‬ ‫⎯‬
‫‪Δ‬‬
‫|‬ ‫|‬
‫‪⎯→ H − C − C − H‬‬
‫‪/‬‬ ‫\‬ ‫‪2‬‬ ‫|‬ ‫|‬ ‫‪/‬‬ ‫‪2‬‬
‫\‬ ‫|‬ ‫|‬
‫‪H H‬‬ ‫‪H H‬‬ ‫‪H H‬‬ ‫‪H H‬‬
‫ﺗﻌﺎﻣﻞ ﻫﻠﻮﺟﻦ ﻫﺎ ﺭﺍﺑﺎ ﺍﻟﻜﻴﻨﻬﺎ ‪Halogenation‬ﮔﻮﻳﻨﺪ ﻭﻣﺮﻛﺒﺎﺕ ﺣﺎﺻﻠﻪ ﺭﺍ ﺑﻪ ﻧﺎﻡ ﺍﻟﻜﺎﻳﻞ ﻫﻼﻳﺪﻫﺎ‬
‫ﻳﺎﺩﻣﻴﻨﻤﺎﻳﻨﺪ‪.‬‬
‫ﺑﻴﺮﻧﮓ ﺳﺎﺧﺘﻦ ﺁﺏ ﺑﺮﻭﻣﻴﻦ ﺍﺯ ﺟﻤﻠﺔ ﺗﻌﺎﻣﻼﺕ ﺗﻮﺻﻴﻔﻰ ﺭﺍﺑﻄﺔ ﺩﻭﮔﺎﻧﻪ ﺍﺳﺖ ‪ .‬ﺑﺮﺍﻯ ﺍﻳﻦ ﻣﻨﻈﻮﺭ ﺍﺯ ﻣﺤﻠﻮﻝ‬
‫ﺑﺮﻭﻣﻴﻦ ﺩﺭ ﻛﺎﺭﺑﻦ ﺗﺘﺮﺍ ﻛﻠﻮﺭﺍﻳﺪ ﻳﺎ ﻛﻠﻮﺭﻭﻓﺎﺭﻡ ﺍﺳﺘﻔﺎﺩﻩ ﻣﻴﻨﻤﺎﻳﻨﺪ‪ ،‬ﺑﻪ ﺍﺳﺎﺱ ﺍﻳﻦ ﺗﻌﺎﻣﻞ ﺩﺭﺟﺔ ﻣﺸﺒﻮﻋﻴﺖ ﺗﻴﻞ‬
‫ﻫﺎﻯ ﻣﺎﻳﻊ ﺗﻌﻴﻴﻦ ﻣﻴﮕﺮﺩﺩ ‪.‬‬
‫‪ – 3‬ﺍﻛﺴﻴﺪﻳﺸﻦ ﺍﻟﻜﻴﻦ ﻫﺎ‬
‫ﺍﻟﻜﻴﻦ ﻫﺎ ﺑﻪ ﺁﺳﺎﻧﻰ ﺗﺤﺖ ﺗﺎﺛﻴﺮ ﺍﻛﺴﻴﺪﺍﻧﺖ ﻫﺎ ﻯ ﻣﺨﺘﻠﻒ ﻗﺮﺍﺭ ﮔﺮﻓﺘﻪ ﻭﺑﺎﺍﻳﻦ ﺧﺎﺻﻴﺖ ﺧﻮﺩ ﺍﺯ ﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ‬
‫ﻭﺳﺎﻳﻜﻠﻮ ﭘﺎﺭﺍﻓﻴﻦ ﻫﺎ ﻓﺮﻕ ﻣﻴﺸﻮﻧﺪ ‪ .‬ﺍﺯ ﺍﻛﺴﻴﺪﻳﺸﻦ ﺍﻟﻜﻴﻦ ﻫﺎ ﻧﻈﺮ ﺑﻪ ﺷﺮﺍﻳﻂ ﻣﺮﻛﺒﺎﺕ ﻣﺨﺘﻠﻒ ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ ‪ ،‬ﺍﺯ‬
‫ﺍﺣﺘﺮﺍﻕ ﺍﻟﻜﻴﻦ ﻫﺎ ‪ ،‬ﻛﺎﺭﺑﻦ ﺩﺍﻯ ﺍﻛﺴﺎﻳﺪ ‪،‬ﺁﺏ ﻭ ﺍﻧﺮژﻯ ﺣﺎﺻﻞ ﻣﻴﺸﻮﺩ ‪:‬‬
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