‫‪Grade12files‬‬

‫اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت‬
‫‪Hydrocarbons‬‬

‫اﻟﻔﻜﺮة اﻟﻌﺎﻣﺔ ﲣﺘﻠﻒ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪ ،‬ﻭﻫﻲ ﻣﺮﻛﺒﺎﺕ‬

‫ﻋﻀﻮﻳﺔ‪ ،‬ﺑﺎﺧﺘﻼﻑ ﺃﻧﻮﺍﻉ ﺍﻟﺮﻭﺍﺑﻂ ﻓﻴﻬﺎ‪.‬‬

‫‪ 8-1‬ﻣﻘﺪﻣﺔ إﻟﻰ اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت‬

‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻳﺔ ﲢﺘﻮﻱ‬
‫ﻣﺼﺪﺭﺍ ﻟﻠﻄﺎﻗﺔ ﻭﺍﳌﻮﺍﺩ ﺍﳋﺎﻡ‪.‬‬
‫ﹰ‬ ‫ﻋﲆ ﻋﻨﴫ ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻭﺗﻌﺪ‬
‫اﻟﻔﻜﺮة اﻟﻌﺎﻣﺔ‬
‫‪ 8-2‬اﻟﻜﺎﻧﺎت‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲢﺘﻮﻱ‬ ‫‪ ‬ﻧﺎﻗﺶ ﺍﻟﻄﻼﺏ ﰲ ﺑﻌﺾ ﺍﻷﺷﻴﺎﺀ ﺍﻟﺘﻲ‬
‫ﻓﻘﻂ ﻋﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ‪.‬‬

‫‪ 8-3‬اﻟﻜﻴﻨﺎت واﻟﻜﺎﻳﻨﺎت‬ ‫ﺗﺒﺪﻭ ﻣﺘﺸـﺎﲠﺔ ﻟﻜﻨﻬﺎ ﳐﺘﻠﻔـﺔ ﻟﺘﻘﺪﻳﻢ ﺍﻟﻔﻜﺮﺓ ﺍﻟﻌﺎﻣـﺔ ﳍﺬﺍ ﺍﻟﻔﺼﻞ‪،‬‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲢﺘﻮﻱ‬
‫ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﻭﺍﺣﺪﺓ ﻋﲆ ﺍﻷﻗﻞ‪ .‬ﺃﻣﺎ ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻓﻬﻲ‬
‫ﺍﳌﻨﻮﻋﺔ؟‬
‫ﻭﺍﺳـﺄﻝ‪ :‬ﻫـﻞ ﺗﻨـﺎﻭﻝ ﺃﺣﺪﻛﻢ ﻳﻮ ﹰﻣـﺎ ﺑﻌـﺾ ﺍﳌﻜـﴪﺍﺕ ﹼ‬
‫ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲢﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﻋﲆ ﺍﻷﻗﻞ‪.‬‬
‫ﻭﻣـﺎ ﻭﺟﻪ ﺍﻟﺸـﺒﻪ ﻭﺍﻻﺧﺘﻼﻑ ﺑـﲔ ﻫﺬﻩ ﺍﻷﻧـﻮﺍﻉ؟ ﺃﺧﱪ ﺍﻟﻄﻼﺏ‬
‫ﺃﻥ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﹰ‬
‫‪ 8-4‬ﻣﺘﺸﻜﻼت اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﻟـﺒـﻌـﺾ ﺍﳍﻴـﺪﺭﻭﻛـﺮﺑﻮﻧﺎﺕ ﺍﻟﺼﻴـﻐـﺔ‬ ‫ﺃﻳﻀـﺎ ﺗﺘﺸـﺎﺑﻪ‪ ،‬ﻭﻟﻜﻨﻬـﺎ ﳐﺘﻠﻔـﺔ‪ .‬ﻭﺗﺘﻜـﻮﻥ‬
‫ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴﻬﺎ‪ ،‬ﻟﻜﻨﻬﺎ ﲣﺘﻠﻒ ﰲ ﺻﻴﻐﻬﺎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲨﻴﻌﻬﺎ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ‪ ،‬ﻭﻣﻊ‬
‫‪ 8-5‬اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت اروﻣﺎﺗﻴﺔ‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺗﺘﺼﻒ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ‬ ‫ﺫﻟﻚ ﻓﻬﻲ ﳐﺘﻠﻔﺔ؛ ﻷﳖﺎ ﲢﺘﻮﻱ ﻋﲆ ﺃﻧﻮﺍﻉ ﳐﺘﻠﻔﺔ ﻣﻦ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺘﻲ‬
‫ﺑﺪﺭﺟﺔ ﻋﺎﻟﻴﺔ ﻣﻦ ﺍﻟﺜﺒﺎﺕ‪ ،‬ﺑﺴﺒﺐ ﺑﻨﺎﺋﻬﺎ ﺍﳊﻠﻘﻲ ﺣﻴﺚ‬
‫ﺗﺘﺸﺎﺭﻙ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﰲ ﻋﺪﺩ ﻣﻦ ﺍﻟﺬﺭﺍﺕ‪.‬‬ ‫ﺗﺰﻭﺩﻫﺎ ﺑﺴﲈﺕ ﻭﺧﺼﺎﺋﺺ ﳐﺘﻠﻔﺔ‪.‬‬
‫ﺣﻘﺎﺋﻖ ﻛﻴﻤﻴﺎﺋﻴﺔ‬
‫• ﺍﳌﺼﺪﺭ ﺍﻟﺮﺋﻴﺲ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻫﻮ ﺍﻟﻨﻔﻂ )ﺍﻟﺒﱰﻭﻝ(‪.‬‬
‫ﻳﻮﻣﻴـﺎ ﻣﻦ ﺟﻮﻑ‬
‫اﻟﺮﺑﻂ ﻣﻊ اﻟﻤﻌﺮﻓﺔ اﻟﺴﺎﺑﻘﺔ‬
‫• ﻳﺘـﻢ ﺿﺦ ﺣـﻮﺍﱄ ‪ 75‬ﻣﻠﻴـﻮﻥ ﺑﺮﻣﻴـﻞ ﻧﻔﻂ ﹼﹰ‬
‫ﺍﻷﺭﺽ‪.‬‬
‫• ﺗﹸﺴـﺘﺨﺪﻡ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﰲ ﺍﻟﻮﻗـﻮﺩ‪ ،‬ﻛـﲈ ﺗﻌـﺪ‬
‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻣﺮﺍﺟﻌـﺔ ﺍﳌﻔﺎﻫﻴـﻢ ﺍﻵﺗﻴـﺔ ﻗﺒﻞ ﺩﺭﺍﺳـﺔ ﻫﺬﺍ‬
‫ﺧﺎﻣـﺎ ﻟﻜﺜـﲑ ﻣـﻦ ﺍﳌﻨﺘﺠـﺎﺕ‪ ،‬ﻭﻣﻨﻬـﺎ ﺍﻟﻠﺪﺍﺋـﻦ‬
‫ﻣـﻮﺍﺩ ﹼﹰ‬
‫)ﺍﻟﺒﻼﺳـﺘﻴﻚ(‪ ،‬ﻭﺍﻷﻟﻴـﺎﻑ ﺍﻟﺼﻨﺎﻋﻴـﺔ‪ ،‬ﻭﺍﳌﺬﻳﺒـﺎﺕ‪،‬‬
‫ﺍﻟﻔﺼﻞ‪:‬‬
‫ﻭﺍﳌﻮﺍﺩ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﺍﻟﺼﻨﺎﻋﻴﺔ‪.‬‬
‫ﺑﻨﺎﺀ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ‬
‫ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺘﺴﺎﳘﻴﺔ ﻭﺍﻟﺒﻨﺎﺀ ﺍﳉﺰﻳﺌﻲ‬
‫ﺗﻐﲑﺍﺕ ﺍﳊﺎﻟﺔ ﺍﻟﻔﻴﺰﻳﺎﺋﻴﺔ ‪ -‬ﺍﻟﻐﻠﻴﺎﻥ ﻭﺍﻻﻧﺼﻬﺎﺭ‬

‫اﺳﺘﻌﻤﺎل اﻟﺼﻮرة‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﲢﺪﻳـﺪ ﻣﺎﻫﻴـﺔ ﺍﻟـﴚﺀ ﺍﳌﻮﺟﻮﺩ ﰲ‬
‫ﺍﻟﺼﻮﺭﺓ‪ .‬ﻣﻨﺸـﺄﺓ ﺣﻔﺮ ﰲ ﺍﻟﺒﺤﺎﺭ‪ .‬ﻭﺍﺳـﺄﳍﻢ ﻋﲈ ﳛﺪﺙ ﰲ ﺍ ﹸﳌﻨﺸﺄﺓ‪.‬‬
‫ﻳﻘﻮﻡ ﻋﲈﻝ ﺍﻟﻨﻔﻂ ﺑﺎﳊﻔﺮ ﻻﺳـﺘﺨﺮﺍﺝ ﺍﻟﻨﻔﻂ‪ ،‬ﻭﺿﺨﻪ ﺇﱃ ﺍﻟﺴﻄﺢ‪،‬‬
‫ﺃﻳﻀﺎ ﲢﺪﻳﺪ ﺍﺳـﺘﺨﺪﺍﻣﺎﺕ‬ ‫ﺛـﻢ ﻧﻘﻠﻪ ﺇﱃ ﺍﳌﺼﻔـﺎﺓ‪ .‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﹰ‬
‫ﺍﻟﻨﻔـﻂ‪ .‬ﺇﺟﺎﺑـﺎﺕ ﳏﺘﻤﻠـﺔ‪ :‬ﻭﻗﻮ ﹰﺩﺍ ﻟﻠﺴـﻴﺎﺭﺍﺕ ﻭﺍﻟﺸـﺎﺣﻨﺎﺕ‪ ،‬ﻭﰲ‬
‫ﺍﺳـﺘﺨﺪﺍﻣﺎﺕ ﺍﳌﻨﺎﺯﻝ‪ ،‬ﻭﻳﺘﺨﺬ ﻣﻮﺍ ﹼﺩ ﺃﻭﻟﻴـﺔ ﻟﻠﻜﺜﲑ ﻣﻦ ﺍﻟﺼﻨﺎﻋﺎﺕ‬
‫ﺍﻟﺘﻲ ﺗﺸﻤﻞ ﺍﻟﺒﻼﺳﺘﻴﻚ‪ ،‬ﻭﺍﻷﻓﻼﻡ‪ ،‬ﻭﺍﻷﻧﺴﺠﺔ ﺍﻟﺼﻨﺎﻋﻴﺔ‪.‬‬

‫‪128‬‬
 ‫‪‬‬

‫‪‬‬ ‫‪‬‬
‫‪‬‬
‫ﺍﻋﻤﻞ ﺍﳌﻄﻮﻳﺔ ﺍﻵﺗﻴﺔ ﻟﺘﺴـﺎﻋﺪﻙ‬ ‫‪‬‬ ‫‪‬‬
‫ﻋـﲆ ﺗﻨﻈﻴـﻢ ﺍﳌﻌﻠﻮﻣـﺎﺕ ﺣﻮﻝ‬ ‫ﺗﺘﻜﻮﻥ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﻦ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﻭﻫﻴﺪﺭﻭﺟﲔ‪.‬‬

‫‪ ‬ﺳﻴﺴـﺘﺨﺪﻡ ﺍﻟﻄﻼﺏ ﻣﻬﺎﺭﺍﺕ ﺑﻨﺎﺀ ﺍﻟﻨﲈﺫﺝ ﳌﺴـﺎﻋﺪﲥﻢ ﰲ‬ ‫ﺍﳌﺮﻛﺒﺎﺕ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﻴﺔ ﺑﺎﺗﺒﺎﻉ‬ ‫ﻭﲢﺘﻮﻱ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﻋﲆ ﺃﺭﺑﻌﺔ ﺇﻟﻜﱰﻭﻧﺎﺕ ﺗﻜﺎﻓﺆ‪ ،‬ﻟﺬﺍ ﻓﺈﳖﺎ‬
‫ﺗﻜﻮﻥ ﺃﺭﺑﻊ ﺭﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ‪.‬‬
‫ﺍﳋﻄﻮﺍﺕ ﺍﻵﺗﻴﺔ‪‬‬ ‫ﺗﺴﺘﻄﻴﻊ ﺃﻥ ﹼ‬

‫ﹶﺗ ﱡ‬
‫ﺼﻮﺭ ﺟﺰﻳﺌﺎﺕ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺒﺴﻴﻄﺔ‪.‬‬ ‫‪1‬ﺍﺛﻦﹺ ﺛﻼﺙ ﺃﻭﺭﺍﻕ‬
‫ﻣﻦ ﻣﻨﺘﺼﻔﻬﺎ ﺑﺼﻮﺭﺓ ﺃﻓﻘﻴﺔ‪ ،‬ﺛﻢ‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻻﻃﻼﻉ ﻋﲆ ﺗﻌﻠﻴﲈﺕ‬ ‫ﻣﻌﺎ‪ ،‬ﻭﺍﻗﻄﻊ ﺧﻂ‬‫ﺃﻣﺴﻚ ﺑﻮﺭﻗﺘﲔ ﹰ‬

‫ﺍﻟﺜﻨﻲ ﺑﻄﻮﻝ ‪.3 cm‬‬ ‫‪‬‬
‫ﺍﻟﺴﻼﻣﺔ ﰲ ﺍﳌﺨﺘﱪ ﻗﺒﻞ ﺑﺪﺀ ﺍﻟﻌﻤﻞ‪.‬‬ ‫‪2‬ﺃﻣﺴﻚ ﺍﻟﻮﺭﻗﺔ ﺍﻟﺜﺎﻟﺜﺔ‪،‬‬
‫‪ .1‬ﺍﻗﺮﺃ ﺗﻌﻠﻴﲈﺕ ﺍﻟﺴﻼﻣﺔ ﰲ ﺍﳌﺨﺘﱪ‪.‬‬
‫‪ .2‬ﺍﺳﺘﺨﺪﻡ ﳎﻤﻮﻋﺎﺕ ﺍﻟﻨﲈﺫﺝ ﺍﳉﺰﻳﺌﻴﺔ )ﺍﻟﻜﺮﺍﺕ ﻭﺍﻟﻮﺻﻼﺕ(‬
‫ﻭﺍﻗﻄﻊ ﻋﲆ ﻃــﻮﻝ ﺧﻂ ﺍﻟﺜﻨﻲ‪،‬‬
‫ﻟﻌﻤـﻞ ﻧﻤـﻮﺫﺝ ﺑﻨﺎﺋﻲ ﻣـﻦ ﺫﺭﰐ ﻛﺮﺑـﻮﻥ ﻣﺮﺗﺒﻄﺘـﲔ ﺑﺮﺍﺑﻄﺔ‬
‫‪‬‬ ‫ﺁﺧﺮ ‪ 3 cm‬ﺩﻭﻥ ﻗﻄﻊ‪.‬‬ ‫ﻭﺍﺗﺮﻙ ﹺ‬
‫ﺃﺣﺎﺩﻳـﺔ‪ ،‬ﻋـﲆ ﺃﻥ ﲤﺜﱠـﻞ ﻛﻞ ﺫﺭﺓ ﻛﺮﺑـﻮﻥ ﺑﻜـﺮﺓ ﻓﻴﻬـﺎ ﺃﺭﺑﻌﺔ‬
‫‪3‬ﺃﺩﺧﻞ ﺃﻭﻝ‬ ‫ﺛﻘﻮﺏ‪ ،‬ﻭﻛﻞ ﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ ﺑﻜﺮﺓ ﻓﻴﻬﺎ ﺛﻘﺐ ﻭﺍﺣﺪ‪.‬‬
‫ﺯﻭﺩ ﺍﻟﻄﻼﺏ ﺑﻜﺮﺍﺕ )ﲢﺘﻮﻱ ﻋﲆ ﺃﺭﺑﻌﺔ ﺛﻘﻮﺏ( ﻟﺘﻤﺜﻴﻞ ﺫﺭﺍﺕ‬‫• ﹼ‬ ‫ﻭﺭﻗﺘﲔ ﺧﻼﻝ ﺍﻟﻘﻄﻊ ﰲ‬ ‫‪ .3‬ﺻﻞ ﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ ﰲ ﻛﻞ ﺛﻘﺐ ﻣﻦ ﺍﻟﺜﻘﻮﺏ ﺍﻟﺸﺎﻏﺮﺓ ﻋﲆ‬
‫ﺍﻟﻮﺭﻗـﺔ ﺍﻟﺜﺎﻟﺜـﺔ‪ ،‬ﻟﻌﻤـﻞ‬
‫ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﻧﲈﺫﺝ ﺭﺑﺎﻋﻴﺔ ﺍﻷﻭﺟﻪ )‪.(tetrahedral‬‬ ‫‪‬‬
‫‪‬‬
‫‪‬‬
‫‪‬‬
‫ﺠـﻞ ﻣـﻦ ‪ 12‬ﺻﻔﺤـﺔ‪،‬‬‫ﹺﺳ ﹼ‬
‫ﺍﻟﻜـﺮﺍﺕ ﺍﻟﺘـﻲ ﲤﺜـﻞ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻋـﲆ ﺃﻥ ﻳﺒﻠﻎ ﳎﻤﻮﻉ‬
‫ﺃﺭﺑﻌﺎ‪.‬‬
‫ﺭﻭﺍﺑﻂ ﻛﻞ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﹰ‬
‫ﻭﻋﻨﻮﻧـﻪ ﺑـ "ﺍﻟـﻤﺮﻛﺒـﺎﺕ‬
‫• ﹶﺫ ﱢﻛﺮ ﺍﻟﻄﻼﺏ ﺑﴬﻭﺭﺓ ﺭﺑﻂ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻋﲆ ﻫﻴﺌﺔ ﺳﻼﺳﻞ‬
‫‪‬‬

‫ﻛـﺮﺭ ﺍﳋﻄﻮﺗﲔ ‪ 3 ، 2‬ﻟﻌﻤﻞ ﻧﲈﺫﺝ ﻣﻦ ﺛﻼﺙ ﻭﺃﺭﺑﻊ ﻭﲬﺲ‬

‫‪‬‬
‫ﹼ‬ ‫‪.4‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﻴﺔ"‪.‬‬
‫ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﰲ ﻛﻞ ﻣﺮﺓ‪ ،‬ﻋﲆ ﺃﻥ ﺗﺮﺗﺒﻂ ﻛﻞ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﻣﻊ‬
‫ﻣﺴﺘﻘﻴﻤﺔ ﺩﻭﻥ ﺗﻔﺮﻋﺎﺕ ﺃﻭ ﺃﺷﻜﺎﻝ ﺣﻠﻘﻴﺔ‪.‬‬ ‫اﻟﻤﻄﻮﻳﺎت ‪    ‬‬
‫‪8-5 ، 8-4 ، 8-3 ، 8-2‬ﻣﻦ ﻫﺬﺍ ﺍﻟﻔﺼﻞ‪ .‬ﻭﺑﻌﺪ‬
‫ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﻛﺤﺪ ﺃﻗﴡ‪.‬‬ ‫ﹼ‬
‫‪‬‬
‫• ﻛﻠﻒ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤﺚ ﻋﻦ ﺃﺳﲈﺀ ﻫﺬﻩ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﰲ ﳏﺘﻮ￯‬ ‫ﺳﺠﻞ ﺳﲈﺕ ﻛﻞ ﻧﻮﻉ ﻣﻦ ﺃﻧﻮﺍﻉ‬
‫ﻭﺃﻣﺜﻠﺔ‬
‫ﻗﺮﺍﺀﺓ ﻫﺬﻩ ﺍﻷﻗﺴﺎﻡ ﹼ‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻭﺧﺼﺎﺋﺼﻪ ﻭﺻﻔﺎﺗﻪ ﺍﳌﻤ ﱢﻴﺰﺓ‪،‬‬
‫‪C21-01A-874637‬‬
‫ﻻ ﻭﺃﺩﺭﺝ ﻓﻴﻪ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ‬‫‪  .1‬ﺟﺪﻭ ﹰ‬
‫‪C21-01A-874637‬‬ ‫ﰲ ﻛﻞ ﻧﻤﻮﺫﺝ ﺑﻨﺎﺋﻲ‪.‬‬
‫ﺍﻟﻔﺼﻞ ﺣﺴﺐ ﺍﻟﻨﻈﺎﻡ ﺍﻟﺪﻭﱄ ﻟﻠﺘﺴﻤﻴﺔ )ﺃﻳﻮﺑﺎﻙ(‪.‬‬ ‫‪C21-01A-874637‬‬
‫ﻣﻦ ﻭﺍﻗﻊ ﺍﳊﻴﺎﺓ‪.‬‬
‫‪  .2‬ﻛﻞ ﻧﻤﻮﺫﺝ ﺑﻨﺎﺋﻲ ﺑﻜﺘﺎﺑﺔ ﺻﻴﻐﺘﻪ ﺍﳉﺰﻳﺌﻴﺔ‪.‬‬
‫‪   .3‬ﺍﻟﻨﻤﻂ ﺍﻟﺬﻱ ﺗﺘﻐﲑ ﻓﻴﻪ ﻧﺴﺒﺔ ﺍﲢﺎﺩ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‬

‫‪ ‬ﻋـﲆ ﺍﻟﻄﻼﺏ ﺑﻨﺎﺀ ﺃﺷـﻜﺎﻝ ﻭﺗﺮﺍﻛﻴﺐ ﹸﳑﹶﺎﺛﻠﺔ ﳌﺎ‬
‫ﻫﻮ ﻣﻮﺟﻮﺩ ﰲ ﺍﳉﺪﻭﻝ ‪.8-1‬‬
‫ﳌﺮﺍﺟﻌﺔ ﳏﺘﻮ￯ ﻫﺬﺍ ﺍﻟﻔﺼﻞ ﻭﻧﺸـﺎﻃﺎﺗﻪ ﺍﺭﺟﻊ ﺇﱃ‬
‫ﺇﱃ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﰲ ﻛﻞ ﺻﻴﻐﺔ ﺟﺰﻳﺌﻴﺔ‪ ،‬ﺛﻢ ﺿﻊ‬
‫ﺻﻴﻐﺔ ﻋﺎ ﹼﻣﺔ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺫﺍﺕ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻷﺣﺎﺩﻳﺔ‪.‬‬
‫ﺍﳌﻮﻗﻊ‪:‬‬
‫‪www.obeikaneducation.com‬‬ ‫‪ ‬ﻛﻴﻒ ﺗﺘﺄﺛﺮ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻋﻨﺪﻣﺎ ﺗﺮﺗﺒﻂ ﺫﺭﺍﺕ‬
‫ﺍﻟﻜﺮﺑﻮﻥ ﺑﺮﻭﺍﺑﻂ ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ؟‬

‫‪‬‬
‫‪.1‬‬
‫ﺫﺭﺍﺕ ‪H‬‬ ‫ﺫﺭﺍﺕ ‪C‬‬
‫‪6‬‬ ‫‪2‬‬
‫‪8‬‬ ‫‪3‬‬
‫‪10‬‬ ‫‪4‬‬
‫‪12‬‬ ‫‪5‬‬

‫‪C5H12 ،C4H10 ،C3H8 ،C2H6 .2‬‬

‫‪CnH2n+2 .3‬‬

‫‪ ‬ﺳـﻴﻘﻞ ﻋـﺪﺩ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟـﲔ ﰲ ﺍﳉـﺰﻱﺀ‪ ،‬ﻭﺳـﺘﻌﻜﺲ‬

‫ﺍﻟﺼﻴﻐﺔ ﻋﺪﺩ ﺫﺭﺍﺕ ﻫﻴﺪﺭﻭﺟﲔ ﺃﻗﻞ‪.‬‬

‫‪129‬‬
 ‫‪8-1‬‬
‫‪8-1‬‬
‫اﻫﺪاف‬
‫ﻣﻘﺪﻣﺔ إﻟﻰ اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت‬ ‫‪  ‬ﺍﳌﻘﺼـﻮﺩ ﺑـﻜﻞ ﻣـﻦ‬
‫‪Introduction to Hydrocarbons‬‬
‫‪ .1‬اﻟﺘﺮﻛﻴﺰ‬
‫ﺍﳌﺮﻛـﺐ ﺍﻟﻌﻀـﻮﻱ ﻭﺍﻟﻜﻴﻤﻴـﺎﺀ‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ‪‬‬ ‫ﺍﻟﻌﻀﻮﻳﺔ‪.‬‬
‫‪ ‬ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻭﺍﻟﻨﲈﺫﺝ ‪ ‬‬ ‫‪ ‬‬
‫ﺳﻴﺎﺭﺓ ﺃﻭ ﺣﺎﻓﻠﺔ ﻓﺈﻧﻚ ﺗﺴﺘﺨﺪﻡ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪.‬‬
‫‪   ‬ﻋﻨﺪﻣﺎ ﺗﺮﻛﺐ ﹼ‬ ‫ﺍﳌﺴﺘﺨﺪﻣﺔ ﻟﺘﻤﺜﻴﻠﻬﺎ‪.‬‬
‫‪‬‬
‫‪ ‬ﺑـﲔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﻓﺎﳉﺎﺯﻭﻟﲔ ﻭﺍﻟﺪﻳﺰﻝ ﺍﻟﻠﺬﺍﻥ ﻳﺴﺘﺨﺪﻣﺎﻥ ﰲ ﺗﺴﻴﲑ ﺍﻟﺴﻴﺎﺭﺍﺕ ﻭﺍﻟﺸﺎﺣﻨﺎﺕ ﻭﺍﳊﺎﻓﻼﺕ ﻣﻦ‬ ‫‪‬‬ ‫‪‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪.‬‬ ‫ﺍﳌﺸﺒﻌﺔ ﻭﻏﲑ ﺍﳌﺸﺒﻌﺔ‪.‬‬ ‫ﻗﺒﻞ ﺑﺪﺀ ﺍﻟـﺪﺭﺱ‪ ،‬ﺍﻋﺮﺽ ﻋﲆ ﺍﻟﻄﻼﺏ ﴍﳛـﺔ ﺍﻟﱰﻛﻴﺰ ﺭﻗﻢ‬
‫‪  ‬ﻣﺼﺪﺭ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ اﻟﻤﺮﻛﺒﺎت اﻟﻌﻀﻮﻳﺔ ‪Organic Compounds‬‬
‫ﻭﻛﻴﻔﻴﺔ ﻓﺼﻠﻬﺎ‪.‬‬
‫ﹼ‬
‫)‪ (27‬ﺍﻟـﻮﺍﺭﺩﺓ ﰲ ﻣﺼﺎﺩﺭ ﺍﻟﺘﻌﻠﻢ ﻟﻠﻔﺼﻮﻝ )‪ ،(5-8‬ﻭﻳﻤﻜﻨﻚ‬
‫ﻋﺮﻑ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﰲ ﺑﺪﺍﻳﺔ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳﻊ ﻋﴩ ﺃﻥ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ‪ .‬ﻭﻣﻨﻬﺎ ‪ -‬ﺍﻟﻨﺒﺎﺗﺎﺕ‬
‫ﻭﻣﺘﻨﻮﻋﺎ ﻣﻦ ﻣﺮﻛﺒﺎﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ .‬ﻭﺃﺷﺎﺭ‬‫ﹰ‬ ‫ﻭﺍﳊﻴﻮﺍﻧﺎﺕ ‪ -‬ﰲ ﺍﻟﺸﻜﻞ ‪ 8-1‬ﺗﹸﻨﺘﹺﺞ ﻗﺪﹾ ﹰﺭﺍ ﻫﺎﺋ ﹰ‬
‫ﻼ‬ ‫اﻟﻤﻔﺮدات‬ ‫ﻣﺮاﺟﻌﺔ‬ ‫ﻋﺮﺿﻬﺎ ﻣﻠﻮﻧﺔ ﻣﻦ ﺧﻼﻝ ﺍﻟﺮﺟﻮﻉ ﺇﱃ ﺍﳌﻮﻗﻊ ﺍﻹﻟﻜﱰﻭﲏ‪ :‬‬
‫‪ ‬ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﺇﱃ ﻫﺬﻩ ﺍﳌﺮﻛﺒﺎﺕ ﺑﺎﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ؛ ﻷﳖﺎ ﻧﺎﲡﺔ ﻋﻦ ﳐﻠﻮﻗﺎﺕ ﺣﻴﺔ )ﻋﻀﻮﻳﺔ(‪.‬‬
‫ﻋﻨﺪﻣﺎ ﻗﺒﻠﺖ ﻧﻈﺮﻳﺔ ﺩﺍﻟﺘﻮﻥ ﰲ ﺑﺪﺍﻳﺔ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳﻊ ﻋﴩ ﺑﺪﺃ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﻳﻔﻬﻤﻮﻥ ﺣﻘﻴﻘﺔ ﺃﻥ‬
‫)‪ :(microorganism‬ﳐﻠﻮﻕ‬ ‫‪www.obeikaneducation.com‬‬
‫ﺣﻲ ﺻﻐﲑ ﺟـﺪﹼﹰ ﺍ ﻻ ﻳﻤﻜـﻦ ﺭﺅﻳﺘﻪ‬
‫ﺍﳌﺮﻛﺒﺎﺕ ـ ﺑﲈ ﻓﻴﻬﺎ ﺗﻠﻚ ﺍ ﹸﳌﺼﻨﹼﻌﺔ ﻣﻦ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ ـ ﺗﺘﺄﻟﻒ ﻣﻦ ﺫﺭﺍﺕ ﻣﺮﺗﺒﺔ ﻭﻣﺮﺗﺒﻄﺔ ﹰ‬
‫ﻣﻌﺎ‬
‫ﺩﻭﻥ ﺍﺳﺘﻌﻤـﺎﻝ ﺍﳌﻴﻜﺮﻭﺳﻜـﻮﺏ‪،‬‬
‫ﺃﻳﻀﺎ ﻣﻦ ﺗﺼﻨﻴﻊ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﻮﺍﺩ ﺍﳉﺪﻳﺪﺓ ﻭﺍﳌﻔﻴﺪﺓ‪ .‬ﻭﻟﻜﻦ‪ ،‬ﱂ‬ ‫ﺑﱰﺍﻛﻴﺐ ﳏﺪﹼ ﺩﺓ‪ .‬ﻭﻗﺪ ﲤﻜﻨﻮﺍ ﹰ‬
‫ﻳﺘﻤﻜﻦ ﺍﻟﻌﻠﲈﺀ ﻣﻦ ﺗﺼﻨﻴﻊ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ‪ .‬ﻭﺑﻨﺎ ﹰﺀ ﻋﲆ ﺫﻟﻚ‪ ،‬ﺍﺳﺘﻨﺘﺞ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﻟﻌﻠﲈﺀ –‬
‫ﻭﻣﻦ ﺫﻟﻚ ﺍﻟﺒﻜﺘﲑﻳﺎ ﻭﺍﻷﻭﻟﻴﺎﺕ‪.‬‬ ‫اﻟﺮﺋﻴﺴﺔ‬ ‫اﻟﻔﻜﺮة‬
‫ﺧﻄﺄ ‪ -‬ﺃﻥ ﻋﺪﻡ ﻣﻘﺪﺭﲥﻢ ﻋﲆ ﺗﺼﻨﻴﻊ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﻋﺎﺋﺪﹲ ﺇﱃ ﺍﻟﻘﻮﺓ ﺍﳊﻴﻮﻳﺔ )ﺃﻭ ﺍﳊﻴﺎﺗﻴﺔ‬ ‫ﹰ‬ ‫اﻟﻤﻔﺮدات اﻟﺠﺪﻳﺪة‬
‫‪ .(Vitalism‬ﻭﻭﻓ ﹰﻘﺎ ﳍﺬﺍ ﺍﳌﺒﺪﺃ‪ ،‬ﻓﺈﻥ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ )ﺍﻟﻌﻀﻮﻳﺔ( ﳍﺎ "ﻗﻮﺓ ﺣﻴﻮ ﹼﻳﺔ" ﻏﺎﻣﻀﺔ‪،‬‬ ‫ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ‬ ‫‪ ‬ﺍﺳﺘﺨﺪﻡ ﳎﻤﻮﻋﺔ ﺍﻟﻨﲈﺫﺝ ﺍﳉﺰﻳﺌﻴﺔ )ﺍﻟﻜﺮﺍﺕ‬
‫ﲤﻜﻨﻬﺎ ﻣﻦ ﺗﺮﻛﻴﺐ ﻣﺮﻛﺒﺎﺕ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬ ‫ﹼ‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ‬
‫ﻛﺎﻥ ﻓﺮﻳﺪﺭﻳﻚ ﻓﻮﻫﻠﺮ ‪1882 – ) Friedrich WÖhler‬‬ ‫‪‬‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳌﺸﺒﻊ‬ ‫ﻭﺍﻟﻮﺻـﻼﺕ( ﻟﺒﻨﺎﺀ ﺟﺰﻱﺀ ﻣﻴﺜـﺎﻥ ‪ ،CH4‬ﻭﺍﻋﺮﺽ ﺍﻟﻨﻤﻮﺫﺝ ﻋﲆ‬
‫‪ 1800‬ﻡ( ﻋﺎﱂ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻷﳌﺎﲏ ﺃﻭﻝ ﻣﻦ ﻗﺎﻡ ﺑﺘﺤﻀﲑ ﻣﺮﻛﺐ ﻋﻀﻮﻱ ﰲ ﺍﳌﺨﺘﱪ‪ .‬ﻭﱂ ﺗﺪﺣﺾ‬
‫ﲡﺮﺑﺔ ﻓﻮﻫﻠﺮ ﻋﲆ ﺍﻟﻔﻮﺭ ﻓﻜﺮﺓ ﺍﻟﻘﻮﺓ ﺍﳊﻴﻮﻳﺔ‪ ،‬ﻭﻟﻜﻨﻬﺎ ﺣﺜﺖ ﻛﻴﻤﻴﺎﺋﻴﲔ ﺃﻭﺭﺑﻴﲔ ﺁﺧﺮﻳﻦ ﻋﲆ‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻏﲑ ﺍﳌﺸﺒﻊ‬
‫ﺍﻟﻄـﻼﺏ‪ ،‬ﻭﺍﺳـﺄﳍﻢ ﻋـﻦ ﺍﳉـﺰﻱﺀ ﺍﻟـﺬﻱ ﻳﻤﺜﻠـﻪ ﻫـﺬﺍ ﺍﻟﻨﻤﻮﺫﺝ‪.‬‬
‫ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ‬
‫ﲑﺍ ﺛﺒﺖ ﹸﺑﻄﻼﻥ ﺍﻟﻔﻜﺮﺓ ﺍﻟﻘﺎﺋﻠﺔ ﺑﺄﻥ ﲢﻀﲑ ﺍﳌﺮﻛﺒﺎﺕ‬
‫ﺍﻟﻘﻴﺎﻡ ﺑﺴﻠﺴﻠﺔ ﻣﻦ ﺍﻟﺘﺠﺎﺭﺏ ﺍﳌﺸﺎﲠﺔ‪ .‬ﻭﺃﺧ ﹰ‬
‫ﺍﻟﻌﻀﻮﻳﺔ ﳛﺘﺎﺝ ﺇﱃ ﻗﻮﺓ ﺣﻴﻮﻳﺔ‪ ،‬ﻭﺃﺩﺭﻙ ﺍﻟﻌﻠﲈﺀ ﺃﻥ ﺑﺎﺳﺘﻄﺎﻋﺘﻬﻢ ﲢﻀﲑ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ‪.‬‬
‫ﺍﻟﺘﻜﺴﲑ ﺍﳊﺮﺍﺭﻱ‬ ‫ﺍﳌﻜﻮﻥ ﺍﻷﺳـﺎﳼ ﻟﻠﻐﺎﺯ‬‫ﻭﺃﺧﱪﻫـﻢ ﺃﻥ ﺍﳉﺰﻱﺀ ﻫﻮ ﺍﳌﻴﺜـﺎﻥ‪ ،‬ﻭﻫﻮ ﱢ‬
‫‪       8-1 ‬‬
‫ﺍﻟﻄﺒﻴﻌـﻲ‪ .‬ﻭﺍﴍﺡ ﳍـﻢ ﺃﻥ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺗﺘﺨﺬ ﻭﻗـﻮ ﹰﺩﺍ ﻷﳖﺎ‬
‫‪   ‬‬ ‫ﺗﺘﺤﺪ ﺑﺎﻷﻛﺴـﺠﲔ ﺑﺴـﻬﻮﻟﺔ ﻭﺗﻨﺘﺞ ﻛﻤﻴﺔ ﻛﺒﲑﺓ ﻣﻦ ﺍﻟﻄﺎﻗﺔ ﰲ ﻫﺬﻩ‬
‫‪    ‬‬
‫‪ ‬‬
‫‪‬‬ ‫ﺍﻟﻌﻤﻠﻴﺔ‪.‬‬
‫‪ ‬‬
‫ﹺ‬
‫ﺍﺑـﻦ ﺟـﺰﻱﺀ ﻣﻴﺜـﺎﻥ ﺁﺧـﺮ‪ ،‬ﻭﺍﻋﺮﺿﻪ ﻋـﲆ ﺍﻟﻄﻼﺏ‪ ،‬ﺛـﻢ ﺃﺯﻝ ﺫﺭﺓ‬
‫ﻣﻌﺎ ﻟﺒﻨﺎﺀ ﺟﺰﻱﺀ ﺍﻹﻳﺜﺎﻥ‪.‬‬
‫ﻫﻴﺪﺭﻭﺟﲔ ﻣﻦ ﻛﻼ ﺍﻟﻨﻤﻮﺫﺟﲔ ﻭﺻﻠﻬﲈ ﹰ‬
‫ﺗﻜﻮﻥ ﻫﺬﺍ ﺍﳉﺰﻱﺀ ﺍﳉﺪﻳﺪ‪.‬‬‫ﻭﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺃﻥ ﻳﻔﴪﻭﺍ ﻛﻴﻒ ﹼ‬
‫ﹸﻧﺰﻋـﺖ ﺫﺭﺗﺎﻥ ﻣﻦ ﺍﳍﻴﺪﺭﻭﺟﲔ‪ ،‬ﻭﺍﺭﺗﺒﻄﺖ ﺫﺭﺗﺎ ﺍﻟﻜﺮﺑﻮﻥ ﹰ‬
‫ﻣﻌﺎ‪ .‬ﺛﻢ‬
‫ﻓـﴪ ﳍﻢ ﺃﻥ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﹸﺗﺘﺨﺬ ﹰ‬
‫ﺃﻳﻀﺎ ﻣـﻮﺍﺩ ﺃﻭﻟﻴﺔ ﻟﻠﻜﺜﲑ ﻣﻦ‬ ‫ﹼ‬
‫ﺍﻟﺼﻨﺎﻋﺎﺕ؛ ﻷﻧﻪ ﻳﻤﻜﻦ ﺭﺑﻂ ﺍﳉﺰﻳﺌﺎﺕ ﺑﻌﻀﻬﺎ ﻣﻊ ﺑﻌﺾ ﺑﺴﻬﻮﻟﺔ‬
‫ﻟﺘﻜﻮﻳﻦ ﺳﻼﺳـﻞ ﻃﻮﻳﻠـﺔ‪ .‬ﻭﻳﻤﻜﻦ ﺍﺳـﺘﺒﺪﺍﻝ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ‬
‫ﺑﻤﺠﻤﻮﻋـﺎﺕ ﺟﺪﻳـﺪﺓ ﻟﺘﻜﻮﻳـﻦ ﺟـﺰﻱﺀ ﺟﺪﻳـﺪ ﲣﺘﻠـﻒ ﺻﻔﺎﺗﻪ‬
‫‪ ‬ﻳﻌﻮﺩ ﺩﺣـﺾ ﻣﺒﺪﺃ ﺍﳊﻴﻮﻳـﺔ )ﺃﻭ ﺍﳊﻴﺎﺗﻴـﺔ( ﺇﱃ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‬
‫ﻭﺧﺼﺎﺋﺼﻪ ﻋﻦ ﺧﺼﺎﺋﺺ ﺍﳉﺰﻱﺀ ﺍﻷﺻﲇ‪  .‬‬
‫ﺍﻷﳌـﺎﲏ ﻓﺮﻳﺪﺭﻳﻚ ﻓﻮﻫﻠﺮ ﻋﻨﺪﻣﺎ ﻗﺎﻡ ﺑﺘﺤﻀﲑ ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ ﺍﳌﻌﺮﻭﻑ‬
‫ﺑﺎﻟﻴﻮﺭﻳـﺎ ﻣﻦ ﻣﺎﺩﺓ ﺳـﻴﺎﻧﺎﺕ ﺍﻷﻣﻮﻧﻴـﻮﻡ ﻏﲑ ﺍﻟﻌﻀﻮﻳﺔ ﻋـﺎﻡ ‪1828‬ﻡ‪ .‬ﻭﻗﺪ‬ ‫— ‪ ‬ﺍﻟﺸـﻜﻞ ‪ 8-1‬ﺇﺟﺎﺑﺎﺕ ﳏﺘﻤﻠـﺔ‪ :‬ﺟﻠﻮﻛﻮﺯ‪ ،‬ﺃﻭ‬
‫ﴏﺡ ﻋـﺎﻡ ‪1835‬ﻡ "ﺑـﺄﻥ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ ﰲ ﻫـﺬﻩ ﺍﻷﻳﺎﻡ ﺗﻜﺎﺩ ﺗﻘﻮﺩﲏ‬ ‫ﺳﻜﺮﻭﺯ‪ ،‬ﺃﻭ ﻣﻴﺜﺎﻥ‪.‬‬
‫ﹼ‬
‫ﺇﱃ ﺍﳉﻨـﻮﻥ‪ .‬ﻓﻬـﻲ ﺗﺒـﺪﻭ ﱄ ﻋﲆ ﺻﻮﺭﺓ ﻏﺎﺑﺔ ﺍﺳـﺘﻮﺍﺋﻴﺔ ﺑﺪﺍﺋﻴـﺔ ﻣﻠﻴﺌﺔ ﺑﺄﻛﺜﺮ‬
‫ﺍﻷﺷﻴﺎﺀ ﺭﻭﻋﺔ‪ ،‬ﻭﺃﳖﺎ ﹸﻣﻔ ﹺﺰﻋﺔ ﻭﻻ ﳖﺎﻳﺔ ﳍﺎ‪ ،‬ﻭﻻ ﳚﺮﺅ ﺍﳌﺮﺀ ﻋﲆ ﺩﺧﻮﳍﺎ؛ ﺇﺫ‬
‫ﻳﺒﺪﻭ ﻻ ﳎﺎﻝ ﻟﻠﺨﺮﻭﺝ ﻣﻨﻬﺎ"‪ .‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻣﻨﺎﻗﺸـﺔ ﺍﻟﺼﻠﺔ ﺍﻟﻮﺛﻴﻘﺔ‬
‫ﺑﲔ ﺗﴫﻳﺢ ﻓﻮﻫﻠﺮ ﻭﺍﻟﻄﻼﺏ ﺍﻟﺬﻳﻦ ﻳﺪﺭﺳﻮﻥ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻴﻮﻡ‪.‬‬
‫‪   ‬‬

‫‪130‬‬
 ‫‪  8-2‬‬ ‫‪ ‬ﻳﻄﻠﻖ ﻣﺼﻄﻠﺢ ﻣﺮﻛﺐ ﻋﻀﻮﻱ ﺍﻟﻴﻮﻡ ﻋﲆ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ‬

‫‪ .2‬اﻟﺘﺪرﻳﺲ‬
‫‪14 ‬‬ ‫ﺍﻟﻜﺮﺑﻮﻥ ﻣﺎ ﻋﺪﺍ ﺃﻛﺎﺳﻴﺪ ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻭﺍﻟﻜﺮﺑﻴﺪﺍﺕ ﻭﺍﻟﻜﺮﺑﻮﻧﺎﺕ؛ ﺣﻴﺚ ﺗﻌﺪ ﻣﺮﻛﺒﺎﺕ ﻏﲑ‬
‫‪   ‬‬ ‫ﻭﻧﻈﺮﺍ ﺇﱃ ﻭﺟﻮﺩ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ‪ ،‬ﹸﺧﺼﺺ ﻓﺮﻉ ﻛﺎﻣﻞ ﻣﻦ ﻓﺮﻭﻉ‬ ‫ﹰ‬ ‫ﻋﻀﻮﻳﺔ‪.‬‬
‫‪‬‬ ‫ﺍﻟﻜﻴﻤﻴﺎﺀ ـ ﹸﺳ ﱢﻤﻲ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ ـ ﻟﺪﺭﺍﺳﺔ ﻫﺬﻩ ﺍﳌﺮﻛﺒﺎﺕ‪ .‬ﺗﺬﻛﺮ ﺃﻥ ﺍﻟﻜﺮﺑﻮﻥ ﻋﻨﴫ ﻳﻘﻊ‬
‫ﰲ ﺍﳌﺠﻤﻮﻋﺔ ‪ 14‬ﻣﻦ ﺍﳉﺪﻭﻝ ﺍﻟﺪﻭﺭﻱ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪ . 8-2‬ﻭﻳﻈﻬﺮ ﻣﻦ ﺍﻟﺘﻮﺯﻳﻊ ﺍﻹﻟﻜﱰﻭﲏ‬
‫ﺗﻄﺒﻴﻘﺎت اﻟﻜﻴﻤﻴﺎء‬ ‫‪‬‬
‫ﻭﻳﻜﻮﻥ ﺃﺭﺑﻊ ﺭﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ‪ .‬ﰲ‬
‫ﹼ‬ ‫ﻟﻠﻜﺮﺑﻮﻥ ‪ 1s2 2s2 2p2‬ﺃﻧﻪ ﻳﺸﺎﺭﻙ ﹰ‬
‫ﺩﺍﺋﲈ ﺑﺈﻟﻜﱰﻭﻧﺎﺗﻪ‪،‬‬
‫ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﺗﺘﺤﺪ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻣﻊ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ‪ ،‬ﺃﻭ ﺫﺭﺍﺕ ﻋﻨﺎﴏ ﺃﺧﺮ￯‬
‫‪14‬‬
‫ﻭﺧﺼﻮﺻﺎ ﺍﻟﻨﻴﱰﻭﺟﲔ ﻭﺍﻷﻛﺴﺠﲔ ﻭﺍﻟﻜﱪﻳﺖ‬‫ﹰ‬ ‫ﺗﻘﻊ ﻗﺮﻳﺒﺔ ﻣﻦ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﳉﺪﻭﻝ ﺍﻟﺪﻭﺭﻱ‪،‬‬
‫‪ ‬ﻳﻨﺒﻌﺚ ﻏﺎﺯ ﺍﳌﻴﺜﺎﻥ ﺍﳌﺘﻜﻮﻥ ﻣﻊ ﺍﻟﻔﺤﻢ‪ ،‬ﻣﻦ ﻣﻨﺎﺟﻢ‬
‫‪Carbon‬‬

‫ﻭﺍﻟﻔﻮﺳﻔﻮﺭ ﻭﺍﳍﺎﻟﻮﺟﻴﻨﺎﺕ‪.‬‬
‫‪6‬‬
‫‪C‬‬
‫‪12.011‬‬
‫ﻭﺗﻜﻮﻥ ﺳﻼﺳﻞ ﺗﱰﺍﻭﺡ ﺃﻃﻮﺍﳍﺎ ﺑﲔ‬ ‫ﺃﻳﻀﺎ ﻣﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﺧﺮ￯‪،‬‬‫ﺗﺘﺤﺪ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﹰ‬
‫ﺍﻟﻔﺤـﻢ ﺍﳌﻨﺸـﺄﺓ ﲢﺖ ﺳـﻄﺢ ﺍﻷﺭﺽ‪ .‬ﻭﺇﺫﺍ ﺗﺮﺍﻛﻢ ﻫـﺬﺍ ﺍﻟﻐﺎﺯ ﻓﺈﻥ‬ ‫‪Silicon‬‬
‫‪14‬‬
‫ﻳﻜﻮﻥ‬
‫ﹼ‬ ‫ﻓﺈﻧﻪ‬ ‫ﺭﻭﺍﺑﻂ‬ ‫ﺃﺭﺑﻊ‬ ‫ﺎ‬ ‫ﹰ‬
‫ﺃﻳﻀ‬ ‫ﻥ‬
‫ﹼ‬
‫ﻳﻜﻮ‬
‫ﹼ‬ ‫ﺍﻟﻜﺮﺑﻮﻥ‬ ‫ﻭﻷﻥ‬ ‫ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬ ‫ﻣﻦ‬ ‫ﺫﺭﺗﲔ ﺇﱃ ﺁﻻﻑ ﺍﻟﺬﺭﺍﺕ‬

‫ﺍﻧﻔﺠـﺎﺭﺍ‪ .‬ﻭﻷﻥ ﺍﳌﻴﺜﺎﻥ ﻻ ﻟـﻮﻥ ﻟﻪ ﻭﻻ‬ ‫ﴍﺍﺭﺓ ﺑﺴـﻴﻄﺔ ﻗـﺪ ﺗﺴـﺒﺐ‬

‫‪Si‬‬
‫ﻣﺮﻛﺒﺎﺕ ﰲ ﺻﻮﺭﺓ ﺗﺮﺍﻛﻴﺐ ﻣﻌﻘﺪﺓ‪ :‬ﺳﻼﺳﻞ ﻣﺘﻔﺮﻋﺔ‪ ،‬ﻭﺗﺮﺍﻛﻴﺐ ﺣﻠﻘﻴﺔ‪ ،‬ﻭﺗﺮﺍﻛﻴﺐ ﺷﺒﻴﻬﺔ‬
‫ﹰ‬
‫‪28.086‬‬

‫‪Germanium‬‬
‫‪32‬‬ ‫ﺗﻌﺮﻑ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ‬
‫ﺃﻳﻀﺎ‪ .‬ﻭﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺍﺣﺘﲈﻻﺕ ﺍﻟﺮﺑﻂ ﻫﺬﻩ‪ ،‬ﻓﻘﺪ ﹼ‬ ‫ﺑﺄﻗﻔﺎﺹ ﺍﻟﻌﺼﺎﻓﲑ ﹰ‬

‫ﺭﺍﺋﺤﺔ ﻭﻻ ﻃﻌﻢ ﻓﻠﻴﺲ ﻣﻦ ﺍﻟﺴﻬﻞ ﺍﻛﺘﺸﺎﻓﻪ‪.‬‬

‫‪Ge‬‬
‫‪72.61‬‬ ‫ﻭﳛﴬﻭﻥ ﺍﳌﺰﻳﺪ ﻣﻨﻬﺎ ﻛﻞ ﻳﻮﻡ‪.‬‬‫ﻳﺘﻌﺮﻓﻮﻥ ﹼ‬ ‫ﻣﻼﻳﲔ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﺍﳌﺨﺘﻠﻔﺔ‪ ،‬ﻭﻣﺎ ﺯﺍﻟﻮﺍ ﹼ‬
‫‪Tin‬‬
‫‪50‬‬
‫ﻳﻜﻮﻥ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ؟‬
‫‪‬ﳌﺎﺫﺍ ﹼ‬
‫‪‬‬ ‫‪‬‬
‫ﻭﻛﺎﻥ ﻋـﲈﻝ ﺍﳌﻨﺎﺟـﻢ ﹰ‬
‫‪Sn‬‬

‫ﻗﺪﻳـﲈ ﻳﺼﻄﺤﺒﻮﻥ ﻋﺼﻔﻮﺭ ﺍﻟﻜﻨـﺎﺭﻱ ﺃﻭ ﺃﻱ‬

‫‪118.710‬‬

‫‪Lead‬‬
‫‪82‬‬
‫اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت ‪Hydrocarbons‬‬

‫ﺣﻴﻮﺍﻥ ﺻﻐﲑ ﺁﺧﺮ ﻻﺧﺘﺒﺎﺭ ﺍﳍﻮﺍﺀ‪ .‬ﱠ‬ ‫ﺗﹸﻌﺪ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ ﻋﻨﴫﻱ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ ﻓﻘﻂ ﺃﺑﺴﻂ ﺍﳌﺮﻛﺒﺎﺕ‬
‫‪Pb‬‬

‫ﺇﻥ ﻫﺬﻩ ﺍﳊﻴﻮﺍﻧﺎﺕ ﺍﻟﺼﻐﲑﺓ ﺃﻭ‬

‫‪207.2‬‬

‫ﺍﻟﻌﻀﻮﻳﺔ‪ .‬ﺗﹸﺮ￯ ﻣﺎ ﻋﺪﺩ ﺍﳌﺮﻛﺒﺎﺕ ﺍﳌﺨﺘﻠﻔﺔ ﺍﻟﺘﻲ ﻳﻤﻜﻦ ﺗﻜﻮﻳﻨﻬﺎ ﻣﻦ ﻫﺬﻳﻦ ﺍﻟﻌﻨﴫﻳﻦ؟ ﻗﺪ‬
‫ﻼ ﳏﺘﻤ ﹰ‬
‫ﺗﻈﻦ ﺃﻥ ﻋﺪﺩﹰﺍ ﻗﻠﻴ ﹰ‬
‫ﺍﻟﻌﺼﺎﻓﲑ ﺃﻛﺜﺮ ﺣﺴﺎﺳﻴﺔ ﳌﺴﺘﻮﻳﺎﺕ ﺍﻷﻛﺴﺠﲔ ﺍﳌﻨﺨﻔﻀﺔ ﺇﺫ ﺗﺰﺩﺍﺩ‬ ‫ﺗﻜﻮﻧﻪ‪ ،‬ﻟﻜﻦ ﻫﻨﺎﻙ ﺁﻻﻑ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﻌﺮﻭﻓﺔ‬
‫ﻼ ﻳﻤﻜﻦ ﹼ‬
‫ﻭﺍﻟﺘﻲ ﺗﺘﻜﻮﻥ ﻣﻦ ﻋﻨﴫﻱ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ ﻓﻘﻂ‪ .‬ﻭﻳﻌﺪ ﺍﳌﻴﺜﺎﻥ ‪ CH4‬ﺃﺑﺴﻂ ﺟﺰﻱﺀ‬
‫‪C22-001C-828378-08‬‬
‫ﴎﻋـﺔ ﻋﻤﻠﻴﺎﺕ ﺍﻷﻳـﺾ ﻟﺪﳞﺎ‪ .‬ﻭﻋﻨﺪﻣﺎ ﻳﻔﻘـﺪ ﻋﺼﻔﻮﺭ ﺍﻟﻜﻨﺎﺭﻱ‬ ‫ﺍﳌﻜﻮﻥ‬
‫ﻫﻴﺪﺭﻭﻛﺮﺑﻮﲏ‪ ،‬ﻳﺘﻜﻮﻥ ﻣﻦ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﻭﺍﺣﺪﺓ ﻣﺘﺤﺪﺓ ﺑﺄﺭﺑﻊ ﺫﺭﺍﺕ ﻫﻴﺪﺭﻭﺟﲔ‪ ،‬ﻭﻫﻮ ﱢ‬
‫ﺍﻟﺮﺋﻴﺲ ﻟﻠﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ‪ ،‬ﻭﻣﻦ ﺃﺟﻮﺩ ﺃﻧﻮﺍﻉ ﺍﻟﻮﻗﻮﺩ‪ ،‬ﻛﲈ ﻳﺒﲔ ﺍﻟﺸﻜﻞ ‪.8-3‬‬
‫ﻭﻋﻴﻪ ﺃﻭ ﻳﻤﻮﺕ ﻓﺈﻥ ﺫﻟﻚ ﻳﻌﺪ ﺇﺷﺎﺭﺓ ﻟﻌﲈﻝ ﺍﳌﻨﺎﺟﻢ ﺑﺈﺧﻼﺀ ﺍﳌﻨﺠﻢ‬ ‫‪‬ﺍﺳﺘﺨﺪﺍﻣﲔ ﻟﻠﻤﻴﺜﺎﻥ ﺃﻭ ﻟﻠﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﰲ ﺑﻴﺘﻚ ﺃﻭ ﳎﺘﻤﻌﻚ‪.‬‬

‫ﺇﱃ ﺃﻥ ﻳﺘﺒﺪﺩ ﺍﳌﻴﺜﺎﻥ‪.‬‬

‫‪ –‬‬ ‫‪8-3‬‬

‫ﻭﺍﻟﻴـﻮﻡ ﺗﺘﻮﺍﻓـﺮ ﺃﺩﻭﺍﺕ ﺣﺪﻳﺜﺔ ﻟﻠﻜﺸـﻒ ﻋﻦ ﺍﳌﻴﺜـﺎﻥ؛ ﻭﻣﻊ ﺫﻟﻚ‪،‬‬ ‫‪‬‬

‫‪ ‬‬
‫ﻳﺘﻄﻠﺐ ﺍﺳﺘﺨﺪﺍﻣﻬﺎ ﻋﻨﺎﻳﺔ ﻓﺎﺋﻘﺔ؛ ﻷﳖﺎ ﻟﻴﺴﺖ ﻓﻌﺎﻟﺔ ‪.100%‬‬ ‫‪ ‬‬

‫ﻜﻮﻥ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ ﻷﻧﻪ ﻗﺎﺩﺭ‬

‫‪ ‬ﹸﻳ ﱢ‬
‫ﻋﲆ ﺗﻜﻮﻳﻦ ‪ 4‬ﺭﻭﺍﺑﻂ ﻣﺸـﱰﻛﺔ ﻣﻊ ﺍﻟـﺬﺭﺍﺕ ﺍﻷﺧﺮ￯‪ ،‬ﺑﲈ ﰲ‬
‫ﺫﻟﻚ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﺧﺮ￯‪.‬‬
‫‪ ‬ﺇﺟﺎﺑﺎﺕ ﳏﺘﻤﻠﺔ‪ :‬ﺍﺳـﺘﺨﺪﺍﻣﻪ ﰲ ﺗﺪﻓﺌﺔ ﺍﳌﻨﺎﺯﻝ‪،‬‬
‫ﻭﰲ ﻃﺒﺦ ﺍﻟﻄﻌﺎﻡ‪.‬‬
‫— ‪  ‬ﺍﻟﺸـﻜﻞ ‪ 8-3‬ﺍﻟﻨﻴﱰﻭﺟـﲔ‪ ،‬ﻭﺍﻷﻛﺴـﺠﲔ‬
‫ﻭﺍﻟﻜﱪﻳﺖ‪ ،‬ﻭﺍﻟﻔﻮﺳﻔﻮﺭ‪ ،‬ﻭﺍﳍﺎﻟﻮﺟﻴﻨﺎﺕ‪.‬‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﳎﻤﻮﻋﺔ ﻣﻦ ﺍﻟﻄﻼﺏ ﺍﳌﺘﻔﻮﻗﲔ ﺍﻟﺒﺤﺚ ﻋﻦ ﻣﺒﺪﺃ‬

‫ﺍﳊﻴﺎﺗﻴﺔ )ﺍﳊﻴﻮﻳﺔ( ﻭﻋﺮﺽ ﻧﺘﺎﺋﺞ ﺑﺤﺜﻬﻢ ﺷﻔﻮ ﹰﻳﺎ ﻋﲆ ﺍﻟﺼﻒ‪ .‬ﻭﻳﺘﻌﲔ ﻋﲆ‬
‫ﺍﻟﻄـﻼﺏ ﺃﻥ ﻳﻔﴪﻭﺍ ﺧﻼﻝ ﻫـﺬﺍ ﺍﻟﻌﺮﺽ ﺍﻟﻨﻈﺮﻳﺔ‪ ،‬ﻭﻛﻴـﻒ ﺗﻢ ﺩﺣﻀﻬﺎ‪،‬‬
‫ﻭﻛﻴﻒ ﺃﺩ￯ ﻋﺪﻡ ﻣﺼﺪﺍﻗﻴﺘﻬﺎ ﺇﱃ ﺗﻐﻴﲑ ﺍﻟﺘﻔﻜﲑ ﺍﻟﻌﻠﻤﻲ‪ .‬ﻭﺷـﺠﻌﻬﻢ ﹰ‬
‫ﺃﻳﻀﺎ‬
‫ﻋﲆ ﺇﻋﺪﺍﺩ ﻣﻮﺍﺩ ﺗﻮﺿﻴﺤﻴﺔ ﻣﺮﺋﻴﺔ ﻻﺳﺘﺨﺪﺍﻣﻬﺎ ﺧﻼﻝ ﺍﻟﻌﺮﺽ‪.‬‬
‫‪   ‬‬

‫‪131‬‬
 ‫‪‬‬ ‫‪‬‬
‫‪H‬‬
‫‪‬‬
‫ﻋﺮض ﺳﺮﻳﻊ‬

‫— —‬
‫‪H— C — H‬‬ ‫‪CH4‬‬
‫‪H‬‬
‫‪‬‬ ‫‪‬‬
‫‪‬‬ ‫‪‬‬
‫‪CH  8-4‬‬
‫‪4‬‬

‫‪A‬‬
‫‪ ‬ﻳﻤﺜﻞ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﺟﺰﻳﺌﺎﺕ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﺑﻄﺮﺍﺋﻖ ﳐﺘﻠﻔﺔ‪.‬‬ ‫‪B‬‬ ‫‪C‬‬ ‫‪D‬‬ ‫‪E‬‬ ‫ﺍﻟﺒﻴﻮﺗﺎﻥ‬
‫‪F AAG‬‬ ‫ﻋـﲆ ‪BBH‬‬
‫ﲢﺘﻮﻱ ‪CC I‬‬
‫ﻋـﺔ ‪DDJ‬‬ ‫ﺍﺳـﺘﺨﺪﻡ‪ FF‬ﹼ‬
‫ﻭﻻ ‪EEK‬‬ ‫‪L GGM HH‬‬‫‪‬‬
‫‪N IO‬‬
‫‪I‬‬ ‫‪JJP KK‬‬ ‫‪LL‬‬ ‫‪M‬‬
‫‪M‬‬
‫‪ 8-5 ‬‬
‫ﻭﻳﺒﲔ ﺍﻟﺸﻜﻞ ‪ 8-4‬ﺃﺭﺑﻊ ﻃﺮﺍﺋﻖ ﳐﺘﻠﻔﺔ ﻟﺘﻤﺜﻴﻞ ﺟﺰﻱﺀ ﺍﳌﻴﺜﺎﻥ‪ ،‬ﺣﻴﺚ ﲤﺜﱠﻞ ﺍﻟﺮﺍﺑﻄﺔ ﺍﳌﺸﱰﻛﺔ‬
‫ﺗﺸﺎﺭﻙ ﺇﻟﻜﱰﻭﻧﲔ‪ .‬ﻭﻳﺴﺘﺨﺪﻡ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﰲ‬ ‫ﹸ‬ ‫)ﺍﻟﺘﺴﺎﳘﻴﺔ( ﺑﺨﻂ ﻭﺍﺣﺪ ﻣﺴﺘﻘﻴﻢ ﻳﺮﻣﺰ ﺇﱃ‬
‫‪  ‬‬
‫‪ ‬‬
‫ﻟﺘﻮﺿﻴﺢ ﺍﻟﻔﺮﻕ ﺍﻟﺸﺎﺳـﻊ ﺑﲔ ﺣﺠـﻢ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﰲ ﺣﺎﻟﺘﻪ‬
‫ﻣﻌﻈﻢ ﺍﻷﺣﻴﺎﻥ ﺍﻟﻨﻤﻮﺫﺝ ﺍﻟﺬﻱ ﻳﻮﺿﺢ ﺍﳌﻌﻠﻮﻣﺎﺕ ﺍﳌﺮﺍﺩ ﺇﻟﻘﺎﺀ ﺍﻟﻀﻮﺀ ﻋﻠﻴﻬﺎ‪ .‬ﻓﻼ ﺗﻌﻄﻲ ﺍﻟﺼﻴﻎ‬
‫ﺍﳉﺰﻳﺌﻴﺔ ﺃﻱ ﻣﻌﻠﻮﻣﺎﺕ ﻋﻦ ﺍﻟﺸﻜﻞ ﺍﳍﻨﺪﳼ ﻟﻠﺠﺰﻱﺀ ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪ ،8-4‬ﰲ ﺣﲔ ﺗﹸﻈﻬﺮ‬
‫‪  ‬‬
‫‪  ‬‬ ‫ﲑﺍ‬
‫ﻣﺪﺭﺟﺎ ﻛﺒ ﹰ‬
‫ﹰ‬ ‫ﳐﺒﺎﺭﺍ‬
‫ﺍﻟﺴﺎﺋﻠﺔ ﻭﺣﺠﻤﻪ ﰲ ﺣﺎﻟﺘﻪ ﺍﻟﻐﺎﺯﻳﺔ‪ .‬ﻭﺍﻣﻸ ﹰ‬
‫ﺛﻢ ﺍﻗﻠﺒﻪ ﰲ ﺣﻮﺽ ﻣﺎﺀ‪ .‬ﹶﺃ ﹺﻣﻞﹺ ﺍﳌﺨﺒﺎﺭ ﻗﻠﻴ ﹰ‬
‫‪‬‬
‫ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﱰﺗﻴﺐ ﺍﻟﻌﺎﻡ ﻟﻠﺬﺭﺍﺕ ﰲ ﺍﳉﺰﻱﺀ‪ ،‬ﻭﻟﻜﻦ ﻻ ﺗﻌﻄﻲ ﺍﻟﺸﻜﻞ ﺍﳍﻨﺪﳼ)ﺍﻟﺜﻼﺛﻲ‬
‫ﺍﻷﺑﻌﺎﺩ( ﺍﻟﺪﻗﻴﻖ‪ .‬ﻭ ﹶﻳﻈﻬﺮ ﺍﻟﺸﻜﻞ ﺍﳍﻨﺪﳼ ﻟﻠﺠﺰﻱﺀ ﺑﻮﺿﻮﺡ ﰲ ﻧﻤﻮﺫﺝ ﺍﻟﻜﺮﺓ ﻭﺍﻟﻌﺼﺎ‪.‬‬
‫‪‬‬ ‫ﻭﻻﻋﺔ‬‫ﻼ ﻭﺿﻊ ﹼ‬ ‫ﺑﺎﳌﺎﺀ‪ ،‬ﹼ‬
‫ﺍﻟﺒﻴﻮﺗﺎﻥ ﰲ ﺍﳌﺎﺀ ﲢﺖ ﺍﳌﺨﺒﺎﺭ‪ ،‬ﻋﲆ ﺃﻥ ﻳﺪﺧﻞ ﺍﻟﺒﻴﻮﺗﺎﻥ ﺍ ﹸﳌﻨﺒﻌﺚ‬
‫‪‬‬
‫ﻭﻟﻜﻦ ﺍﻟﻨﻤﻮﺫﺝ ﺍﻟﻔﺮﺍﻏﻲ ﹸﻳﻌﻄﻲ ﺻﻮﺭﺓ ﺃﻛﺜﺮ ﻭﺍﻗﻌﻴﺔ ﻋﻦ ﺍﻟﻜﻴﻔﻴﺔ ﺍﻟﺘﻲ ﻳﺒﺪﻭ ﻓﻴﻬﺎ ﺍﳉﺰﻱﺀ ﻟﻮ‬
‫ﺃﻣﻜﻦ ﺭﺅﻳﺘﻪ ﺣﻘﻴﻘ ﹰﺔ‪ .‬ﻟﺬﺍ ﻋﻠﻴﻚ ﺃﻥ ﺗﺘﺬﻛﺮ ﻭﺃﻧﺖ ﺗﻨﻈﺮ ﺇﱃ ﻫﺬﻩ ﺍﻟﻨﲈﺫﺝ ﺃﻥ ﺍﻟﺬﺭﺍﺕ ﻣﺘﺼﻠﺔ ﹰ‬
‫ﻣﻌﺎ‬ ‫‪‬‬
‫ﺑﺮﻭﺍﺑﻂ ﺗﺸﱰﻙ ﻓﻴﻬﺎ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ‪.‬‬ ‫‪C C‬‬
‫ﻓـﺮﻍ ﳏﺘﻮﻳﺎﺕ‬ ‫ﺍﻟﻮﻻﻋـﺔ ﰲ ﺍﳌﺨﺒﺎﺭ‪ ،‬ﻭﳛﻞ ﳏـﻞ ﺍﳌﺎﺀ‪ .‬ﺛﻢ ﹼ‬ ‫ﻣـﻦ ﹼ‬
‫‪ ‬ﺗﺮﺗﺒﻂ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺑﻌﻀﻬﺎ ﻣﻊ ﺑﻌﺾ ﻟﻴﺲ‬

‫—‬
‫—‬
‫ﹼ‬
‫—‪—C—C‬‬
‫ﻓﻘﻂ ﺑﺮﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ ﺃﺣﺎﺩﻳﺔ‪ ،‬ﺑﻞ ﹰ‬
‫ﺃﻳﻀﺎ ﺑﺮﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ ﺛﻨﺎﺋﻴﺔ ﻭﺛﻼﺛﻴﺔ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪.8-5‬‬
‫ﺍﻟﻮﻻﻋﺔ ﰲ ﺍﳌﺨﺒﺎﺭ‪ ،‬ﻭﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﺴﺠﻴﻞ ﺣﺠﻢ ﺍﻟﻐﺎﺯ‬
‫—‬
‫—‬
‫‪‬‬
‫ﻭﻗﺒﻞ ﺃﻥ ﻳﺘﻤﻜﻦ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﰲ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳﻊ ﻋﴩ ﻣﻦ ﻓﻬﻢ ﺍﻟﺮﻭﺍﺑﻂ ﻭﺍﻟﺒﻨﺎﺀ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‬
‫ﻟﻠﻤﻮﺍﺩ ﺍﻟﻌﻀﻮﻳﺔ‪ ،‬ﻗﺎﻣﻮﺍ ﺑﺈﺟﺮﺍﺀ ﺍﺧﺘﺒﺎﺭﺍﺕ ﻋﲆ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﻨﺎﲡﺔ ﻋﻦ ﺗﺴﺨﲔ ﺍﻟﺪﻫﻮﻥ‬ ‫‪‬‬ ‫ﺍﻟﻮﻻﻋﺔ ﺍﻟﻔﺎﺭﻏﺔ‪ ،‬ﻭﻗﺲ ﺣﺠﻢ ﺍﳌﺎﺀ ﺍﻟﴬﻭﺭﻱ‬ ‫ﺍﻟﻨﺎﺗﺞ‪ .‬ﻭﺍﻓﺘﺢ ﹼ‬
‫ﺍﳊﻴﻮﺍﻧﻴﺔ ﻭﺍﻟﺰﻳﻮﺕ ﺍﻟﻨﺒﺎﺗﻴﺔ‪ ،‬ﻭﺻﻨﹼﻔﻮﺍ ﻫﺬﻩ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺑﻨﺎ ﹰﺀ ﻋﲆ ﺍﺧﺘﺒﺎﺭ ﻛﻴﻤﻴﺎﺋﻲ ﹸﳜﻠﻂ‬
‫ﻟﺘﻌﺒﺌﺘﻬـﺎ ﺑﺼﻮﺭﺓ ﻛﺎﻣﻠﺔ‪ .‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺍﳌﻘﺎﺭﻧﺔ ﺑﲔ ﺣﺠﻢ ﻛﻞ‬
‫‪C‬‬ ‫‪C‬‬
‫ﺛﻢ ﹸﻳﻘﺎﺱ ﻣﻘﺪﺍﺭ ﺍﻟﱪﻭﻡ ﺍﻟﺬﻱ ﺗﻔﺎﻋﻞ ﻣﻊ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ‪ .‬ﻓﻘﺪ‬ ‫ﻓﻴﻪ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺑﺎﻟﱪﻭﻡ‪ ،‬ﹼ‬
‫ﺗﺘﻔﺎﻋﻞ ﺑﻌﺾ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﻊ ﻛﻤﻴﺔ ﻗﻠﻴﻠﺔ ﻣﻦ ﺍﻟﱪﻭﻡ‪ ،‬ﻭﺑﻌﻀﻬﺎ ﻣﻊ ﻛﻤﻴﺔ ﺃﻛﱪ‪ ،‬ﻭﻗﺪ ﻻ‬ ‫‪C —C‬‬
‫ﻳﺘﻔﺎﻋﻞ ﺑﻌﻀﻬﺎ ﻣﻊ ﺃﻱ ﻛﻤﻴﺔ ﻣﻦ ﺍﻟﱪﻭﻡ‪ .‬ﻟﺬﺍ ﺃﻃﻠﻖ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﻋﲆ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺘﻲ‬ ‫‪‬‬ ‫ﻣﻦ ﺍﻟﺴﺎﺋﻞ ﻭﺍﻟﻐﺎﺯ‪.‬‬
‫ﺗﻔﺎﻋﻠﺖ ﻣﻊ ﺍﻟﱪﻭﻡ ﺍﺳﻢ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ ﻣﺘﺄ ﹼﺛﺮﻳﻦ ﺑﻤﻔﻬﻮﻡ ﺃﻥ ﺍﳌﺤﻠﻮﻝ ﺍﳌﺎﺋﻲ‬
‫ﻏﲑ ﺍﳌﺸﺒﻊ ﻗﺎﺩﺭ ﻋﲆ ﺇﺫﺍﺑﺔ ﺍﳌﺰﻳﺪ ﻣﻦ ﺍﳌﺬﺍﺏ‪ .‬ﺃﻣﺎ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺘﻲ ﱂ ﺗﺘﻔﺎﻋﻞ ﻣﻊ ﺍﻟﱪﻭﻡ‬ ‫‪‬‬ ‫ﲢﺬﻳـﺮ‪ :‬ﺗﺄﻛـﺪ ﻣﻦ ﻋـﺪﻡ ﻭﺟﻮﺩ ﺃﻱ ﳍـﺐ ﻣﺸـﺘﻌﻞ ﰲ ﺍﳌﺨﺘﱪ‪.‬‬
‫ﻓﺴ ﹼﻤﻴﺖ ﺑﺎﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸﺒﻌﺔ‪.‬‬ ‫ﹸ‬
‫ﻭﻧﻔـﺬ ﻫـﺬﺍ ﺍﻟﻌﺮﺽ ﺍﻟﻌﻤـﲇ ﰲ ﻏﺮﻓﺔ ﺟﻴﺪﺓ ﺍﻟﺘﻬﻮﻳـﺔ ﺃﻭ ﺩﺍﺧﻞ‬
‫‪C‬‬ ‫‪C‬‬
‫ﻳﺴﺘﻄﻴﻊ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﺍﻟﻴﻮﻡ ﺗﻔﺴﲑ ﻧﺘﺎﺋﺞ ﺍﻻﺧﺘﺒﺎﺭﺍﺕ ﺍﻟﺘﻲ ﺗﻌﻮﺩ ﺇﱃ ﻣﺌﺔ ﻭﺳﺒﻌﲔ ﻋﺎ ﹰﻣﺎ ﻣﻀﺖ‪.‬‬ ‫—‪—C‬‬
‫—‪—C‬‬
‫ﺣﻴﺚ ﲢﺘﻮﻱ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺘﻲ ﺗﻔﺎﻋﻠﺖ ﻣﻊ ﺍﻟﱪﻭﻡ ﻋﲆ ﺭﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ‪.‬‬
‫ﺧﺰﺍﻧﺔ ﺍﻷﺑﺨﺮﺓ‪ .‬‬
‫‪‬‬
‫ﺃﻣﺎ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺘﻲ ﱂ ﺗﺘﻔﺎﻋﻞ ﻣﻊ ﺍﻟﱪﻭﻡ ﻓﻘﺪ ﺍﺣﺘﻮﺕ ﻓﻘﻂ ﻋﲆ ﺭﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ ﺃﺣﺎﺩﻳﺔ‪.‬‬
‫‪‬‬
‫ﻭﺍﻟﻴﻮﻡ ﹸﻳﻌﺮﻑ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﻟﺬﻱ ﳛﺘﻮﻱ ﻋﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ ﻓﻘﻂ ﺑﺎﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳌﺸﺒﻊ‪ .‬ﺃﻣﺎ‬ ‫‪‬‬
‫ﺍﻟﺬﻱ ﳛﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﻋﲆ ﺍﻷﻗﻞ ﻓ ﹸﻴﻌﺮﻑ ﺑﺎﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻏﲑ ﺍﳌﺸﺒﻊ‪.‬‬
‫‪‬ﻣﺎ ﺃﺻﻞ ﻣﺼﻄﻠﺤﻲ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸﺒﻌﺔ ﻭﻏﲑ ﺍﳌﺸﺒﻌﺔ؟‬
‫‪‬‬ ‫‪‬‬

‫‪ ‬ﻗـﺎﻡ ﺍﻟﻜﻴﻤﻴﺎﺋﻴـﻮﻥ ﰲ ﺑﺪﺍﻳﺎﺕ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳـﻊ‬

‫‪C22-119C-828378-08‬‬ ‫ﻋﴩ ﺑﺎﺧﺘﺒﺎﺭ ﺍﻟﺪﻫﻮﻥ ﺍﳊﻴﻮﺍﻧﻴﺔ ﻭﺍﻟﺰﻳﻮﺕ ﺍﻟﻨﺒﺎﺗﻴﺔ ﳌﻌﺮﻓﺔ ﻫﻞ‬
‫ﺗﺘﻔﺎﻋـﻼﻥ ﻣﻊ ﺍﻟـﱪﻭﻡ‪ .‬ﻭﻗﺪ ﺳـﻤﻴﺖ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺘﻲ‬
‫ﺗﻔﺎﻋﻠﺖ ﻣﻊ ﺍﻟﱪﻭﻡ ﺑﺎﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ‪ ،‬ﰲ ﺣﲔ‬
‫ﺳﻤﻴﺖ ﺗﻠﻚ ﺍﻟﺘﻲ ﱂ ﺗﺘﻔﺎﻋﻞ ﻣﻌﻪ ﺑﺎﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸﺒﻌﺔ‪.‬‬

‫ﺼﻄﻠﺤﲔ "ﻣﺸﺒﻊ" ﻭ"ﻏﲑ‬ ‫ﹶ‬ ‫‪ ‬ﺳﻴﺴـﺘﻮﻋﺐ ﺑﻌﺾ ﺍﻟﻄﻼﺏ ﺍ ﹸﳌ‬

‫ﻣﺸـﺒﻊ" ﻋﲆ ﻧﺤﻮ ﺃﻓﻀـﻞ ﻋﻨﺪ ﺗﻄﺒﻴﻘﻬﲈ ﻋـﲆ ﻣﺜﺎﻝ ﻣﻨﺎﻇﺮ‪ .‬ﻟﺬﺍ ﹶﺷـ ﱢﺒﻪ ﻋﺪﻡ‬
‫ﺍﻹﺷـﺒﺎﻉ ﺑﻤﻨﺸـﻔﺔ ﻭﺭﻗﻴﺔ ﺟﺎﻓﺔ ﻻ ﺗﺰﺍﻝ ﻗﺎﺩﺭﺓ ﻋـﲆ ﺍﻣﺘﺼﺎﺹ ﺍﳌﺎﺀ ﺑﺄﻟﻜﲔ‬
‫ﺃﻭ ﺃﻟﻜﺎﻳﻦ ﻳﺴـﺘﻄﻴﻊ ﺍﻣﺘﺼﺎﺹ ﺍﳌﺰﻳﺪ ﻣـﻦ ﺍﳍﻴﺪﺭﻭﺟﲔ ﻋﻦ ﻃﺮﻳﻖ ﺗﻜﻮﻳﻦ‬
‫ﺭﻭﺍﺑﻂ ‪ C- H‬ﺇﺿﺎﻓﻴﺔ ﻋﲆ ﺣﺴـﺎﺏ ﺍﻟﺮﻭﺍﺑـﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﺃﻭ ﺍﻟﺜﻼﺛﻴﺔ‪ .‬ﻭﺑﺘﻌﺒﲑ‬
‫ﺁﺧـﺮ‪ ،‬ﳛﺘﻮﻱ ﺍﳌﺮﻛـﺐ ﻋﲆ ﻋﺪﺩ ﺫﺭﺍﺕ ﻫﻴﺪﺭﻭﺟﲔ ﺃﻗـﻞ ﻣﻦ ﺍﻟﻌﺪﺩ ﺍﻟﺬﻱ‬
‫ﺷﺒﻪ ﺇﺷﺒﺎﻉ ﺍﳌﻨﺸـﻔﺔ ﺍﻟﻮﺭﻗﻴﺔ ﺑﺎﳌﺎﺀ‬‫ﺗﺴـﺘﻄﻴﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﺳـﺘﻴﻌﺎﺑﻪ‪ .‬ﺛﻢ ﹼ‬
‫ﺑﺄﻟﻜﺎﻥ ﳛﺘﻮﻱ ﻣﺴـﺒ ﹰﻘﺎ ﻋﲆ ﲨﻴﻊ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﺍﻟﺘﻲ ﺗﺴـﺘﻄﻴﻊ ﺫﺭﺍﺕ‬
‫ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﻷﻟﻜﺎﻥ ﺍﺳﺘﻴﻌﺎﲠﺎ‪ .‬‬

‫‪132‬‬
 ‫ﺗﻨﻘﻴﺔ اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت ‪Refining Hydrocarbons‬‬
‫ﹼ‬
‫ﺴﻤﻰ ﺍﻟﻨﻔﻂ )ﺍﻟﺒﱰﻭﻝ(‪ .‬ﻭﻗﺪ ﺗﺸﻜﻞ‬ ‫ﲑ ﻣﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﻦ ﺍﻟﻮﻗﻮﺩ ﺍﻷﺣﻔﻮﺭﻱ ﺍ ﹸﳌ ﹼ‬ ‫ﺍﻟﻴﻮﻡ ﺍﻟﻜﺜ ﹸ‬
‫ﹶ‬ ‫ﻳﻨﺘﺞ‬
‫ﹸ‬
‫اﻟﺘﻌﻠﻢ اﻟﺒﺼﺮي‬ ‫ﺍﻟﻨﻔﻂ ﻣﻦ ﺑﻘﺎﻳﺎ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ ﺍﻟﺘﻲ ﻋﺎﺷﺖ ﰲ ﺍﳌﺤﻴﻄﺎﺕ ﻣﻨﺬ ﻣﻼﻳﲔ ﺍﻟﺴﻨﲔ‪ .‬ﻭﻣﻊ ﻣﺮﻭﺭ ﺍﻟﺰﻣﻦ ﻛﻮﻧﺖ‬
‫ﲢﻮﻟﺖ ﺑﻔﻌﻞ ﺍﳊﺮﺍﺭﺓ‬ ‫ﺑﻘﺎﻳﺎ ﻫﺬﻩ ﺍﳌﺨﻠﻮﻗﺎﺕ ﰲ ﻗﺎﻉ ﺍﳌﺤﻴﻂ ﻃﺒﻘﺎﺕ ﺳﻤﻴﻜﺔ ﻣﻦ ﺗﺮﺳﺒﺎﺕ ﺷﺒﻪ ﻃﻴﻨﻴﺔ‪ ،‬ﹼ‬

‫‪ 8-6 ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﻔﺤﺺ ﺍﻟﺸـﻜﻞ ﺍﻟﺬﻱ ﻳﻮﺿﺢ‬

‫ﺍﳌﻨﺒﻌﺜﺔ ﻣﻦ ﺑﺎﻃﻦ ﺍﻷﺭﺽ ﻭﺍﻟﻀﻐﻂ ﺍﳍﺎﺋﻞ ﻣﻦ ﺍﻟﺮﻭﺍﺳﺐ ﺍﻟﻜﺜﲑﺓ ﺇﱃ ﺻﺨﺮ ﺯﻳﺘﻲ ﻭﻏﺎﺯ ﻃﺒﻴﻌﻲ‪ .‬ﻭﻳﻨﻔﺬ‬
‫ﺍﻟﻨﻔﻂ ﻣﻦ ﺧﻼﻝ ﺃﻧﻮﺍﻉ ﻣﻌﻴﻨﺔ ﻣﻦ ﺍﻟﺼﺨﻮﺭ ﺫﺍﺕ ﻣﺴﺎﻣﺎﺕ‪ ،‬ﻭﻳﺘﺠﻤﻊ ﰲ ﺃﻋﲈﻕ ﺍﻟﻘﴩﺓ ﺍﻷﺭﺿﻴﺔ ﰲ ﺻﻮﺭﺓ‬

‫ﺍﳌﻜﻮﻧـﺎﺕ )ﺍﻷﺟﺰﺍﺀ( ﺍﻟﺮﺋﻴﺴـﺔ ﺍﻟﺘﻲ ﻳﺘﻢ ﺍﳊﺼـﻮﻝ ﻋﻠﻴﻬﺎ ﻣﻦ ﺑﺮﺝ‬

‫ﹼ‬ ‫ﺃﻳﻀﺎ ﻋﲆ ﻛﻤﻴﺎﺕ‬
‫ﺑﹺ ﹶﺮﻙ‪ .‬ﻭﻋﺎﺩﺓ ﻣﺎ ﻳﻮﺟﺪ ﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﻣﺼﺎﺣ ﹰﺒﺎ ﻟﻠﱰﺳﺒﺎﺕ ﺍﻟﻨﻔﻄﻴﺔ‪ ،‬ﺣﻴﺚ ﻳﺘﺸﻜﻼﻥ ﹰ‬
‫ﻣﻌﺎ ﰲ ﺍﻟﻮﻗﺖ ﻧﻔﺴﻪ‬
‫ﻭﺑﺎﻟﻄﺮﻳﻘﺔ ﻧﻔﺴﻬﺎ‪ .‬ﻭﻳﺘﻜﻮﻥ ﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﺑﺼﻮﺭﺓ ﺃﺳﺎﺳﻴﺔ ﻣﻦ ﺍﳌﻴﺜﺎﻥ‪ ،‬ﻭﻟﻜﻨﻪ ﳛﺘﻮﻱ ﹰ‬

‫ﺍﻟﺘﻘﻄـﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ ﰲ ﻣﺼﻔﺎﺓ ﺍﻟﺒﱰﻭﻝ‪ .‬ﻭﻭﺿﺢ ﺃﻥ ﻋﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ‬
‫ﺍﻟﺒﺴـﻴﻂ ﲤﺜﻞ ﻓﻘﻂ ﺍﳋﻄﻮﺓ ﺍﻷﻭﱃ ﰲ ﲢﻮﻳـﻞ ﺍﻟﻨﻔﻂ ﺍﳋﺎﻡ ﺇﱃ ﻣﻮﺍﺩ‬
‫ﺍﳌﻜﻮﻧﺎﺕ ﲣﻀـﻊ ﳌﻌﺎﳉﺔ ﺇﺿﺎﻓﻴﺔ ﻟﻔﺼﻠﻬﺎ‬‫ﻣﻔﻴـﺪﺓ‪ ،‬ﻭﺃﻥ ﺍﻟﻜﺜﲑ ﻣﻦ ﹼ‬
‫ﻛﻴﻤﻴﺎﺋﻴﺎ ﺇﱃ ﻣﺮﻛﺒﺎﺕ ﺃﺧﺮ￯‪.‬‬
‫ﹼﹰ‬ ‫ﺑﺼﻮﺭﺓ ﺃﻓﻀﻞ‪ ،‬ﺃﻭ ﺣﺘﻰ ﲢﻮﻳﻠﻬﺎ‬
‫ﻫـﺬﺍ ﻭﻳﺘﻢ ﺇﻋﺎﺩﺓ ﺗﻘﻄﲑ ﺑﻌﺾ ﺍﳌﺨﻠﻔـﺎﺕ ﺍﻟﺜﻘﻴﻠﺔ ﻣﻦ ﺑﺮﺝ ﺍﻟﺘﻘﻄﲑ‬
‫ﲢﺖ ﺗﺄﺛﲑ ﺍﻟﺘﻔﺮﻳﻎ؛ ﺣﻴﺚ ﺇﻥ ﺗﻘﻠﻴﻞ ﺍﻟﻀﻐﻂ ﻓﻮﻕ ﺳـﻄﺢ ﺍﻟﺴـﺎﺋﻞ‬
‫ﻳـﺆﺩﻱ ﺇﱃ ﺧﻔـﺾ ﺩﺭﺟـﺔ ﻏﻠﻴﺎﻧـﻪ‪ .‬ﻭﻫـﺬﺍ ﻳﻌﻨـﻲ ﺇﻣﻜﺎﻧﻴـﺔ ﻓﺼﻞ‬
‫‪C4H10  CH4‬‬
‫ﺍﳌﻜﻮﻧﺎﺕ ﺍﻟﺜﻘﻴﻠﺔ ﻣﺮﺓ ﺃﺧﺮ￯ ﺩﻭﻥ ﺍﺳـﺘﻌﲈﻝ ﺩﺭﺟﺎﺕ ﺣﺮﺍﺭﺓ ﻋﺎﻟﻴﺔ‬
‫ﹼ‬
‫ﺿﺌﻴﻠﺔ ﻣﻦ ﺃﻧﻮﺍﻉ ﺃﺧﺮ￯ ﻣﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲢﺘﻮﻱ ﻋﲆ ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﺇﱃ ﲬﺲ ﺫﺭﺍﺕ‪.‬‬
‫‪ ‬ﹸﻳﻌﺪ ﺍﻟﻨﻔﻂ ـ ﻋﲆ ﺍﻟﻌﻜﺲ ﻣﻦ ﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ـ ﹰ‬
‫ﺧﻠﻴﻄﺎ ﹸﻣﻌﻘﹼﺪﹰ ﺍ ﳛﺘﻮﻱ ﻋﲆ ﺃﻛﺜﺮ ﻣﻦ ﺃﻟﻒ‬
‫ﻼ ﻣﺎ ﹸﻳﺴﺘﺨﺪﻡ ﰲ ﺻﻮﺭﺗﻪ ﺍﳋﺎﻡ‪ ،‬ﻓﻬﻮ ﺃﻛﺜﺮ ﻓﺎﺋﺪﺓ ﻟﻺﻧﺴﺎﻥ‬ ‫ﻣﺮﻛﺐ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﳌﺨﺘﻠﻔﺔ‪ .‬ﻟﺬﺍ ﻓﺈﻥ ﺍﻟﻨﻔﻂ ﻗﻠﻴ ﹰ‬ ‫ﹼ‬
‫ﻣﻜﻮﻧﺎﺕ ﺃﻭ ﺃﺟﺰﺍﺀ ﺃﺑﺴﻂ‪ .‬ﻭﳛﺪﺙ ﻫﺬﺍ ﺍﻟﻔﺼﻞ ﻣﻦ ﺧﻼﻝ ﻋﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ‪،‬‬ ‫ﻋﻨﺪﻣﺎ ﻳﻔﺼﻞ ﺇﱃ ﹼ‬
‫ﺍﻟﺘﻲ ﺗﺘﻀﻤﻦ ﺗﺒﺨﲑ ﺍﻟﻨﻔﻂ ﻋﻨﺪ ﺩﺭﺟﺔ ﺍﻟﻐﻠﻴﺎﻥ‪ ،‬ﺛﻢ ﲡﻤﻊ ﺍﳌﺸﺘﻘﺎﺕ ﺃﻭ ﺍﳌﻜﻮﻧﺎﺕ ﺍﳌﺨﺘﻠﻔﺔ ﰲ ﺃﺛﻨﺎﺀ ﺗﻜﺜﻔﻬﺎ‬
‫ﻋﻨﺪ ﺩﺭﺟﺎﺕ ﺣﺮﺍﺭﺓ ﻣﺘﺒﺎﻳﻨﺔ‪ .‬ﻭﳚﺮﻱ ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ ﰲ ﺃﺑﺮﺍﺝ ﻟﻠﺘﺠﺰﺋﺔ ﺷﺒﻴﻬﺔ ﺑﲈ ﰲ ﺍﻟﺸﻜﻞ ‪.8-6‬‬
‫ﻭﻳﺘﻢ ﺍﻟﺘﺤﻜﻢ ﰲ ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ ﺩﺍﺧﻞ ﺑﺮﺝ ﺍﻟﺘﺠﺰﺋﺔ‪ ،‬ﻓﺘﻜﻮﻥ ﻗﺮﻳﺒﺔ ﻣﻦ ‪ 400°C‬ﰲ ﺃﺳﻔﻞ ﺍﻟﱪﺝ‪ ،‬ﻭﻫﻮ ﺍﳌﻜﺎﻥ‬
‫ﺗﺪﺭﳚﻴﺎ ﰲ ﺍﲡﺎﻩ ﺃﻋﲆ ﺍﻟﱪﺝ‪ .‬ﻭﻋﻤﻮ ﹰﻣﺎ ﺗﻨﺨﻔﺾ ﺩﺭﺟﺎﺕ ﺣﺮﺍﺭﺓ ﺗﻜﺜﹼﻒ‬ ‫ﹼﹰ‬ ‫ﺍﻟﺬﻱ ﻳﻐﲇ ﻓﻴﻪ ﺍﻟﻨﻔﻂ‪ ،‬ﻭﺗﻨﺨﻔﺾ‬
‫ﺍﳌﻮﺍﺩ )ﺩﺭﺟﺎﺕ ﺍﻟﻐﻠﻴﺎﻥ( ﻣﻊ ﺍﻧﺨﻔﺎﺽ ﺍﻟﻜﺘﻠﺔ ﺍﳉﺰﻳﺌﻴﺔ ﳍﺎ‪ .‬ﻟﺬﺍ ﺗﺘﻜﺜﻒ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻭ ﹸﺗﹸﺴﺤﺐ ﰲ ﺃﺛﻨﺎﺀ‬
‫ﺗﺼﺎﻋﺪ ﺍﻷﺑﺨﺮﺓ ﺍﳌﺨﺘﻠﻔﺔ ﺩﺍﺧﻞ ﺍﻟﱪﺝ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪.8-6‬‬
‫‪  8-6‬‬
‫‪  ‬‬
‫‪‬‬
‫‪C12H26  C5H12‬‬
‫‪40°C‬‬

‫‪‬‬
‫‪‬‬

‫ﻗﺪ ﺗﺆﺩﻱ ﺇﱃ ﲢﻠﻠﻬﺎ‪ .‬ﺛﻢ ﹸﺗﺴﺘﺨﺪﻡ ﻫﺬﻩ ﹼ‬

‫ﺍﳌﻜﻮﻧﺎﺕ ﺍﻟﺜﻘﻴﻠﺔ ﻟﻠﺤﺼﻮﻝ‬
‫‪40 – 100°C‬‬ ‫‪    ‬‬
‫‪C16H34  C12H26‬‬ ‫‪‬‬ ‫‪ ‬‬

‫ﻋﲆ ﺯﻳﻮﺕ ﺍﻟﺘﺸﺤﻴﻢ‪ ،‬ﺃﻭ ﹸﲤﺰﺝ ﺑﺎﻟﻮﻗﻮﺩ ﺍﳌﺴﺘﺨﺪﻡ ﰲ ﺍﻟﺼﻨﺎﻋﺔ‪ ،‬ﺃﻭ‬

‫‪105 – 275°C‬‬

‫‪C18H38  C15H32‬‬ ‫‪‬‬

‫‪240 – 300°C‬‬ ‫‪‬‬

‫ﻛﻴﻤﻴﺎﺋﻴﺎ ﺑﺎﺳـﺘﺨﺪﺍﻡ‬
‫ﹼﹰ‬ ‫ﹸﲤ ﱠﺮﺭ ﺩﺍﺧﻞ ﻭﺣﺪﺓ ﺍﻟﺘﻜﺴـﲑ ﺍﳊﺮﺍﺭﻱ ﻟ ﹸﺘ ﱠ‬
‫ﺤﻮﻝ‬ ‫‪C22H46  C17H36‬‬ ‫‪‬‬
‫‪‬‬
‫ﺍﳊﺮﺍﺭﺓ ﻭﻋﻮﺍﻣﻞ ﻣﺴﺎﻋﺪﺓ ﺇﱃ ﺃﻟﻜﻴﻨﺎﺕ‪ .‬‬ ‫‪‬‬
‫‪300°C‬‬
‫‪400°C‬‬
‫‪‬‬
‫‪‬‬
‫‪‬‬
‫‪C20H42‬‬

‫‪‬‬ ‫‪ ‬‬

‫‪‬‬ ‫‪‬‬

‫ﻋﺮض ﺳﺮﻳﻊ‬

‫‪E‬‬ ‫‪F‬‬ ‫ﻟﻌﺮﺽ‬

‫‪AAG‬‬ ‫ﺍﳌﺨﺘﱪ ‪BBH‬‬
‫ﰲ ‪CC I‬‬
‫ﺍﳌﻮﺟﻮﺩ‪DDJ‬‬
‫ﺍﻟﺘﻘﻄﲑ ‪EEK‬‬
‫ﺟﻬﺎﺯ‪FF L GG‬‬
‫‪M HHN‬‬‫ﺍﺳـﺘﺨﺪﻡ‬
‫‪IO‬‬
‫‪I‬‬ ‫‪‬‬
‫‪JJP KK‬‬ ‫‪LL‬‬ ‫‪M‬‬
‫‪M‬‬ ‫‪NN‬‬ ‫‪OO‬‬ ‫‪PP‬‬

‫ﻭﺗﻮﺿﻴـﺢ ﻛﻴﻒ ﹸﻳﻔﺼﻞ ﺍﳋﻠﻴﻂ ﺇﱃ ﻣﻜﻮﻧﺎﺗﻪ‪ .‬ﻭﺍﺳـﺘﺨﺪﻡ ﺍﳌﺎﺀ‬

‫ﹰ‬
‫ﺧﻠﻴﻄـﺎ‪ ،‬ﻭﺍﻓﺼﻠﻪ ﺇﱃ ﻣﻠﺢ ﻭﻣـﺎﺀ ﻣﻘﻄﺮ‪ .‬ﻭﻋﻨﺪ‬ ‫ﺍﳌﺎﻟـﺢ ﺑﻮﺻﻔﻪ‬ ‫اﻟﺘﻨﻮع اﻟﺜﻘﺎﻓﻲ‬
‫ﺍﻗﱰﺍﺏ ﻋﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ ﻋﲆ ﺍﻻﻧﺘﻬﺎﺀ‪ ،‬ﺍﺳﺄﻝ ﺍﻟﻄﻼﺏ‪ :‬ﻣﺎ ﺍﻟﺬﻱ‬
‫‪ ‬ﺗﻢ ﺗﻄﺒﻴـﻖ ﺍﻟﻤﻌﺮﻓﺔ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﻣﻨﺬ‬
‫ﺗﺒﻘـﻰ ﰲ ﺍﻟﻜﺄﺱ ﺍﻟﺰﺟﺎﺟﻴـﺔ؟ ﻣﺎﺀ ﻣﺎﻟﺢ ﻣﺮﻛﺰ‪ .‬ﻭﺍﺳـﺄﳍﻢ‪ :‬ﻣﺎ‬
‫ﺃﻗﺪﻡ ﺍﻟﻌﺼﻮﺭ ﻋﻠﻰ ﺗﻘﻄﻴﺮ ﺍﻟﻌﻄﻮﺭ ﻭﺍﻟﻤﺮﺍﻫﻢ ﻓﻲ ﻣﻨﻄﻘﺔ ﻭﺍﺩﻱ ﺍﻹﻧﺪﻭﺱ‪،‬‬
‫ﺗﺮﻛﻴﺐ ﺍﻟﺴﺎﺋﻞ ﺍﳌﻘﻄﺮ؟ ﻣﺎﺀ ﻣﻘﻄﺮ‪.‬‬
‫ﻓـﻲ ﻛﻞ ﻣـﻦ ﺍﻟﺒﺎﻛﺴـﺘﺎﻥ‪ ،‬ﻭﺍﻟﻬﻨـﺪ‪ ،‬ﻭﺃﻓﻐﺎﻧﺴـﺘﺎﻥ‪ .‬ﻭﺷـﻤﻠﺖ ﺍﻟﻌﻄـﻮﺭ‬
‫ﻭﻣﺴـﻚ ﺍﻟﺘﻤـﺮ ﺍﻟﻬﻨﺪﻱ‪،‬‬ ‫ﺍﻟﻤﺤﻀـﺮﺓ ﺑﺎﻟﺘﻘﻄﻴـﺮ ﺯﻳـﺖ ﺧﺸـﺐ ﺍﻟﺼﻨﺪﻝ‪ ،‬ﹺ‬ ‫ﹼ‬
‫ﻭﺍﻟﻜﺎﻓـﻮﺭ‪ .‬ﻭﻛﺎﻧﺖ ﹸﺗ ﹶﺮﺵ ﻫـﺬﻩ ﺍﻟﻌﻄﻮﺭ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﻋﻠـﻰ ﺍﻟﻤﻠﻮﻙ ﺧﻼﻝ‬
‫ﻣﺮﺍﺳـﻢ ﺍﻟﺘﺘﻮﻳﺞ‪ ،‬ﻭﺍﺳﺘﺨﺪﻡ ﻋﻄﺮ ﺍﻟﻤﺮﻫﻢ ﺍﻟﻤﺸـﺘﻖ ﻣﻦ ﺧﺸﺐ ﺍﻟﺼﻨﺪﻝ‬
‫ﻓﻲ ﻃﻘﻮﺱ ﺍﻻﺳﺘﺤﻤﺎﻡ‪ .‬ﻭﻳﺆﺩﻱ ﻛﻞ ﻣﻦ ﺍﻟﻤﻌﺎﺟﻴﻦ ﻭﺍﻟﻤﺮﻫﻢ ﺍﻷﺭﻭﻣﺎﺗﻲ‬
‫ﻣﻬﻤـﺎ ﺧﻼﻝ ﺑﻌﺾ ﺍﻟﻤﻬﺮﺟﺎﻧﺎﺕ ﺍﻟﺘﻲ ﹸﺗﻘـﺎﻡ ﺣﺘﻰ ﻫﺬﻩ ﺍﻷﻳﺎﻡ‪ ،‬ﻣﺜﻞ‬ ‫ﺩﻭﺭﺍ ﹼﹰ‬
‫ﹰ‬
‫ﻣﻬﺮﺟﺎﻥ ﺩﻳﻮﺍﻟﻲ )‪ ،(Diwali‬ﻭﻣﻬﺮﺟﺎﻥ ﺍﻟﻬﻨﺪﻭﺱ ﻟﻸﺿﻮﺍﺀ‪.‬‬

‫‪133‬‬
‫ﻳﺒﲔ ﺍﻟﺸﻜﻞ ‪ 8-6‬ﺃﺳﲈﺀ ﺍﳌﺸﺘﻘﺎﺕ ﺃﻭ ﺍﳌﻜﻮﻧﺎﺕ ﺍﻷﺳﺎﺳﻴﺔ ﺍﻟﺘﻲ ﹸﺗﹸﻔﺼﻞ ﻋﻦ ﺍﻟﻨﻔﻂ‬ ‫‪ 8-7‬‬
‫ﻣﺼﺤﻮﺑﺔ ﺑﺪﺭﺟﺔ ﻏﻠﻴﺎﳖﺎ‪ ،‬ﻭﺍﳌﺪ￯ ﺍﻟﺬﻱ ﻳﱰﺍﻭﺡ ﻓﻴﻪ ﺣﺠﻢ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻭﺍﺳﺘﺨﺪﺍﻣﺎﺗﻪ‬
‫اﻟﺨﻠﻔﻴﺔ اﻟﻨﻈﺮﻳﺔ ﻟﻠﻤﺤﺘﻮى‬
‫‪ ‬‬
‫ﺍﻟﺸﺎﺋﻌﺔ‪ .‬ﻭﻗﺪ ﻳﻜﻮﻥ ﺑﻌﺾ ﻫﺬﻩ ﺍﳌﺸﺘﻘﺎﺕ ﺃﻭ ﺍﳌﻜﻮﻧﺎﺕ ﻣﺄﻟﻮ ﹰﻓﺎ ﻟﺪﻳﻚ؛ ﺣﻴﺚ ﺇﻧﻚ‬ ‫‪‬‬
‫ﻳﻮﻣﻴﺎ‪ ،‬ﺇﻻ ﺃﻥ ﺃﺑﺮﺍﺝ ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ ﺍﳌﺒﻴﻨﺔ ﰲ ﺍﻟﺸﻜﻞ ‪ 8-7‬ﻻ ﺗﹸﻨﺘﹺﺞ‬‫ﺗﺴﺘﺨﺪﻣﻬﺎ ﹼﹰ‬ ‫‪  ‬‬
‫ﻧﺎﺩﺭﺍ ﻣﺎ ﹸﻳﻨﺘﹺﺞ‬
‫ﺍﳌﻜﻮﻧﺎﺕ‪ .‬ﻓﻌﲆ ﺳﺒﻴﻞ ﺍﳌﺜﺎﻝ‪ ،‬ﹰ‬
‫ﺍﳌﻜﻮﻧﺎﺕ ﺑﺎﻟﻨﺴﺐ ﺍﻟﺘﻲ ﻧﺤﺘﺎﺝ ﺇﻟﻴﻬﺎ ﻣﻦ ﻫﺬﻩ ﹼ‬
‫‪ ‬ﻗﺪ ﻳﺘﻔﺎﺟﺄ ﺍﻟﻄﻼﺏ ﻋﻨﺪﻣﺎ ﻳﻌﺮﻓﻮﻥ ﺃﻥ ﺗﺼﻨﻴﻒ‬
‫‪   ‬‬
‫ﺍﻟﺘﻘﻄﲑ ﺍﻟﻜﻤﻴﺔ ﺍﳌﺮﻏﻮﺏ ﻓﻴﻬﺎ ﻣﻦ ﺍﳉﺎﺯﻭﻟﲔ‪ ،‬ﻭﻟﻜﻨﻪ ﹸﻳﻨﺘﹺﺞ ﰲ ﺍﳌﻘﺎﺑﻞ ﺍﻟﺰﻳﻮﺕ ﺍﻟﺜﻘﻴﻠﺔ‬ ‫‪  ‬‬
‫ﺑﻜﻤﻴﺎﺕ ﺗﻔﻮﻕ ﺣﺎﺟﺔ ﺍﻟﺴﻮﻕ‪.‬‬
‫ﻃﻮﺭ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﻭﺍﳌﻬﻨﺪﺳﻮﻥ ﺍﻟﻌﺎﻣﻠﻮﻥ ﰲ ﻗﻄﺎﻉ ﺍﻟﻨﻔﻂ ﻗﺒﻞ ﺳﻨﻮﺍﺕ ﻋﺪﻳﺪﺓ ﻋﻤﻠﻴﺔ‬
‫ﻟﻘﺪ ﹼ‬
‫‪‬‬
‫‪‬‬
‫ﺍﻷﻭﻛﺘـﺎﻥ ﻻ ﻳﺮﺗﺒـﻂ ﻣﺒﺎﴍﺓ ﺑﺎﻷﻭﻛﺘـﺎﻥ؛ ﺍﻷﻟﻜﺎﻥ ﺫﻱ ﺍﻟﺴﻠﺴـﻠﺔ‬
‫ﻃﻠﻖ ﻋﲆ ﻫﺬﻩ ﺍﻟﻌﻤﻠﻴﺔ ﺍﻟﺘﻲ ﹸﲢ ﹼﻮﻝ ﻓﻴﻬﺎ‬ ‫ﺗﺴﺎﻋﺪ ﻋﲆ ﻣﻮﺍﺀﻣﺔ ﺍﻟﻌﺮﺽ ﻣﻊ ﺍﻟﻄﻠﺐ‪ ،‬ﹸ‬
‫ﻭﺃ ﹺ‬
‫ﺍﳌﻜﻮﻧﺎﺕ ﺍﻟﺜﻘﻴﻠﺔ ﺇﱃ ﺟﺎﺯﻭﻟﲔ ﻋﻦ ﻃﺮﻳﻖ ﺗﻜﺴﲑ ﺍﳉﺰﻳﺌﺎﺕ ﺍﻟﻜﺒﲑﺓ ﺇﱃ ﺟﺰﻳﺌﺎﺕ ﺃﺻﻐﺮ‬
‫‪‬‬ ‫ﺍﳌﺴﺘﻘﻴﻤﺔ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ ‪ 8‬ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ .‬ﻟﻘﺪ ﻭﺿﻌﺖ ﺗﺼﻨﻴﻔﺎﺕ‬
‫‪‬‬
‫ﻋﻤﻠﻴﺔ ﺍﻟﺘﻜﺴﲑ ﺍﳊﺮﺍﺭﻱ‪ .‬ﻭﲢﺪﺙ ﻋﻤﻠﻴﺔ ﺍﻟﺘﻜﺴﲑ ﺍﳊﺮﺍﺭﻱ ﻋﻨﺪ ﻏﻴﺎﺏ ﺍﻷﻛﺴﺠﲔ‬
‫ﻭﻭﺟﻮﺩ ﻋﺎﻣﻞ ﻣﺴﺎﻋﺪ‪ .‬ﻭﺑﺎﻹﺿﺎﻓﺔ ﺇﱃ ﺗﻜﺴﲑ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺜﻘﻴﻠﺔ ﺇﱃ ﺟﺰﻳﺌﺎﺕ‬
‫ﺍﻷﻭﻛﺘﺎﻥ ﰲ ﺍﻟﺒﺪﺍﻳﺔ‪ ،‬ﺑﺈﻋﻄﺎﺀ ﻗﻴﻤﺔ "ﺻﻔﺮ" ﻟﻠﻬﺒﺘﺎﻥ‪ ،‬ﺍﻟﺬﻱ ﻳﺴـﺒﺐ‬
‫ﺃﻳﻀﺎ ﺍﳌﻮﺍﺩ ﺍﻷﻭﻟﻴﺔ ﻟﺼﻨﺎﻋﺔ‬ ‫ﺑﺎﳊﺠﻢ ﺍﳌﻄﻠﻮﺏ ﰲ ﺍﳉﺎﺯﻭﻟﲔ ﻓﺈﻥ ﻫﺬﻩ ﺍﻟﻌﻤﻠﻴﺔ ﺗﻨﺘﺞ ﹰ‬
‫ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﻨﺘﺠﺎﺕ ﺍﳌﺨﺘﻠﻔﺔ‪ ،‬ﻭﻣﻨﻬﺎ ﺍﳌﻨﺘﺠﺎﺕ ﺍﻟﺒﻼﺳﺘﻴﻜﻴﺔ ﻭﺃﻓﻼﻡ ﺍﻟﺘﺼﻮﻳﺮ ﻭﺍﻷﻟﻴﺎﻑ‬
‫ﺍﻻﺷـﺘﻌﺎﻝ ﺍﳌﺒﻜﺮ ﰲ ﺍﺳﻄﻮﺍﻧﺔ ﺍﻻﺣﱰﺍﻕ )‪ (cylinder‬ﰲ ﺍﳌﺤﺮﻙ‪،‬‬
‫ﺍﻟﺼﻨﺎﻋﻴﺔ‪.‬‬ ‫ﻭﻗﻴﻤـﺔ ‪ 100‬ﻟـ ﹺ‪ -4،2،2‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘـﺎﻥ‪ ،‬ﺍﻟﺬﻱ ﻛﺎﻥ ﻟﻪ ﺃﻓﻀﻞ‬
‫‪‬ﺍﻟﻌﻤﻠﻴﺔ ﺍﻟﺘﻲ ﳛﺪﺙ ﻣﻦ ﺧﻼﳍﺎ ﺗﻜﺴﲑ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‬
‫ﺫﺍﺕ ﺍﻟﺴﻼﺳﻞ ﺍﻟﻜﺒﲑﺓ ﺇﱃ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﺮﻏﻮﺑﺔ ﺃﻛﺜﺮ ﻭﺫﺍﺕ ﺳﻼﺳﻞ ﺃﺻﻐﺮ‪.‬‬ ‫ﻧﻮﻋﻴﺔ ﺍﺷـﺘﻌﺎﻝ ﻋﻨﺪﻣﺎ ﺃﺟﺮﻳﺖ ﺍﻻﺧﺘﺒﺎﺭﺍﺕ ﻷﻭﻝ ﻣﺮﺓ‪ .‬ﺇﻥ ﺍﻻﺳﻢ‬
‫ﺍﻟﺸـﺎﺋﻊ ﻟـ ﹺ‪ -4،2،2‬ﺛﻼﺛـﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ ﻫﻮ ﺃﻳﺰﻭﺃﻭﻛﺘﺎﻥ‪ ،‬ﹸ‬
‫‪ ‬ﻻ ﺗﹸﻌﺪ ﺃﻱ ﻣﻦ ﺍﳌﺸﺘﻘﺎﺕ ﺍﻟﻨﺎﲡﺔ ﻋﻦ ﺗﻜﺮﻳﺮ ﺍﻟﻨﻔﻂ ﺍﳋﺎﻡ ﻣﺎﺩﺓ ﻧﻘﻴﺔ‪.‬‬
‫ﺧﻠﻴﻄﺎ ﻣﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪ ،‬ﻭﻟﻴﺲ‬ ‫ﹰ‬ ‫ﻓﻜﲈ ﻫﻮ ﻣﻮﺿﺢ ﰲ ﺍﻟﺸﻜﻞ ‪ ،8-6‬ﹸﻳﻌﺪ ﺍﳉﺎﺯﻭﻟﲔ‬ ‫ﻭﺳـﻤﻲ‬
‫ﻣﺎﺩﺓ ﻧﻘﻴﺔ؛ ﺇﺫ ﺗﺘﻜﻮﻥ ﻣﻌﻈﻢ ﺟﺰﻳﺌﺎﺕ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﰲ ﺍﳉﺎﺯﻭﻟﲔ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ‬ ‫ﹰ‬
‫ﺧﻄﺄ ﺑﺎﻷﻭﻛﺘﺎﻥ ﻋﲆ ﻳﺪ ﺍﻟﻔﻨﱢﻴﲔ ﺍﻟﺬﻳﻦ ﻗﺎﻣﻮﺍ ﺑﺎﺧﺘﺒﺎﺭ ﺍﳉﺎﺯﻭﻟﲔ‪ .‬ﺇﺫ‬
‫ﺭﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ ﺃﺣﺎﺩﻳﺔ ﻣﻦ ‪ 12-5‬ﺫﺭﺓ ﻛﺮﺑﻮﻥ‪ .‬ﻭﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺫﻟﻚ‪ ،‬ﻓﺈﻥ ﺍﳉﺎﺯﻭﻟﲔ‬
‫ﻋﲈ ﺍﺳ ﹸﺘ ﹺ‬
‫ﹸﺨﺪﻡ ﰲ ﺍﳌﺮﻛﺒﺎﺕ ﰲ ﺑﺪﺍﻳﺎﺕ ﺍﻟﻘﺮﻥ‬ ‫ﺍﳌﺴﺘﺨﺪﻡ ﺍﻟﻴﻮﻡ ﰲ ﺍﻟﺴﻴﺎﺭﺍﺕ ﳜﺘﻠﻒ ﹼ‬
‫ﺍﻟﻌﴩﻳﻦ‪ .‬ﻓﺎﻟﻴﻮﻡ ﳚﺮ￯ ﺗﻌﺪﻳﻞ ﺍﳉﺎﺯﻭﻟﲔ ﺍﳌﺴﺘﺨﻠﺺ ﻣﻦ ﺍﻟﻨﻔﻂ ﺑﻌﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ ﻣﻦ‬ ‫ﻣﻬﻦ ﻓﻲ اﻟﻜﻴﻤﻴﺎء‬ ‫ﻳﺆﺩﻱ ﺍﳉﺎﺯﻭﻟﲔ ﺫﻭ ﺍﻟﺘﺼﻨﻴﻒ ‪ 90‬ﺍﻟﺪﻭﺭ ﻧﻔﺴﻪ ﳋﻠﻴﻂ ﻣﻜﻮﻥ ﻣﻦ‬
‫ﺧﻼﻝ ﺿﺒﻂ ﺗﺮﻛﻴﺒﻪ ﻭﺇﺿﺎﻓﺔ ﻣﻮﺍﺩ ﺗﺆﺩﻱ ﺇﱃ ﲢﺴﲔ ﺃﺩﺍﺋﻪ ﰲ ﳏﺮﻙ ﺍﳌﺮﻛﺒﺎﺕ‪ ،‬ﻭﺗﺆﺩﻱ‬
‫ﹰ‬
‫ﺃﻳﻀﺎ ﺇﱃ ﺗﻘﻠﻴﻞ ﺍﻟﺘﻠﻮﺙ ﺍﻟﻨﺎﺗﺞ ﻋﻦ ﻋﻮﺍﺩﻡ ﺍﻟﺴﻴﺎﺭﺍﺕ‪.‬‬
‫‪‬‬
‫‪     ‬‬
‫‪ 90%‬ﺃﻳﺰﻭﺃﻭﻛﺘـﺎﻥ ﻭ ‪ 10%‬ﻫﺒﺘﺎﻥ‪ .‬ﻭﺍﻟﻴﻮﻡ ﻳﻤﻜﻦ ﺇﺿﺎﻓﺔ ﻣﺮﻛﺒﺎﺕ‬
‫ﻟﺬﺍ ﻓﻤﻦ ﺍﻟﴬﻭﺭﻱ ﺟﺪﹼﹰ ﺍ ﺃﻥ ﳛﺪﺙ ﺍﺷﺘﻌﺎﻝ ﺧﻠﻴﻂ ﺍﳉﺎﺯﻭﻟﲔ ﻭﺍﳍﻮﺍﺀ ﰲ ﺃﺳﻄﻮﺍﻧﺔ ﳏﺮﻙ‬ ‫‪   ‬‬
‫‪ ‬‬
‫ﺇﱃ ﺍﳉﺎﺯﻭﻟﲔ ﻟﻠﺤﺼﻮﻝ ﻋﲆ ﺗﺼﻨﻴﻔﺎﺕ ﺃﻭﻛﺘﺎﻥ ﺃﻋﲆ ﻣﻦ ‪.100‬‬
‫ﺍﳌﺮﻛﺒﺔ ﰲ ﺍﻟﻠﺤﻈﺔ ﺍﳌﻨﺎﺳﺒﺔ‪ ،‬ﻭﺃﻥ ﳚﺮﻱ ﺍﺣﱰﺍﻗﻪ ﲤﺎ ﹰﻣﺎ‪ .‬ﻓﺈﺫﺍ ﺣﺪﺙ ﺍﻻﺷﺘﻌﺎﻝ ﻗﺒﻞ ﺍﳌﻮﻋﺪ‬
‫‪     ‬‬
‫ﺍﳌﻨﺎﺳﺐ ﺃﻭ ﺑﻌﺪﻩ ﻓﺈﻥ ﺫﻟﻚ ﻳﺆﺩﻱ ﺇﱃ ﺧﺴﺎﺭﺓ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﻟﻄﺎﻗﺔ‪ ،‬ﻭﺍﻧﺨﻔﺎﺽ ﻓﺎﻋﻠﻴﺔ‬
‫‪ ‬‬
‫ﺍﻟﻮﻗﻮﺩ‪ ،‬ﻭﻓﻘﺪﺍﻥ ﻛﻔﺎﺀﺓ ﺍﳌﺤﺮﻙ‪ .‬ﻻ ﲢﱰﻕ ﻣﻌﻈﻢ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺫﺍﺕ ﺍﻟﺴﻼﺳﻞ‬ ‫‪‬‬ ‫اﻟﺘﻘﻮﻳﻢ‬
‫ﺍﳌﺘﻔﺮﻋﺔ( ﲤﺎ ﹰﻣﺎ‪ ،‬ﻭﲤﻴﻞ ﺑﻔﻌﻞ ﺍﳊﺮﺍﺭﺓ ﻭﺍﻟﻀﻐﻂ ﺇﱃ ﺍﻻﺷﺘﻌﺎﻝ ﺍﳌﺒﻜﺮ ﻗﺒﻞ‬
‫ﺍﳌﺴﺘﻘﻴﻤﺔ )ﻏﲑ ﹼ‬
‫ﺃﻥ ﻳﺼﺒﺢ ﺍﳌﻜﺒﺲ ﰲ ﺍﳌﻮﺿﻊ ﺍﻟﺼﺤﻴﺢ‪ ،‬ﻭﻗﺒﻞ ﺍﺷﺘﻌﺎﻝ ﺷﻤﻌﺔ ﺍﻻﺣﱰﺍﻕ؛ ﺇﺫ ﻳﻜﻮﻥ ﻫﺬﺍ‬
‫ﺍﻻﺣﱰﺍﻕ ﺍﳌﺒﻜﺮ ﻣﺼﺤﻮ ﹰﺑﺎ ﺑﻔﺮﻗﻌﺔ )‪.(knocking‬‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺇﺟﺮﺍﺀ ﺑﺤﺚ ﻭﲢﻀﲑ ﻭﺳـﻴﻠﺔ ﻣﺮﺋﻴﺔ‪،‬‬
‫ﻣﺜـﻞ ﻣﻠﺼـﻖ‪ ،‬ﺃﻭ ﻋـﺮﺽ ﴍﺍﺋـﺢ ﺣﺎﺳـﻮﺑﻴﺔ ﺗﻔـﴪ ﺗﺼﻨﻴﻔـﺎﺕ‬
‫ﺍﻷﻭﻛﺘﺎﻥ‪ ،‬ﻋﲆ ﺃﻥ ﲢﺘﻮﻱ ﻫﺬﻩ ﺍﻟﻮﺳﻴﻠﺔ ﻋﲆ ﻣﻌﻠﻮﻣﺎﺕ ﺣﻮﻝ ﻣﺎﺩﺓ‬
‫"ﺭﺑﺎﻋﻲ ﺇﻳﺜﻴﻞ ﺍﻟﺮﺻﺎﺹ" ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﳉﺎﺯﻭﻟﲔ‪ ،‬ﻭﻛﻴﻒ ﺗﺆﺛﺮ ﰲ‬
‫ﻣﺸﺮوع اﻟﻜﻴﻤﻴﺎء‬
‫ﺗﺼﻨﻴﻔﺎﺕ ﺍﻷﻭﻛﺘﺎﻥ‪   .‬‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺇﺟﺮﺍﺀ ﺑﺤﺚ ﻳﺘﻌﻠﻖ ﺑﺎﻟﻔﺮﻭﻕ ﺑﲔ ﺃﻧﻮﺍﻉ‬ ‫— ‪ ‬ﺍﻟﺸـﻜﻞ ‪ 8-7‬ﺇﺟﺎﺑـﺎﺕ ﳏﺘﻤﻠـﺔ‪ :‬ﺛﺎﲏ ﺃﻛﺴـﻴﺪ‬
‫ﺍﻟﻮﻗﻮﺩ‪ ،‬ﻋﲆ ﺃﻥ ﻳﺸـﺘﻤﻞ ﻫـﺬﺍ ﺍﻟﺒﺤﺚ ﻣﻌﻠﻮﻣﺎﺕ ﺗﺘﻌﻠـﻖ ﺑﺄﻧﻮﺍﻉ ﺍﳉﺎﺯﻭﻟﲔ‬ ‫ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻭﺃﻛﺎﺳـﻴﺪ ﺍﻟﻜﱪﻳﺖ‪ ،‬ﻭﺃﻛﺎﺳﻴﺪ ﺍﻟﻨﻴﱰﻭﺟﲔ‪ ،‬ﻭﻣﺮﻛﺒﺎﺕ‬
‫ﺍﳌﺨﺘﻠﻔﺔ ﺍﳌﺴـﺘﺨﺪﻣﺔ ﰲ ﺍﻟﺴﻴﺎﺭﺍﺕ ﻭﺍﻟﺸـﺎﺣﻨﺎﺕ‪ ،‬ﻭﻭﻗﻮﺩ ﺍﻟﺪﻳﺰﻝ ﻭﺍﻟﻮﻗﻮﺩ‬ ‫ﺍﻟﺮﺻﺎﺹ‪.‬‬
‫ﻭﺣﺜﱠﻬﻢ ﻋﲆ ﺇﺩﺭﺍﺝ ﺃﻧﻮﺍﻉ‬
‫ﺍﳌﺴـﺘﺨﺪﻡ ﰲ ﺍﻟﻄﺎﺋﺮﺍﺕ ﻭﰲ ﺳـﻴﺎﺭﺍﺕ ﺍﻟﺴـﺒﺎﻕ‪ .‬ﹸ‬ ‫‪ ‬ﺍﻟﺘﻜﺴـﲑ ﺍﳊـﺮﺍﺭﻱ ﻋﻤﻠﻴـﺔ ﳛـﺪﺙ ﺧﻼﳍـﺎ‬
‫ﺍﻟﻮﻗـﻮﺩ ﺍﻷﺧـﺮ￯ ﺍﻟﺘـﻲ ﳚﺪﻭﳖﺎ ﺧـﻼﻝ ﺍﻟﺒﺤـﺚ‪ .‬ﻭﺍﻃﻠـﺐ ﺇﻟﻴﻬﻢ ﲢﻀﲑ‬ ‫ﺗﻜﺴـﲑ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺫﺍﺕ ﺍﻟﺴﻼﺳـﻞ ﺍﻟﻜﺒـﲑﺓ ﺇﱃ‬
‫ﻣﻠﺼﻖ ﻳﻮﺿﺢ ﺗﺮﻛﻴﺐ ﱟ‬
‫ﻛﻞ ﻣﻦ ﺃﻧﻮﺍﻉ ﺍﻟﻮﻗﻮﺩ ﺍﳌﺨﺘﻠﻔﺔ‪ .‬‬ ‫ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺫﺍﺕ ﺳﻼﺳـﻞ ﺃﺻﻐـﺮ‪ .‬ﻭﲢـﺪﺙ ﻫـﺬﻩ‬
‫ﺍﻟﻌﻤﻠﻴﺔ ﺑﻮﺟﻮﺩ ﻋﺎﻣﻞ ﳏﻔﺰ ﻭﰲ ﻏﻴﺎﺏ ﺍﻷﻛﺴﺠﲔ‪.‬‬
‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﲢﺪﻳـﺪ ﻣﻮﺍﻗـﻊ ﻣﺼـﺎﰲ ﺍﻟﻨﻔﻂ ﰲ‬

‫ﺍﳌﻤﻠﻜـﺔ‪ .‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺯﻳﺎﺭﺓ ﺃﻗﺮﺏ ﻣﺼﻔﺎﺓ ﳍﻢ ﺃﻭ ﺍﻻﺗﺼﺎﻝ ﺑﺄﻱ ﻣﺼﻔﺎﺓ‬
‫ﻟﻠﺤﺼﻮﻝ ﻋﲆ ﻣﻌﻠﻮﻣﺎﺕ ﺗﺘﻌﻠﻖ ﺑﲈﻫﻴﺔ ﺍﳌﻮﺍﺩ ﺍﻟﺘﻲ ﺗﻨﺘﺠﻬﺎ‪ ،‬ﻭﻛﻤﻴﺔ ﺑﺮﺍﻣﻴﻞ‬
‫ﺍﻟﻨﻔـﻂ ﺍﳋﺎﻡ ﺍﻟﺘﻲ ﺗﻜﺮﺭﻫﺎ ﺷـﻬﺮ ﹼﹰﻳﺎ‪ .‬ﻭﻋﲆ ﺍﻟﻄـﻼﺏ ﺗﻠﺨﻴﺺ ﻧﺘﺎﺋﺠﻬﻢ ﰲ‬
‫ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ‪ .‬‬

‫‪134‬‬
 ‫ﹸﺃﻧﺸﺊ ﻧﻈﺎﻡ ﺗﺼﻨﻴﻒ ﺍﻷﻭﻛﺘﺎﻥ‪ ،‬ﺃﻭ ﻣﻨﻊ ﺍﻟﻔﺮﻗﻌﺔ‪ ،‬ﻟﻠﺒﻨﺰﻳﻦ ﰲ ﺃﻭﺍﺧﺮ ﺍﻟﻌﴩﻳﻨﻴﺎﺕ‪،‬‬
‫ﳑﺎ ﺃﺩ￯ ﺇﱃ ﺇﺩﺭﺍﺝ ﺗﺼﻨﻴﻒ ﺍﻷﻭﻛﺘﺎﻥ ﻋﲆ ﻣﻀﺨﺎﺕ ﺍﻟﺒﻨﺰﻳﻦ ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪.8-8‬‬
‫اﻟﺘﻘﻮﻳﻢ‬ ‫ﻓﻠﻠﺒﻨﺰﻳﻦ ﺍﳌﺘﻮﺳﻂ ﺍﻟﺪﺭﺟﺔ ﺗﺼﻨﻴﻒ ﺃﻭﻛﺘﺎﻥ ﻳﻘﺎﺭﺏ ‪ ،89‬ﰲ ﺣﲔ ﻟﻠﺒﻨﺰﻳﻦ ﺍﳌﻤﺘﺎﺯ‬
‫ﻭﲢﺪﺩ ﻛﺜﲑ ﻣﻦ ﺍﻟﻌﻮﺍﻣﻞ ﺍﻟﺘﺼﻨﻴﻒ ﺍﻷﻭﻛﺘﺎﲏ ﺍﻟﺬﻱ‬ ‫ﻗﻴﻤﺔ ﺃﻋﲆ ﺗﺼﻞ ‪ 91‬ﺃﻭ ﺃﻛﺜﺮ‪ .‬ﹸ‬
‫ﲢﺘﺎﺝ ﺇﻟﻴﻪ ﺍﻟﺴﻴﺎﺭﺓ‪ ،‬ﻓﻤﻨﻬﺎ ﺿﻐﻂ ﺍﳌﻜﺒﺲ ﻋﲆ ﺧﻠﻴﻂ ﺍﻟﻮﻗﻮﺩ ﻭﺍﳍﻮﺍﺀ‪ ،‬ﻭﺩﻓﻊ‬
‫ﺃﻳﻀﺎ‪ .‬ﻭﰲ ﺍﳌﻤﻠﻜﺔ ﺍﻟﻌﺮﺑﻴﺔ ﺍﻟﺴﻌﻮﺩﻳﺔ ﺗﻢ ﺗﺼﻨﻴﻒ ﺍﻷﻭﻛﺘﺎﻥ ﻋﲆ ﻣﻀﺨﺎﺕ‬ ‫ﺍﻟﺴﻴﺎﺭﺓ ﹰ‬
‫ﺑﺎﳌﻜﻮﻧﺎﺕ ﺍﻟﺘﻲ ﹸﺗﻔﺼﻞ‬
‫ﹼ‬ ‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺇﻋﺪﺍﺩ ﻗﺎﺋﻤﺔ‬ ‫ﺍﻟﺒﻨﺰﻳﻦ ‪.95 ،91‬‬
‫ﺃﻗﺪﻡ ﺍﻟﻌﺼﻮﺭ‪‬ﺃﻥ ﺍﻟﻨﻔﻂ ﻳﺴﻴﻞ‬
‫ﻭﺟﺪ ﺍﻟﻨﺎﺱ ﻣﻨﺬ ‪‬‬ ‫‪  ‬‬ ‫‪ ‬‬
‫ﻣـﻦ ﺍﻟﻨﻔـﻂ ﺩﺍﺧﻞ ﻋﻤـﻮﺩ ﺍﻟﺘﺠﺰﺋـﺔ‪ ،‬ﻭﺗﺮﺗﻴﺒﻬـﺎ ﺗﺼﺎﻋﺪ ﹼﹰﻳﺎ ﺣﺴـﺐ‬ ‫‪  8-8‬‬ ‫ﻣﻦ ﺍﻟﺸﻘﻮﻕ ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﻟﺼﺨﻮﺭ‪ .‬ﻭﺗﺸﲑ ﺍﻟﺴﺠﻼﺕ ﺍﻟﺘﺎﺭﳜﻴﺔ ﺇﱃ ﺃﻥ ﺍﻟﻨﻔﻂ ﻗﺪ‬
‫ﺍﺳﺘﹸﺨﺪﻡ ﻣﻨﺬ ﺃﻛﺜﺮ ﻣﻦ ‪ 5000‬ﺳﻨﺔ‪ .‬ﻭﰲ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳﻊ ﻋﴩ ﻋﻨﺪﻣﺎ ﺩﺧﻞ ﺍﻟﻌﺎﱂ‬
‫ﺍﳌﻜﻮﻧﺎﺕ ﻫﻲ‪ :‬ﻏﺎﺯﺍﺕ ﺍﻟﻨﻔﻂ )‪ 1‬ﺇﱃ ‪4‬‬ ‫ﺍﻟﺰﻳـﺎﺩﺓ ﰲ ﺩﺭﺟﺔ ﺍﻟﻐﻠﻴﺎﻥ‪ .‬ﹼ‬
‫‪   ‬‬
‫‪antiknock‬‬ ‫ﻭﺑﺨﺎﺻﺔ‬
‫ﹼ‬ ‫ﻋﴫ ﺍﻵﻻﺕ ﻭﺍﺯﺩﺍﺩ ﻋﺪﺩ ﺳﻜﺎﻧﻪ‪ ،‬ﻓﺎﺯﺩﺍﺩ ﺍﻟﻄﻠﺐ ﻋﲆ ﻣﻨﺘﺠﺎﺕ ﺍﻟﻨﻔﻂ‬

‫ﺫﺭﺍﺕ ﻛﺮﺑـﻮﻥ(؛ ﺍﳉﺎﺯﻭﻟﲔ )‪ 5‬ﺇﱃ ‪ 12‬ﺫﺭﺓ ﻛﺮﺑﻮﻥ(؛ ﺍﻟﻜﲑﻭﺳـﲔ‬ ‫‪‬‬

‫‪89‬‬
‫ﺍﻟﻜﲑﻭﺳﲔ ﻻﺳﺘﺨﺪﺍﻣﻪ ﰲ ﺍﻹﻧﺎﺭﺓ ﻭﺗﺸﺤﻴﻢ ﺍﻵﻻﺕ‪ .‬ﻗﺎﻡ ﺇﺩﻭﻳﻦ ﺩﺭﻳﻚ ‪Edwin‬‬
‫‪- Drake‬ﰲ ﳏﺎﻭﻟﺔ ﻣﻨﻪ ﻟﻠﻌﺜﻮﺭ ﻋﲆ ﳐﺰﻭﻥ ﺩﺍﺋﻢ ﻣﻦ ﺍﻟﻨﻔﻂ‪ -‬ﺑﺤﻔﺮ ﺃﻭﻝ ﺑﺌﺮ ﻧﻔﻂ ﰲ‬

‫)‪ 12‬ﺇﱃ ‪ 16‬ﺫﺭﺓ ﻛﺮﺑـﻮﻥ(؛ ﺯﻳﺖ ﺍﻟﺘﺪﻓﺌﺔ )‪ 15‬ﺇﱃ ‪ 18‬ﺫﺭﺓ ﻛﺮﺑﻮﻥ(؛‬ ‫‪ 100 ‬‬ ‫ﺍﻟﻮﻻﻳﺎﺕ ﺍﳌﺘﺤﺪﺓ ﰲ ﻭﻻﻳﺔ ﺑﻨﺴﻠﻔﺎﻧﻴﺎ ﻋﺎﻡ ‪1859‬ﻡ‪ .‬ﻭﺍﺯﺩﻫﺮﺕ ﺻﻨﺎﻋﺔ ﺍﻟﻨﻔﻂ ﻟﻔﱰﺓ‬
‫ﻣﻦ ﺍﻟﺰﻣﻦ‪ ،‬ﻭﻟﻜﻦ ﺣﲔ ﺍﻛﺘﺸﻒ ﺗﻮﻣﺎﺱ ﺃﺩﻳﺴﻮﻥ ‪ Thomas Edison‬ﺍﳌﺼﺒﺎﺡ‬
‫‪110‬‬
‫ﺯﻳﺖ ﺍﻟﺘﺸﺤﻴﻢ )‪ 17‬ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﺃﻭ ﺃﻛﺜﺮ(؛ ﻭﺍﳌﺨ ﹼﻠﻔﺎﺕ ﺍﻟﺜﻘﻴﻠﺔ )‪20‬‬ ‫ﺍﻟﻜﻬﺮﺑﺎﺋﻲ ﰲ ﻋﺎﻡ ‪1882‬ﻡ‪ ،‬ﺧﴚ ﺍﳌﺴﺘﺜﻤﺮﻭﻥ ﻣﻦ ﺍﻟﻘﻀﺎﺀ ﻋﲆ ﻫﺬﻩ ﺍﻟﺼﻨﺎﻋﺔ‪ .‬ﻏﲑ‬
‫ﺃﻥ ﺍﺧﱰﺍﻉ ﺍﻟﺴﻴﺎﺭﺍﺕ ﰲ ﺍﻟﻌﻘﺪ ﺍﻷﺧﲑ ﻣﻦ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳﻊ ﻋﴩ ﺃﻧﻌﺶ ﻫﺬﻩ ﺍﻟﺼﻨﺎﻋﺔ‬
‫ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﺃﻭ ﺃﻛﺜﺮ(‪ .‬‬ ‫ﲑﺍ‪.‬‬
‫ﻛﺜ ﹰ‬

‫اﻟﺘﻘﻮﻳﻢ ‪8-1‬‬
‫‪ .3‬اﻟﺘﻘﻮﻳﻢ‬ ‫‪ .1‬اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺍﺫﻛﺮ ﺛﻼﺛﺔ ﺗﻄﺒﻴﻘﺎﺕ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ؟‬ ‫اﻟﺨﻼﺻﺔ‬
‫ﺳﻢ ﹼ‬
‫ﻣﺮﻛ ﹰﺒﺎ ﻋﻀﻮ ﹼﹰﻳﺎ‪ ،‬ﻭﻭﺿﺢ ﻣﺎ ﻳﺪﺭﺳﻪ ﻋﺎﱂ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ‪.‬‬ ‫ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﻋﲆ ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﺇﺫ ‪ .2‬ﱢ‬
‫ﲢﺘﻮﻱ ﹼ‬
‫ﻳﻤﻜﻨﻪ ﺗﻜﻮﻳﻦ ﺳـﻼﺳﻞ ﻣﺴﺘﻘﻴﻤـﺔ ﻭﺃﺧـﺮ￯ ‪ .3‬ﺣﺪﹼ ﺩ ﺍﳌﻌﻠﻮﻣﺎﺕ ﺍﻟﺘﻲ ﱢ‬
‫ﺗﺮﻛﺰ ﻋﻠﻴﻬﺎ ﻛﻞ ﻣﻦ ﺍﻟﻨﲈﺫﺝ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳉﺰﻳﺌﻴﺔ ﺍﻷﺭﺑﻌﺔ‪.‬‬
‫اﻟﺘﺤﻘﻖ ﻣﻦ اﻟﻔﻬﻢ‬ ‫‪ .4‬ﻗﺎﺭﻥ ﺑﲔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸﺒﻌﺔ ﻭﻏﲑ ﺍﳌﺸﺒﻌﺔ‪.‬‬ ‫ﻣﺘﻔﺮﻋﺔ‪.‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﻮﺍﺩ ﻋﻀﻮﻳﺔ ﺗﺘﺄﻟﻒ ﻣﻦ ‪ .5‬ﺻﻒ ﻋﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ‪.‬‬
‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﳌﻘﺎﺭﻧـﺔ ﺑـﲔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺍﳌﺸـﺒﻌﺔ‬ ‫‪ .6‬ﺍﺳﺘﻨﺘﺞ ﺗﻮﺻﻒ ﺑﻌﺾ ﺍﳌﻨﺘﺠﺎﺕ ﺍﻟﺪﻫﻨﻴﺔ ﺑﺄﳖﺎ ﺯﻳﻮﺕ ﻧﺒﺎﺗﻴﺔ ﹸﻣ ﹶﻬﺪﹾ ﹶﺭﺟﺔ‪،‬‬ ‫ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ‪.‬‬
‫ﻭﻫﻲ ﺯﻳﻮﺕ ﺗﻔﺎﻋﻠﺖ ﻣﻊ ﺍﳍﻴﺪﺭﻭﺟﲔ ﺑﻮﺟﻮﺩ ﻋﺎﻣﻞ ﳏﻔﺰ‪ .‬ﻣﺎ ﺳﺒﺐ ﺗﻔﺎﻋﻞ‬ ‫ﺍﳌﺼﺪﺭﺍﻥ ﺍﻟﺮﺋﻴﺴﺎﻥ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﳘﺎ‬
‫ﻭﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ‪ .‬‬ ‫ﺍﳍﻴﺪﺭﻭﺟﲔ ﻣﻊ ﻫﺬﻩ ﺍﻟﺰﻳﻮﺕ؟‬ ‫ﺍﻟﻨﻔﻂ ﻭﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ‪.‬‬
‫ﻓﴪ ﺍﻟﺒﻴﺎﻧﺎﺕ ﺍﻋﺘﲈﺩﹰﺍ ﻋﲆ ﺍﻟﺸﻜﻞ ‪ .8-6‬ﻣﺎ ﺗﺄﺛﲑ ﺃﻋﺪﺍﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ‬ ‫ﻣﻜﻮﻧﺎﺗﻪ ﻋﻦ ﻃﺮﻳﻖ ‪ .7‬ﹼ‬
‫ﻳﻤﻜﻦ ﻓﺼﻞ ﺍﻟﻨﻔﻂ ﺇﱃ ﹼ‬
‫ﻣﻜﻮﻥ ﻧﻔﻄﻲ ﻋﻨﺪﻣﺎ ﹸﻳ ﱠﱪﺩ ﺇﱃ ﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ – ﰲ ﻟﺰﻭﺟﺔ ﺃﻱ ﹼ‬ ‫ﻋﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ‪.‬‬
‫إﻋﺎدة اﻟﺘﺪرﻳﺲ‬ ‫ﺍﻟﻐﺮﻓﺔ؟‬

‫ﺍﺳـﺄﻝ ﺍﻟﻄﻼﺏ ﳌـﺎﺫﺍ ﻳﺴـﺘﺨﺪﻡ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﺃﺭﺑـﻊ ﻃﺮﺍﺋﻖ ﳐﺘﻠﻔﺔ‬

‫ﺃﻧﻮﺍﻋﺎ‬
‫ﻟﻨﻤﺬﺟﺔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪ .‬ﺗﻌﻄﻲ ﺍﻟﻨﲈﺫﺝ ﺍﳌﺨﺘﻠﻔﺔ ﺍﻷﺭﺑﻌﺔ ﹰ‬
‫ﳐﺘﻠﻔﺔ ﻣﻦ ﺍﳌﻌﻠﻮﻣﺎﺕ ﻋﻦ ﺍﳉﺰﻱﺀ‪ .‬‬

‫اﻟﺘﻮﺳﻊ‬
‫ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺭﺳﻢ ﺛﻼﺛﺔ ﻧﲈﺫﺝ ﳐﺘﻠﻔﺔ ﻟﻠﻤﻴﺜﺎﻥ‪ ،‬ﻭﺍﺫﻛﺮ ﻣﻴﺰﺓ‬

‫اﻟﺘﻘﻮﻳﻢ ‪8-1‬‬
‫ﻭﺍﺣﺪﺓ ﻟﻜﻞ ﻧﻤﻮﺫﺝ‪ .‬‬

‫ﻋـﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ‪ .‬ﻭﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‬ ‫ﺗﻄﺒﻴﻘـﺎﺕ ﳏﺘﻤﻠﺔ‪ :‬ﻭﻗﻮﺩ ﻟﺘﺪﻓﺌﺔ ﺍﳌﻨـﺎﺯﻝ‪ ،‬ﻭﻣﻮﺍﺩ ﺃﻭﻟﻴﺔ ﻟﺘﺼﻨﻴﻊ‬ ‫‪.1‬‬
‫ﻏـﲑ ﺍﳌﺸـﺒﻌﺔ ﻫﻲ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﲢﺘﻮﻱ ﻋـﲆ ﺍﻷﻗﻞ ﺭﺍﺑﻄﺔ‬ ‫ﺍﳌﻨﺘﺠﺎﺕ ﺍﻟﺒﻼﺳﺘﻴﻜﻴﺔ‪ ،‬ﻭﺍﻷﻓﻼﻡ‪ ،‬ﻭﺍﻷﻧﺴﺠﺔ ﺍﻟﺼﻨﺎﻋﻴﺔ‪.‬‬
‫ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬ ‫ﺇﺟﺎﺑﺔ ﳏﺘﻤﻠﺔ‪ :‬ﻣﻴﺜﺎﻥ؛ ﻳﺪﺭﺱ ﻋﺎﱂ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ ﺍﳌﺮﻛﺒﺎﺕ‬ ‫‪.2‬‬
‫ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌـﻲ‪ :‬ﻋﻤﻠﻴﺔ ﻓﺼﻞ ﺍﻟﻨﻔﻂ ﺇﱃ ﻣﻜﻮﻧﺎﺗﻪ ﺑﺎﻻﻋﺘﲈﺩ‬ ‫‪.5‬‬ ‫ﺍﳌﺤﺘﻮﻳـﺔ ﻋـﲆ ﺍﻟﻜﺮﺑـﻮﻥ ﲨﻴﻌﻬـﺎ ﻣﺎ ﻋـﺪﺍ ﺃﻛﺎﺳـﻴﺪ ﺍﻟﻜﺮﺑﻮﻥ‪،‬‬
‫ﻋﲆ ﺍﺧﺘﻼﻑ ﺩﺭﺟﺎﺕ ﺍﻟﻐﻠﻴﺎﻥ ﺑﻮﺻﻔﻬﺎ ﻃﺮﻳﻘﺔ ﻟﻠﻔﺼﻞ‪.‬‬ ‫ﻭﺍﻟﻜﺮﺑﻴﺪﺍﺕ‪ ،‬ﻭﺍﻟﻜﺮﺑﻮﻧﺎﺕ‪.‬‬
‫ﻓﺮﺿﻴﺔ ﳏﺘﻤﻠﺔ‪ :‬ﺗﺘﻔﺎﻋﻞ ﺍﻟﺰﻳﻮﺕ ﻣﻊ ﺍﳍﻴﺪﺭﻭﺟﲔ ﻋﻨﺪﻣﺎ ﺗﻨﻜﴪ‬ ‫‪.6‬‬ ‫ﺗﻮﺿﺢ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧـﻮﻉ ﺍﻟﺬﺭﺍﺕ ﰲ ﺍﳉﺰﻱﺀ‪ ،‬ﺃﻣﺎ ﺍﻟﺼﻴﻐﺔ‬ ‫‪.3‬‬
‫ﺍﻟﺮﻭﺍﺑـﻂ ﺍﻟﺜﻨﺎﺋﻴـﺔ ﺃﻭ ﺍﻟﺜﻼﺛﻴـﺔ‪ ،‬ﻭﺗﺮﺗﺒـﻂ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟـﲔ‬ ‫ﺍﻟﺒﻨﺎﺋﻴـﺔ ﻓﺘﻮﺿﺢ ﺍﻟﱰﺗﻴـﺐ ﺍﻟﻌﺎﻡ ﻟﻠﺬﺭﺍﺕ‪ .‬ﻛـﲈ ﻳﻮﺿﺢ ﻧﻤﻮﺫﺝ‬
‫ﺑﺎﳉﺰﻱﺀ‪.‬‬ ‫ﲑﺍ ﻳﻮﺿﺢ ﺍﻟﻨﻤﻮﺫﺝ ﺍﻟﻔﺮﺍﻏﻲ‬
‫ﺍﻟﻜﺮﺓ ﻭﺍﻟﻌﺼﺎ ﺷﻜﻞ ﺍﳉﺰﻱﺀ‪ .‬ﻭﺃﺧ ﹰ‬
‫ﻛﻠـﲈ ﺯﺍﺩ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺳﻠﺴـﻠﺔ ﺍﳉـﺰﻱﺀ‪ ،‬ﺍﺯﺩﺍﺩﺕ‬ ‫‪.7‬‬ ‫ﺻﻮﺭﺓ ﻭﺍﻗﻌﻴﺔ ﻋﻦ ﺍﳍﻴﺌﺔ ﺍﻟﺘﻲ ﻳﺒﺪﻭ ﻋﻠﻴﻬﺎ ﺍﳉﺰﻱﺀ‪.‬‬
‫ﺍﳌﻜﻮﻥ‪.‬‬
‫ﻟﺰﻭﺟﺔ ﹼ‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸـﺒﻌﺔ ﻫﻲ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﲢﺘﻮﻱ ﻓﻘﻂ‬ ‫‪.4‬‬

‫‪135‬‬
 ‫‪8-2‬‬
‫‪8-2‬‬
‫اﻫﺪاف‬
‫ا“ﻟﻜﺎﻧﺎت ‪Alkanes‬‬ ‫‪  ‬ﺍﻷﻟﻜﺎﻧﺎﺕ ﻣﻦ ﺧﻼﻝ ﹼ‬
‫ﺗﻔﺤﺺ‬
‫‪‬‬
‫‪ .1‬اﻟﺘﺮﻛﻴﺰ‬
‫اﻟﺮﺋﻴﺴﺔ‬ ‫اﻟﻔﻜﺮة‬
‫ﺻﻴﻐﻬﺎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫‪‬‬
‫‪  ‬ﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻸﻟـﻜﺎﻥ ﺇﺫﺍ‬
‫‪ ‬ﻫﻞ ﺳﺒﻖ ﺃﻥ ﺍﺳﺘﺨﺪﻣﺖ ﳍﺐ ﺑﻨﺰﻥ ﺃﻭ ﺷﻮﺍﻳﺔ ﻏﺎﺯ؟ ﺇﺫﺍ ﻓﻌﻠﺖ ﺫﻟﻚ‬ ‫ﹸﺃﻋﻄﻴﺖ ﺍﺳﻤﻪ‪.‬‬
‫ﺗﻜﻮﻥ ﻗﺪ ﺍﺳﺘﺨﺪﻣﺖ ﺃﻟﻜﺎﻧ ﹰﺎ‪ .‬ﻓﺎﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﻭﺍﻟﱪﻭﺑﺎﻥ ﳘﺎ ﺍﻟﻐﺎﺯﺍﻥ ﺍﻷﻛﺜﺮ ﺍﺳﺘﺨﺪﺍ ﹰﻣﺎ‪،‬‬
‫ﻭﻛﻼﳘﺎ ﺃﻟﻜﺎﻥ‪.‬‬
‫‪  ‬ﺧﺼﺎﺋﺺ ﺍﻷﻟﻜﺎﻧﺎﺕ‪.‬‬ ‫‪‬‬
‫ﻣﺮاﺟﻌﺔ اﻟﻤﻔﺮدات‬
‫‪ ‬ا¶ﻟﻜﺎﻧﺎت ذات اﻟﺴﻼﺳﻞ اﻟﻤﺴﺘﻘﻴﻤﺔ‬ ‫ﻗﺒﻞ ﺑﺪﺀ ﺍﻟـﺪﺭﺱ‪ ،‬ﺍﻋﺮﺽ ﻋﲆ ﺍﻟﻄﻼﺏ ﴍﳛـﺔ ﺍﻟﱰﻛﻴﺰ ﺭﻗﻢ‬
‫‪Straight-Chain Alkanes IUPAC‬‬
‫ﹸﻳﻌﺪﹼ ﺍﳌﻴﺜﺎﻥ ﺃﺻﻐﺮ ﻣﺮﻛﺐ ﰲ ﺳﻠﺴﻠﺔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﻌﺮﻭﻓﺔ ﺑﺎﻷﻟﻜﺎﻧﺎﺕ‪ .‬ﻭﻳﺘﺨﺬ‬ ‫ﻣﻨﻈﻤﺔ ﺩﻭﻟﻴﺔ ﺗﺴﺎﻋﺪ ﻋﲆ ﺍﻟﺘﻮﺍﺻﻞ ﺑﲔ‬
‫)‪ (28‬ﺍﻟـﻮﺍﺭﺩﺓ ﰲ ﻣﺼﺎﺩﺭ ﺍﻟﺘﻌﻠﻢ ﻟﻠﻔﺼﻮﻝ )‪ ،(5-8‬ﻭﻳﻤﻜﻨﻚ‬
‫ﻭﻗﻮﺩﹰﺍ ﰲ ﺍﳌﻨﺎﺯﻝ ﻭﳐﺘﱪﺍﺕ ﺍﻟﻌﻠﻮﻡ‪ ،‬ﻭﻫﻮ ﻳﻨﺘﺞ ﻋﻦ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﻟﻌﻤﻠﻴﺎﺕ ﺍﳊﻴﻮﻳﺔ‪ .‬ﻭﲢﺘﻮﻱ‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻭﻫﻲ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪ ،‬ﻋﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ ﻓﻘﻂ ﺑﲔ ﺍﻟﺬﺭﺍﺕ‪ .‬ﺍﻧﻈﺮ ﺇﱃ ﺍﻟﻨﲈﺫﺝ‬
‫ﺍﻟﻜﻴﻤﻴﺎﺋﻴﲔ ﻣﻦ ﺧﻼﻝ ﻭﺿﻊ ﻗﻮﺍﻋﺪ‬ ‫ﻋﺮﺿﻬﺎ ﻣﻠﻮﻧﺔ ﻣﻦ ﺧﻼﻝ ﺍﻟﺮﺟﻮﻉ ﺇﱃ ﺍﳌﻮﻗﻊ ﺍﻹﻟﻜﱰﻭﲏ‪ :‬‬
‫ﻭﻣﻌﺎﻳﲑ ﻟﺒﻌﺾ ﺍﳌﺠﺎﻻﺕ ﻣﺜﻞ ﺍﻟﺘﺴﻤـﻴـﺔ‬
‫ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﻴﺜﺎﻥ ﺍﻟﺘﻲ ﺩﺭﺳﺘﻬﺎ ﺳﺎﺑ ﹰﻘﺎ‪ .‬ﻛﲈ ﻳﺒﲔ ﺍﳉﺪﻭﻝ ‪ 8-1‬ﺍﻟﻨﲈﺫﺝ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻺﻳﺜﺎﻥ ‪C2H6‬‬
‫ﻣﻌﺎ ﺑﺮﺍﺑﻄﺔ‬
‫ﺍﻟﻜﻴـﻤﻴﺎﺋﻴﺔ‪ ،‬ﻭﺍﳌﺼﻄﻠﺤـﺎﺕ‪ ،‬ﻭﺍﻟﻄـﺮﺍﺋﻖ‬
‫‪www.obeikaneducation.com‬‬
‫ﺍﳌﺮﻛﺐ ﺍﻟﺜﺎﲏ ﰲ ﺳﻠﺴﻠﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ .‬ﻭﻳﺘﺄﻟﻒ ﺍﻹﻳﺜﺎﻥ ﻣﻦ ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﻣﺮﺗﺒﻄﺘﲔ ﹰ‬ ‫ﺍﳌﻌـﻴﺎﺭﻳﺔ‪.‬‬
‫ﺃﺣﺎﺩﻳﺔ‪ ،‬ﻭﺳﺖ ﺫﺭﺍﺕ ﻫﻴﺪﺭﻭﺟﲔ ﺗﺘﺸﺎﺭﻙ ﰲ ﺇﻟﻜﱰﻭﻧﺎﺕ ﺍﻟﺘﻜﺎﻓﺆ ﺍﳌﺘﺒﻘﻴﺔ ﻟﺬﺭﰐ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬
‫اﻟﻤﻔﺮدات اﻟﺠﺪﻳﺪة‬
‫ﺍﳌﺮﻛﺐ ﺍﻟﺜﺎﻟﺚ ﰲ ﺳﻠﺴﻠﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﺍﻟﱪﻭﺑﺎﻥ‪ ،‬ﻣﻦ ﺛﻼﺙ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﻭﺛﲈﲏ‬ ‫ﻭﻳﺘﻜﻮﻥ ﹼ‬ ‫اﻟﺮﺋﻴﺴﺔ‬ ‫اﻟﻔﻜﺮة‬
‫ﺍﻷﻟﻜﺎﻥ‬
‫ﺫﺭﺍﺕ ﻫﻴﺪﺭﻭﺟﲔ‪ ،‬ﳑﺎ ﻳﻌﻄﻴﻪ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ‪ .C3H8‬ﺃﻣﺎ ﻣﺮﻛﺐ ﺍﻟﺒﻴﻮﺗﺎﻥ ﻓﻴﺘﻜﻮﻥ ﻣﻦ ﺃﺭﺑﻊ‬‫ﹼ‬
‫ﺍﻟﺴﻠﺴﻠﺔ ﺍﳌﺘﲈﺛﻠﺔ‬
‫ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﻭﺻﻴﻐﺘﻪ ‪ .C4H10‬ﻗﺎﺭﻥ ﺑﲔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻜﻞ ﻣﻦ ﺍﻹﻳﺜﺎﻥ‪ ،‬ﻭﺍﻟﱪﻭﺑﺎﻥ‪،‬‬
‫ﻭﺍﻟﺒﻴﻮﺗﺎﻥ‪ ،‬ﺍﳌﺒﻴﻨﺔ ﰲ ﺍﳉﺪﻭﻝ ‪.8-1‬‬ ‫ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ‬ ‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺗﻌﺮﻳـﻒ ﺍﻟﺮﺍﺑﻄـﺔ‬
‫ﺍﳌﺠﻤﻮﻋﺔ ﺍﻟﺒﺪﻳﻠﺔ‬
‫‪‬‬ ‫‪81‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳊﻠﻘﻲ‬
‫ﺸـﺎﺭﻙ ﺯﻭﺝ ﻣﻦ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺑﲔ ﺫﺭﺗﲔ‪ .‬ﻭﺍﺳـﺄﻝ‪:‬‬‫ﺍﻷﺣﺎﺩﻳـﺔ‪ .‬ﹶﺗ ﹸ‬
‫ﻛﻴﻒ ﹸ ﹶﲤﺜﱠـﻞ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻷﺣﺎﺩﻳﺔ ﰲ ﺍﻟﻨﲈﺫﺝ ﺍﻟﺒﻨﺎﺋﻴﺔ؟ ﻣﻦ ﺧﻼﻝ ﺧﻂ‬
‫— —— — —‬
‫—‬

‫‪H‬‬ ‫‪H‬‬ ‫‪¿ÉãjE’G‬‬

‫‪H — CH— CH— H‬‬
‫‪‬‬ ‫‪‬‬ ‫‪‬‬ ‫‪‬‬ ‫ﺍﻷﻟﻜﺎﻥ ﺍﳊﻠﻘﻲ‬
‫— —— ——‬
‫— —— ——‬

‫‪¿ÉãjE’G‬‬ ‫‪(C‬‬ ‫’‪2H‬‬ ‫‪6)G‬‬

‫—‬

‫‪H —HC —HC — H‬‬ ‫‪¿ÉãjE‬‬

‫—‬

‫‪(C2H‬‬
‫‪¿ÉãjE‬‬ ‫)‪’6G‬‬ ‫—‪H‬‬
‫‪H C —HC — H‬‬
‫‪H —HH‬‬
‫‪C —HC‬‬ ‫—‬
‫‪H H‬‬
‫)‪(C2H6‬‬ ‫‪H‬‬ ‫‪H‬‬
‫—‬

‫‪H H HH‬‬ ‫)‪(C2H6‬‬

‫ﻗﺼـﲑ ﺃﻭ ﴍﻃﺔ )‪ (-‬ﺗﺮﺑﻂ ﺑﲔ ﺫﺭﺗﲔ‪ ،‬ﺃﻭ ﺯﻭﺝ ﻣﻦ ﺍﻟﻨﻘﻂ)‪ (:‬ﺑﲔ‬

‫‪H‬‬ ‫‪H‬‬
‫—‬

‫‪¿ÉãjE’G‬‬
‫—‬
‫—‬

‫‪¿ÉãjE¿ÉãjE‬‬
‫‪’G ’G‬‬ ‫‪¿ÉãjE’G‬‬
‫—‬
‫—‬

‫‪(C2(C‬‬
‫‪H62)H6) ¿ÉãjE’G‬‬
‫——‬
‫‪HH‬‬ ‫——‬
‫‪CC‬‬ ‫‪CHC——HHH‬‬ ‫‪H —H‬‬
‫‪C — CH— H‬‬ ‫‪H—C—C—H‬‬
‫)‪(C2H6‬‬ ‫)‪(C2H6‬‬
‫—‬
‫—‬
‫—‬

‫— —‬
‫—‬
‫—‬

‫—‬
‫—‬
‫—‬
‫—‬

‫— ‪H HH‬‬
‫‪HCH— C — H‬‬
‫)‪(C2H6‬‬ ‫‪H H‬‬ ‫‪HH HHH‬‬
‫—‬

‫‪H‬‬ ‫‪H‬‬ ‫‪H H H‬‬ ‫‪¿ÉHhÈdG‬‬

‫ﺫﺭﺗـﲔ‪ .‬ﻭﺃﺧﱪﻫـﻢ ﺃﻥ ﺍﳍﻴﺪﺭﻭﻛﺮﺑـﻮﻥ ﺍﻟﺬﻱ ﳛﺘـﻮﻱ ﻋﲆ ﺭﻭﺍﺑﻂ‬

‫— —‬
‫— —‬
‫—‬

‫‪¿ÉHhÈdG‬‬
‫— —— —‬
‫— —— —‬
‫— —— —‬

‫‪H —HC —H‬‬ ‫‪C —HC — H‬‬ ‫)‪(C3H8‬‬ ‫‪H — CH— CH— CH— H‬‬
‫‪H H H H HH‬‬ ‫‪¿ÉHhÈdG‬‬
‫)‪(C3H8‬‬ ‫‪¿ÉHhÈdG‬‬
‫—‬
‫—‬
‫—‬
‫—‬

‫‪¿ÉHhÈdG‬‬
‫‪¿ÉHhÈdG‬‬
‫— —‬
‫— ———‬

‫—‬

‫‪H H H‬‬
‫‪H —HCH —HC‬‬
‫‪H —HC‬‬
‫‪H— H‬‬
‫— —‬
‫— —‬

‫—— ——‬

‫‪—— C‬‬
‫‪¿ÉHhÈdG H‬‬ ‫‪—— C‬‬‫‪—— C—— H‬‬ ‫)‪(C3H8‬‬ ‫‪HC —HC —HC — H‬‬
‫‪H —H‬‬
‫—‬

‫‪H83)H8) (C H ) H C H —CC —CC — CH— H‬‬

‫‪(C3(C‬‬ ‫‪¿ÉHhÈdG‬‬ ‫)‪(C3H8‬‬ ‫‪H H‬‬
‫—‬

‫—‬
‫—‬
‫—‬

‫ﺃﺣﺎﺩﻳﺔ ﻓﻘﻂ ﰲ ﺑﻨﺎﺋﻪ ﻳﺴﻤﻰ ﺍﻷﻟﻜﺎﻥ‪ .‬‬

‫——‬

‫—‬
‫—‬

‫‪3 8‬‬
‫‪H H H H HH‬‬ ‫‪H — CH— CH — H‬‬ ‫‪¿ÉHhÈdG‬‬
‫—‬
‫—‬

‫‪H—C‬‬
‫—‬

‫)‪(C3H8‬‬ ‫‪H — CH— CH— CH— H‬‬

‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫—‬
‫—‬
‫—‬

‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫)‪(C3H8‬‬

‫—‬
‫—‬
‫—‬

‫‪¿ÉJƒ«ÑdG‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H HH HH HH‬‬

‫‪¿ÉJƒ«ÑdG‬‬ ‫‪H H H HH H‬‬
‫‪H HH HH H‬‬ ‫‪¿ÉJƒ«ÑdG‬‬
‫— —‬
‫— —‬
‫— —‬
‫— —‬

‫‪¿ÉJƒ«ÑdG ¿ÉJƒ«ÑdG‬‬
‫— ——‬
‫— ——‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬

‫‪H —H‬‬
‫‪C —H‬‬
‫‪C —H‬‬
‫‪C —H‬‬
‫—‬
‫——‬
‫——‬
‫—‬

‫‪C—H‬‬
‫—‬
‫—‬

‫‪(C H )(C HH) H‬‬ ‫—‪—C‬‬

‫‪—CH‬‬
‫—‪— C‬‬
‫——‪— C——CC‬‬
‫‪— CC— CC— C‬‬
‫‪H‬‬
‫—‬
‫‪— CH H‬‬ ‫‪¿ÉJƒ«ÑdG‬‬
‫)‪(C4H10‬‬
‫)‪(C4H10‬‬ ‫‪H—C—C—C—C—H‬‬
‫‪(C4H104 ) 10 4 10‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫— —‬
‫— —‬
‫— —‬
‫— —‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫——‬
‫——‬
‫—‬

‫‪ .2‬اﻟﺘﺪرﻳﺲ‬
‫‪H —H‬‬
‫‪CH— H‬‬
‫‪CH—HC‬‬
‫‪H —HC‬‬
‫‪H—H‬‬ ‫‪¿ÉJƒ«ÑdG‬‬
‫—‬
‫—‬
‫—‬
‫—‬

‫‪H HH HH HH H‬‬ ‫‪(C‬‬ ‫)‪4H10‬‬

‫‪¿ÉJƒ«ÑdG‬‬
‫—‬
‫—‬

‫‪H H H H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬

‫—‬
‫—‬
‫—‬

‫)‪(C4H10‬‬ ‫‪H — CH— CH— CH— CH— H‬‬ ‫‪(C‬‬ ‫)‪4H10‬‬

‫‪¿ÉJƒ«ÑdG‬‬ ‫‪H —HC —HC —HC —H C — H‬‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬
‫—‬

‫‪C22-106C-828378-08‬‬
‫‪C22-106C-828378-08‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫)‪(C4H10‬‬ ‫‪H — CH— CH— CH— CH— H‬‬
‫‪06C-828378-08‬‬
‫‪6C-828378-08‬‬ ‫‪C22-106C-828378-08‬‬ ‫‪C22-106C-828378-08‬‬
‫—‬
‫—‬
‫—‬
‫—‬

‫‪-828378-08‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H C22-106C-828378-08‬‬

‫‪C22-106C-828378-08‬‬
‫‪C22-106C-828378-08‬‬
‫‪C22-106C-828378-08‬‬
‫‪C22-106C-828378-08‬‬

‫ﻋﺮض ﺳﺮﻳﻊ‬

‫‪A‬‬ ‫‪B‬‬ ‫‪C‬‬ ‫‪D‬‬ ‫ﺍﳌﺴـﺘﺨﺪﻡ‪E A F BAG ACB‬‬

‫ﺍﻟﻐﺎﺯ‪C I CED‬‬
‫‪H BD‬‬ ‫‪J DFE‬‬‫ﻧـﻮﻉ‬
‫‪K EG‬‬‫ﻋـﻦ‬
‫ﺍﺑﺤـﺚ ‪F L‬‬ ‫‪‬‬
‫‪FHGM GHIN‬‬ ‫‪HJIO IK‬‬‫‪‬‬
‫‪JP JLK KML‬‬ ‫‪N‬‬
‫‪LM‬‬ ‫‪ON‬‬
‫‪M‬‬
‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬
‫ﰲ ﺍﳌﺨﺘـﱪ‪ .‬ﺗﺴـﺘﺨﺪﻡ ﻣﻌﻈـﻢ ﺍﳌﺨﺘـﱪﺍﺕ ﺍﻟﻐـﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﺃﻭ‬
‫‪ ‬ﺍﻟﻔﺖ ﻧﻈـﺮ ﺍﻟﻄﻼﺏ ﺇﱃ ﺃﻧﻪ ﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺃﻥ ﺃﺳـﲈﺀ‬ ‫ﺍﻟﱪﻭﺑـﺎﻥ‪ .‬ﺍﺷـﻌﻞ ﻣﻮﻗﺪ ﺑﻨـﺰﻥ ﺃﻣـﺎﻡ ﺍﻟﻄـﻼﺏ ﹼ‬
‫ﺑﺎﻟﻮﻻﻋﺔ‪ ،‬ﺛﻢ‬
‫ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﻟﺘـﻲ ﺗﺘﻜﻮﻥ ﻣﻦ ﲬـﺲ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﻭ ﺃﻛﺜـﺮ ﻭﲢﺘﻮﻱ ﻋﲆ‬ ‫ﻛﻼ ﻣﻦ ﹼ‬
‫ﺍﻟﻮﻻﻋﺔ ﻭﻣﻮﻗﺪ ﺑﻨﺰﻥ ﻳﺴﺘﺨﺪﻡ ﻓﻴﻪ ﺃﻟﻜﺎﻥ‬ ‫ﺃﺧﱪﻫﻢ ﺃﻥ ﹼﹰ‬
‫ﺑﺎﺩﺋﺎﺕ ﻣﺸﺘﻘﺔ ﻣﻦ ﺍﻟﻴﻮﻧﺎﻧﻴﺔ ﺃﻭ ﺍﻹﻏﺮﻳﻘﻴﺔ‪ ،‬ﺇﻻ ﺃﻥ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ‬ ‫ﺑﻮﺻﻔـﻪ ﻭﻗـﻮ ﹰﺩﺍ‪ .‬ﻓﻴﺴـﺘﺨﺪﻡ ﰲ ﹼ‬
‫ﺍﻟﻮﻻﻋـﺔ ﺍﻟﺒﻴﻮﺗـﺎﻥ‪ ،‬ﰲ ﺣـﲔ‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﻷﺻﻐﺮ ﺳـﻤﻴﺖ ﻭﻓﻖ ﻣﺼﺎﺩﺭ ﳐﺘﻠﻔﺔ‪ .‬ﻟﺬﺍ ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ‬ ‫ﻳﺴـﺘﺨﺪﻡ ﰲ ﻣﻮﻗﺪ ﺑﻨﺰﻥ ﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﺃﻭ ﺍﻟﱪﻭﺑﺎﻥ‪ .‬ﻭﺍﻃﻠﺐ‬
‫ﺍﻟﺒﺤـﺚ ﻋﻦ ﺃﺻﻞ ﺍﻟﺒﺎﺩﺋﺎﺕ ﺍﳌﺴـﺘﺨﺪﻣﺔ ﰲ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ‬ ‫ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﳌﻘﺎﺭﻧـﺔ ﺑـﲔ ﺍﻟﻠﻬﺒـﲔ‪ .‬ﳚﺐ ﺃﻥ ﻳﺒـﺪﻭ ﻛﻞ ﻣﻨﻬﲈ‬
‫ﺫﺭﺓ ﺇﱃ ﺃﺭﺑﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﰲ ﺻﻮﺭﺓ ﺳﻠﺴﻠﺔ ﻣﺴﺘﻘﻴﻤﺔ‪ .‬ﻭﻋﻠﻴﻬﻢ ﺗﺴﺠﻴﻞ‬ ‫ﻣﺜﻞ ﺍﻵﺧﺮ‪ .‬ﻭﺗﻌﻮﺩ ﺍﺧﺘﻼﻓﺎﺕ ﺍﻟﻠﻮﻥ ﺇﱃ ﻧﺴـﺒﺔ ﺍﻷﻛﺴﺠﲔ ﰲ‬
‫ﺍﳌﻌﻠﻮﻣﺎﺕ ﺍﻟﺘﻲ ﺗﻮﺻﻠﻮﺍ ﺇﻟﻴﻬﺎ ﰲ ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ‪ .‬‬ ‫ﳐﻠﻮﻁ ﺍﻷﻛﺴﺠﲔ ﻭﺍﻟﻐﺎﺯ‪ .‬‬

‫‪136‬‬
 ‫‪‬‬ ‫‪82‬‬

‫اﺳﺘﺨﺪام اﻟﻤﻔﺮدات اﻟﻌﻠﻤﻴﺔ‬ ‫‪‬‬

‫‪‬‬
‫‪‬‬
‫‪‬‬

‫‪CH 4‬‬ ‫‪CH 4‬‬ ‫ﻣﻴﺜﺎﻥ‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻛﺘﺎﺑﺔ ﻋﺒﺎﺭﺍﺕ ﺗﻔﴪ ﻣﻌﻨﻰ‬ ‫‪CH 3CH 3‬‬ ‫‪C 2H 6‬‬ ‫ﺇﻳﺜﺎﻥ‬
‫ﺑﺮﻭﺑﺎﻥ‬
‫ﱟ‬
‫‪CH 3CH 2CH 3‬‬ ‫‪C 3H 8‬‬
‫ﻛﻞ ﻣﻦ ﺍﳌﺼﻄﻠﺤﲔ "ﺳﻠﺴﻠﺔ ﻣﺘﲈﺛﻠﺔ" ﻭ" ﳎﻤﻮﻋﺔ ﺑﺪﻳﻠﺔ"‪ .‬‬ ‫‪CH 3CH 2CH 2CH 3‬‬ ‫‪C 4H 10‬‬ ‫ﺑﻴﻮﺗﺎﻥ‬
‫‪CH 3CH 2CH 2CH 2CH 3‬‬ ‫‪C 5H 12‬‬ ‫ﺑﻨﺘﺎﻥ‬
‫‪CH 3CH 2CH 2CH 2CH 2CH 3‬‬ ‫‪C 6H 14‬‬ ‫ﻫﻜﺴﺎﻥ‬
‫‪CH 3CH 2CH 2CH 2CH 2CH 2CH 3‬‬ ‫‪C 7H 16‬‬ ‫ﻫﺒﺘﺎﻥ‬
‫ﺃﻭﻛﺘﺎﻥ‬
‫اﻟﺘﻘﻮﻳﻢ‬ ‫‪CH 3(CH 2) 6CH 3‬‬
‫‪CH 3(CH 2) 7CH 3‬‬
‫‪C 8H 18‬‬
‫‪C 9H 20‬‬ ‫ﻧﻮﻧﺎﻥ‬
‫‪CH 3(CH 2) 8CH 3‬‬ ‫‪C 10H 22‬‬ ‫ﺩﻳﻜﺎﻥ‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﻛﻞ ﻃﺎﻟﺐ ﻛﺘﺎﺑﺔ ﺳـﺆﺍﻝ ﻋﻦ ﳏﺘﻮ￯ ﺍﻟﺪﺭﺱ‪،‬‬ ‫ﺃﻳﻀﺎ ﺑﻐﺎﺯ )ﺍﻟﱪﻭﺑﺎﻥ ﺍ ﹸﳌﺴﺎﻝ( ‪ (LP) Liquified Propan‬ـ‬
‫ﹸﻳﺒﺎﻉ ﺍﻟﱪﻭﺑﺎﻥ ـ ﻭﺍﳌﻌﺮﻭﻑ ﹰ‬

‫ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺗﺒﺎﺩﻝ ﺍﻷﺳـﺌﻠﺔ ﻓﻴـﲈ ﺑﻴﻨﻬﻢ ﻭﺍﺧﺘﺒﺎﺭ ﺑﻌﻀﻬﻢ ﹰ‬

‫ﺑﻌﻀﺎ‪.‬‬ ‫ﰲ ﺻﻮﺭﺓ ﻭﻗﻮﺩ ﻟﻠﻄﺒﺦ ﻭﺍﻟﺘﺴﺨﲔ‪ .‬ﻭﻳﺴﺘﺨﺪﻡ ﺍﻟﺒﻴﻮﺗﺎﻥ ﰲ ﺍﻟﻘﺪﹼ ﺍﺣﺎﺕ ﺍﻟﺼﻐﲑﺓ‪ ،‬ﻭﰲ‬
‫ﺃﻳﻀﺎ ﰲ ﺗﺼﻨﻴﻊ ﺍﳌﻄﺎﻁ ﺍﻟﺼﻨﺎﻋﻲ‪.‬‬‫ﺑﻌﺾ ﺍﳌﺸﺎﻋﻞ‪ ،‬ﻛﲈ ﻳﺴﺘﺨﺪﻡ ﹰ‬
‫‪‬‬ ‫‪‬‬ ‫‪ ‬ﻟﻘﺪ ﻻﺣﻈﺖ ﻋﲆ ﺍﻷﻏﻠﺐ ﺃﻥ ﺃﺳﲈﺀ‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ ﺗﻨﺘﻬﻲ ﺑـ ﺍﳌﻘﻄﻊ "ﺍﻥ"‪ ،‬ﻭﺃﻥ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﻟﺘﻲ ﲢﻮﻱ ﲬﺲ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﻭ‬
‫ﺃﻛﺜﺮ ﺗﺒﺪﺃ ﺃﺳﲈﺅﻫﺎ ﺑﻤﻘﺎﻃﻊ ﻣﺸﺘﻘﺔ ﻣﻦ ﺃﺭﻗﺎﻡ ﻳﻮﻧﺎﻧﻴﺔ ﺃﻭ ﻻﺗﻴﻨﻴﺔ ﹸﲤﺜﻞ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‬
‫ﻣﺜﻼ ﻟﻪ ﲬﺲ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ ،‬ﲤﺎ ﹰﻣﺎ ﻛﺎﻟﺸﻜﻞ ﺍﳌﺨﻤﺲ ﺫﻱ ﺍﻷﻭﺟﻪ‬ ‫ﰲ ﻛﻞ ﺳﻠﺴﻠﺔ‪ .‬ﻓﺎﻟﺒﻨﺘﺎﻥ ﹰ‬
‫‪‬‬
‫ﺍﳋﻤﺴﺔ‪ ،‬ﻭﺍﻷﻭﻛﺘﺎﻥ ﳛﺘﻮﻱ ﻋﲆ ﺛﲈﻧﻴﺔ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﻣﺜﻞ ﺍﻷﺧﻄﺒﻮﻁ )‪ (octopus‬ﺫﻱ‬
‫‪‬‬
‫ﻳﻤﻜﻨـﻚ ﺗﻨﻔﻴﺬ ﳐﺘـﱪ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﳌﻮﺟﻮﺩ ﰲ‬ ‫ﹸﻣﺘﲈﺛﻞ ‪Homologous‬‬
‫ﺍﳌﺠ ﱠﺴﺎﺕ ﺍﻟﺜﲈﻧﻴﺔ‪ .‬ﺃﻣﺎ ﻣﺮﻛﺒﺎﺕ ﺍﳌﻴﺜﺎﻥ‪ ،‬ﻭﺍﻹﻳﺜﺎﻥ‪ ،‬ﻭﺍﻟﱪﻭﺑﺎﻥ‪ ،‬ﻭﺍﻟﺒﻴﻮﺗﺎﻥ ﻓﻘﺪ ﹸﺳﻤﻴﺖ ﹶ‬
‫ﻗﺒﻞ‬
‫ﻣﻌﺮﻓﺔ ﺑﻨﺎﺀ )ﺗﺮﻛﻴﺐ( ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻟﺬﺍ ﻓﺈﻥ ﺍﳌﻘﺎﻃﻊ ﺍﻷﻭﱃ ﻣﻦ ﺃﺳﲈﺋﻬﺎ ﻟﻴﺴﺖ ﻣﺸﺘﻘﺔ ﻣﻦ‬
‫ﹶ‬
‫ﺟﺎﺀﺕ ﻣﻦ ﺍﻟﻜﻠﻤﺔ ﺍﻹﻏﺮﻳﻘﻴﺔ‬
‫ﳖﺎﻳﺔ ﺍﻟﻔﺼﻞ ﰲ ﻫﺬﻩ ﺍﳌﺮﺣﻠﺔ ﻣﻦ ﺍﻟﺪﺭﺱ‪.‬‬ ‫)‪ (homologos‬ﻭﺗﻌﻨﻲ ﹸﻣﺘ ﹺﹼﻔﻖ‪.‬‬ ‫ﺑﺎﺩﺋﺔ ﺭﻗﻤﻴﺔ‪ .‬ﻭ ﹸﻳﻈﻬﺮ ﺍﳉﺪﻭﻝ ‪ 8-2‬ﺃﺳﲈﺀ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﻟﻌﴩﺓ ﺍﻷﻭﱃ ﻭﺻﻴﻐﻬﺎ‪ .‬ﻻﺣﻆ ﺃﻥ‬
‫ﺍﳌﻘﻄﻊ ﺍﻷﻭﻝ ﺍﳌﺨﻄﻮﻁ ﲢﺘﻪ ﻳﻤﺜﻞ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﳉﺰﻱﺀ‪.‬‬
‫ﻋﲈ ﻫﻲ ﻋﻠﻴﻪ ﰲ‬ ‫ﻭﻳﺒﲔ ﺍﳉﺪﻭﻝ ‪ 8-2‬ﺃﻥ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻗﺪ ﹸﻛﺘﺒﺖ ﺑﻄﺮﻳﻘﺔ ﳐﺘﻠﻔﺔ ﹼ‬
‫ﺍﳉﺪﻭﻝ ‪ .8-1‬ﻭﺗﹸﺴﻤﻰ ﻫﺬﻩ ﺍﻟﺼﻴﻎ ﺑﺎﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﻜﺜﻔﺔ‪ ،‬ﺣﻴﺚ ﺗﻮﻓﺮ ﺍﳊﻴﺰ ﻟﻜﻮﳖﺎ ﻻ‬
‫ﺗﻈﻬﺮ ﺗﻔﺮﻉ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ .‬ﻭﻳﻤﻜﻦ ﻛﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﳌﻜﺜﻔﺔ ﺑﻄﺮﺍﺋﻖ‬
‫ﻋﺪﺓ‪ .‬ﻓﻔﻲ ﺍﳉﺪﻭﻝ ‪ 8-2‬ﺣﺬﻓﺖ ﺍﳋﻄﻮﻁ ﺍﻟﺘﻲ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻟﺘﻮﻓﲑ ﺍﳌﺴﺎﺣﺔ‪.‬‬
‫اﻟﺘﻘﻮﻳﻢ‬ ‫ﺃﻳﻀﺎ ﰲ ﻫﺬﺍ ﺍﳉﺪﻭﻝ ‪ ،8-2‬ﻣﻼﺣﻈﺔ ﺃﻥ‪ -CH2 -‬ﻫﻲ ﺍﻟﻮﺣﺪﺓ ﺍﳌﺘﻜﺮﺭﺓ ﰲ‬ ‫ﻭﺗﺴﺘﻄﻴﻊ ﹰ‬
‫ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﻜﺮﺑﻮﻧﻴﺔ‪ .‬ﻓﻌﲆ ﺳﺒﻴﻞ ﺍﳌﺜﺎﻝ‪ ،‬ﻳﺰﻳﺪ ﺍﻟﺒﻨﺘﺎﻥ ﻋﻦ ﺍﻟﺒﻴﻮﺗﺎﻥ ﺑﻮﺣﺪﺓ ‪ -CH2-‬ﻭﺍﺣﺪﺓ‪.‬‬

‫‪ ‬ﺑﻌـﺪ ﺃﻥ ﺗﻌﻠﻢ ﺍﻟﻄﻼﺏ ﺃﺳـﲈﺀ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﻟﻌﴩﺓ ﺍﻷﻭﱃ‬

‫ﺫﺍﺕ ﺍﻟﺴﻼﺳـﻞ ﺍﳌﺴـﺘﻘﻴﻤﺔ‪ ،‬ﺣﺪﱢ ﺩ ﻟـﻜﻞ ﻃﺎﻟﺐ ﺍﺳـﻤﻲ ﺃﻟﻜﺎﻧﲔ‪،‬‬
‫ﻭﺍﻃﻠـﺐ ﺇﻟﻴﻬﻢ ﻛﺘﺎﺑﺔ ﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﻜﺎﻣﻠﺔ ﻭﺍﳌﻜﺜﻔﺔ ﳍﲈ ﻭﻋﻤﻞ‬
‫ﻧﲈﺫﺝ ﲤﺜﻞ ﺟﺰﻳﺌﺎﲥﲈ‪ .‬‬

‫‪ ‬ﺳﻴﺠﺪ ﺑﻌﺾ ﺍﻟﻄﻼﺏ ﺃﻥ ﻣﻦ ﺍﻷﺳﻬﻞ ﺗﻌﻠﻢ ﻣﻌﻨﻰ ﺍﻟﺼﻴﻐﺔ‬

‫ﺍﻟﻌﺎﻣﺔ ﻟﻸﻟﻜﺎﻧﺎﺕ )‪ (C2H2n+2‬ﺇﺫﺍ ﺍﺳـﺘﺨﺪﻣﻮﻫﺎ ﰲ ﻋﻤﻞ ﻧﲈﺫﺝ ﻷﺷـﻜﺎﻝ‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ‪ .‬ﻟﺬﺍ ﺣﺪﹼ ﺩ ﻟﻜﻞ ﻃﺎﻟﺐ ﺃﻟﻜﺎ ﹰﻧﺎ ﻣﻌﻴﻨﹰﺎ‪ ،‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺍﺳـﺘﺨﺪﺍﻡ‬
‫ﺍﻟﺼﻴﻐـﺔ ﺍﻟﻌﺎﻣﺔ ﻟﺘﻮﻗـﻊ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ ﺍﻟﺬﻱ ﺳـﻮﻑ‬
‫ﳛﺘﺎﺟـﻮﻥ ﺇﻟﻴﻪ ﻟﻌﻤﻞ ﻧﻤﻮﺫﺝ ﺍﻷﻟـﻜﺎﻥ ﺍﳌﻌﻄﻰ ﳍﻢ‪ ،‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﻋﻤﻞ‬
‫ﺍﻟﻨﲈﺫﺝ ﻭﺍﺧﺘﺒﺎﺭ ﺗﻮﻗﻌﺎﲥﻢ‪ .‬‬

‫‪137‬‬
‫ﻭﺗﺴﺘﻄﻴﻊ ﺯﻳﺎﺩﺓ ﺗﻜﺜﻴﻒ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺑﻜﺘﺎﺑﺔ ﻭﺣﺪﺓ ‪ – CH2-‬ﺑﲔ ﻗﻮﺳﲔ‬ ‫‪ 8-9‬‬
‫ﻳﺘﺒﻌﻬﺎ ﺭﻗﻢ ﺳﻔﲇ ﻳﻤﺜﻞ ﻋﺪﺩ ﻫﺬﻩ ﺍﻟﻮﺣﺪﺍﺕ‪ ،‬ﻛﲈ ﻫﻮ ﺍﳊﺎﻝ ﻣﻊ ﺍﻷﻭﻛﺘﺎﻥ‪،‬‬
‫ﻭﺍﻟﻨﻮﻧﺎﻥ‪ ،‬ﻭﺍﻟﺪﻳﻜﺎﻥ‪.‬‬
‫‪‬‬ ‫‪.C13H28 ‬‬
‫‪‬‬
‫ﻭﺗﹸﺴﻤﻰ ﺳﻠﺴﻠﺔ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﺘﻲ ﳜﺘﻠﻒ ﺑﻌﻀﻬﺎ ﻋﻦ ﺑﻌﺾ ﰲ ﻋﺪﺩ ﺍﻟﻮﺣﺪﺓ‬
‫ﺍﳌﺘﻜﺮﺭﺓ ﺍﻟﺴﻠﺴﻠﺔ ﺍ ﹸﳌﺘﲈﺛﻠﺔ‪ .‬ﻭﳍﺬﻩ ﺍﻟﺴﻠﺴﻠﺔ ﺻﻴﻐﺔ ﺭﻗﻤﻴﺔ ﺛﺎﺑﺘﺔ ﺑﲔ ﺃﻋﺪﺍﺩ‬
‫ﺍﻟﺬﺭﺍﺕ‪ .‬ﻓﻔﻲ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻳﻤﻜﻦ ﻛﺘﺎﺑﺔ ﺍﻟﺼﻴﻐﺔ ﺍﻟﻌﺎﻣﺔ ﺍﻟﺘﻲ ﺗﺮﺑﻂ ﺑﲔ ﻋﺪﺩ‬
‫اﻟﺘﻮﺳﻊ‬
‫ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ ﻋﲆ ﺍﻟﻨﺤﻮ ﺍﻟﺘﺎﱄ ‪CnH2n+2‬؛ ﺣﻴﺚ ‪ n‬ﻋﺪﺩ‬
‫ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﻷﻟﻜﺎﻥ‪ .‬ﻭﺍﻵﻥ ﺗﺴﺘﻄﻴﻊ ﻛﺘﺎﺑﺔ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻷﻱ‬ ‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤﺚ ﻋﻦ ﻣﺼﺪﺭ ﺍﻟﻄﺎﻗﺔ ﺍﳌﺴﺘﺨﺪﻡ‬
‫ﺃﻟﻜﺎﻥ ﺇﺫﺍ ﺃﻋﻄﻴﺖ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻓﻴﻪ‪ .‬ﻓﻌﲆ ﺳﺒﻴﻞ ﺍﳌﺜﺎﻝ‪ ،‬ﳛﺘﻮﻱ‬
‫ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ ،‬ﻟﺬﺍ ﻓﺈﻥ ﺻﻴﻐﺘﻪ ﻫﻲ ‪ C7H2(7)+2‬ﺃﻭ ‪.C7H16‬‬
‫ﺍﳍﺒﺘﺎﻥ ﻋﲆ ﺳﺒﻊ‪‬‬ ‫‪‬‬ ‫ﰲ ﺗﺪﻓﺌﺔ ﺑﻴﻮﲥﻢ ﻭﺗﺴﺠﻴﻞ ﺍﳌﻌﻠﻮﻣﺎﺕ ﺍﻟﺘﻲ ﳛﺼﻠﻮﻥ ﻋﻠﻴﻬﺎ ﰲ ﺩﻓﱰ‬
‫‪C H‬‬ ‫‪‬‬
‫‪‬ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻷﻟﻜﺎﻥ ﳛﺘﻮﻱ ﻋﲆ ‪ 13‬ﺫﺭﺓ‬ ‫‪‬‬ ‫‪C4H10 ‬‬

‫ﺍﻟﻜﻴﻤﻴﺎﺀ‪ .‬ﻓﺈﺫﺍ ﻛﺎﻥ ﺫﻟﻚ ﻋﻦ ﻃﺮﻳﻖ ﺣﺮﻕ ﻭﻗﻮﺩ ﻣﺎ‪ ،‬ﻓﻌﻠﻴﻬﻢ ﲢﺪﻳﺪ‬
‫‪4 10‬‬

‫ﻛﺮﺑﻮﻥ ﰲ ﺻﻴﻐﺘﻪ ﺍﳉﺰﻳﺌﻴﺔ‪.‬‬

‫ا¶ﻟﻜﺎﻧﺎت ذات اﻟﺴﻼﺳﻞ اﻟﻤﺘﻔﺮّ ﻋﺔ‬ ‫ﻫﺬﺍ ﺍﻟﻮﻗﻮﺩ ﻭﺗﺴـﺠﻴﻞ ﺗﺮﻛﻴﺒﻪ‪ .‬ﻭﺇﺫﺍ ﺍﺳﺘﺨﺪﻣﻮﺍ ﺍﻟﻜﻬﺮﺑﺎﺀ ﻓﺎﻃﻠﺐ‬
‫ﹸﺴﻤﻰ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﻟﺘﻲ ﻧﺎﻗﺸﻨﺎﻫﺎ ﺣﺘﻰ ﺍﻵﻥ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺫﺍﺕ ﺍﻟﺴﻼﺳﻞ‬ ‫ﺗ ﹼ‬
‫ﻣﻌﺎ ﺑﺨﻂ ﻭﺍﺣﺪ‪ .‬ﻭﺍﻵﻥ ﺍﻧﻈﺮ‬
‫ﹰ‬ ‫ﺗﺮﺗﺒﻂ‬ ‫ﻓﻴﻬﺎ‬ ‫ﺍﻟﻜﺮﺑﻮﻥ‬ ‫ﺫﺭﺍﺕ‬ ‫ﻷﻥ‬ ‫ﺍﳌﺴﺘﻘﻴﻤﺔ؛‬ ‫ﺇﻟﻴﻬـﻢ ﺍﳌﺰﻳﺪ ﻣﻦ ﺍﻟﺒﺤﺚ ﳌﻌﺮﻓﺔ ﻧﻮﻉ ﺍﻟﻮﻗـﻮﺩ )ﺇﻥ ﻭﺟﺪ( ﺍﻟﺬﻱ ﺗﻢ‬
‫ﺇﱃ ﺍﻟﺼﻴﻐﺘﲔ ﰲ ﺍﻟﺸﻜﻞ ‪ ،8-9‬ﻓﺈﺫﺍ ﻋﺪﺩﺕ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ‬
‫ﻓﺴﺘﻜﺘﺸﻒ ﺃﻥ ﻛﻠﺘﻴﻬﲈ ﳍﺎ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴﻬﺎ ‪ ،C4H10‬ﻓﻬﻞ ﳘﺎ ﺍﳌﺎﺩﺓ‬ ‫ﺣﺮﻗﻪ ﻹﻧﺘﺎﺝ ﻫﺬﻩ ﺍﻟﻜﻬﺮﺑﺎﺀ‪ ،‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺭﺳﻢ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‬
‫ﻧﻔﺴﻬﺎ؟‬
‫ﻓﺈﺫﺍ ﺍﻋﺘﻘﺪﺕ ﺃﻥ ﺍﻟﺒﻨﺎﺋﻴﺘﲔ ﲤﺜﹼﻼﻥ ﻣﺎﺩﺗﲔ ﳐﺘﻠﻔﺘﲔ ﻓﺄﻧﺖ ﻋﲆ ﺻﻮﺍﺏ‪.‬‬
‫‪‬‬ ‫ﻟﻠﻤﻜﻮﻧﺎﺕ ﺍﻟﺮﺋﻴﺴﺔ ﰲ ﺍﻟﻮﻗﻮﺩ ﺍﳌﺴﺘﺨﺪﻡ‪ .‬‬
‫ﹼ‬
‫‪ C22-113C-828378-08‬ﺇﺫ ﲤﺜﻞ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﰲ ﺍﳉﺎﻧﺐ ﺍﻟﺴﻔﲇ ﺍﻟﺒﻴﻮﺗﺎﻥ‪ ،‬ﰲ ﺣﲔ ﻳﻤﺜﻞ ﺍﻟﺒﻨﺎﺀ‬
‫ﻣﺘﻔﺮ ﹰﻋﺎ ﻳﻌﺮﻑ ﺑﺎﻷﻳﺰﻭﺑﻴﻮﺗﺎﻥ‪ ،‬ﻭﻫﻲ ﻣﺎﺩﺓ ﳍﺎ‬ ‫ﹼ‬ ‫ﰲ ﺍﳉﺎﻧﺐ ﺍﻟﻌﻠﻮﻱ ﺃﻟﻜﺎ ﹰﻧﺎ‬
‫ﺧﺼﺎﺋﺺ ﻛﻴﻤﻴﺎﺋﻴﺔ ﻭﻓﻴﺰﻳﺎﺋﻴﺔ ﳐﺘﻠﻔﺔ ﻋﻦ ﺍﻟﺒﻴﻮﺗﺎﻥ ﲤﺎ ﹰﻣﺎ‪ .‬ﻭﺗﺴﺘﻄﻴﻊ ﺃﻥ ﺗﺮﺗﺒﻂ‬ ‫اﻟﺘﻌﻠﻢ اﻟﺒﺼﺮي‬
‫ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﻣﻊ ﺫﺭﺓ ﺃﻭ ﺫﺭﺗﲔ ﺃﻭ ﺛﻼﺙ ﺃﻭ ﺣﺘﻰ ﺃﺭﺑﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﺧﺮ￯‪،‬‬
‫ﳑﹼﺎ ﻳﻨﺠﻢ ﻋﻦ ﻫﺬﻩ ﺍﳋﺎﺻﻴﺔ ﻭﺟﻮﺩ ﳎﻤﻮﻋﺔ ﻣﺘﻨﻮﻋﺔ ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺫﺍﺕ‬
‫ﺍﻟﺴﻼﺳﻞ ﺍﳌﺘﻔﺮﻋﺔ‪.‬‬ ‫‪‬‬ ‫‪‬‬ ‫‪ 83  89 ‬ﺍﺳـﺘﻌﻤﻞ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴـﺔ‬
‫‪C4H10 ‬‬ ‫‪C4H10 ‬‬
‫ﻟﻘﺪ ﻋﺮﻓﺖ ﺳﺎﺑ ﹰﻘﺎ ﺃﻥ ﺍﻟﺒﻴﻮﺗﺎﻥ ﹸﻳﺴﺘﺨﺪﻡ ﰲ ﺍﻟﻘﺪﹼ ﺍﺣﺎﺕ ﻭﺍﳌﺸﺎﻋﻞ‪ .‬ﻭﺃﻣﺎ‬
‫ﺑﻴﺌﻴﺎ ﻓﻴﺴﺘﺨﺪﻡ ﰲ ﺍﻟﺘﱪﻳﺪ‪ ،‬ﻭﻳﺘﺨﺬ ﻣﺎﺩﺓ ﺩﺍﻓﻌﺔ‬
‫ﺍﻷﻳﺰﻭﺑﻴﻮﺗﺎﻥ ﺑﻮﺻﻔﻪ ﻣﺎﺩﺓ ﺁﻣﻨﺔ ﹼﹰ‬
‫ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺫﺍﺕ ﺍﻟﺴﻼﺳـﻞ ﺍﳌﺴـﺘﻘﻴﻤﺔ ﻭﺍﳌﺘﻔﺮﻋﺔ ﻟﺘﻘﺪﻳﻢ‬
‫ﰲ ﻣﻨﺘﺠﺎﺕ ﳑﺎﺛﻠﺔ ﳉﻞ ﺍﳊﻼﻗﺔ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪ .8-9‬ﻭﺑﺎﻹﺿﺎﻓﺔ ﺇﱃ ﻫﺬﻩ‬
‫ﻛﻼ ﻣﻦ ﺍﻟﺒﻴﻮﺗﺎﻥ ﻭﺍﻷﻳﺰﻭﺑﻴﻮﺗﺎﻥ ﻳﺴﺘﺨﺪﻡ ﰲ ﺻﻮﺭﺓ ﻣﺎﺩﺓ‬ ‫ﺍﻟﺘﻄﺒﻴﻘﺎﺕ ﻓﺈﻥ ﹼﹰ‬
‫ﺷـﺠﻊ‬
‫ﻣﻔﻬـﻮﻡ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﻟﻠﻄـﻼﺏ‪ .‬ﻭﻟﺘﺤﻘﻴـﻖ ﺫﻟﻚ ﱠ‬
‫ﺧﺎﻡ ﰲ ﻋﻤﻠﻴﺎﺕ ﺗﺼﻨﻴﻊ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﻮﺍﺩ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ‪.‬‬
‫ﺍﻟﻄﻼﺏ ﻋﲆ ﻛﺘﺎﺑﺔ ﺻﻴﻎ ﺑﻨﺎﺋﻴﺔ ﺃﻭ ﻋﻤﻞ ﻧﲈﺫﺝ ﻟﻠﺠﺰﻳﺌﺎﺕ ﺍﳌﺤﺘﻤﻠﺔ‬
‫‪‬ﺍﻟﻔﺮﻕ ﺑـﲔ ﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻜﻞ ﻣـﻦ ﺍﻟﺒﻴﻮﺗﺎﻥ‬
‫ﻭﺍﻷﻳﺰﻭﺑﻴﻮﺗﺎﻥ‪.‬‬ ‫ﺫﺍﺕ ﺍﻟﺼﻴﻐﺔ ‪ C5H12‬ﲨﻴﻌﻬﺎ‪ .‬ﹼ‬
‫ﻭﺫﻛﺮﻫﻢ ﺑﺄﻥ ﻛﻞ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﳚﺐ ﺃﻥ‬
‫‪‬‬
‫‪C22-113C-828378-08‬‬
‫ﻳﻜﻮﻥ ﳍﺎ ﺃﺭﺑﻊ ﺭﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ ﺃﺣﺎﺩﻳﺔ ﺗﺮﺑﻄﻬﺎ ﺑﺎﻟﺬﺭﺍﺕ ﺍﻷﺧﺮ￯‪.‬‬
‫ﻭﻳﺘﻌﲔ ﻋﻠﻴﻬﻢ ﻛﺘﺎﺑﺔ ﺛﻼﺛﺔ ﺻﻴﻎ ﺑﻨﺎﺋﻴﺔ ﳏﺘﻤﻠﺔ ﻭﻫﻲ ﺗﻠﻚ ﺍﳌﻮﺟﻮﺩﺓ ﰲ‬
‫ﺍﻟﺸﻜﻞ ‪ .8-17‬‬

‫ﻋﺮض ﺗﻮﺿﻴﺤﻲ‬

‫‪‬‬ ‫‪‬‬
‫ﺻﺎﺑﻮﻧﻴـﺎ ﺑﺈﺿﺎﻓـﺔ ‪ 25 ml‬ﻣـﻦ ﺳـﺎﺋﻞ ﺍﻟﺘﻨﻈﻴـﻒ‪،‬‬
‫ﹼﹰ‬ ‫ﺣـﴬ ﳏﻠـﻮ ﹰ‬
‫ﻻ‬ ‫‪‬‬
‫ﻭ‪ 160 ml‬ﻣﻦ ﺍﳌﺎﺀ‪ ،‬ﻭ ‪ 5 ml‬ﻣﻦ ﺍﳉﻠﻴﴪﻳﻦ ﺇﱃ ﻛﺄﺱ ﻣﺪﺭﺟﺔ ﺳﻌﺘﻬﺎ‬ ‫ﻣﻼﺣﻈﺔ ﺍﺣﱰﺍﻕ ﺍﳌﻴﺜﺎﻥ‪.‬‬
‫‪ .400 ml‬ﻭﺃﺫﺏ ‪ 5 g‬ﺳﻜﺮﻭﺯ ﰲ ‪ 160 ml‬ﻣﻦ ﺍﳌﺎﺀ ﰲ ﻛﺄﺱ ﺯﺟﺎﺟﻴﺔ‬ ‫‪‬‬
‫ﻣﻌﺎ ﺑﺮﻓﻖ ﰲ ﻛﺄﺱ ﺳﻌﺘﻬﺎ ‪.400 ml‬‬
‫ﺃﺧﺮ￯‪ .‬ﺛﻢ ﺍﺧﻠﻂ ﺍﳌﺤﻠﻮﻟﲔ ﹰ‬ ‫ﻛﺄﺱ ﻣﺪﺭﺟﺔ ﺳﻌﺔ ‪400 ml‬؛ ﻭﺃﺧﺮ￯ ﺳﻌﺔ ‪150 ml‬؛ ﺳﺎﺋﻞ ﺗﻨﻈﻴﻒ‬
‫ﹺﺻـﻞ ﺃﺣﺪ ﻃـﺮﰲ ﺍﻷﻧﺒﻮﺏ ﺍﳌﻄﺎﻃـﻲ ﺑﻔﺘﺤﺔ ﺍﻟﻐـﺎﺯ ﻭﺍﻟﻄﺮﻑ ﺍﻵﺧﺮ‬ ‫‪25 ml‬؛ ﺟﻠﻴﴪﻳﻦ ‪5 ml‬؛ ﺳﻜﺮﻭﺯ ‪5 g‬؛ ﺃﻧﺒﻮﺏ ﻣﻄﺎﻃﻲ ﻃﻮﻟﻪ ‪1m‬؛‬
‫ﺑﺴـﺎﻕ ﻗﻤﻊ ﺻﻐﲑ‪ .‬ﻭﺍﻏﻤﺮ ﺍﻟﻘﻤﻊ ﰲ ﺍﳋﻠﻴـﻂ ﺍﻟﺼﺎﺑﻮﲏ‪ ،‬ﺛﻢ ﺍﺭﻓﻌﻪ‪.‬‬ ‫ﻗﻤﻊ ﺻﻐﲑ؛ ﻣﺴـﻄﺮﺓ ﻣﱰﻳﺔ؛ ﺷـﻤﻌﺔ؛ ﺃﻋﻮﺍﺩ ﺛﻘﺎﺏ؛ ﺟﺮﻳﺪﺓ؛ ﻻﺻﻖ‬
‫ﺛﻢ ﺍﻓﺘﺢ ﺍﻟﻐﺎﺯ ﺑﺮﻓﻖ ﻣﺪﺓ ﺛﺎﻧﻴﺔ ﻟﻌﻤﻞ ﻓﻘﺎﻋﺎﺕ‪ .‬ﻭﻋﺘﱢﻢ ﺍﻟﻐﺮﻓﺔ‪.‬‬ ‫ﺷﻔﺎﻑ‪.‬‬
‫ﻃﺒﻴﻌﻴﺎ( ﺃﻭ ﺳﻘﻄﺖ ﻧﺤﻮ ﺍﻷﺭﺽ )ﻏﺎﺯ‬‫ﹼﹰ‬ ‫ﻛﻠﲈ ﺍﺭﺗﻔﻌﺖ ﺍﻟﻔﻘﺎﻋﺔ ﹰ‬
‫)ﻏﺎﺯﺍ‬ ‫‪‬‬
‫ﳏﱰﻗﺔ‪B‬ﻣﺜﺒﺘﺔ‪A‬ﺑﻄﺮﻑ ﻣﺴﻄﺮﺓ‬‫ﺷﻤﻌﺔ ‪C‬‬‫ﺑﻠﻬﺐ ‪D‬‬
‫ﺍﻟﻔﻘﺎﻋﺔ ‪E‬‬ ‫ﺃﺷـﻌﻞ‬
‫‪A F BAG‬‬ ‫ﺑﺮﻭﺑﺎﻥ(‪ACBH ،‬‬
‫‪C I CEDJ‬‬
‫‪BD‬‬ ‫‪DFEK EGF L FHGM GHIN HJO‬‬
‫‪I‬‬
‫ﺍﻟﻨﻔﺎﻳﺎﺕ ﻳﻤﻜﻦ‬
‫‪JP JLK KML N‬‬
‫ﺳﻜﺐ‪ IK‬ﺍﳌﺤﻠﻮﻝ ﰲ ﺍﳌﻐﺴﻠﺔ‪.‬‬ ‫‪LM M‬‬
‫ﺍﻟﺘﺨﻠﺺ ﻣﻦ‬
‫‪ON NPO OP‬‬ ‫‪P‬‬

‫ﻣﱰﻳﺔ‪ .‬ﻭﻳﺴﺘﺤﺴـﻦ ﺍﻻﺳﺘﻌﺎﻧﺔ ﺑﺸﺨﺺ ﺁﺧﺮ ﻟﻜﻲ ﹸﻳﻤﺴﻚ ﺑﺎﳌﺴﻄﺮﺓ‬

‫ﺍﳌﱰﻳﺔ ﺍﳌﺜﺒﺘﺔ ﻋﻠﻴﻬﺎ ﺍﻟﺸﻤﻌﺔ ﺍﳌﺤﱰﻗﺔ ﰲ ﺃﺛﻨﺎﺀ ﻋﻤﻞ ﺍﻟﻔﻘﺎﻋﺎﺕ‪.‬‬

‫‪138‬‬
 ‫‪‬‬ ‫‪83‬‬

‫اﻟﺘﻌﺰﻳﺰ‬ ‫ﺍﻟﺒﻴﻮﺗﻴﻞ‬ ‫ﺍﻷﻳﺰﻭﺑﺮﻭﺑﻴﻞ‬ ‫ﺍﻟﱪﻭﺑﻴﻞ‬ ‫ﺍﻹﻳﺜﻴﻞ‬ ‫ﺍﳌﻴﺜﻴﻞ‬ ‫‪‬‬

‫‪‬‬
‫—‪CH3‬‬ ‫—‪CH3CH2‬‬ ‫—‪— 2‬‬
‫‪CH3CH23CH‬‬ ‫‪CHCH‬‬‫—‪3CH23‬‬
‫‪3CHCH‬‬ ‫‪CH‬‬
‫‪CH‬‬
‫‪CH‬‬
‫‪33‬‬‫—‬
‫‪CH‬‬‫‪3CH‬‬
‫‪2CH‬‬
‫‪2CH‬‬ ‫—‪2‬‬
‫‪2CH‬‬ ‫‪2— CHCH‬‬
‫‪3CH‬‬‫—‪2‬‬
‫‪3CHCH‬‬‫‪3‬‬ ‫‪CH‬‬
‫‪CH3CH‬‬‫‪—32CH‬‬
‫‪3CH‬‬ ‫‪— 2CHCH‬‬
‫‪CH22CH‬‬ ‫‪— 33CH‬‬
‫‪2CH‬‬ ‫‪2— 3‬‬
‫‪CHCH‬‬ ‫‪CH‬‬
‫‪CH‬‬‫—‪33‬‬
‫‪CH‬‬ ‫‪CH‬‬
‫‪3CH‬‬
‫‪2CH‬‬‫—‪2‬‬
‫‪2CH‬‬‫—‪2CH2‬‬
‫‪CH‬‬‫‪CH‬‬
‫‪3CH‬‬ ‫‪2— 3‬‬
‫‪3CHCH‬‬ ‫‪CHCH‬‬
‫‪3CH‬‬
‫‪3CH‬‬
‫‪2CH‬‬ ‫‪2—2C‬‬
‫‪2CH‬‬
‫‪‬‬
‫‪ ‬ﺍﺳﺄﻝ ﺍﻟﻄﻼﺏ ﻋﲈ ﺇﺫﺍ ﻛﺎﻥ ﻫﻨﺎﻙ ﺃﻟﻜﺎﻥ ﳛﻤﻞ‬
‫‪H‬‬

‫ﺍﻻﺳـﻢ ‪ -2‬ﺇﻳﺜﻴـﻞ ﺑﻴﻮﺗﺎﻥ‪ .‬ﻭﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻗﺒﻞ ﺍﻹﺟﺎﺑﺔ ﻋﻦ‬

‫‪H‬‬

‫—‬
‫‪H‬‬
‫‪H—C—H‬‬

‫—‬
‫‪H‬‬

‫—‬
‫‪H—C—H‬‬

‫—‬
‫‪H—C—H‬‬ ‫‪H‬‬

‫—‬
‫ﺍﻟﺘﺴـﺎﺅﻝ ﻛﺘﺎﺑـﺔ ﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﺠـﺰﻱﺀ ﺍﻟﺬﻱ ﻟﻪ ﻫﺬﺍ ﺍﻻﺳـﻢ‬
‫‪H—C—H‬‬ ‫‪H—C—H‬‬

‫—‬

‫—‬
‫—‬
‫‪—C—H‬‬ ‫‪‬‬

‫—‬
‫‪H—C—H‬‬ ‫‪H—C—H‬‬

‫—‬
‫‪H—C—H‬‬ ‫‪H—C—H‬‬

‫—‬

‫—‬
‫—‬
‫‪H—C—H‬‬

‫—‬
‫‪H—C—H‬‬
‫ﻭﲢﺪﻳﺪ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ‪.‬‬

‫—‬
‫‪H—C—H‬‬

‫—‬

‫—‬
‫‪H‬‬

‫—‬
‫ﻻ‪ .‬ﺑﺎﺗﺒـﺎﻉ ﻗﻮﺍﻋـﺪ ﺃﻳﻮﺑـﺎﻙ )‪ (IUPAC‬ﻳﻈﻬـﺮ ﺃﻥ ﻫﺬﺍ ﺍﻻﺳـﻢ ﻫﻮ‬
‫‪C22-035C-828378-08‬‬
‫‪C22-034C-828378-08‬‬
‫‪C22-038C-828378-08‬‬ ‫‪C22-036C-828378-08‬‬
‫‪  ‬ﻟﻘﺪ ﺭﺃﻳﺖ ﺃﻥ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳌﺘﻔﺮﻋﺔ ﻭﺍﳌﺴﺘﻘﻴﻤﺔ ﳍﺎ ﺍﻟﺼﻴﻐﺔ‬
‫‪C22-037C-828378-08‬‬
‫‪‬‬ ‫ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴﻬﺎ‪ .‬ﻭﺗﻮﺿﺢ ﻫﺬﻩ ﺍﳊﻘﻴﻘﺔ ﹰ‬
‫ﻟﺒﻨـﺎﺀ ﳛﺘـﻮﻱ ﻋﲆ ﺳﻠﺴـﻠﺔ ﻛﺮﺑﻮﻧﻴـﺔ ﻣﻜﻮﻧﺔ ﻣﻦ ﺫﺭﺗـﲔ ﻣﺘﺼﻠﺘﲔ‬
‫ﺃﺳﺎﺳﻴﺎ ﰲ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ "ﳛﺪﺩ‬
‫ﹼﹰ‬ ‫ﻣﺒﺪﺃ‬
‫‪‬‬ ‫ﺗﻨﻈﻴﻢ ﺍﻟﺬﺭﺍﺕ ﻭﺗﺮﺗﻴﺒﻬﺎ ﰲ ﺍﳉﺰﻱﺀ ﺍﻟﻌﻀﻮﻱ ﻫﻮﻳﺘﻪ"‪ .‬ﻟﺬﺍ ﳚﺐ ﺃﻥ ﻳﺼﻒ ﺍﺳﻢ‬

‫ﺑـﺬﺭﺓ ﺍﻟﻜﺮﺑـﻮﻥ ﺍﻟﺜﺎﻧﻴﺔ ﰲ ﺳﻠﺴـﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﻣﻜﻮﻧﺔ ﻣـﻦ ‪ 4‬ﺫﺭﺍﺕ‪،‬‬ ‫ﺍﳌﻔﺮﺩﺍﺕ ﺍﻷﻛﺎﺩﻳﻤﻴﺔ‬
‫ﺍﻟﺒﺪﻳﻞ )‪(Substitute‬‬
‫ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ ﺍﻟﱰﻛﻴﺐ ﺍﻟﺒﻨﺎﺋﻲ ﻟﻠﻤﺮﻛﺐ ﺑﺪﻗﺔ‪.‬‬
‫ﻳﻄﻠـﻖ ﻋـﲆ ﺃﻃـﻮﻝ ﺳﻠﺴـﻠﺔ ﻛﺮﺑﻮﻧﻴـﺔ ﻣﺘﺼﻠﺔ )ﻣﺴـﺘﻤﺮﺓ( ﻋﻨـﺪ ﺗﺴـﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ‬
‫ﻫﻮ ﺍﻟﺸﺨﺺ ﺃﻭ ﺍﻟﴚﺀ ﺍﻟﺬﻱ ﳛﻞ ﹶﳏ ﱠﻞ‬
‫ﺃﻥ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﻣﺘﺼﻠﺔ ﲢﺘﻮﻱ ﻋﲆ‬ ‫ﻭﻟﻜﻦ ﰲ ﻫﺬﻩ ﺍﳊﺎﻟﺔ ﹼ‬ ‫ﻏﲑﻩ‪.‬‬
‫ﺍﳌﺘﻔﺮﻋـﺔ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴـﺔ‪ .‬ﻭﺗﹸﺴـﻤﻰ ﻛﻞ ﺍﻟﺘﻔﺮﻋـﺎﺕ ﺍﳉﺎﻧﺒﻴـﺔ ﺍﳌﺠﻤﻮﻋـﺎﺕ‬
‫ﻣﺜـﺎﻝ‪ :‬ﹸﻳﺘﺨﺬ ﺍﳊﺮﻳـﺮ ﺍﻟﺼﻨﺎﻋـﻲ ﺑﺪﻳ ﹰ‬ ‫ﺍﻟﺒﺪﻳﻠـﺔ؛ ﻷﳖـﺎ ﺗﻈﻬـﺮ ﻛﺄﳖـﺎ ﺑﺪﻳﻠـﺔ ﻟـﺬﺭﺓ ﺍﳍﻴﺪﺭﻭﺟـﲔ ﰲ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﳌﺴـﺘﻘﻴﻤﺔ‬
‫ﻼ‬
‫ﲬـﺲ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ .‬ﺛﻢ ﺍﻃﻠـﺐ ﹰ‬
‫ﺃﻳﻀﺎ ﺇﱃ ﺍﻟﻄﻼﺏ ﻛﺘﺎﺑﺔ ﺍﻻﺳـﻢ‬ ‫ﻋﻦ ﺍﳊﺮﻳﺮ ﺍﻟﻄﺒﻴﻌﻲ‪.‬‬ ‫)ﻏـﲑ ﺍﳌﺘﻔﺮﻋـﺔ(‪ .‬ﻭ ﹸﻳﻨﺴـﺐ ﺍﺳـﻢ ﺍﳌﺠﻤﻮﻋـﺔ ﺍﻟﺒﺪﻳﻠـﺔ ﺍﳌﺸـﺘﻘﺔ ﻣـﻦ ﺍﻷﻟـﻜﺎﻥ‪،‬‬
‫ﻭﺍﻟﺘـﻲ ﺗﺘﻔـﺮﻉ ﻣـﻦ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴـﺔ‪ ،‬ﺇﱃ ﺍﺳـﻢ ﺍﻷﻟـﻜﺎﻥ ﺍﻟـﺬﻱ ﳛﺘـﻮﻱ ﻋـﲆ‬
‫ﺍﻟﺼﺤﻴﺢ ﻟﻠﻤﺮﻛﺐ‪ – 3 .‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‪ .‬‬ ‫ﻋـﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ ﻧﻔﺴـﻬﺎ‪ ،‬ﻭﻳﺘـﻢ ﺗﻐﻴـﲑ ﺍﳌﻘﻄـﻊ ﺍﻷﺧـﲑ ﻣـﻦ "ﺍﻥ" ﺇﱃ "ﻳﻞ"‪.‬‬
‫ﻭﺗﹸﺴـﻤﻰ ﺍﳌﺠﻤﻮﻋـﺔ ﺍﻟﺒﺪﻳﻠـﺔ ﺍﳌﺸـﺘﻘﺔ ﻣـﻦ ﺍﻷﻟـﻜﺎﻥ ﺑﻤﺠﻤﻮﻋـﺔ ﺍﻷﻟﻜﻴـﻞ‪ .‬ﻭ ﹸﻳﺒﲔ‬
‫ﺍﳉﺪﻭﻝ ‪ 8-3‬ﺑﻌﺾ ﳎﻤﻮﻋﺎﺕ ﺍﻷﻟﻜﻴﻞ‪.‬‬
‫‪ ‬ﺍﺳﺘﺨﺪﻡ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﺍﻟﻘﻮﺍﻋﺪ‬
‫‪ ‬ﺍﻟﺒﻴﻮﺗﺎﻥ ﻫﻮ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺫﻭ ﺳﻠﺴﻠﺔ ﻣﺴﺘﻘﻴﻤﺔ‪،‬‬ ‫ﺍﻟﻨﻈﺎﻣﻴﺔ ﺍﻟﺘﺎﻟﻴﺔ ﺍﳌﺘﻔﻖ ﻋﻠﻴﻬﺎ ﻣﻦ ﺍﻻﲢﺎﺩ ﺍﻟﺪﻭﱄ ﻟﻠﻜﻴﻤﻴﺎﺀ ﺍﻟﺒﺤﺘﺔ ﻭﺍﻟﺘﻄﺒﻴﻘﻴﺔ ﺃﻳﻮﺑﺎﻙ‪،‬‬
‫)‪ (IUPAC‬ﰲ ﺗﺴﻤﻴﺔ ﻣﺮﻛﺒﺎﺕ ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ‪.‬‬
‫ﺃﻣﺎ ﺍﻷﻳﺰﻭﺑﻴﻮﺗﺎﻥ ﻓﻬﻮ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺫﻭ ﺳﻠﺴﻠﺔ ﻣﺘﻔﺮﻋﺔ‪.‬‬ ‫ﺍﳋﻄـﻮﺓ‪ .1‬ﺣﺪﺩ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺃﻃﻮﻝ ﺳﻠﺴـﻠﺔ ﻣﺘﺼﻠﺔ‪ ،‬ﻣﺴـﺘﺨﺪ ﹰﻣﺎ ﺍﺳـﻢ‬
‫ﺍﻷﻟـﻜﺎﻥ ﺍﻟﺬﻱ ﳛﺘﻮﻱ ﻋﲆ ﻫﺬﺍ ﺍﻟﻌﺪﺩ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻋﲆ ﺃﻧﻪ ﺍﺳـﻢ ﻟﻠﺴﻠﺴـﻠﺔ‬
‫ﺍﻟﺮﺋﻴﺴﺔ ﰲ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫ﺍﳋﻄـﻮﺓ ‪ .2‬ﺭ ﱢﻗـﻢ ﻛﻞ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﰲ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴـﺔ‪ ،‬ﻣﺒﺘﺪﺋﹰـﺎ ﺍﻟﱰﻗﻴﻢ ﻣﻦ ﻃﺮﻑ‬
‫ﻣﻮﺍﻗـﻊ ﲨﻴﻊ‬
‫ﹶ‬ ‫ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻷﻗـﺮﺏ ﺇﱃ ﺍﳌﺠﻤﻮﻋـﺔ ﺍﻟﺒﺪﻳﻠـﺔ؛ ﺇﺫ ﺗﹸﻌﻄـﻲ ﻫـﺬﻩ ﺍﳋﻄـﻮﺓ‬
‫ﺃﺻﻐﺮ ﺃﺭﻗﺎﻡ ﳑﻜﻨﺔ‪.‬‬
‫ﹶ‬ ‫ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ‬

‫ﺃﻛﺴـﻴﺪ ﺍﻟﻜﺮﺑـﻮﻥ‪ ،‬ﺿـﻮﺀ‪ ،‬ﺣـﺮﺍﺭﺓ‪ ،‬ﺑﺨﺎﺭ ﻣﺎﺀ‪ ،‬ﺳـﻨﺎﺝ )ﺳـﻮﺍﺩ‬ ‫ﲢﺬﻳـﺮ‪ :‬ﻻ ﺗﻘﻢ ﲠـﺬﺍ ﺍﻟﻌـﺮﺽ ﹸﻗﺮﺏ ﻣـﻮﺍﺩ ﻗﺎﺑﻠﺔ ﻟﻼﺷـﺘﻌﺎﻝ‪ ،‬ﻭﺿﻊ‬
‫ﺍﻟﺪﺧﺎﻥ‪ ،‬ﺷﺤﺒﺎﺭ(‪.‬‬ ‫ﻭﺭﻕ ﺟﺮﺍﺋـﺪ ﻋﲆ ﺍﻷﺭﺽ ﻻﻟﺘﻘﺎﻁ ﺍﻟﺸـﻤﻊ ﺍ ﹸﳌﻨﺼﻬﺮ ﺍﻟﺬﻱ ﹶﻳ ﹸ‬
‫ﻘﻄﺮ ﻣﻦ‬
‫ﻫـﻞ ﺗﻔﺎﻋـﻞ ﺍﻻﺣـﱰﺍﻕ ﻃـﺎﺭﺩ ﻟﻠﺤـﺮﺍﺭﺓ ﺃﻡ ﻣﺎﺹ ﳍـﺎ؟ ﻃﺎﺭﺩ‬ ‫‪.3‬‬ ‫ﺍﻟﺸﻤﻌﺔ‪.‬‬
‫ﻟﻠﺤﺮﺍﺭﺓ‪.‬‬ ‫‪‬‬
‫ﳛﺪﺙ ﺗﻮﻫﺞ ﻋﻨﺪ ﺍﻧﻔﺠﺎﺭ ﻛﻞ ﻓﻘﺎﻋﺔ‪ .‬ﳛﱰﻕ ﺍﻟﻐﺎﺯ ﺍﳌﺤﺼﻮﺭ ﻭ ﹸﻳ ﹾﻨﺘﹺ ﹸﺞ‬
‫اﻟﺘﻘﻮﻳﻢ‬
‫ﳍ ﹰﺒﺎ ﺃﺻﻔﺮ ﻣﻀﻴﺌﹰﺎ‪.‬‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻛﺘﺎﺑـﺔ ﺍﳌﻌﺎﺩﻟـﺔ ﺍﳌﻮﺯﻭﻧـﺔ ﻟﺘﻔﺎﻋـﻞ‬ ‫‪‬‬

‫ﺍﻻﺣﱰﺍﻕ‪.‬‬ ‫ﺍﻃﺮﺡ ﺍﻷﺳﺌﻠﺔ ﺍﻟﺘﺎﻟﻴﺔ‪:‬‬
‫‪CH4 + 2O2 → CO2 + 2H2O‬‬ ‫ﻣـﺎ ﺍﳌﺎﺩﺗـﺎﻥ ﺍﳌﺘﻔﺎﻋﻠﺘـﺎﻥ ﺍﻟﻠﺘـﺎﻥ ﻧﺠـﻢ ﻋﻨﻬـﲈ ﺍﻻﺣـﱰﺍﻕ ﺍﻟﺬﻱ‬ ‫‪.1‬‬

‫ﺃﻭ‬ ‫ﺷﺎﻫﺪﲤﻮﻩ؟ ﺍﻷﻛﺴﺠﲔ ﻭﺍﳌﻴﺜﺎﻥ ﺃﻭ ﺍﻟﱪﻭﺑﺎﻥ‪.‬‬

‫‪C3H8 + 5O2 → 3CO2 + 4H2O‬‬ ‫ﻣﺎﺫﺍ ﺃﻧﺘﺞ ﺗﻔﺎﻋﻞ ﺍﻻﺣﱰﺍﻕ؟ ﺛﺎﲏ ﺃﻛﺴـﻴﺪ ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻭﺭﺑﲈ ﺃﻭﻝ‬ ‫‪.2‬‬

‫‪139‬‬
 ‫ﺍﳋﻄﻮﺓ ‪ .3‬ﱢ‬
‫ﺳـﻢ ﻛﻞ ﳎﻤﻮﻋﺔ ﺃﻟﻜﻴﻞ ﺑﺪﻳﻠﺔ‪ .‬ﻭﺿﻊ ﺍﺳﻢ ﺍﳌﺠﻤﻮﻋﺔ ﻗﺒﻞ ﺍﺳﻢ ﺍﻟﺴﻠﺴﻠﺔ‬
‫ﺍﻟﺮﺋﻴﺴﺔ‪.‬‬
‫ﺍﳋﻄـﻮﺓ ‪ .4‬ﺇﺫﺍ ﺗﻜـﺮﺭﺕ ﳎﻤﻮﻋﺔ ﺍﻷﻟﻜﻴﻞ ﻧﻔﺴـﻬﺎ ﺃﻛﺜﺮ ﻣﻦ ﻣـﺮﺓ ﺑﻮﺻﻔﻬﺎ ﹰ‬
‫ﺗﻔﺮﻋﺎ ﻋﻦ‬
‫ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴـﺔ ﻓﺎﺳـﺘﺨﺪﻡ ﺑﺎﺩﺋﺔ )ﺛﻨﺎﺋﻲ ‪ ،‬ﺛﻼﺛﻲ‪ ،‬ﺭﺑﺎﻋﻲ ‪ ،‬ﻭﻫﻜﺬﺍ‪ (...‬ﻗﺒﻞ ﺍﺳﻢ‬
‫‪‬‬
‫ﺍﳌﺠﻤﻮﻋـﺔ ﻟﻠﺪﻻﻟﺔ ﻋﲆ ﻋﺪﺩ ﺍﳌﺮﺍﺕ ﺍﻟﺘﻲ ﺗﻈﻬﺮ ﻓﻴﻬﺎ‪ ،‬ﻭﺍﺳـﺘﺨﺪﻡ ﺭﻗﻢ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ‬
‫ﺍﻟﺘﻲ ﺗﺘﺼﻞ ﲠﺎ ﺍﳌﺠﻤﻮﻋﺔ ﻟﻠﺪﻻﻟﺔ ﻋﲆ ﻣﻮﻗﻌﻬﺎ‪.‬‬ ‫ﻗـﺪ ﻳﻌﺘﻘﺪ ﺍﻟﻄﻼﺏ ﺃﻥ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ ﺍﳌﺘﺼﻠﺔ ﰲ ﺻﻮﺭﺓ ﺧﻂ‬
‫ﺍﳋﻄﻮﺓ ‪ .5‬ﻋﻨﺪﻣﺎ ﺗﺘﺼﻞ ﳎﻤﻮﻋﺎﺕ ﺃﻟﻜﻴﻞ ﳐﺘﻠﻔﺔ ﻋﲆ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻧﻔﺴﻬﺎ ﺿﻊ‬
‫ﺃﺳـﲈﺀﻫﺎ ﺑﺎﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ ﺑﺎﻟﻠﻐﺔ ﺍﻻﻧﺠﻠﻴﺰﻳﺔ‪ .‬ﻭﻻ ﺗﹸﺆﺧﺬ ﺍﻟﺒﺎﺩﺋﺎﺕ )ﺛﻨﺎﺋﻲ‪ ،‬ﺛﻼﺛﻲ‪،‬‬ ‫ﺃﻓﻘﻲ ﰲ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻫﻲ ﹰ‬
‫ﺩﺍﺋﲈ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﺍﳌﺴﺘﺨﺪﻣﺔ‬
‫ﻭﻫﻜﺬﺍ( ﰲ ﺍﳊﺴﺒﺎﻥ ﻋﻨﺪ ﲢﺪﻳﺪ ﺍﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ‪.‬‬
‫ﻼ‪ ،‬ﹸﻣﺴﺘﺨﺪ ﹰﻣﺎ ﺍﻟﴩﻃﺎﺕ ﻟﻔﺼﻞ ﺍﻷﺭﻗﺎﻡ ﻋﻦ ﺍﻟﻜﻠﲈﺕ‪،‬‬ ‫ﺍﳋﻄﻮﺓ ‪ .6‬ﺍﻛﺘﺐ ﺍﻻﺳﻢ ﻛﺎﻣ ﹰ‬ ‫ﰲ ﺗﺴﻤﻴﺔ ﺍﳌﺎﺩﺓ‪.‬‬
‫ﻭﺍﻟﻔﻮﺍﺻﻞ ﻟﻠﻔﺼﻞ ﺑﲔ ﺍﻷﺭﻗﺎﻡ‪ .‬ﻭﻻ ﺗﱰﻙ ﹰ‬
‫ﻓﺮﺍﻏﺎ ﺑﲔ ﺍﺳﻢ ﺍﳌﺠﻤﻮﻋﺔ ﻭﺍﺳﻢ ﺍﻟﺴﻠﺴﻠﺔ‬
‫ﺍﻟﺮﺋﻴﺴﺔ‪.‬‬
‫‪‬‬
‫‪81‬‬
‫ﺍﻛﺘﺐ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻸﻟﻜﺎﻥ ﺍﻟﺘﺎﱄ ﻋﲆ ﺍﻟﺴـﺒﻮﺭﺓ‪ -6 :‬ﺫﺭﺍﺕ‬
‫‪CH3‬‬ ‫‪‬‬
‫‪CH2‬‬ ‫ﺍﳌﺒﲔ ﰲ ﺍﻟﺸﻜﻞ ﺃﺩﻧﺎﻩ‪.‬‬
‫ﺳﻢ ﺍﻷﻟﻜﺎﻥ ﱠ‬
‫ﱢ‬ ‫ﻛﺮﺑـﻮﻥ ﻣﺘﺼﻠﺔ ﰲ ﺻﻮﺭﺓ ﺧﻂ ﺃﻓﻘﻲ ﻣﻊ ﳎﻤﻮﻋﺔ ﺑﺮﻭﺑﻴﻞ) ﺫﺍﺕ‬
‫ﺛﻼﺛﺔ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ( ﻣﺘﻔﺮﻋﺔ ﻋﻤﻮﺩ ﹼﹰﻳﺎ ﻣﻦ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺜﺎﻧﻴﺔ‪،‬‬
‫‪CH 3CH 2CH 2CHCHCHCH 2CH 3‬‬
‫‪CH 3‬‬ ‫‪CH 3‬‬ ‫ﺗﺤﻠﻴﻞ اﻟﻤﺴﺄﻟﺔ‬ ‫‪1‬‬

‫ﺃﻋﻄﻴﺖ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﺍﺗﺒﻊ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻟﺘﺴﻤﻴﺔ ﺍﻷﻳﻮﺑﺎﻙ ‪ IUPAC‬ﻟﺘﺤﺪﻳﺪ ﺍﺳﻢ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻭﺃﺳﲈﺀ ﺍﻟﺘﻔﺮﻋﺎﺕ‬
‫ﻭﻣﻮﺍﻗﻌﻬﺎ ﰲ ﺍﻟﺸﻜﻞ ﺍﳌﻌﻄﻰ‪.‬‬ ‫ﺛﻢ ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻛﺘﺎﺑﺔ ﺍﺳﻢ ﻫﺬﺍ ﺍﻷﻟﻜﺎﻥ‪.‬‬
‫ﺣﺴﺎب اﻟﻤﻄﻠﻮب‬ ‫‪2‬‬

‫ﺍﳋﻄﻮﺓ ‪ .1‬ﺣﺪﹼ ﺩ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻣﺘﺼﻠﺔ‪ .‬ﹸﻳﻤﻜﻦ ﺗﻮﺟﻴﻪ ﺍﻟﺴﻼﺳﻞ ﰲ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺑﻄﺮﺍﺋﻖ ﻋﺪﻳﺪﺓ؛ ﻟﺬﺍ‬
‫ﻼ؛ ﺣﻴﺚ ﺇﻥ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﲢﺘﻮﻱ‬ ‫ﻋﻠﻴﻚ ﺍﻻﻧﺘﺒﺎﻩ ﺧﻼﻝ ﺍﻟﺒﺤﺚ ﻋﻦ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ‪ .‬ﻭﰲ ﻫﺬﻩ ﺍﳊﺎﻟﺔ ﻳﻜﻮﻥ ﺍﻟﻮﺿﻊ ﺳﻬ ﹰ‬ ‫‪‬‬
‫ﻋﲆ ﺛﲈﲏ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ ،‬ﻟﺬﺍ ﻓﺈﻥ ﺍﻻﺳﻢ ﺍﻟﺮﺋﻴﺲ ﻫﻮ ﺃﻭﻛﺘﺎﻥ‪.‬‬
‫ﺍﳋﻄﻮﺓ ‪ .2‬ﺭ ﹼﻗﻢ ﻛﻞ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﰲ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ‪ .‬ﻭﺭ ﹼﻗﻢ ﺍﻟﺴﻠﺴﻠﺔ ﰲ ﻛﻼ ﺍﻻﲡﺎﻫﲔ‪ ،‬ﻛﲈ ﻫﻮ ﹸﻣ ﱠ‬
‫ﻮﺿﺢ ﺃﺩﻧﺎﻩ ﻣﺒﺘﺪﺋﹰﺎ ﻣﻦ ﺍﻟﻴﺴﺎﺭ‬
‫ﺍﺳـﺄﻝ ﺍﻟﻄﻼﺏ ﻗﺒﻞ ﺍﻟﻜﺸـﻒ ﻋﻦ ﺍﻻﺳـﻢ ﺍﻟﺼﺤﻴﺢ )ﺃﻳﻮﺑﺎﻙ(‬
‫ﺑﻮﺿﻊ ﳎﻤﻮﻋﺎﺕ ﺍﻷﻟﻜﻴﻞ ﻋﲆ ﺍﳌﻮﺍﻗﻊ ‪ 4‬ﻭ ‪ 5‬ﻭ‪ ،6‬ﺛﻢ ﻣﻦ ﺍﻟﻴﻤﲔ ﺑﻮﺿﻊ ﳎﻤﻮﻋﺎﺕ ﺍﻷﻟﻜﻴﻞ ﻋﲆ ﺍﳌﻮﺍﻗﻊ ‪ 3‬ﻭ ‪ 4‬ﻭ‪ .5‬ﻭﻷﻥ ﺃﺭﻗﺎﻡ‬
‫ﺍﳌﻮﺍﻗﻊ ‪ 3‬ﻭ‪ 4‬ﻭ‪ 5‬ﻫﻲ ﺍﻷﺻﻐﺮ ﻟﺬﺍ ﳚﺐ ﺍﺳﺘﺨﺪﺍﻣﻬﺎ ﰲ ﺍﻻﺳﻢ‪.‬‬
‫ﺳـﻤﻰ ﺍﳌﺮﻛﺐ ﺑـ ‪ -2‬ﺑﺮﻭﺑﻴﻞ ﻫﻜﺴـﺎﻥ؟‬
‫ﻟﻠﻤﺮﻛـﺐ‪ :‬ﻛـﻢ ﻃﺎﻟ ﹰﺒﺎ ﹼ‬
‫‪CH3‬‬ ‫‪CH3‬‬ ‫ﻭﻛـﻢ ﻃﺎﻟ ﹰﺒـﺎ ﺃﻃﻠﻖ ﻋﲆ ﺍﳌﺮﻛﺐ ﹰ‬
‫ﺍﺳـﲈ ﺁﺧﺮ‪ .‬ﺛـﻢ ﺍﻃﻠﺐ ﺇﱃ ﺃﺣﺪ‬
‫‪CH2‬‬ ‫‪CH2‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫‪CH3CH2CH2CHCHCHCH2CH3‬‬
‫‪5‬‬
‫‪6‬‬ ‫‪7‬‬ ‫‪8‬‬ ‫‪8‬‬ ‫‪7‬‬ ‫‪6‬‬ ‫‪5‬‬
‫‪CH3CH2CH2CHCHCHCH2CH3‬‬
‫‪4‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪1‬‬
‫ﺍﻟﻄـﻼﺏ ﳑـﻦ ﺃﺧﻄﺆﻭﺍ ﰲ ﺍﻟﺘﺴـﻤﻴﺔ ﺃﻥ ﻳﻔﴪ ﻛﻴـﻒ ﺗﻮﺻﻞ ﺇﱃ‬
‫ﺫﻟﻚ ﺍﻻﺳـﻢ؟ ﻭﺍﻃﻠـﺐ ﺇﱃ ﺃﺣﺪ ﺍﻟﻄﻼﺏ ﺍﻟﺬﻳﻦ ﻛﺘﺒﻮﺍ ﺍﻻﺳـﻢ‬
‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬

‫ﺍﻟﺼﺤﻴﺢ ﻟﻠﻤﺮﻛﺐ ‪ -4‬ﻣﻴﺜﻴﻞ ﺃﻭﻛﺘﺎﻥ‪ ،‬ﺗﺮﻗﻴﻢ ﺍﻟﺴﻠﺴﻠﺔ ﺑﺼﻮﺭﺓ‬

‫ﺻﺤﻴﺤﺔ ﻋﲆ ﺍﻟﺴﺒﻮﺭﺓ‪.‬‬

‫‪‬‬
‫ﺍﻛﺘـﺐ ﺳﻼﺳـﻞ ﻛﺮﺑﻮﻧﻴﺔ ﲤﺜـﻞ ﺃﻟﻜﺎﻧـﺎﺕ ﻣﺘﻔﺮﻋـﺔ ﺃﺧﺮ￯ ﻋﲆ‬
‫ﺍﻟﺴـﺒﻮﺭﺓ‪ ،‬ﻭﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺇﳚـﺎﺩ ﺍﻟﱰﻗﻴـﻢ ﺍﻟﺼﺤﻴﺢ ﳍﺎ‬
‫ﻭﻛﺘﺎﺑﺔ ﺃﺳـﲈﺀ ﻫـﺬﻩ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ .‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬـﻢ ﻛﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ‬
‫ﺍﳍﻴﻜﻠﻴﺔ ﻭﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﻜﺎﻣﻠﺔ ﳌﺮﻛﺒﺎﺕ ﻳﹸﻌﻄﻮﻥ ﺃﺳﲈﺀﻫﺎ‪ .‬‬

‫‪140‬‬
 ‫ﻭﺳﻤﻬﺎ‪ .‬ﻫﻨﺎﻙ ﳎﻤﻮﻋﺘﺎﻥ ﻣﻴﺜﻴﻞ‪ -‬ﻣﻮﺟﻮﺩﺗﺎﻥ ﻋﲆ ﺍﳌﻮﻗﻌﲔ ‪3‬‬
‫ﻋﲔ ﳎﻤﻮﻋﺎﺕ ﺍﻷﻟﻜﻴﻞ ﺍﳌﺘﻔﺮﻋﺔ ﻋﻦ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﹼ‬
‫ﺍﳋﻄﻮﺓ ‪ .3‬ﹼ‬
‫ﻭ ‪ ،5‬ﻭﳎﻤﻮﻋﺔ ﺇﻳﺜﻴﻞ ﻋﲆ ﺍﳌﻮﻗﻊ ‪.4‬‬
‫‪‬‬ ‫‪‬‬
‫‪CH 3‬‬
‫‪CH 2‬‬
‫‪8‬‬ ‫‪7‬‬ ‫‪6‬‬ ‫‪5‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪1‬‬
‫‪CH 3CH 2CH 2CHCHCHCH 2CH 3‬‬

‫ﺳﻢ ﺍﻷﻟﻜﺎﻥ ﺃﺩﻧﺎﻩ‪.‬‬

‫‪4‬‬

‫‪ ‬ﱢ‬
‫‪CH 3‬‬ ‫‪CH 3‬‬
‫‪ ‬‬
‫ﺍﳋﻄﻮﺓ ‪ .4‬ﺇﺫﺍ ﺗﻜﺮﺭﺕ ﳎﻤﻮﻋﺔ ﺍﻷﻟﻜﻴﻞ ﻧﻔﺴﻬﺎ ﺃﻛﺜﺮ ﻣﻦ ﻣﺮﺓ ﺑﻮﺻﻔﻬﺎ ﻓﺮﻋﹰ ﺎ ﻋﲆ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻓﺎﺳﺘﺨﺪﻡ ﺍﻟﺒﺎﺩﺋﺎﺕ )ﺛﻨﺎﺋﻲ‪،‬‬
‫‪CH 3‬‬ ‫ﺛﻼﺛﻲ‪ ،‬ﺭﺑﺎﻋﻲ‪ ،‬ﻭﻫﻜﺬﺍ‪ (...‬ﻗﺒﻞ ﺍﺳﻢ ﺍﳌﺠﻤﻮﻋﺔ ﻟﻠﺪﻻﻟﺔ ﻋﲆ ﻋﺪﺩ ﺍﳌﺮﺍﺕ ﺍﻟﺘﻲ ﺗﻈﻬﺮ ﻓﻴﻬﺎ‪ ،‬ﻭﺍﺑﺤﺚ ﻋﻦ ﳎﻤﻮﻋﺎﺕ ﺍﻷﻟﻜﻴﻞ ﺍﻟﺘﻲ‬
‫ﻭﺃﺣﺺ ﻋﺪﺩﻫﺎ‪ .‬ﺛﻢ ﺣﺪﹼ ﺩ ﺍﻟﺒﺎﺩﺋﺔ ﺍﻟﺘﻲ ﺗ ﹾﹸﻈ ﹺﻬﺮ ﻋﺪﺩ ﺍﳌﺮﺍﺕ ﺍﻟﺘﻲ ﺗﻈﻬﺮ ﻓﻴﻬﺎ ﻛﻞ ﳎﻤﻮﻋﺔ ﻭﺍﺳﺘﺨﺪﻣﻬﺎ‪ .‬ﻭﺳﻮﻑ‬
‫ﹺ‬ ‫ﺗﻜﺮﺭﺕ ﺃﻛﺜﺮ ﻣﻦ ﻣﺮﺓ‬
‫ﺗﻀﺎﻑ ﰲ ﻫﺬﺍ ﺍﳌﺜﺎﻝ ﺍﻟﺒﺎﺩﺋﺔ "ﺛﻨﺎﺋﻲ" ﺇﱃ ﺍﻻﺳﻢ ﻣﻴﺜﻴﻞ؛ ﻷﻥ ﻫﻨﺎﻙ ﳎﻤﻮﻋﺘﻲ ﻣﻴﺜﻴﻞ‪ .‬ﻭﻻ ﻳﺘﻄﻠﺐ ﺫﻟﻚ ﺇﺿﺎﻓﺔ ﺃﻱ ﺑﺎﺩﺋﺔ ﺇﱃ ﳎﻤﻮﻋﺔ‬
‫‪CH 3CHCHCH 2CH 2CH 3‬‬ ‫ﺍﻹﻳﺜﻴﻞ ﺍﻟﻮﺣﻴﺪﺓ‪ .‬ﹼﺑﲔ ﺍﻵﻥ ﻣﻮﻗﻊ ﻛﻞ ﳎﻤﻮﻋﺔ ﺑﺎﺳﺘﺨﺪﺍﻡ ﺍﻟﺮﻗﻢ ﺍﳌﻨﺎﺳﺐ‪.‬‬
‫‪CH 3‬‬ ‫‪‬‬
‫‪CH 3‬‬ ‫‪CH 2‬‬ ‫‪– 4‬‬
‫‪5‬‬ ‫‪3‬‬
‫‪‬‬ ‫‪CH 3CH 2CH 2CHCHCHCH 2CH 3‬‬
‫‪‬‬ ‫‪CH 3‬‬
‫‪4‬‬
‫‪CH 3‬‬
‫‪‬‬
‫‪ -3 ،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ‬ ‫‪–5،3 ‬‬

‫ﺍﳋﻄﻮﺓ ‪ .5‬ﻋﻨﺪﻣﺎ ﺗﺘﺼﻞ ﳎﻤﻮﻋﺎﺕ ﺃﻟﻜﻴﻞ ﳐﺘﻠﻔﺔ ﺑﺎﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﺿﻊ ﺃﺳﲈﺀﻫﺎ ﺣﺴﺐ ﺍﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ‪ ،‬ﻭﺿﻊ ﺃﺳﲈﺀ ﺗﻔﺮﻋﺎﺕ‬
‫ﺍﻷﻟﻜﻴﻞ ﺣﺴﺐ ﺍﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ ﻣﻊ ﲡﺎﻫﻞ ﺍﻟﺒﺎﺩﺋﺎﺕ؛ ﺣﻴﺚ ﻳﻀﻊ ﺍﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ ﺍﻻﺳﻢ ﺇﻳﺜﻴﻞ ﻗﺒﻞ ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ) ﺇ ﻗﺒﻞ ﻡ (‪.‬‬
‫ﻼ‪ ،‬ﻭﺍﺳﺘﺨﺪﻡ ﺍﻟﴩﻃﺎﺕ ﻟﻔﺼﻞ ﺍﻷﺭﻗﺎﻡ ﻋﻦ ﺍﻟﻜﻠﲈﺕ ﻭﺍﻟﻔﻮﺍﺻﻞ ﻟﻠﻔﺼﻞ ﺑﲔ ﺍﻷﺭﻗﺎﻡ‪ ،‬ﻭﺍﻛﺘﺐ ﺍﺳﻢ‬ ‫ﺍﳋﻄﻮﺓ ‪ .6‬ﺍﻛﺘﺐ ﺍﻻﺳﻢ ﻛﺎﻣ ﹰ‬
‫ﺍﻟﺸﻜﻞ )ﺍﳌﺮﻛﺐ( ﻣﺴﺘﺨﺪ ﹰﻣﺎ ﺍﻟﴩﻃﺎﺕ ﻭﺍﻟﻔﻮﺍﺻﻞ ﺣﺴﺐ ﺍﳊﺎﺟﺔ‪ .‬ﻭﻳﺘﻌﲔ ﻛﺘﺎﺑﺔ ﺍﻻﺳﻢ ﻋﲆ ﺍﻟﻨﺤﻮ ﺍﻟﺘﺎﱄ‪:‬‬
‫‪ –4‬ﺇﻳﺜﻴﻞ– ‪ – 5،3‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺃﻭﻛﺘﺎﻥ‪.‬‬
‫‪‬‬ ‫ﺗﻘﻮﻳﻢ اﺟﺎﺑﺔ‬ ‫‪3‬‬

‫ﺗﻢ ﺇﳚﺎﺩ ﻭﺗﺮﻗﻴﻢ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﻣﺘﺼﻠﺔ ﺑﺼﻮﺭﺓ ﺻﺤﻴﺤﺔ‪ ،‬ﻭﺗ ﱠﹶﻢ ﺗﻌﻴﲔ ﲨﻴﻊ ﺍﻟﺘﻔﺮﻋﺎﺕ ﺑﺎﻟﺒﺎﺩﺋﺎﺕ‪ ،‬ﻭﺃﺳﲈﺀ ﳎﻤﻮﻋﺎﺕ‬
‫‪ - 4 ،2 .a‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ‬ ‫‪.8‬‬ ‫‪CH3 CH3‬‬ ‫ﺃﻟﻜﻴﻞ ﺍﻟﺼﺤﻴﺤﺔ‪ .‬ﺍﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ ﻭﻋﻼﻣﺎﺕ ﺍﻟﱰﻗﻴﻢ ﺻﺤﻴﺤﺎﻥ‪CH3 CH3 .‬‬
‫‪CH3CHCH2CHCH2CH3‬‬ ‫‪CH3CCH2CHCH3‬‬ ‫‪‬‬
‫‪ - 4 ،2 ،2‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‬ ‫‪.b‬‬ ‫ﺍﻟﺒﻨﺎﺋﻴﺔ‪CH‬ﻟﻠﻤﺮﻛﺒﺎﺕ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪3‬‬
‫‪ .8‬ﺍﺳﺘﺨﺪﻡ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻟﺘﺴﻤﻴﺔ ﺍﻷﻳﻮﺑﺎﻙ ‪ IUPAC‬ﻟﺘﺴﻤﻴﺔ ﺍﻟﺼﻴﻐﺔ‬
‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪.c‬‬ ‫‪CH3 CH3‬‬ ‫‪.b‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪.a‬‬ ‫‪CH3 CH3‬‬

‫‪ - 7 ،4 ،2‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﻧﻮﻧﺎﻥ‬ ‫‪.c‬‬ ‫‪CH2 CH3CHCH‬‬

‫‪CH3 2CHCH‬‬
‫‪CH3 2CH3‬‬ ‫‪CH3CCH2CHCH3‬‬ ‫‪CH3CHCH2CHCH2CH3‬‬ ‫‪CH3CCH2CHCH3‬‬
‫‪CH3CHCH2CH2CHCH2CHCH3‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬

‫ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻭﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬ ‫‪.9‬‬ ‫‪CH3‬‬ ‫ﺍﻟﺒﻨﺎﺋﻴﺔ‪CH‬ﻟﻠﻤﺮﻛﺒﺎﺕ ﺍﻟﺘﺎﻟﻴﺔ‪:‬‬

‫‪3‬‬
‫‪  .9‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ‬
‫‪CH2‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪ –5CH‬ﺑﺮﻭﺑﻴﻞ ﺩﻳﻜﺎﻥ‬
‫ﻣﻴﺜﻴﻞ–‬ ‫‪CH‬ﺛﻨﺎﺋﻲ‬
‫‪–33،2CH‬‬
‫‪.a 3‬‬
‫ﺳﻠﺴـﻠﺔ ﺭﺋﻴﺴـﺔ ﻣﻦ ‪ 10‬ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ ،‬ﻭﳎﻤﻮﻋﺘﺎ ﻣﻴﺜﻴﻞ‬
‫‪2‬‬

‫‪.a‬‬ ‫‪CH3CHCH2CH2CHCH2CHCH3‬‬ ‫ﺃﻭﻛﺘﺎﻥ‬

‫ﺇﻳﺜﻴﻞ‪CH‬‬ ‫ﺛﻼﺛﻲ‬
‫‪3CHCH‬‬ ‫‪2CH‬‬ ‫‪5، 4، 32CHCH‬‬
‫‪–2CHCH‬‬ ‫‪.b 3‬‬

‫ﻋـﲆ ﺫﺭﰐ ﺍﻟﻜﺮﺑـﻮﻥ ‪ 2‬ﻭ‪ ،3‬ﻭﳎﻤﻮﻋـﺔ ﺑﺮﻭﺑﻴـﻞ ﻋﲆ ﺫﺭﺓ‬

‫ﺍﻟﻜﺮﺑﻮﻥ ﺭﻗﻢ ‪.5‬‬
‫ﺳﻠﺴﻠﺔ ﺭﺋﻴﺴﺔ ﻣﻦ ‪ 8‬ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ ،‬ﻣﻊ ﳎﻤﻮﻋﺎﺕ ﺇﻳﺜﻴﻞ‬ ‫‪.b‬‬
‫ﻋﲆ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ‪ 3‬ﻭ ‪ 4‬ﻭ‪.5‬‬

‫اﻟﺘﻘﻮﻳﻢ‬ ‫ﻣﺸﺮوع اﻟﻜﻴﻤﻴﺎء‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤﺚ‬

‫‪ ‬ﺍﳍﻜﺘﺎﻥ ﻫﻮ ﺍﺳﻢ ﺃﻳﻮﺑﺎﻙ ﻟﻸﻟﻜﺎﻥ ﺫﻱ ﺍﻟﺴﻠﺴﻠﺔ ﺍﳌﺴﺘﻘﻴﻤﺔ‬
‫ﻋـﻦ ﺍﻻﺳـﺘﻌﲈﻻﺕ ﺍﻟﺼﻨﺎﻋﻴـﺔ ﻟﻸﻟﻜﺎﻧـﺎﺕ ﺍﳊﻠﻘﻴـﺔ‪ ،‬ﻭﲢﻀـﲑ ﻣﻠﺼـﻖ‬
‫ﺯﻭﺩ ﺍﻟﻄـﻼﺏ ﲠﺬﻩ ﺍﳌﻌﻠﻮﻣﺔ‪ ،‬ﺛﻢ‬
‫ﺍﳌﺤﺘﻮﻳﺔ ﻋـﲆ ‪ 100‬ﺫﺭﺓ ﻛﺮﺑﻮﻥ‪ .‬ﹼ‬ ‫ﺍﺳـﺘ ﹾﻌ ﹺﻤﻞ ﻓﻴﻬﺎ‬
‫ﹸﻳﻈﻬـﺮ ﻣﻨﺘﺠﺎﺕ ﲢﺘـﻮﻱ ﻋﲆ ﻫﺬﻩ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﺃﻭ ﻣﻨﺘﺠﺎﺕ ﹸ‬
‫ﺍﺳﺄﻝ‪ :‬ﻣﺎ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻟﻠﻬﻜﺘﺎﻥ؟ ‪C100H202‬‬
‫ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﳊﻠﻘﻴﺔ ﺧـﻼﻝ ﻋﻤﻠﻴﺔ ﺗﺼﻨﻴﻌﻬﺎ‪ .‬ﻭﺍﻋـﺮﺽ ﺍﳌﻠﺼﻘﺎﺕ ﺩﺍﺧﻞ‬
‫ﺍﻟﺼﻒ ﺑﻮﺻﻔﻬﺎ ﺃﺩﺍﺓ ﺗﻌﻠﻴﻤﻴﺔ ﳉﻤﻴﻊ ﺍﻟﻄﻼﺏ‪   .‬‬

‫‪141‬‬
 ‫اﻟﻜﺎﻧﺎت اﻟﺤﻠﻘﻴﺔ ‪Cycloalkanes‬‬
‫ﺗﹸﻌـﺪ ﻗـﺪﺭﺓ ﺫﺭﺓ ﺍﻟﻜﺮﺑـﻮﻥ ﻋﲆ ﺗﻜﻮﻳـﻦ ﺗﺮﺍﻛﻴﺐ ﺑﻨﺎﺋﻴـﺔ ﺣﻠﻘﻴﺔ ﻣﻦ ﺃﺳـﺒﺎﺏ ﻭﺟﻮﺩ‬
‫ﻫـﺬﺍ ﺍﻟﺘﻨﻮﻉ ﰲ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ‪ .‬ﻭ ﹸﻳﺴـﻤﻰ ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀـﻮﻱ ﺍﻟﺬﻱ ﳛﺘﻮﻱ ﻋﲆ‬ ‫‪  8-10‬‬ ‫اﻟﺘﻌﺰﻳﺰ‬
‫ﺣﻠﻘﺔ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﻴﺔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳊﻠﻘﻲ‪ .‬ﻭﺗﹸﺴـﺘﺨﺪﻡ ﺍﻟﺒﺎﺩﺋﺔ ﺣﻠﻘﻲ )‪(cyclo‬‬ ‫‪‬‬

‫‪ ‬ﺃﴍ ﺇﱃ ﻭﺟﻮﺩ ﺳـﺖ ﻃﺮﺍﺋﻖ ﳐﺘﻠﻔﺔ‬

‫ﻣـﻊ ﺍﺳـﻢ ﺍﳍﻴﺪﺭﻭﻛﺮﺑـﻮﻥ ﻟﻺﺷـﺎﺭﺓ ﺇﱃ ﺍﺣﺘـﻮﺍﺀ ﺍﳍﻴﺪﺭﻭﻛﺮﺑـﻮﻥ ﻋﲆ ﺑﻨـﺎﺀ ﺣﻠﻘﻲ‪.‬‬ ‫‪CH 2 CH 2 CH 2‬‬
‫ﻟـﺬﺍ ﻓـﺈﻥ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺍﳊﻠﻘﻴـﺔ ﺍﳌﺤﺘﻮﻳـﺔ ﻋـﲆ ﺭﻭﺍﺑـﻂ ﺃﺣﺎﺩﻳﺔ ﻓﻘﻂ ﺗﹸﺴـﻤﻰ‬ ‫‪CH 2 CH 2 CH‬‬
‫‪CH‬‬‫‪2 2 CH 2 CH 2‬‬
‫ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﳊﻠﻘﻴﺔ‪ .‬ﻭﺗﺘﻜﻮﻥ ﺍﳊﻠﻘﺎﺕ ﰲ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ ﻣﻦ ﺛﻼﺙ‪ ،‬ﺃﻭ ﺃﺭﺑﻊ‪،‬‬
‫ﺃﻭ ﲬﺲ‪ ،‬ﺃﻭ ﺳـﺖ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﻭ ﺃﻛﺜﺮ‪ .‬ﺇﻥ ﺍﺳـﻢ ﺍﻷﻟـﻜﺎﻥ ﺍﳊﻠﻘﻲ ﺫﻱ ﺍﻟﺬﺭﺍﺕ‬
‫‪CH 2 CH 2 CH‬‬
‫‪CH‬‬‫‪2 2 CH 2 CH 2‬‬ ‫ﻟﱰﻗﻴـﻢ ﺍﳊﻠﻘﺔ ﺍﻟﺴﺪﺍﺳـﻴﺔ‪ .‬ﻗﺪ ﺗﻜـﻮﻥ ﺃﺭﻗﺎﻡ ﻣﻮﺍﻗـﻊ ﺍﳌﺠﻤﻮﻋﺎﺕ‬
‫‪CH 2 CH 2 CH 2‬‬
‫ﺍﻟﺴـﺖ ﻣﻦ ﺍﻟﻜﺮﺑﻮﻥ ﻫﻮ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ‪ .‬ﻭﻳﺴـﺘﺨﺪﻡ ﺍﳍﻜﺴﺎﻥ ﺍﳊﻠﻘﻲ ﺍﳌﺴﺘﺨﺮﺝ‬
‫ﻣﻦ ﺍﻟﺒﱰﻭﻝ ﰲ ﹸﻣﺰﻳﻼﺕ ﺍﻟﺪﻫﺎﻥ‪ ،‬ﻭﺍﺳﺘﺨﻼﺹ ﺍﻟﺰﻳﻮﺕ ﱠ‬
‫ﺍﻟﻄ ﱠﻴﺎﺭﺓ ﻟﺘﺤﻀﲑ ﺍﻟﻌﻄﻮﺭ‪.‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬
‫‪‬‬
‫ﺍﻟﺒﺪﻳﻠـﺔ ﺍﺑﺘـﺪﺍ ﹰﺀ ﻣﻦ ﺃﻋﲆ ﻫـﻲ‪ 4 ،2 ،1 :‬ﺃﻭ ﺍﻷﺭﻗـﺎﻡ ‪ .6 ،4 ،1‬ﻭﻗﺪ‬
‫ﻭﻻﺣﻆ ﺃﻥ ﺍﳍﻜﺴﺎﻥ ﺍﳊﻠﻘﻲ ‪ C6H12‬ﻳﻘﻞ ﻋﻦ ﺍﳍﻜﺴﺎﻥ ‪ C6H14‬ﻏﲑ ﺍﳌﺘﻔﺮﻉ ﺑﺬﺭﰐ‬
‫ﻫﻴﺪﺭﻭﺟـﲔ؛ ﻭﺫﻟـﻚ ﻷﻥ ﺇﻟﻜـﱰﻭﻥ ﺗﻜﺎﻓﺆ ﻭﺍﺣـﺪﹰ ﺍ ﻣﻦ ﻛﻞ ﻣـﻦ ﺫﺭﰐ ﺍﻟﻜﺮﺑﻮﻥ ﰲ‬
‫‪C‬‬ ‫‪C CC‬‬ ‫‪C‬‬ ‫‪C‬‬
‫ﺗﻜـﻮﻥ ﺍﻷﺭﻗـﺎﻡ ﺍﺑﺘـﺪﺍﺀ ﻣﻦ ﺍﻟﻴﻤـﲔ ﻫـﻲ‪ 5 ،2 ،1:‬ﺃﻭ ‪ .6 ،3 ،1‬ﺃ ﹼﻣﺎ‬
‫‪C‬‬ ‫‪C CC‬‬ ‫‪C‬‬ ‫‪C‬‬
‫ﻳﻜـﻮﻥ ﺭﺍﺑﻄـﺔ ﻛﺮﺑـﻮﻥ‪ -‬ﻛﺮﺑـﻮﻥ ﹰ‬
‫ﻋﻮﺿﺎ ﻋـﻦ ﺭﺍﺑﻄـﺔ ﻛﺮﺑﻮﻥ‪-‬‬ ‫ﺍﻷﻟـﻜﺎﻥ ﺍﳊﻠﻘـﻲ ﱢ‬
‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬
‫‪‬‬ ‫‪‬‬ ‫ﺍﺑﺘﺪﺍ ﹰﺀ ﻣﻦ ﺃﺳﻔﻞ‪ ،‬ﻓﺘﻜﻮﻥ ﺍﻷﺭﻗﺎﻡ ﻫﻲ‪ 4 ،3 ،1 :‬ﺃﻭ ‪ .5 ،4 ،1‬‬
‫ﻫﻴﺪﺭﻭﺟﲔ‪.‬‬
‫‪ ‬ﺇﺫﺍ ﻭﺟﺪﺕ )ﺣﻠﻘﻲ( ﰲ ﺍﺳﻢ ﺍﻷﻟﻜﺎﻥ‪ ،‬ﻓﲈ ﺍﻟﺬﻱ ﺳﺘﻌﺮﻓﻪ‬
‫ﻋﻦ ﻫﺬﺍ ﺍﻷﻟﻜﺎﻥ؟‬ ‫اﻟﺘﻘﻮﻳﻢ‬
‫‪ C22-107C-828378-08‬ﹸﲤﺜﱠﻞ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪ 8-10‬ﺍﳍﻜﺴﺎﻥ ﺍﳊﻠﻘﻲ ﺑﺄﺷﻜﺎﻝ‬
‫‪C22-107C-828378-08‬‬
‫‪C22-107C-828378-08‬‬
‫ﻣﻜﺜﻔﺔ ﻭﻫﻴﻜﻠﻴﺔ ﻭﺧﻄﻴﺔ ﻋﺪﻳﺪﺓ؛ ﻭﺗﹸﻈﻬﺮ ﺍﻷﺷﻜﺎﻝ ﺍﳋﻄﻴﺔ ﺍﻟﺮﻭﺍﺑﻂ ﺑﲔ ﺫﺭﺍﺕ‬
‫ﺍﻟﻜﺮﺑﻮﻥ ﻓﻘﻂ‪ ،‬ﻭﺗﹸﻔﴪ ﺍﻟﺰﻭﺍﻳﺎ ﰲ ﺍﻟﺸﻜﻞ ﻋﲆ ﺃﳖﺎ ﻣﻮﺍﻗﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ .‬ﺃﻣﺎ‬
‫ﺑﺎﻟﻨﺴﺒﺔ ﻟﺬﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﻓﻴﻔﱰﺽ ﺃﳖﺎ ﲢﺘﻞ ﺑﻘﻴﺔ ﻣﻮﺍﻗﻊ ﺍﻟﺮﺑﻂ ﺇ ﹼ‬
‫ﻻ ﺇﺫﺍ ﹸﻭﺟﺪﺕ‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﻛﻞ ﻃﺎﻟـﺐ ﻛﺘﺎﺑﺔ ﺻﻴﻐﺔ ﺑﻨﺎﺋﻴـﺔ ﻷﻟﻜﺎﻥ ﺣﻠﻘﻲ‬
‫ﺍﻟﺘﻔﺮﻋﺎﺕ )ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ(‪ .‬ﻭﻻ ﺗﻈﻬﺮ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﰲ ﺍﻟﺸﻜﻞ‬
‫ﺍﳍﻴﻜﲇ‪.‬‬
‫ﻣﺘﻔـﺮﻉ ﰲ ﺃﻋـﲆ ﻭﺭﻗـﺔ‪ ،‬ﻭﻛﺘﺎﺑﺔ ﺍﺳـﻢ ﺍﻷﻟـﻜﺎﻥ ﰲ ﺃﺳـﻔﻞ ﺍﻟﻮﺭﻗﺔ‬
‫‪ ‬ﻳﻤﻜﻦ ﺃﻥ‬ ‫ﻧﻔﺴـﻬﺎ‪ .‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﹶﺛ ﹾﻨﻲ ﺍﻟﻮﺭﻗﺔ ﻣـﻦ ﺍﻟﻨﺼﻒ‪ ،‬ﻋﲆ ﺃﻻ ﻳﻈﻬﺮ‬
‫ﻳﻜـﻮﻥ ﻟﻸﻟﻜﺎﻧـﺎﺕ ﺍﳊﻠﻘﻴـﺔ ﳎﻤﻮﻋﺎﺕ ﺑﺪﻳﻠﺔ ﻛﺴـﺎﺋﺮ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﻷﺧﺮ￯‪ .‬ﻭﺗﺘﻢ‬
‫ﺗﺴﻤﻴﺘﻬﺎ ﺑﺎﺗﺒﺎﻉ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ )‪ (IUPCA‬ﺍﳌﺴﺘﺨﺪﻣﺔ ﰲ ﺗﺴﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ‬ ‫ﺍﺳـﻢ ﺍﻷﻟﻜﺎﻥ ﺍﳊﻠﻘﻲ‪ ،‬ﻭﺩﻋﻬـﻢ ﻳﺘﺒﺎﺩﻟﻮﺍ ﺍﻷﻭﺭﺍﻕ ﻓﻴـﲈ ﺑﻴﻨﻬﻢ‪ .‬ﺛﻢ‬
‫ﻏﲑ ﺍﳌﺘﻔﺮﻋﺔ ﻧﻔﺴـﻬﺎ‪ ،‬ﻭﻟﻜﻦ ﺑﺈﺟـﺮﺍﺀ ﺗﻌﺪﻳﻞ ﳏﺪﻭﺩ؛ ﻓﻠﻴﺲ ﻫﻨـﺎﻙ ﺣﺎﺟﺔ ﺇﱃ ﺇﳚﺎﺩ‬
‫ﺩﺍﺋﲈ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ‪ .‬ﻭﻷﻥ ﺍﻟﺸﻜﻞ ﺍﳊﻠﻘﻲ ﻟﻴﺲ‬‫ﺃﻃﻮﻝ ﺳﻠﺴـﻠﺔ؛ ﺇﺫ ﺗﻌﺪ ﺍﳊﻠﻘﺔ ﹰ‬ ‫ﺍﻃﻠـﺐ ﺇﱃ ﻛﻞ ﻃﺎﻟـﺐ ﺃﻥ ﳛـﺎﻭﻝ ﺗﺴـﻤﻴﺔ ﺍﻷﻟـﻜﺎﻥ‪ ،‬ﻭﺑﻌﺪ ﺫﻟﻚ‪،‬‬
‫ﻟـﻪ ﺃﻃﺮﺍﻑ ﻟﺬﺍ ﻳﺒﺪﺃ ﺍﻟﱰﻗﻴـﻢ ﻣﻦ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﺍﳌﺮﺗﺒﻄـﺔ ﺑﺎﳌﺠﻤﻮﻋﺔ ﺍﻟﺒﺪﻳﻠﺔ‪ .‬ﻭﻋﻨﺪ‬
‫ﻭﺟـﻮﺩ ﺃﻛﺜﺮ ﻣﻦ ﳎﻤﻮﻋﺔ ﺑﺪﻳﻠﺔ ﺗﹸﺮﻗﻢ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺣﻮﻝ ﺍﳊﻠﻘﺔ‪ ،‬ﻋﲆ ﺃﻥ ﲢﺼﻞ‬ ‫ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺍﻟﻮﻗﻮﻑ ﻋﲆ ﻣﺪ￯ ﺗﻄﺎﺑﻖ ﺍﻷﺳﲈﺀ‪ ،‬ﺛﻢ ﺩﻋﻬﻢ ﻳﻌﻤﻠﻮﺍ‬
‫ﺍﳌﺠﻤﻮﻋـﺎﺕ ﺍﻟﺒﺪﻳﻠـﺔ ﻋـﲆ ﺃﺻﻐﺮ ﳎﻤﻮﻋﺔ ﺃﺭﻗـﺎﻡ ﳑﻜﻨـﺔ‪ .‬ﻭﺇﺫﺍ ﻛﺎﻥ ﻫﻨﺎﻙ ﳎﻤﻮﻋﺔ‬
‫ﹴ‬
‫ﻋﻨﺪﺋﺬ ﻟﻠﱰﻗﻴـﻢ‪ .‬ﻭ ﹸﻳﻮﺿﺢ ﺍﳌﺜﺎﻝ ﺍﻵﰐ‬ ‫ﺑﺪﻳﻠـﺔ ﻭﺍﺣـﺪﺓ ﻣﺘﺼﻠﺔ ﺑﺎﳊﻠﻘﺔ ﻓـﻼ ﴐﻭﺭﺓ‬ ‫ﻣﻌﺎ ﻟﺘﺴـﻤﻴﺔ ﺍﻷﻟـﻜﺎﻥ ﺑﺼـﻮﺭﺓ ﺻﺤﻴﺤﺔ‪ ،‬ﻭﺷـﺠﻌﻬﻢ ﻋﲆ ﻃﻠﺐ‬ ‫ﹰ‬
‫ﻋﻤﻠﻴﺔ ﺗﺴﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ‪.‬‬
‫ﺍﳌﺴﺎﻋﺪﺓ ﻋﻨﺪ ﺍﳊﺎﺟﺔ‪ .‬‬

‫ا¬ﺛﺮاء‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﻟﺒﺤـﺚ ﰲ ﺣﺠـﻮﻡ‬
‫ﺷﻴﻮﻋﺎ ﺑﲔ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ‪ ،‬ﻭﲢﺪﻳﺪ‬
‫ﹰ‬ ‫ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ ﺍﻷﻛﺜﺮ‬
‫ﺳﺒﺐ ﺃﳘﻴﺔ ﺣﺠﻢ ﺍﻷﻟﻜﺎﻥ ﺍﳊﻠﻘﻲ‪.‬‬
‫ﹸﻳﻌـﺪﹼ ﺣﺠـﻢ ﺍﳊﻠﻘﺔ ﰲ ﻛﻞ ﻣﻦ ﺍﻟﺒﻨﺘﺎﻥ ﺍﳊﻠﻘﻲ ﻭﺍﳍﻜﺴـﺎﻥ ﺍﳊﻠﻘﻲ‬
‫ﺗﻜﻮﻥ‬
‫ﺷـﻴﻮﻋﺎ؛ ﻷﻥ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﻫﺬﻩ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﹼ‬
‫ﹰ‬ ‫ﺍﻷﻛﺜﺮ‬
‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺑﻨﺎﺀ ﻧﻤﻮﺫﺝ ﻷﻟﻜﺎﻥ ﻛﺜﲑ ﺍﻟﺘﻔﺮﻉ ﳛﻤﻞ‬
‫ﺭﻭﺍﺑـﻂ ﳍﺎ ﺃﻗـﻞ ﺍﻧﻀﻐـﺎﻁ ﻣﻘﺎﺭﻧـﺔ ﺑﺎﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﰲ ﺍﳊﻠﻘﺎﺕ‬
‫ﺍﻟﺼﻴﻐـﺔ ‪ ،C18H38‬ﺛـﻢ ﺗﺴـﻤﻴﺔ ﻫـﺬﺍ ﺍﻟﻨﻤﻮﺫﺝ ﺑﺎﺳـﺘﺨﺪﺍﻡ ﻗﻮﺍﻋـﺪ ﺃﻳﻮﺑﺎﻙ‬
‫)‪ .(IUPAC‬‬
‫ﺍﻟﺼﻐـﺮ￯ ﺃﻭ ﺍﻟﻜـﱪ￯‪ .‬ﺇﻥ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺃﺣﺎﺩﻳـﺔ ﺍﻟﺮﺑﻂ ﹸﺗ ﹶﻜ ﱢﻮﻥ‬
‫ﺃﻗﻮ￯ ﺭﻭﺍﺑـﻂ ﳑﻜﻨﺔ ﻋﻨﺪﻣﺎ ﺗﻜﻮﻥ ﺍﻟﺰﻭﺍﻳﺎ ﺑـﲔ ﺍﻟﺮﻭﺍﺑﻂ ‪،109.5°‬‬
‫ﻛﲈ ﻫﻮ ﺍﳊﺎﻝ ﰲ ﺍﳌﻴﺜﺎﻥ‪ .‬‬
‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬ ‫‪ ‬ﳛﺘﻮﻱ ﺍﻷﻟﻜﺎﻥ ﻋﲆ ﺣﻠﻘﺔ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﻴﺔ‪.‬‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻛﺘﺎﺑﺔ ﻓﻘﺮﺓ ﹼ‬

‫ﻋـﲈ ﻳﺘﻮﻗﻌﻮﻥ ﺣﺪﻭﺛﻪ ﻋﻨﺪ‬
‫ﺧﻠـﻂ ﻛﻤﻴﺔ ﻗﻠﻴﻠﺔ ﻣﻦ ﺯﻳﺖ ﺍﳌﺤﺮﻛﺎﺕ‪ ،‬ﺃﻭ ﺃﻱ ﺧﻠﻴﻂ ﺁﺧﺮ ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ‬
‫ﺑﺎﳌـﺎﺀ‪ .‬ﻭﻳﺘﻌﲔ ﻋﲆ ﺍﻟﻄـﻼﺏ ﺑﻌﺪ ﺫﻟﻚ ﺃﻥ ﻳﺼﻔﻮﺍ ﻣﺎ ﺣﺪﺙ ﻋﻨﺪﻣﺎ ﺟﺮﺑﻮﺍ‬
‫ﺫﻟﻚ‪ .‬ﻭﻋﻠﻴﻬﻢ ﹰ‬
‫ﺃﻳﻀﺎ ﺃﻥ ﻳﻜﺘﺒﻮﺍ ﻫﺎﺗﲔ ﺍﻟﻔﻘﺮﺗﲔ ﰲ ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ‪ .‬‬

‫‪142‬‬
 ‫‪82‬‬

‫‪‬‬ ‫‪CH3‬‬ ‫‪‬‬

‫ﺳﻢ ﺍﻷﻟﻜﺎﻥ ﺍﳊﻠﻘﻲ ﺍﳌﺠﺎﻭﺭ‪.‬‬
‫ﹼ‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫ﺗﺤﻠﻴﻞ اﻟﻤﺴﺄﻟﺔ‬ ‫‪1‬‬
‫‪ ‬ﺍﺳﺘﺨﺪﻡ ﻗﻮﺍﻋﺪ ﺃﻳﻮﺑﺎﻙ ﻟﺘﺴﻤﻴﺔ ﺍﳌﺮﻛﺐ ﺍﻵﰐ‪:‬‬ ‫ﺃﻋﻄﻴﺖ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﻋﻠﻴﻚ ﺍﺗﺒﺎﻉ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ ﻟﺘﺤﺪﻳﺪ ﺍﻟﺸﻜﻞ ﺍﳊﻠﻘﻲ ﺍﻟﺮﺋﻴﺲ ﻭﻣﻮﺍﻗﻊ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ‬
‫)ﺍﻟﺘﻔﺮﻋﺎﺕ( ﻟﻠﺸﻜﻞ ﺍﳌﻌﻄﻰ‪.‬‬
‫‪C22-130C-828378-08‬‬
‫‪CH 3‬‬ ‫ﺣﺴﺎب اﻟﻤﻄﻠﻮب‬ ‫‪2‬‬

‫ﺍﳋﻄﻮﺓ ‪ .1‬ﺣﺪﹼ ﺩ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﳊﻠﻘﺔ‪ ،‬ﻭﺍﺳﺘﺨﺪﻡ ﺍﺳﻢ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳊﻠﻘﻲ ﺍﻟﺮﺋﻴﺲ‪ .‬ﺣﻴﺚ ﺗﺘﺄﻟﻒ ﺍﳊﻠﻘﺔ ﰲ ﻫﺬﻩ‬
‫ﺍﳊﺎﻟﺔ‪ ،‬ﻣﻦ ﺳﺖ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ .‬ﻟﺬﺍ ﻓﺈﻥ ﺍﻻﺳﻢ ﺍﻟﺮﺋﻴﺲ ﻫﻮ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ‪.‬‬
‫‪CH 3‬‬ ‫ﻭﺟﺪ ﺍﻟﱰﻗﻴﻢ ﺍﻟﺬﻱ ﻳﻌﻄﻲ ﺃﻗﻞ ﳎﻤﻮﻋﺔ ﺃﺭﻗﺎ ﹰﻣﺎ ﳑﻜﻨﺔ ﻟﻠﺘﻔﺮﻋﺎﺕ‪.‬‬ ‫ﺍﳋﻄﻮﺓ ‪ .2‬ﺭ ﱢﻗﻢ ﺍﳊﻠﻘﺔ ﺍﺑﺘﺪﺍ ﹰﺀ ﻣﻦ ﺃﺣﺪ ﹼ‬
‫ﺗﻔﺮﻋﺎﺕ )‪ ،(-CH3‬ﹺ‬
‫ﻭﻓﻴﲈ ﻳﲇ ﻃﺮﻳﻘﺘﺎﻥ ﻟﱰﻗﻴﻢ ﺍﳊﻠﻘﺔ ﳘﺎ‪:‬‬
‫‪‬‬ ‫‪CH 3‬‬
‫‪B‬‬
‫‪CH 3‬‬
‫‪A‬‬

‫‪ - 2 ،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﺮﻭﺑﺎﻥ ﺣﻠﻘﻲ‬

‫‪1‬‬ ‫‪4‬‬
‫‪6‬‬
‫‪2‬‬ ‫‪CH 3‬‬ ‫‪3‬‬ ‫‪CH 3‬‬
‫‪5‬‬

‫‪5‬‬ ‫‪3‬‬ ‫‪6‬‬ ‫‪2‬‬

‫‪4‬‬ ‫‪1‬‬
‫‪CH 3‬‬ ‫‪CH 3‬‬
‫‪1,2,4‬‬ ‫‪1,3,4‬‬

‫ﳎﻤﻮﻋﺎﺕ ‪ –CH3‬ﻋﲆ ﺍﳌﻮﺍﻗﻊ ‪ 1‬ﻭ‪ 3‬ﻭ‪ 4‬ﰲ ﺍﻟﺸﻜﻞ ‪ ،A‬ﰲ ﺣﲔ ﻳﻀﻊ‬‫ﹺ‬ ‫ﻳﻀﻊ ﺍﻟﱰﻗﻴﻢ ﺑﺪ ﹰﺀﺍ ﻣﻦ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺃﺳﻔﻞ ﺍﳊﻠﻘﺔ‬
‫ﹺ‬
‫ﳎﻤﻮﻋﺎﺕ ‪ CH3‬ﻋﲆ ﺍﳌﻮﺍﻗﻊ ‪1‬ﻭ ‪ 2‬ﻭ ‪ .4‬ﻭﺗﻀﻊ ﻃﺮﺍﺋﻖ ﺍﻟﱰﻗﻴﻢ ﺍﻷﺧﺮ￯ ﳎﻤﻮﻋﺎﺕ‬ ‫ﺍﻟﱰﻗﻴﻢ ﺑﺪ ﹰﺀﺍ ﻣﻦ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺃﻋﲆ ﺍﳊﻠﻘﺔ‬
‫‪ -CH3‬ﻋﲆ ﻣﻮﺍﻗﻊ ﺫﺍﺕ ﺃﺭﻗﺎﻡ ﺃﻋﲆ‪ .‬ﻟﺬﺍ ﻓﺈﻥ ‪ 1‬ﻭ ‪ 2‬ﻭ ‪ 4‬ﻫﻲ ﺃﻗﻞ ﺃﺭﻗﺎﻡ ﳑﻜﻨﺔ‪ .‬ﻟﺬﻟﻚ ﺗﹸﺴﺘﺨﺪﻡ ﰲ ﺍﻻﺳﻢ‪.‬‬
‫ﻋﻠﲈ ﺑﺄﻥ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺜﻼﺙ ﲨﻴﻌﻬﺎ ﳎﻤﻮﻋﺎﺕ ﻣﻴﺜﻴﻞ‪.‬‬ ‫ﺳﻢ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ‪ .‬ﹰ‬ ‫ﺍﳋﻄﻮﺓ ‪ .3‬ﱢ‬
‫ﺍﳋﻄﻮﺓ ‪ .4‬ﺃﺿﻒ ﺍﻟﺒﺎﺩﺋﺔ ﻹﻇﻬﺎﺭ ﻋﺪﺩ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﳌﻮﺟﻮﺩﺓ‪ ،‬ﺣﻴﺚ ﺗﻮﺟﺪ ﺛﻼﺙ ﳎﻤﻮﻋﺎﺕ ﻣﻴﺜﻴﻞ‪ ،‬ﻟﺬﺍ ﻓﺈﻥ ﺍﻟﺒﺎﺩﺋﺔ )ﺛﻼﺛﻲ(‬
‫ﺗﹸﻀﺎﻑ ﺇﱃ ﺍﺳﻢ ﺍﳌﺠﻤﻮﻋﺔ ﻣﻴﺜﻴﻞ‪ ،‬ﻓﺘﺼﺒﺢ ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ‪.‬‬
‫ﺍﳋﻄﻮﺓ ‪ .5‬ﻳﻤﻜﻦ ﲡﺎﻫﻞ ﺍﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ ﺑﺴﺒﺐ ﻭﺟﻮﺩ ﻧﻮﻉ ﻭﺍﺣﺪ ﻣﻦ ﺍﳌﺠﻤﻮﻋﺎﺕ‪.‬‬
‫‪C22-052C-828378-08‬ﺍﺳﻢ ﺍﻷﻟﻜﺎﻥ ﺍﳊﻠﻘﻲ ﺍﻟﺮﺋﻴﺲ‪ ،‬ﻣﺴﺘﺨﺪ ﹰﻣﺎ ﺍﻟﻔﻮﺍﺻﻞ ﻟﻠﻔﺼﻞ ﺑﲔ ﺍﻷﺭﻗﺎﻡ‪ ،‬ﻭﺍﻟﴩﻃﺎﺕ‬
‫ﲨﻊ ﺍﻻﺳﻢ ﺑﺎﺳﺘﺨﺪﺍﻡ‬‫ﺍﳋﻄﻮﺓ ‪ .6‬ﹶ ﹼ‬
‫ﻟﻠﻔﺼﻞ ﺑﲔ ﺍﻷﺭﻗﺎﻡ ﻭﺍﻟﻜﻠﲈﺕ‪ .‬ﻭﺍﻛﺘﺐ ﺍﻻﺳﻢ ﻋﲆ ﺍﻟﻨﺤﻮ ﺍﻵﰐ‪:‬‬
‫‪ – 4 ،2 ،1‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ‬
‫ﺗﻘﻮﻳﻢ اﺟﺎﺑﺔ‬ ‫‪3‬‬

‫ﹸﻳﺮ ﹼﻗﻢ ﺍﻟﺸﻜﻞ ﺍﳊﻠﻘﻲ ﺍﻟﺮﺋﻴﺲ ﻋﲆ ﺃﻥ ﻳﻌﻄﻲ ﺍﻟﺘﻔﺮﻋﺎﺕ ﺃﻗﻞ ﳎﻤﻮﻋﺔ ﺃﺭﻗﺎﻡ ﳑﻜﻨﺔ‪ .‬ﻭﺗﺸﲑ ﺍﻟﺒﺎﺩﺋﺔ )ﺛﻼﺛﻲ( ﺇﱃ ﻭﺟﻮﺩ ﺛﻼﺙ‬
‫ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ .‬ﻭﻷﻥ ﺍﻟﺘﻔﺮﻋﺎﺕ ﻛﻠﻬﺎ ﻫﻲ ﳎﻤﻮﻋﺎﺕ ﻣﻴﺜﻴﻞ‪ ،‬ﻟﺬﺍ ﻓﻼ ﴐﻭﺭﺓ ﻟﻠﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ‪.‬‬

‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬

‫‪ ‬ﻋﺎﺩﺓ ﻣـﺎ ﺗﻜﻮﻥ‬

‫ﺧﺎﺻـﺎ‪ ،‬ﺃﻛﺜﺮ ﺩﻗﺔ ﻣـﻦ ﺃﺟﻬﺰﺓ‬
‫ﺍﻟـﻜﻼﺏ ﺍﻟﺒﻮﻟﻴﺴـﻴﺔ ‪ K-9‬ﺍﳌﺪﺭﺑـﺔ ﺗﺪﺭﻳ ﹰﺒـﺎ ﹼﹰ‬
‫ﴪﻋﺎﺕ ﺍﳊﺮﻳﻖ ﰲ ﻣﻮﻗﻊ ﺍﳊﺮﻳﻖ‪.‬‬ ‫ﺍﻟﻜﺸـﻒ ﺍﻹﻟﻜﱰﻭﻧﻴﺔ ﰲ ﺍﻟﻌﺜﻮﺭ ﻋﲆ ﹸﻣ ﹶ ﱢ‬
‫ﻣﻜﻮﻧـﺎﺕ‬
‫ﺣﺴﺎﺳـﺔ ﲡـﺎﻩ ﹼ‬ ‫ﺇﻥ ﺃﺟﻬـﺰﺓ ﺍﻟﻜﺸـﻒ ﻋـﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﹼ‬
‫ﺍﳉﺎﺯﻭﻟـﲔ ﰲ ﻣﺪ￯ ﺃﺟﺰﺍﺀ ﻣﻦ ﺍﳌﻠﻴـﻮﻥ )‪ .(ppm‬ﻭﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺫﻟﻚ‪،‬‬
‫ﺁﺛﺎﺭﺍ ﺿﺌﻴﻠﺔ ﺟﺪﹼﹰ ﺍ ﻗﺪ ﺗﻐﻔﻞ ﻋﻨﻬﺎ ﺍﻷﺟﻬﺰﺓ‬‫ﺗﺴـﺘﻄﻴﻊ ﺍﻟﻜﻼﺏ ﺃﻥ ﲢﺪﱢ ﺩ ﺑﺪﻗﺔ ﹰ‬
‫ﺍﻹﻟﻜﱰﻭﻧﻴـﺔ‪ ،‬ﻭﻋﺎﺩﺓ ﻣﺎ ﺗﻜﻮﻥ ﺿﺌﻴﻠﺔ ﺟﺪﹼﹰ ﺍ ﺗﺼـﻞ ﺇﱃ ‪0.01 microliter‬‬
‫ﹶﺒﺨﺮ‪ .‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ‬ ‫ﻣـﻦ ﳐﻠﻮﻁ ﳛﺘﻮﻱ ﻋـﲆ ‪ 50%‬ﻣﻦ ﺍﳉﺎﺯﻭﻟﲔ ﺍ ﹸﳌﺘ ﱢ‬
‫ﺨﺪﻣﺖ ﻓﻴﻬﺎ ﺍﻟﻜﻼﺏ ﻹﺛﺒـﺎﺕ ﺃﻥ ﺍﳊﺮﻳﻖ‬ ‫ﺍﻟﺒﺤـﺚ ﰲ ﻗﻀﻴﺔ ﺣﻘﻴﻘﻴﺔ ﺍﺳـ ﹸﺘ ﹺ‬
‫ﹸﻣﻔﺘﹶﻌﻞ‪ .‬‬

‫‪143‬‬
 ‫‪‬‬
‫‪ .10‬ﺍﺳﺘﺨﺪﻡ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ ﻟﺘﺴﻤﻴﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪CH2CH3 .c‬‬
‫‪CH3‬‬
‫‪.b‬‬ ‫‪.a‬‬ ‫‪‬‬
‫‪CH3‬‬

‫‪ .a .10‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ ﺣﻠﻘﻲ‬

‫‪CH3‬‬ ‫‪CH2CH3‬‬
‫‪CH3CH2‬‬

‫‪ - 2‬ﺇﻳﺜﻴﻞ‪ -4،1-‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ‬

‫‪  .11‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻸﻟﻜﺎﻧﺎﺕ ﺍﻟﺘﺎﻟﻴﺔ‪:‬‬
‫‪C22-053C-828378-08‬‬
‫‪ –1 .a‬ﺇﻳﺜﻴﻞ– ‪ –3‬ﺑﺮﻭﺑﻴﻞ ﺑﻨﺘﺎﻥ ﺣﻠﻘﻲ‪.‬‬
‫‪.b‬‬
‫‪C22-055C-828378-08‬‬
‫‪ – 4،2،2،1 .b‬ﺭﺑﺎﻋﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ‪.‬‬
‫‪C22-054C-828378-08‬‬ ‫‪ -3.1‬ﺛﻨﺎﺋﻲ ﺇﻳﺜﻴﻞ ﺑﻴﻮﺗﺎﻥ ﺣﻠﻘﻲ‬ ‫‪.c‬‬
‫ﺧﺼﺎﺋﺺ ا¶ﻟﻜﺎﻧﺎت‬ ‫‪ .11‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫ﻼ ﺭﺍﺑﻄﺔ ‪ O-H‬ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﳌﺎﺀ‬ ‫ﻋﺮﻓﺖ ﺳﺎﺑ ﹰﻘﺎ ﺃﻥ ﺑﻨﺎﺀ ﺍﳉﺰﻱﺀ ﻳﺆﺛﺮ ﰲ ﺧﺼﺎﺋﺼﻪ‪ .‬ﻓﻤﺜ ﹰ‬
‫ﺭﺍﺑﻄﺔ ﹸﻗﻄﺒﻴﺔ‪ ،‬ﻭﻷﻥ ﺟﺰﻱﺀ ‪ H-O-H‬ﻟﻪ ﺷﻜﻞ ﻫﻨﺪﳼ ﻣﻨﺤﻦﹴ ﻓﺈﻥ ﺍﳉﺰﻱﺀ ﻧﻔﺴﻪ ﻗﻄﺒﻲ‪،‬‬ ‫ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴـﺔ ﻫـﻲ ﺣﻠﻘﺔ ﻣـﻦ ‪ 5‬ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ ،‬ﻣﻊ‬ ‫‪.a‬‬
‫ﻣﻌﺎ‪ .‬ﻟﺬﺍ ﻓﺈﻥ‬
‫ﻭﺗﻜﻮﻥ ﺭﻭﺍﺑﻂ ﻫﻴﺪﺭﻭﺟﻴﻨﻴﺔ ﹰ‬ ‫ﹼ‬ ‫ﻟﺬﺍ ﺗﻨﺠﺬﺏ ﺟﺰﻳﺌﺎﺕ ﺍﳌﺎﺀ ﺑﻌﻀﻬﺎ ﺇﱃ ﺑﻌﺾ‪،‬‬
‫ﲑﺍ ﻣﻦ ﺳﺎﺋﺮ ﺍﳌﻮﺍﺩ ﺍﳌﺸﺎﲠﺔ ﻟﻪ ﰲ ﺍﻟﻜﺘﻠﺔ ﺍﳉﺰﻳﺌﻴﺔ‬
‫ﺩﺭﺟﺎﺕ ﺍﻟﻐﻠﻴﺎﻥ ﻭﺍﻻﻧﺼﻬﺎﺭ ﻟﻠﲈﺀ ﺃﻋﲆ ﻛﺜ ﹰ‬ ‫ﳎﻤﻮﻋـﺔ ﺇﻳﺜﻴﻞ ﻋـﲆ ﺫﺭﺓ ﺍﻟﻜﺮﺑـﻮﻥ ‪ ،1‬ﻭﳎﻤﻮﻋﺔ ﺑﺮﻭﺑﻴﻞ‬
‫ﻭﰲ ﺍﳊﺠﻢ‪.‬‬
‫ﺗﺮ￯‪ ،‬ﻣﺎ ﺧﺼﺎﺋﺺ ﺍﻷﻟﻜﺎﻧﺎﺕ؟ ﺗﺘﻜﻮﻥ ﲨﻴﻊ ﺍﻟﺮﻭﺍﺑﻂ ﰲ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﻦ ﺫﺭﺓ ﻛﺮﺑﻮﻥ‬ ‫ﻋﲆ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ‪.3‬‬
‫ﻭﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ‪ ،‬ﺃﻭ ﺫﺭﰐ ﻛﺮﺑﻮﻥ‪ .‬ﻭﻳﺘﻌﺬﺭ ﺃﻥ ﺗﻜﻮﻥ ﺍﻟﺮﺍﺑﻄﺔ ﺑﲔ ﺫﺭﺗﲔ ﻣﻦ ﺍﻟﻨﻮﻉ ﻧﻔﺴﻪ‬
‫‪ -‬ﻣﺜﻞ ﺍﻟﻜﺮﺑﻮﻥ ‪ -‬ﺭﺍﺑﻄﺔ ﻗﻄﺒﻴﺔ‪ .‬ﻟﺬﺍ ﺗﹸﻌﺪ ﺟﺰﻳﺌﺎﺕ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻏﲑ ﻗﻄﺒﻴﺔ؛ ﻷﻥ ﺭﻭﺍﺑﻄﻬﺎ‬ ‫ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴـﺔ ﻫـﻲ ﺣﻠﻘﺔ ﻣـﻦ ‪ 6‬ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ ،‬ﻣﻊ‬ ‫‪.b‬‬
‫ﲨﻴﻌﺎ ﻏﲑ ﻗﻄﺒﻴﺔ‪ ،‬ﳑﺎ ﳚﻌﻠﻬﺎ ﻣﺬﻳﺒﺎﺕ ﺟﻴﺪﺓ ﳌﻮﺍﺩ ﺃﺧﺮ￯ ﻏﲑ ﻗﻄﺒﻴﺔ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪.8-11‬‬
‫ﹰ‬
‫ﹸﻘﺎﺭﻥ ﺧﺼﺎﺋﺺ ﺍﳌﺮﻛﺐ ﺍﻟﻘﻄﺒﻲ ﺑﺨﺼﺎﺋﺺ‬ ‫‪ ‬ﻛﻴﻒ ﺗ ﹶ‬ ‫ﳎﻤﻮﻋﺎﺕ ﻣﻴﺜﻴﻞ ﻋﲆ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ‪.4، 2، 2،1‬‬
‫ﺍﳌﺮﻛﺐ ﻏﲑ ﺍﻟﻘﻄﺒﻲ؟ ﺍﻧﻈﺮ ﺇﱃ ﺍﳉﺪﻭﻝ ‪ ،8-4‬ﻭﻻﺣﻆ ﺃﻥ ﺍﻟﻜﺘﻠﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻟﻠﻤﻴﺜﺎﻥ )‪(16 amu‬‬
‫ﻗﺮﻳﺒﺔ ﻣﻦ ﺍﻟﻜﺘﻠﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻟﻠﲈﺀ )‪ ،(18 amu‬ﻛﺬﻟﻚ ﻓﺈﻥ ﺟﺰﻳﺌﺎﺕ ﺍﳌﺎﺀ ﻭﺍﳌﻴﺜﺎﻥ ﻣﺘﻘﺎﺭﺑﺔ‬
‫ﰲ ﺍﳊﺠﻢ‪ .‬ﻭﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺫﻟﻚ‪ ،‬ﻋﻨﺪﻣﺎ ﺗﹸﻘﺎﺭﻥ ﺩﺭﺟﺎﺕ ﺍﻟﻐﻠﻴﺎﻥ ﻭﺍﻻﻧﺼﻬﺎﺭ ﻟﻠﻤﻴﺜﺎﻥ‬

‫‪    8-11 ‬‬

‫‪ ‬‬
‫‪ ‬‬
‫‪     ‬‬
‫‪‬‬

‫‪144‬‬
 ‫ﻭﺍﺿﺤﺎ ﻭ ﺟﻮﻫﺮ ﹼﹰﻳﺎ‪.‬‬
‫ﹰ‬ ‫ﻼ ﻋﲆ ﺃﻥ ﺍﳉﺰﻳﺌﺎﺕ ﲣﺘﻠﻒ ﺍﺧﺘﻼ ﹰﻓﺎ‬ ‫ﺑﲈ ﻟﻠﲈﺀ ﺗﺮ￯ ﺩﻟﻴ ﹰ‬
‫‪‬‬
‫‪84‬‬ ‫ﻭﻳﻌﻮﺩ ﺳﺒﺐ ﺍﻻﺧﺘﻼﻑ ﺍﻟﻜﺒﲑ ﰲ ﺩﺭﺟﺎﺕ ﺍﳊﺮﺍﺭﺓ ﺇﱃ ﺃﻥ ﺍﻟﺘﺠﺎﺫﺏ ﺑﲔ‬
‫‪‬‬
‫اﻟﺘﻘﻮﻳﻢ‬ ‫ﺍﳌﻴﺜﺎﻥ‬ ‫ﺍﳌﺎﺀ‬
‫ﺟﺰﻳﺌﺎﺕ ﺍﳌﻴﺜﺎﻥ ﺿﻌﻴﻒ ﻣﻘﺎﺭﻧﺔ ﺑﺎﻟﺘﺠﺎﺫﺏ ﺑﲔ ﺟﺰﻳﺌﺎﺕ ﺍﳌﺎﺀ‪ .‬ﻭﻳﻤﻜﻦ‬
‫‪‬‬ ‫ﺗﻔﺴﲑ ﻫﺬﺍ ﺍﻻﺧﺘﻼﻑ ﰲ ﺍﻟﺘﺠﺎﺫﺏ ﺇﱃ ﺃﻥ ﺟﺰﻳﺌﺎﺕ ﺍﳌﻴﺜﺎﻥ ﻏﲑ ﻗﻄﺒﻴﺔ‪ ،‬ﻭﻻ‬
‫‪CH4‬‬ ‫‪H2O‬‬
‫ﹸﻜﻮﻥ ﺭﻭﺍﺑﻂ‬‫ﹸﻜﻮﻥ ﺭﻭﺍﺑﻂ ﻫﻴﺪﺭﻭﺟﻴﻨﻴﺔ ﺑﻴﻨﻬﺎ‪ ،‬ﺃﻣﺎ ﺟﺰﻳﺌﺎﺕ ﺍﳌﺎﺀ ﻓﻘﻄﺒﻴﺔ ﻭﺗ ﱢ‬
‫ﺗ ﱢ‬
‫‪16 amu‬‬ ‫‪18 amu‬‬ ‫‪‬‬ ‫ﻫﻴﺪﺭﻭﺟﻴﻨﻴﺔ‪.‬‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻛﺘﺎﺑـﺔ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﻟـﻜﻞ ﻣـﻦ‬ ‫ﻏﺎﺯ‬ ‫ﺳﺎﺋﻞ‬
‫‪‬‬
‫‪‬‬
‫ﻳﻔﴪ ﺍﻟﻔﺮﻕ ﰲ ﺍﻟﻘﻄﺒﻴﺔ ﻭﺍﻟﺮﻭﺍﺑﻂ ﺍﳍﻴﺪﺭﻭﺟﻴﻨﻴﺔ ﹰ‬
‫ﺃﻳﻀﺎ ﻋﺪﻡ ﺍﻣﺘﺰﺍﺝ ﺃﻭ‬ ‫ﹼ‬
‫ﺍﺧﺘﻼﻁ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻭﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺧﺮ￯ ﺑﺎﳌﺎﺀ‪ .‬ﻓﺈﺫﺍ ﺣﺎﻭﻟﺖ‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ ﺍﻟﺘﺎﻟﻴﺔ‪ :‬ﺑﺮﻭﺑﺎﻥ ﺣﻠﻘﻲ‪C3H6 ،‬؛ ﺑﻴﻮﺗﺎﻥ ﺣﻠﻘﻲ‪،‬‬ ‫‪-162°C‬‬ ‫‪100°C‬‬ ‫‪‬‬
‫ﺇﺫﺍﺑﺔ ﺃﻟﻜﺎﻧﺎﺕ ـ ﻣﺜﻞ ﺯﻳﻮﺕ ﺍﻟﺘﺸﺤﻴﻢ ـ ﰲ ﺍﳌﺎﺀ ﻳﻨﻔﺼﻞ ﺍﻟﺴﺎﺋﻼﻥ‬
‫‪-182°C‬‬ ‫‪0°C‬‬ ‫‪‬‬
‫‪C4H8‬؛ ﺑﻨﺘﺎﻥ ﺣﻠﻘﻲ‪C5H10 ،‬؛ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ ‪ .C6H12‬‬ ‫ﻓــﻮﺭﺍ ﺇﱃ ﻃﺒﻘﺘﲔ‪ .‬ﻭﳛــﺪﺙ ﻫــﺬﺍ ﺍﻻﻧﻔﺼﺎﻝ ﻷﻥ ﻗــﻮ￯ ﺍﻟﺘﺠﺎﺫﺏ‬
‫ﺑﲔ ﺟﺰﻳﺌﺎﺕ ﺍﻷﻟﻜﺎﻥ ﺃﻗــﻮ￯ ﻣﻦ ﻗــﻮ￯ ﺍﻟﺘﺠﺎﺫﺏ ﺑﲔ ﺟﺰﻳﺌﺎﺕ‬
‫ﹰ‬

‫ﺍﳌﻜﻮﻧﺔ ﻣﻦ ﺟﺰﻳﺌﺎﺕ ﻏﲑ ﻗﻄﺒﻴﺔ‪.‬‬

‫ﱠ‬ ‫ﺍﻷﻟﻜﺎﻥ ﻭﺍﳌﺎﺀ‪ .‬ﻟﺬﺍ ﻓﺈﻥ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺗﺬﻭﺏ ﰲ ﺍﳌﺬﻳﺒﺎﺕ‬
‫اﻟﻤﻄﻮﻳﺎت‬ ‫اﻟﻤﻄﻮﻳﺎت‬
‫‪ ‬ﺇﻥ ﺍﳋﺎﺻﻴﺔ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻟﻸﻟﻜﺎﻧﺎﺕ ﻫﻲ ﺿﻌﻒ‬
‫ﺃﺩﺧﻞ ﻣﻌﻠﻮﻣﺎﺕ ﻣﻦ ﻫﺬﺍ‬
‫ﻧﺸﺎﻃﻬﺎ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‪ .‬ﻭﻛﲈ ﻋﺮﻓﺖ ﺳﺎﺑ ﹰﻘﺎ ﻓﺈﻥ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﻟﺘﻔﺎﻋﻼﺕ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﲢﺪﺙ ﻋﻨﺪﻣﺎ‬
‫ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﻠﺨﻴﺺ ﻣﻌﻠﻮﻣﺎﺕ ﻫﺬﺍ ﺍﻟﻘﺴﻢ ﰲ ﻣﻄﻮﻳﺎﲥﻢ‪.‬‬ ‫ﺍﻟﻘﺴﻢ ﰲ ﻣﻄﻮﻳﺘﻚ‪.‬‬
‫ﺗﻨﺠﺬﺏ ﻣﺎﺩﺓ ﻣﺘﻔﺎﻋﻠﺔ ﺫﺍﺕ ﺷﺤﻨﺔ ﻛﻬﺮﺑﺎﺋﻴﺔ ﻛﺎﻣﻠﺔ‪ ،‬ﻣﺜﻞ ﺍﻷﻳﻮﻥ‪ ،‬ﺃﻭ ﺫﺍﺕ ﺷﺤﻨﺔ ﹸﺟﺰﺋﻴﺔ‪،‬‬
‫ﻣﺜﻞ ﺟﺰﻱﺀ ﻗﻄﺒﻲ‪ ،‬ﺇﱃ ﻣﺎﺩﺓ ﻣﺘﻔﺎﻋﻠﺔ ﺃﺧﺮ￯ ﺫﺍﺕ ﺷﺤﻨﺔ ﻣﻌﺎﻛﺴﺔ‪ .‬ﺍﳉﺰﻳﺌﺎﺕ ﺍﻟﺘﻲ ﺗﻜﻮﻥ ﻓﻴﻬﺎ‬

‫‪ .3‬اﻟﺘﻘﻮﻳﻢ‬
‫ﺍﻟﺬﺭﺍﺕ ﻣﺮﺗﺒﻄﺔ ﺑﺮﻭﺍﺑﻂ ﻏﲑ ﻗﻄﺒﻴﺔ ـ ﻛﲈ ﰲ ﺍﻷﻟﻜﺎﻧﺎﺕ ـ ﺗﻜﻮﻥ ﻏﲑ ﻗﻄﺒﻴﺔ‪ .‬ﻟﺬﺍ ﻳﻜﻮﻥ ﺍﻧﺠﺬﺍﺏ‬
‫ﻫﺬﻩ ﺍﳉﺰﻳﺌﺎﺕ ﻧﺤﻮ ﺍﻷﻳﻮﻧﺎﺕ ﺃﻭ ﺍﳉﺰﻳﺌﺎﺕ ﺍﻟﻘﻄﺒﻴﺔ ﺿﻌﻴ ﹰﻔﺎ ﺟﺪﹼﹰ ﺍ‪ .‬ﻭﻳﻤﻜﻦ ﺇﺭﺟﺎﻉ ﺿﻌﻒ ﻧﺸﺎﻁ‬
‫ﻧﺴﺒﻴﺎ‪.‬‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ ﺇﱃ ﺭﻭﺍﺑﻂ ‪ C - C‬ﻭ ‪ C - H‬ﺍﻟﻘﻮﻳﺔ ﹼﹰ‬

‫·‬
‫اﻟﺘﺤﻘﻖ ﻣﻦ اﻟﻔﻬﻢ‬ ‫اﻟﺘﻘﻮﻳﻢ ‪8-2‬‬
‫اﻟﺮﺋﻴﺴﺔ ﹺﺻﻒ ﺍﳌﻴﺰﺍﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﺮﺋﻴﺴﺔ ﳉﺰﻳﺌﺎﺕ ﺍﻷﻟﻜﺎﻧﺎﺕ‪.‬‬
‫ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﻔﺴـﲑ ﳌﺎﺫﺍ ﻳﻌﺪ ﺍﳌﺮﻛﺐ ﺣﻠﻘﻲ ﺑﺮﻭﺑﺎﻥ ﺃﺻﻐﺮ‬ ‫اﻟﻔﻜﺮة‬

‫ﺳﻢ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﺘﺎﻟﻴﺔ ﺑﺎﺳﺘﺨﺪﺍﻡ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ‪.‬‬

‫‪ .13‬ﱢ‬
‫‪.12‬‬ ‫اﻟﺨﻼﺻﺔ‬
‫ﲢﺘﻮﻱ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻋﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ‬
‫ﺃﻟـﻜﺎﻥ ﺣﻠﻘـﻲ ﳏﺘﻤـﻞ‪ .‬ﻻ ﻳﻤﻜـﻦ ﺑﻨﺎﺀ ﺍﻟﺸـﻜﻞ ﺍﳊﻠﻘـﻲ ﻣﻦ ﺫﺭﺓ‬ ‫‪CH3‬‬ ‫‪CH3 .c‬‬ ‫‪CH3‬‬ ‫‪.b‬‬ ‫‪CH3‬‬ ‫‪.a‬‬ ‫ﻓﻘﻂ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬

‫—‬

‫—‬
‫‪CH3CCH3‬‬ ‫‪CH3CHCH2CH2CH3‬‬ ‫ﺗﻌـﺪ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺃﻓﻀـﻞ ﲤﺜﻴـﻞ‬
‫ﻛﺮﺑـﻮﻥ ﻭﺍﺣﺪﺓ ﺃﻭ ﺫﺭﺗﲔ‪ ،‬ﻟﺬﺍ ﳚﺐ ﺃﻥ ﺗﺘﻮﻓﺮ ﺛﻼﺙ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‬ ‫‪CH3‬‬ ‫‪CH2CH3‬‬

‫—‬
‫‪CH3‬‬ ‫ﻟﻸﻟﻜﺎﻧـﺎﺕ ﻭﺍﳌﺮﻛﺒــﺎﺕ ﺍﻟﻌﻀﻮﻳـﺔ‬
‫ﺍﻷﺧـــﺮ￯‪ .‬ﻭﻳﻤﻜـﻦ ﺗﺴـﻤﻴﺔ ﻫـﺬﻩ ‪ .14‬ﺻﻒ ﺍﳋﺼﺎﺋﺺ ﺍﻟﻌﺎﻣﺔ ﻟﻸﻟﻜﺎﻧﺎﺕ‪.‬‬
‫ﺃﻭ ﺃﻛﺜﺮ‪ .‬‬ ‫‪C22-172C-828378-08‬‬ ‫ﺍﳌﺮﻛﺒﺎﺕ ﺑﺎﺳـﺘﺨﺪﺍﻡ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻣﻴﺔ ‪ .15‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻜﻞ ﳑﺎ ﻳﺄﰐ‪:‬‬
‫‪C22-057C-828378-08‬‬ ‫‪C22-056C-828378-08‬‬
‫‪ –1 .c‬ﺇﻳﺜﻴﻞ–‪ –4‬ﻣﻴﺜﻴﻞ ﺣﻠﻘﻲ ﻫﻜﺴﺎﻥ‬ ‫ﹸﺣﺪﱢ ﺩﺕ ﻣﻦ ﺍﻻﲢﺎﺩ ﺍﻟﺪﻭﱄ ﻟﻠﻜﻴﻤﻴﺎﺀ ‪ -3،4 .a‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﻫﺒﺘﺎﻥ‬
‫‪ –1،2 .d‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺣﻠﻘﻲ ﺑﺮﻭﺑﺎﻥ‬ ‫‪-4 .b‬ﺃﻳﺰﻭﺑﺮﻭﺑﻴﻞ– ‪ -3‬ﻣﻴﺜﻴﻞ ﺩﻳﻜﺎﻥ‬ ‫ﺍﻟﺒﺤﺘﺔ ﻭﺍﻟﺘﻄﺒﻴﻘﻴﺔ )‪.(IUPAC‬‬
‫إﻋﺎدة اﻟﺘﺪرﻳﺲ‬ ‫‪ .16‬ﺗﻔﺴﲑ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﳌﺎﺫﺍ ﻳﻌﺪ ﺍﻻﺳﻢ ‪–3‬ﺑﻴﻮﺗﻴﻞ ﺑﻨﺘﺎﻥ ﻏﲑ ﺻﺤﻴﺢ؟‬ ‫ﻋـﲆ‬ ‫ﺗﺴـﻤﻰ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﳌﺤﺘﻮﻳـﺔ‬‫ﹼ‬
‫ﺍﻛﺘﺐ ﺑﻨﺎ ﹰﺀ ﻋﲆ ﻫﺬﺍ ﺍﻻﺳﻢ‪ ،‬ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﺮﻛﺐ‪ .‬ﻣﺎ ﺍﻻﺳﻢ ﺍﻟﻨﻈﺎﻣﻲ )ﺍﻷﻳﻮﺑﺎﻙ(‬ ‫ﺣﻠﻘـﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ‬

‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻛﺘﺎﺑـﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﻟﻜﻞ ﻣـﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ‬ ‫ﺍﻟﺼﺤﻴﺢ ﻟﻠﻤﺮﻛﺐ ‪ –3‬ﺑﻴﻮﺗﻴﻞ ﺑﻨﺘﺎﻥ؟‬ ‫ﺍﳊﻠﻘﻴﺔ‪.‬‬

‫ﺍﻟﻌﴩﺓ ﺍﻷﻭﱃ ﻋﲆ ﺍﻟﺴﺒﻮﺭﺓ‪ .‬‬

‫اﻟﺘﻮﺳﻊ‬
‫ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﻌ ﱡﻠﻢ ﺃﺳﲈﺀ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺫﺍﺕ ﺍﻟﺴﻼﺳﻞ ﺍﳌﺴﺘﻘﻴﻤﺔ‬
‫ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ ‪ 20 - 11‬ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﻟﻜﻞ ﺟﺰﻱﺀ‪ .‬‬

‫اﻟﺘﻘﻮﻳﻢ ‪8-2‬‬
‫‪ .15‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟـﺪﺭﺱ ﻭﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ ،‬ﺃﻭ ﺇﱃ ﺩﻟﻴﻞ ﺣﻠﻮﻝ‬ ‫‪ .12‬ﺍﻷﻟﻜﺎﻧـﺎﺕ ﻫـﻲ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺫﺍﺕ ﺳﻼﺳـﻞ ﺃﻭ ﺣﻠﻘﺎﺕ‬
‫ﺍﳌﺴﺎﺋﻞ ﺹ ‪.79‬‬ ‫ﲢﺘﻮﻱ ﻓﻘﻂ ﻋﲆ ﺭﻭﺍﺑﻂ ‪ C-C‬ﻭ ‪ C-H‬ﻣﺸﱰﻛﺔ ﺃﺣﺎﺩﻳﺔ‪.‬‬
‫‪ .16‬ﲢﺘﻮﻱ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﻣﺘﺼﻠﺔ ﻋﲆ ﺳﺒﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪،‬‬ ‫‪-2 .a .13‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‬
‫ﻭﻟﻴﺲ ﲬﺲ ﺫﺭﺍﺕ ﰲ ﻫﺬﺍ ﺍﳌﺮﻛﺐ‪ .‬ﻭﺑﺎﻟﺘﺎﱄ ﲢﺘﻮﻱ ﺍﻟﺴﻠﺴـﻠﺔ‬ ‫‪ - 2 ،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﺮﻭﺑﺎﻥ‬ ‫‪.b‬‬
‫ﺍﻟﺮﺋﻴﺴـﺔ ﻋﲆ ﺳـﺒﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﻣﻊ ﳎﻤﻮﻋـﺔ ﺇﻳﺜﻴﻞ ﻋﲆ ﺫﺭﺓ‬ ‫‪ - 1‬ﺇﻳﺜﻴﻞ‪ - 5 ،4 ،2 -‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ‬ ‫‪.c‬‬
‫ﺍﻟﻜﺮﺑﻮﻥ ‪ .3‬ﻭﺍﻷﺳﻢ ﺍﻟﺼﺤﻴﺢ ﳍﺬﺍ ﺍﳌﺮﻛﺐ‪ -3 :‬ﺇﻳﺜﻴﻞ ﻫﺒﺘﺎﻥ‪.‬‬
‫‪ .14‬ﺇﻥ ﺭﻭﺍﺑـﻂ ‪ C-C‬ﻭ ‪ C-H‬ﻏـﲑ ﻗﻄﺒﻴـﺔ‪ ،‬ﳑﺎ ﳚﻌـﻞ ﺍﻷﻟﻜﺎﻧﺎﺕ‬
‫ﻏـﲑ ﺫﺍﺋﺒﺔ ﰲ ﺍﳌﺎﺀ‪-‬ﺍﳌﺬﻳﺐ ﺍﻟﻘﻄﺒﻲ‪ .‬ﻭﻫﺬﻩ ﺍﻟﺮﻭﺍﺑﻂ ﹰ‬
‫ﺃﻳﻀﺎ ﻗﻮﻳﺔ‬
‫ﻛﻴﻤﻴﺎﺋﻴـﺎ‪ ،‬ﺑﺼﻮﺭﺓ‬
‫ﹼﹰ‬ ‫ﻭﺛﺎﺑﺘـﺔ‪ ،‬ﳑﺎ ﳚﻌـﻞ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﻏﲑ ﻧﺸـﻄﺔ‬
‫ﻧﺴﺒﻴﺔ‪.‬‬

‫‪145‬‬
 ‫‪8-3‬‬
‫‪8-3‬‬
‫ا“ﻟﻜﻴﻨﺎت و ا“ﻟﻜﺎﻳﻨﺎت‬ ‫اﻫﺪاف‬
‫‪  ‬ﺍﻟـﺼـﻴـﻎ ﺍﻟﺒـﻨـﺎﺋـﻴـﺔ‬
‫‪Alkenes and Alkynes‬‬
‫‪ .1‬اﻟﺘﺮﻛﻴﺰ‬
‫ﻟﻸﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ‪.‬‬
‫‪   ‬ﺍﻷﻟﻜـﲔ ﺃﻭ ﺍﻷﻟﻜـﺎﻳـﻦ اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ‪‬‬
‫‪‬‬ ‫ﺍﻋﺘﲈ ﹰﺩﺍ ﻋﲆ ﺻﻴﻐﺘﻪ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫‪  ‬ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻸﻟﻜﲔ ‪‬‬
‫ﺃﻭ ﺍﻷﻟﻜﺎﻳﻦ ﺇﻥ ﹸﺃﻋﻄﻴﺖ ﺍﺳﻤﻪ‪  .‬ﺗﹸﻨﺘﺞ ﺍﻟﻨﺒﺎﺗﺎﺕ ﺍﻹﻳﺜﲔ ﰲ ﺻﻮﺭﺓ ﻫﺮﻣﻮﻥ ﹸﻧﻀﺞ ﻃﺒﻴﻌﻲ‪ .‬ﻭﻋﺎﺩ ﹰﺓ ﻣﺎ ﺗ ﹶ‬
‫‪‬‬
‫ﹸﻘﻄﻒ‬
‫ﹸﻌﺮﺽ ﻟﻺﻳﺜﲔ ﺣﺘﻰ ﺗﻨﻀﺞ‪.‬‬
‫‪  ‬ﺧﺼﺎﺋـﺺ ﺍﻷﻟﻜـﻴﻨﺎﺕ ﺍﻟﻔﻮﺍﻛﻪ ﻭﺍﳋﴬﺍﻭﺍﺕ ﻗﺒﻞ ﲤﺎﻡ ﻧﻀﺠﻬﺎ‪ ،‬ﻓﺘ ﱠ‬ ‫ﻗﺒﻞ ﺑﺪﺀ ﺍﻟـﺪﺭﺱ‪ ،‬ﺍﻋﺮﺽ ﻋﲆ ﺍﻟﻄﻼﺏ ﴍﳛـﺔ ﺍﻟﱰﻛﻴﺰ ﺭﻗﻢ‬
‫ﻭﺍﻷﻟﻜـﺎﻳـﻨــﺎﺕ ﺑﺨـﺼـﺎﺋﺺ ا¶ﻟﻜﻴﻨﺎت ‪Alkenes‬‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ‪.‬‬
‫)‪ (29‬ﺍﻟـﻮﺍﺭﺩﺓ ﰲ ﻣﺼﺎﺩﺭ ﺍﻟﺘﻌﻠﻢ ﻟﻠﻔﺼﻮﻝ )‪ ،(5-8‬ﻭﻳﻤﻜﻨﻚ‬
‫ﹼ‬
‫ﺗﺬﻛﺮ ﺃﻥ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﺸﺒﻌﺔ؛ ﻷﳖﺎ ﲢﺘﻮﻱ ﻋﲆ ﺭﻭﺍﺑﻂ ﺗﺴﺎﳘﻴﺔ ﺃﺣﺎﺩﻳﺔ ﺑﲔ‬
‫ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻭﺃﻥ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ ﳍﺎ ﻋﲆ ﺍﻷﻗﻞ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ‬ ‫ﻣﺮاﺟﻌﺔ اﻟﻤﻔﺮدات‬ ‫ﻋﺮﺿﻬﺎ ﻣﻠﻮﻧﺔ ﻣﻦ ﺧﻼﻝ ﺍﻟﺮﺟﻮﻉ ﺇﱃ ﺍﳌﻮﻗﻊ ﺍﻹﻟﻜﱰﻭﲏ‪ :‬‬
‫ﻭﺗﺴﻤﻰ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ ﺍﳌﺤﺘﻮﻳﺔ ﻋﲆ ﺭﺍﺑﻄﺔ ﺗﺴﺎﳘﻴﺔ ﺛﻨﺎﺋﻴﺔ‬
‫ﹼ‬ ‫‪ ‬ﻣﺎﺩﺓ ﻛﻴﻤﻴﺎﺋﻴﺔ ﺗﹸﻨﺘﹶﺞ ﰲ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬
‫ﺟﺰﺀ ﻣﻦ ﺍﳌﺨﻠﻮﻕ ﺍﳊﻲ ﻭﺗﹸﻨﻘﻞ ﻭﺍﺣﺪﺓ ﺃﻭ ﺃﻛﺜﺮ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺑﺎﻷﻟﻜﻴﻨﺎﺕ‪ .‬ﻭﻷﻥ ﺍﻷﻟﻜﲔ ﳚﺐ ﺃﻥ ﳛﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ‬ ‫‪www.obeikaneducation.com‬‬
‫ﺇﱃ ﺟﺰﺀ ﺁﺧــﺮ‪ ،‬ﻭﺗــﺆﺩﻱ ﺇﱃ ﺗﻐﲑ ﺛﻨﺎﺋﻴﺔ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻟﺬﺍ ﻻ ﻳﻮﺟﺪ ﺃﻟﻜﲔ ﺑﺬﺭﺓ ﻛﺮﺑﻮﻥ ﻭﺍﺣﺪﺓ‪ .‬ﻭﻋﻠﻴﻪ ﻓﺈﻥ ﺃﺑﺴﻂ ﺃﻟﻜﲔ‬
‫ﳛﺘﻮﻱ ﻋﲆ ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﺗﺮﺗﺒﻄﺎﻥ ﺑﺮﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ‪ .‬ﻭﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺍﻷﺭﺑﻌﺔ ﺍﳌﺘﺒﻘﻴﺔ – ﺍﺛﻨﺎﻥ ﻣﻦ‬ ‫ﻓﺴﻴﻮﻟﻮﺟﻲﻓﻴﻪ‪.‬‬
‫ﻛﻞ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ‪ -‬ﺗﺸﱰﻙ ﻣﻊ ﺃﺭﺑﻊ ﺫﺭﺍﺕ ﻫﻴﺪﺭﻭﺟﲔ ﻟﺘﻌﻄﻲ ﺟﺰﻱﺀ ﺍﻹﻳﺜﲔ ‪.C2H4‬‬ ‫اﻟﻤﻔﺮدات اﻟﺠﺪﻳﺪة‬ ‫اﻟﺮﺋﻴﺴﺔ‬ ‫اﻟﻔﻜﺮة‬
‫ﺗﻜﻮﻥ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺍﳌﺤﺘﻮﻳﺔ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﻭﺍﺣﺪﺓ ﺳﻼﺳﻞ ﻣﺘﲈﺛﻠﺔ‪ .‬ﻭﻟﻠﺴﻠﺴﻠﺔ ﺍﳌﺘﲈﺛﻠﺔ ﺻﻴﻐﺔ‬
‫ﹼ‬ ‫ﺍﻷﻟﻜﲔ‬
‫ﺭﻗﻤﻴﺔ ﺛﺎﺑﺘﺔ ﺑﲔ ﺃﻋﺪﺍﺩ ﺍﻟﺬﺭﺍﺕ‪ .‬ﻓﺈﺫﺍ ﺩﺭﺳﺖ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﻮﺍﺩ ﺍﻟﻈﺎﻫﺮﺓ ﰲ ﺍﳉﺪﻭﻝ ‪8-5‬‬ ‫‪ ‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻺﻳﺜﺎﻥ‪ ،‬ﻭﺍﻹﻳﺜﲔ‪،‬‬
‫ﺍﻷﻟﻜﺎﻳﻦ‬
‫ﻟﻜﻞ ﻣﻨﻬﺎ ﻫﻮ ﺿﻌﻒ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ .‬ﻟﺬﺍ‬ ‫ﻓﺴﻮﻑ ﺗﺮ￯ ﺃﻥ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﱟ‬
‫ﺗﻜﻮﻥ ﺍﻟﺼﻴﻐﺔ ﺍﻟﻌﺎﻣﺔ ﻟﻸﻟﻜﻴﻨﺎﺕ ﻫﻲ ‪ .CnH2n‬ﹶﻳﻘﻞ ﻛﻞ ﺃﻟﻜﲔ ﻋﻦ ﺍﻷﻟﻜﺎﻥ ﺍﳌﻨﺎﻇﺮ ﻟﻪ ﺑﺬﺭﰐ‬ ‫ﻭﺍﻹﻳﺜﺎﻳـﻦ ﺟﻨ ﹰﺒـﺎ ﺇﱃ ﺟﻨـﺐ ﻋـﲆ ﺍﻟﺴـﺒﻮﺭﺓ‪ .‬ﻭﺍﻛﺘـﺐ ﺃﺳـﲈﺀ ﻫﺬﻩ‬
‫ﻳﻜﻮﻧﺎﻥ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺘﺴﺎﳘﻴﺔ ﺍﻟﺜﺎﻧﻴﺔ‪ ،‬ﻭﳘﺎ ﻏﲑ ﻣﺘﻮﺍﻓﺮﻳﻦ ﻟﻠﺮﺑﻂ‬
‫ﻫﻴﺪﺭﻭﺟﲔ؛ ﻷﻥ ﺇﻟﻜﱰﻭﻧﲔ ﺍﺛﻨﲔ ﱢ‬
‫ﺑﺬﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ‪ .‬ﻣﺎ ﺍﻟﺼﻴﻎ ﺍﳉﺰﻳﺌﻴﺔ ﻟﻸﻟﻜﻴﻨﺎﺕ ﺫﺍﺕ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴﺖ ﻭﺍﻟﺘﺴﻊ؟‬ ‫ﺍﳌﺮﻛﺒـﺎﺕ ﲢـﺖ ﺻﻴﻐﻬـﺎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ ،‬ﺛـﻢ ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﲢﺪﻳﺪ‬
‫‪‬‬ ‫‪85‬‬
‫ﺍﻟﻔـﺮﻭﻕ ﺑﲔ ﻫـﺬﻩ ﺍﻟﺼﻴﻎ‪ .‬ﻋﲆ ﺍﻟﻄﻼﺏ ﺃﻥ ﻳﻼﺣﻈـﻮﺍ ﺃﻥ ﺍﻹﻳﺜﺎﻥ‬
‫‪ -2‬ﺑﻴﻮﺗﲔ‬ ‫‪ -1‬ﺑﻴﻮﺗﲔ‬ ‫ﺑﺮﻭﺑﲔ‬ ‫ﺇﻳﺜﲔ‬ ‫‪‬‬ ‫ﳛﺘـﻮﻱ ﻋـﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳـﺔ ﻓﻘﻂ‪ ،‬ﻭﺍﻹﻳﺜـﲔ ﳛﻮﻱ ﺭﺍﺑﻄـﺔ ﺛﻨﺎﺋﻴﺔ‬
‫‪CH‬‬ ‫‪CH‬‬ ‫‪CH CH‬‬ ‫‪C HC H‬‬ ‫‪CH‬‬ ‫‪C CH H‬‬ ‫‪‬‬
‫‪CC‬‬ ‫‪HH‬‬ ‫‪CH‬‬ ‫‪CH‬‬

‫ﻭﻋﲆ‬ ‫ﻭﺍﺣـﺪﺓ‪.‬‬ ‫ﻭﺍﺣـﺪﺓ‪ .‬ﻭﺃﻣـﺎ ﺍﻹﻳﺜﺎﻳـﻦ ﻓﻴﺤـﻮﻱ ﺭﺍﺑﻄـﺔ ﺛﻼﺛﻴـﺔ‬

‫‪4‬‬ ‫‪8‬‬ ‫‪2‬‬ ‫‪4‬‬ ‫‪4‬‬ ‫‪8‬‬ ‫‪3‬‬ ‫‪6‬‬ ‫‪4‬‬ ‫‪8 2‬‬ ‫‪4‬‬ ‫‪3‬‬
‫‪4‬‬ ‫‪6‬‬
‫‪8‬‬ ‫‪4 28 4‬‬ ‫‪3 46 8‬‬ ‫‪4‬‬ ‫‪8‬‬ ‫‪4‬‬ ‫‪8‬‬

‫‪CH‬‬
‫‪4‬‬ ‫‪CH‬‬‫‪8‬‬
‫‪HH C‬‬
‫‪C‬‬ ‫‪2‬‬
‫‪HH‬‬ ‫‪4‬‬ ‫‪CHH C‬‬‫‪HH‬‬
‫‪4‬‬ ‫‪8‬‬ ‫‪3‬‬ ‫‪C CH H H‬‬
‫‪6‬‬ ‫‪C HC H‬‬ ‫‪4‬‬ ‫‪8‬‬ ‫‪2‬‬ ‫‪CC HH‬‬ ‫‪4‬‬ ‫‪CH‬‬ ‫‪4 38 6‬‬ ‫‪CH‬‬ ‫‪4‬‬ ‫‪82‬‬ ‫‪4‬‬ ‫‪34 68‬‬ ‫‪4‬‬ ‫‪8‬‬ ‫‪4‬‬ ‫‪8‬‬
‫‪C‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬

‫ﺍﻟﻄـﻼﺏ ﺃﻥ ﻳﻼﺣﻈـﻮﺍ ﹰ‬
‫‪C‬‬ ‫‪H‬‬
‫ﺃﻳﻀـﺎ ﺃﻥ ﻟﻺﻳﺜـﺎﻥ ﺃﻛـﱪ ﻋﺪﺩ ﻣـﻦ ﺫﺭﺍﺕ‬
‫‪C‬‬
‫‪H‬‬ ‫‪C C‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪C‬‬ ‫‪H‬‬ ‫—‬
‫—‬ ‫‪C C‬‬ ‫‪C —C‬‬ ‫‪‬‬ ‫—‬
‫—‬
‫‪H‬‬
‫‪H‬‬ ‫‪C‬‬ ‫‪H‬‬ ‫‪C C‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫—‬
‫—‬
‫‪H‬‬ ‫‪CH CH CH‬‬‫— —‪CH‬‬
‫‪CHCH CHHCH‬‬ ‫—‪CH‬‬
‫‪HCH‬‬ ‫‪— CH‬‬
‫‪CHCH‬‬ ‫‪CH‬‬
‫‪H CH CH‬‬
‫‪— CH‬‬
‫‪H‬‬
‫‪— CH‬‬ ‫‪CH CH — CH‬‬
‫‪CHCH CH‬‬ ‫‪CHCH—CH‬‬
‫‪CH— CH CHCH‬‬ ‫‪CHCH‬‬‫——‬ ‫‪CHCHCHCH CH CH — CH‬‬ ‫‪CH CH — CHCH‬‬

‫ﻣﻦ‪CH‬ﺫﺭﺍﺕ‬‫ﻋـﺪﺩ— ‪CH‬‬
‫ﺍﳍﻴﺪﺭﻭﺟـﲔ‪ ،‬ﻭﺃﻣـﺎ ﺍﻹﻳﺜﺎﻳﻦ ﻓﻴﺤﺘـﻮﻱ ﻋﲆ ﺃﻗﻞ ‪CHCH‬‬
‫‪2‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2 2‬‬ ‫‪3‬‬ ‫‪3‬‬ ‫‪3 2‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪3 2 2‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3 3‬‬ ‫‪2‬‬ ‫‪3 3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪3‬‬

‫‪‬‬
‫‪3‬‬ ‫— —‪CH‬‬
‫‪CH CH CH‬‬ ‫‪CHCH CH CH‬‬
‫‪2‬‬ ‫‪CH—CH‬‬
‫‪2‬‬
‫‪— CH‬‬
‫‪CHCH‬‬ ‫‪2 2‬‬ ‫‪CH CHCH‬‬‫‪CH——CH‬‬
‫‪3‬‬ ‫‪CH‬‬ ‫‪CH‬‬
‫‪3‬‬‫‪CHCH‬‬ ‫‪CH‬‬‫——‬
‫‪CHCH‬‬ ‫‪3 2‬‬‫— ‪CH‬‬ ‫‪— CH‬‬
‫‪CH C22-061C-828378-08‬‬
‫‪CH CH‬‬ ‫‪CHCH‬‬‫‪3‬‬ ‫‪CH‬‬
‫‪2 2‬‬‫‪CH CH‬‬ ‫‪CH——CH‬‬‫‪CHCH CH CH CH — CH‬‬
‫‪22‬‬ ‫‪3 3‬‬ ‫‪23‬‬ ‫‪3‬‬ ‫‪22‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪33‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪3‬‬ ‫‪2‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪3‬‬
‫‪C22-062C-828378-08‬‬ ‫‪‬‬
‫‪C22-064C-828378-08 C22-063C-828378-08‬‬
‫ﺍﳍﻴﺪﺭﻭﺟـﲔ‪ .‬ﻟـﺬﺍ ﻧ ﱢﺒﻪ ﺍﻟﻄـﻼﺏ ﻋـﲆ ﺃﻥ ﺍﻹﻳﺜﲔ ﻫـﻮ ﺃﻟﻜﲔ ﻷﻧﻪ‬
‫ﳛﺘﻮﻱ ﻋـﲆ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﰲ ﺑﻨﺎﺋـﻪ‪ ،‬ﻭﺃﻥ ﺍﻹﻳﺜﺎﻳﻦ ﻫﻮ ﺃﻟﻜﺎﻳﻦ؛ ﻷﻧﻪ‬
‫ﳛﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ ﰲ ﺑﻨﺎﺋﻪ‪ .‬‬

‫‪ .2‬اﻟﺘﺪرﻳﺲ‬
‫— ‪ C6H12 ‬ﻭ ‪C9H18‬‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﳎﻤﻮﻋـﺔ ﻣـﻦ ﺍﻟﻄـﻼﺏ ﺗﺼﻤﻴـﻢ ﻓﺤﻮﺻﺎﺕ‬ ‫ا¬ﺛﺮاء‬

‫ﻛﻴﻤﻴﺎﺋﻴـﺔ ﹸﲤ ﱢﻴﺰ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻋـﻦ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨـﺎﺕ‪ .‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﻟﺒﺤـﺚ ﻋﻦ ﺃﺻﻞ‬
‫ﺍﻟﺒﺤﺚ ﻋﻦ ﺍﻟﻨﺸـﺎﻁ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸـﺒﻌﺔ ﻭﻏﲑ ﺍﳌﺸﺒﻌﺔ‬ ‫ﺍﺳـﺘ ﹺ‬
‫ﺨﺪﻣﺖ ﻟﻮﺻﻒ ﺃﻧﻮﺍﻉ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪.‬‬ ‫ﺍﳌﺼﻄﻠﺤﺎﺕ ﺍﻟﺘﻲ ﹸ‬
‫ﻭﺍﳌﻘﺎﺭﻧﺔ ﺑﻴﻨﻬﲈ‪ .‬‬
‫ﻻ ﺗـﺰﺍﻝ ﹸﺗ ﹼ‬
‫ﺴـﻤﻰ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﰲ ﺑﻌـﺾ ﺍﻷﺣﻴـﺎﻥ ﺑﺎﻟﺒﺎﺭﺍﻓﻴﻨـﺎﺕ‬
‫)‪ ،(Paraffins‬ﰲ ﺣـﲔ ﹸﻳﺸـﺎﺭ ﺇﱃ ﺍﻷﻟﻜﻴﻨـﺎﺕ ﺑـﲔ ﺣـﲔ ﻭﺁﺧـﺮ‬
‫ﻣﺸﺮوع اﻟﻜﻴﻤﻴﺎء‬
‫ﺑﺎﻷﻭﻟﻴﻔﻴﻨـﺎﺕ )‪ .(olefins‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺗﺴـﺠﻴﻞ ﻧﺘﺎﺋﺠﻬﻢ ﰲ‬
‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤﺚ ﻋﻦ ﺑﻌﺾ ﺍﻷﻟﻜﻴﻨﺎﺕ‬ ‫ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ‪.‬‬
‫ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﻟﻄﺒﻴﻌﺔ‪ ،‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﲢﻀﲑ ﻣﻠﺼﻖ ﹸﻳ ﹶﺒ ﱢﻴﻨﻮﻥ ﻓﻴﻪ‬
‫ﺃﻳﻦ ﺗﻮﺟﺪ ﻫـﺬﻩ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻭﺍﻷﺷـﻜﺎﻝ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﺮﻛﺒﺎﺕ‪.‬‬
‫‪‬‬

‫‪146‬‬
 ‫‪      a‬‬ ‫‪ ‬ﺗﹸﺴﻤﻰ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺑﺎﻟﻄﺮﻳﻘﺔ ﺍﳌﺘﺒﻌﺔ ﰲ ﺗﺴﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻧﻔﺴﻬﺎ ﺗﻘﺮﻳ ﹰﺒﺎ‪.‬‬
‫ﺣﻴﺚ ﺗﻜﺘﺐ ﺃﺳﲈﺅﻫﺎ ﺑﺘﻐﻴﲑ ﺍﳌﻘﻄﻊ ﺍﻷﺧﲑ )ﺍﻥ( ﻟﻸﻟﻜﺎﻥ ﺍﳌﻨﺎﻇﺮ ﺇﱃ ﺍﳌﻘﻄﻊ )ﻳﻦ(‪ .‬ﻭ ﹸﻳﺴﻤﻰ‬
‫ﻋﺮض ﺳﺮﻳﻊ‬
‫‪‬‬
‫‪1‬‬
‫‪C —C—C—C‬‬
‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫ﺍﻷﻟﻜﺎﻥ ﺍﻟﺬﻱ ﻳﺘﻜﻮﻥ ﻣﻦ ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﺍﻹﻳﺜﺎﻥ‪ ،‬ﰲ ﺣﲔ ﻳﺴﻤﻰ ﺍﻷﻟﻜﲔ ﺍﻟﺬﻱ ﳛﺘﻮﻱ ﻋﲆ‬
‫‪1‬‬ ‫ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﺍﻹﻳﺜﲔ‪ .‬ﻭﺑﻄﺮﻳﻘﺔ ﳑﺎﺛﻠﺔ‪ ،‬ﻓﺎﻷﻟﻜﲔ ﺍﻟﺬﻱ ﳛﺘﻮﻱ ﺛﻼﺙ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﻳﺴﻤﻰ‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫ﺷﻴﻮﻋﺎ‪ ،‬ﳘﺎ ﺍﻹﻳﺜﻴﻠﲔ ﻭﺍﻟﱪﻭﺑﻴﻠﲔ‪.‬‬
‫ﹰ‬ ‫ﺑﺮﻭﺑﲔ‪ .‬ﻭﻟﻺﻳﺜﲔ ﻭﺍﻟﱪﻭﺑﲔ ﺍﺳﲈﻥ ﻗﺪﻳﲈﻥ ﺃﻛﺜﺮ‬
‫‪C — C —C — C‬‬
‫‪2‬‬
‫ﻳﺘﻌﲔ ﲢﺪﻳﺪ ﻣﻮﻗﻊ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ ﻟﺘﺴﻤﻴﺔ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺫﺍﺕ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻷﺭﺑﻊ ﺃﻭ ﺃﻛﺜﺮ ﰲ‬
‫ﺍﻟﺴﻠﺴﻠﺔ‪ ،‬ﻛﲈ ﰲ ﺍﻷﻣﺜﻠﺔ ﰲ ﺍﻟﺸﻜﻞ ‪ .8-12a‬ﻭﻳﺘﻢ ﻫﺬﺍ ﺑﱰﻗﻴﻢ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﻟﺴﻠﺴﻠﺔ‬
‫ﺍﻟﻔﺎﻛﻬﺔ‪A F BAG ACB‬‬
‫ﻣﻦ ‪C I‬‬
‫ﺣﺒﺎﺕ‪CED‬‬
‫ﺛﻼﺙ‪J DFEK‬‬
‫ﺘﲔ‪FH‬ﺃﻭ‪EGF L‬‬
‫ﺣﺒ‪GM‬‬
‫ﺿـﻊ‪GHI‬‬ ‫‪IIKJ‬‬
‫‪P ‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫‪H BD‬‬ ‫‪N HJO‬‬ ‫‪JLK KML‬‬ ‫‪N‬‬ ‫‪ON‬‬
‫‪LM M‬‬ ‫‪NPO‬‬ ‫‪OPC — CP‬‬
‫ﱠ‬ ‫—‪C—C‬‬
‫‪3‬‬
‫ﺍﻟﺮﺋﻴﺴﺔ ﺍﺑﺘﺪﺍ ﹰﺀ ﻣﻦ ﻃﺮﻑ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺬﻱ ﻳﻌﻄﻲ ﺃﺻﻐﺮ ﺭﻗﻢ ﻷﻭﻝ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﰲ ﺍﻟﺮﺍﺑﻄﺔ‬
‫ﺍﻟﺜﻨﺎﺋﻴﺔ‪ .‬ﺛﻢ ﹸﻳﺴﺘﺨﺪﻡ ﻫﺬﺍ ﺍﻟﻌﺪﺩ ﰲ ﺍﻻﺳﻢ‪.‬‬
‫ﺍﻟﻨﺎﺿﺠـﺔ ﰲ ﻛﻴﺲ ﺑﺠﺎﻧﺐ ﻛﺄﺱ ﻣﺪﺭﺟﺔ ﲢﺘﻮﻱ ﻋﲆ ‪20 ml‬‬ ‫‪4‬‬
‫‪C—C—C —C‬‬
‫‪3‬‬ ‫‪2‬‬ ‫‪1‬‬
‫ﻻﺣﻆ ﺃﻥ ﺍﻟﺒﻨﺎﺀ ﺍﻟﺜﺎﻟﺚ ﻟﻴﺲ "‪–3‬ﺑﻴﻮﺗﲔ" ﻷﻧﻪ ﻣﻄﺎﺑﻖ ﻟﻠﺒﻨﺎﺀ ﺍﻷﻭﻝ‪–1 ،‬ﺑﻴﻮﺗﲔ‪ .‬ﻟﺬﺍ ﻣﻦ‬
‫ﻟﻜﻞ ﻣﻨﻬﲈ ﺻﻔﺎﺗﻪ ﺍﳋﺎﺻﺔ‪.‬‬‫ﺍﻟﴬﻭﺭﻱ ﺃﻥ ﺗﹸﺪﺭﻙ ﺃﻥﹼ ‪–1‬ﺑﻴﻮﺗﲔ ﻭ ‪–2‬ﺑﻴﻮﺗﲔ ﻣﺎﺩﺗﺎﻥ ﳐﺘﻠﻔﺘﺎﻥ‪ ،‬ﱟ‬
‫ﻣﻦ ﳏﻠﻮﻝ ﺍﻟﻴﻮﺩ ﺍﳌﺨ ﱠﻔﻒ )ﳏﻠﻮﻝ ﺻﺒﻐﺔ ﺍﻟﻴﻮﺩ ﺃﻭ ﺣﺘﻰ ﳏﻠﻮﻝ‬
‫‪1‬‬

‫‪b‬‬ ‫ﻭ ﹸﺗ ﹼ‬
‫ﹸﺴﻤﻰ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺍﳊﻠﻘﻴﺔ ﺗﻘﺮﻳ ﹰﺒﺎ ﺑﺎﻟﻄﺮﻳﻘﺔ ﻧﻔﺴﻬﺎ ﺍﻟﺘﻲ ﺗﹸﺴﻤﻰ ﲠﺎ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ‪ ،‬ﻋﲆ‬
‫ﺫﺭﰐ ﺍﻟﻜﺮﺑﻮﻥ ﺍﳌﺮﺗﺒﻄﺘﲔ ﺑﺎﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ‪ .‬ﻻﺣﻆ‬
‫ﺃﻥ ﺗﻜﻮﻥ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﺭﻗﻢ ‪ 1‬ﻫﻲ ﺇﺣﺪ￯ ﹼ‬
‫ﺍﻟﻴـﻮﺩ ﺍﳌﺮﻛﺰ ﺍﻷﺻـﲇ ‪ stock solution‬ﺫﻱ ﻟﻮﻥ ﺑﻨﻲ ﻣﺼﻔﺮ‬
‫‪5‬‬

‫‪4‬‬
‫‪1‬‬ ‫‪CH3‬‬ ‫ﺗﺮﻗﻴﻢ ﺍﳌﺮﻛﺐ ﰲ ﺍﻟﺸﻜﻞ ‪ .8-12b‬ﺇﻥ ﺍﺳﻢ ﻫﺬﺍ ﺍﳌﺮﻛﺐ ﻫﻮ ‪ –3،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘﲔ ﺣﻠﻘﻲ‪.‬‬
‫‪‬ﳌﺎﺫﺍ ﻳﻌﺪ ﻣﻦ ﺍﻟﴬﻭﺭﻱ ﺗﻌﻴﲔ ﻣﻮﻗﻊ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ ﰲ ﺍﺳﻢ‬
‫ﻓﺎﺗﺢ ﻭﺷـﻔﺎﻑ(‪ ،‬ﺛﻢ ﻏﻂ ﺍﻟﻜﺄﺱ ﺍﻟﺘـﻲ ﲢﺘﻮﻱ ﺍﻟﻴﻮﺩ ﻭﺣﺒﺎﺕ‬
‫‪C22-065C-828378-08‬‬
‫‪3‬‬ ‫‪2‬‬
‫‪CH3‬‬ ‫ﺍﻷﻟﻜﲔ؟‬

‫ﻣﻌﺎ ﺑﻜﺄﺱ ﻛﺒﲑﺓ‪ ،‬ﻭﺃﺣﻜﻢ ﺇﻏﻼﻕ ﺃﺳـﻔﻞ ﺍﻟﻜﺄﺱ ﻣﻊ‬ ‫ﺍﻟﻔﺎﻛﻬﺔ ﹰ‬

‫‪ ‬ﺍﺗﺒﻊ ﻋﻨﺪ ﺗﺴﻤﻴﺘﻬﺎ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ‬
‫‪  8-12‬‬ ‫ﺍﳌﺴﺘﺨﺪﻣﺔ ﰲ ﺗﺴﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳌﺘﻔﺮﻋﺔ‪ ،‬ﻋﲆ ﺃﻥ ﻳﺆﺧﺬ ﰲ ﺍﳊﺴﺒﺎﻥ ﺃﻣﺮﺍﻥ‪ ،‬ﺃﻭﳍﲈ ﺃﻥ ﺗﻜﻮﻥ‬
‫ﹰ‬
‫ﺍﳌﻨﻀـﺪﺓ ﺑﺎﺳـﺘﺨﺪﺍﻡ ﴍﻳـﻂ ﻻﺻﻖ‪ .‬ﺿـﻊ‪ 20 ml‬ﻣﻦ ﳏﻠﻮﻝ‬ ‫ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﰲ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺩﺍﺋﲈ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﲢﺘﻮﻱ ﻋﲆ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ‪ ،‬ﺳﻮﺍﺀ ﺃﻛﺎﻧﺖ ‪C22-158C-828378-08‬‬
‫‪‬‬ ‫‪‬‬ ‫‪‬‬ ‫‪‬‬
‫‪‬‬
‫‪‬‬ ‫‪‬‬
‫ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺃﻡ ﱂ ﺗﻜﻦ‪ .‬ﻭﺛﺎﻧﻴﻬﲈ ﺃﻥ ﳛﺪﺩ ﻣﻮﻗﻊ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ –‬

‫ﺍﻟﻴـﻮﺩ ﺍﳌﺨ ﱠﻔـﻒ ﻧﻔﺴـﻪ ﰲ ﻛﺄﺱ ﳑﺎﺛﻞ ﹰ‬

‫ﺃﻳﻀـﺎ‪ ،‬ﻭﻟﻜﻦ ﻣﻦ ﺩﻭﻥ‬ ‫‪‬‬ ‫ﻭﻟﻴﺲ ﺍﻟﺘﻔﺮﻋﺎﺕ – ﻛﻴﻔﻴﺔ ﺗﺮﻗﻴﻢ ﺍﻟﺴﻠﺴﻠﺔ‪ .‬ﻻﺣﻆ ﻭﺟﻮﺩ ﺳﻠﺴﻠﺘﲔ ﻣﻦ ‪ – 4‬ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﰲ‬
‫ﺍﳉﺰﻱﺀ ﺍ ﹸﳌﺒﲔ ﰲ ﺍﻟﺸﻜﻞ ‪ ،8-13a‬ﺇﻻ ﺃﻥ ﺍﻟﺴﻠﺴﻠﺔ ﺍﳌﺤﺘﻮﻳﺔ ﻋﲆ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ ﺍﺳﺘﺨﺪﻣﺖ‬

‫ﻭﺿـﻊ ﺣﺒـﺎﺕ ﺍﻟﻔﺎﻛﻬﺔ ﺑﺠﺎﻧﺒﻪ‪ ،‬ﻭﻏﻄﻪ ﺑـﻜﺄﺱ ﻛﺒﲑﺓ ﻭﺃﺣﻜﻢ‬

‫ﺍﳌﺘﻔﺮﻉ ﻫﻮ ‪ –2‬ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗﲔ‪.‬‬
‫ﺃﺳﺎﺳﺎ ﻟﻠﺘﺴﻤﻴﺔ‪ .‬ﺇﻥ ﻫﺬﺍ ﺍﻷﻟﻜﲔ ﱢ‬
‫ﹰ‬ ‫ﻭﺣﺪﻫﺎ‬
‫ﲢﺘﻮﻱ ﺑﻌﺾ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ ﻋﲆ ﺃﻛﺜﺮ ﻣﻦ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ‪ .‬ﻭﻳﻈﻬﺮ ﻋﺪﺩ‬

‫ﺇﻏﻼﻕ ﺃﺳـﻔﻞ ﺍﻟﻜﺄﺱ ﻣﻊ ﺍﳌﻨﻀﺪﺓ ﺑﺎﺳﺘﺨﺪﺍﻡ ﴍﻳﻂ ﻻﺻﻖ‪،‬‬ ‫ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﰲ ﺟﺰﻳﺌﺎﺕ ﻣﻦ ﻫﺬﺍ ﺍﻟﻨﻮﻉ ﺑﺎﺳﺘﺨﺪﺍﻡ ﺍﻟﺒﺎﺩﺋﺔ )ﺩﺍﻱ‪ ،‬ﺗﺮﺍﻱ‪ ،‬ﺗﻴﱰﺍ‪ ،‬ﻭﻫﻜﺬﺍ(‬
‫ﻗﺒﻞ ﺍﳌﻘﻄﻊ )ﻳﻦ(‪ .‬ﻭﺗﹸﺮ ﹼﻗﻢ ﻣﻮﺍﻗﻊ ﺍﻟﺮﻭﺍﺑﻂ ﻋﲆ ﺃﻥ ﺗﹸﻨﺘﺞ ﺃﺻﻐﺮ ﳎﻤﻮﻋﺔ ﻣﻦ ﺍﻷﺭﻗﺎﻡ‪ .‬ﺃﻱ ﻧﻈﺎﻡ‬

‫ﻋﲆ ﺃﻥ ﻳﻤﺜﻞ ﻋﻴﻨﺔ ﺿﺎﺑﻄﺔ‪ .‬ﻭﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻣﻼﺣﻈﺔ ﻟﻮﻥ‬ ‫ﺗﺮﻗﻴﻢ ﺳﺘﺴﺘﺨﺪﻡ ﰲ ﺍﳌﺜﺎﻝ ﰲ ﺍﻟﺸﻜﻞ ‪8-13b‬؟ ﺳﺘﺴﺘﺨﺪﻡ ﺍﻟﺒﺎﺩﺋﺔ )ﻫﺒﺘﺎ(؛ ﻷﻥ ﺍﳉﺰﻱﺀ‬
‫ﳛﺘﻮﻱ ﻋﲆ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﹸﺳﺒﺎﻋﻴﺔ‪ .‬ﻭﻷﳖﺎ ﲢﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺘﲔ ﺛﻨﺎﺋﻴﺘﲔ ﻓﺈﻧﻚ ﺗﺴﺘﺨﺪﻡ‬

‫ﻳﻮﻣﻴﺎ ﻟﺒﻀﻌﺔ ﺃﻳﺎﻡ ﻭﺗﻔﺴـﲑ ﻣﺎ ﺣﺪﺙ‪ .‬ﺇﻥ ﺍﻹﻳﺜﲔ‬

‫ﳏﻠﻮﻝ ﺍﻟﻴﻮﺩ ﹼﹰ‬
‫ﺍﻟﺒﺎﺩﺋﺔ )ﺛﻨﺎﺋﻲ( ﻗﺒﻞ ﺍﳌﻘﻄﻊ )ﻳﻦ(‪ ،‬ﺗﹸﻌﻄﻲ ﺍﻻﺳﻢ ﻫﺒﺘﺎﺩﺍﻳﲔ‪ .‬ﻭﺑﺈﺿﺎﻓﺔ ﺍﻟﺮﻗﻤﲔ ‪ 2‬ﻭ‪ 4‬ﻟﺘﻌﻴﲔ‬
‫ﻣﻮﺍﻗﻊ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﻳﺼﺒﺢ ﺍﻻﺳﻢ ‪ -4 ،2‬ﻫﺒﺘﺎﺩﺍﻳﲔ‪.‬‬

‫ﺍﻟﻨﺎﺗﺞ ﻋـﻦ ﺍﻟﻔﺎﻛﻬﺔ ﺍﻟﻨﺎﺿﺠﺔ ﻫﻮ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻏﲑ ﻣﺸـﺒﻊ‪.‬‬ ‫‪     8-13‬‬
‫—‪— C —C‬‬
‫—‪C —C —C‬‬ ‫‪—C — C‬‬
‫‪CH 3‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫‪5‬‬ ‫‪6‬‬ ‫‪7‬‬

‫ﻟﻴﻜﻮﻥ ﻧﻮﺍﺗﺞ ﻫﺎﻟﻴﺪﺍﺕ ﺍﻷﻟﻜﻴﻞ ﺍﻟﻌﺪﻳﻤﺔ‬

‫ﻭﻳﺘﻔﺎﻋﻞ ﻣﻊ ﺍﻟﻴـﻮﺩ ﹼ‬ ‫‪    ‬‬ ‫‪‬‬ ‫‪CH 2 — C — CH 2 — CH 3‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫‪     ‬‬ ‫—‪— C —C‬‬
‫—‪C —C —C‬‬ ‫‪—C — C‬‬ ‫‪2‬‬
‫ﺍﻟﻠـﻮﻥ‪ ،‬ﻭﻋﻠﻴﻪ ﻓﻴﺨﻒ )ﻳﺒﻬـﺖ( ﻟﻮﻥ ﳏﻠﻮﻝ ﺍﻟﻴـﻮﺩ ﺍﳌﻮﺿﻮﻉ‬ ‫‪‬‬ ‫‪7‬‬ ‫‪6‬‬ ‫‪5‬‬ ‫‪4‬‬ ‫‪3‬‬
‫‪42‬‬
‫‪2‬‬ ‫‪1‬‬

‫‪b‬‬ ‫‪a‬‬
‫ﺑﺠﺎﻧﺐ ﺍﻟﻔﺎﻛﻬﺔ‪ ،‬ﰲ ﺣﲔ ﻳﺒﻘﻰ ﻟﻮﻥ ﺍﳌﺤﻠﻮﻝ ﺍﻟﻀﺎﺑﻂ ﻛﲈ ﻫﻮ‪.‬‬

‫‪ ‬ﺇﺫﺍ ﱂ ﹸﳛـﺪﺩ ﻣﻮﻗـﻊ ﺍﻟﺮﺍﺑﻄـﺔ ﺍﻟﺜﻨﺎﺋﻴـﺔ‪ ،‬ﻓـﻼ‬

‫ﻳﻤﻜـﻦ ﺍﳉﺰﻡ ﺑﺼـﻮﺭﺓ ﻗﻄﻌﻴﺔ ﺃﻱ ﻣﺮﻛﺐ ﻫﻮ ﺍﳌﹶ ﹼ‬
‫ﻌﻨﻲ ﺑﺎﻻﺳـﻢ‬
‫ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‪.‬‬
‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬
‫اﻟﺘﻘﻮﻳﻢ‬
‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻛﺘﺎﺑﺔ ﺍﻷﺳـﺌﻠﺔ‬
‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﲢﺪﻳﺪ ﺍﳌﻌﻠﻮﻣﺔ ﺍﻹﺿﺎﻓﻴﺔ ﺍﳌﻄﻠﻮﺑﺔ ﳊﻞ‬ ‫ﺍﻵﺗﻴﺔ ﰲ ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ ﻭﺍﻹﺟﺎﺑﺔ ﻋﻨﻬﺎ ﺑﻌﺪ ﻗﺮﺍﺀﺓ ﺍﻟﻘﺴﻢ ‪.8-3‬‬
‫ﺍﳌﺴﺄﻟﺔ ﺍﻟﺘﺎﻟﻴﺔ‪:‬‬ ‫ﻛﻴـﻒ ﲣﺘﻠـﻒ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻷﻟـﻜﺎﻥ ﻋﻨﻬﺎ ﻷﻟﻜـﲔ ﳛﺘﻮﻱ ﺍﻟﻌﺪﺩ‬ ‫‪.1‬‬
‫ﻳﻤﻜـﻦ ﲢﻮﻳـﻞ ﺍﻷﻟﻜﻴﻨـﺎﺕ ﺇﱃ ﺃﻟﻜﺎﻧـﺎﺕ ﺑﺎﺳـﺘﺨﺪﺍﻡ ﺍﻟﺘﻔﺎﻋـﻞ‬ ‫ﻧﻔﺴـﻪ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ؟ ﳛﺘﻮﻱ ﺍﻷﻟﻜﺎﻥ ﻋـﲆ ﺫﺭﰐ ﻫﻴﺪﺭﻭﺟﲔ‬
‫ﺍﻟﻜﻴﻤﻴﺎﺋـﻲ ﺍ ﹸﳌ ﱠ‬
‫ﺴـﻤﻰ ﺑﺎ ﹶﳍﺪﹾ ﹶﺭﺟﺔ‪ ،‬ﺣﻴﺚ ﹸﻳﻀﺦ ﻏـﺎﺯ ﺍﳍﻴﺪﺭﻭﺟﲔ ﰲ‬ ‫ﺇﺿﺎﻓﻴﺘﲔ )‪ (CnH2n+2‬ﻣﻘﺎﺭﻧﺔ ﺑﺎﻷﻟﻜﲔ )‪.(CnH2n‬‬
‫ﳏﻠـﻮﻝ ﻣـﻦ ﺍﻷﻟﻜﲔ ﺑﻮﺟـﻮﺩ ﻋﺎﻣﻞ ﳏﻔـﺰ‪ .‬ﻓﲈ ﻋﺪﺩ ﻣـﻮﻻﺕ ﻏﺎﺯ‬ ‫ﻛﻴـﻒ ﲣﺘﻠﻒ ﺍﻟﺼﻴﻐـﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻷﻟﻜﺎﻥ ﻋﻨﻬﺎ ﻷﻟﻜﺎﻳـﻦ ﳛﺘﻮﻱ ﺍﻟﻌﺪﺩ‬ ‫‪.2‬‬
‫ﺍﳍﻴﺪﺭﻭﺟﲔ ﺍﻟﺘﻲ ﻳﺘﻌﲔ ﺇﺿﺎﻓﺘﻬﺎ ﺇﱃ ‪ 1mol‬ﻣﻦ ﺃﻟﻜﲔ ﳛﺘﻮﻱ ﻋﲆ‬ ‫ﻧﻔﺴـﻪ ﻣـﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ؟ ﳛﺘـﻮﻱ ﺍﻷﻟـﻜﺎﻥ ﻋـﲆ ﺃﺭﺑـﻊ ﺫﺭﺍﺕ‬
‫ﺃﻛﺜﺮ ﻣﻦ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﻟﺘﺤﻮﻳﻠﻪ ﻛﺎﻣ ﹰ‬
‫ﻼ ﺇﱃ ﺃﻟﻜﺎﻥ؟‬ ‫ﻫﻴﺪﺭﻭﺟـﲔ ﺇﺿﺎﻓﻴـﺔ )‪ (CnH2n+2‬ﻣﻘﺎﺭﻧـﺔ ﺑﺎﻷﻟﻜﺎﻳـﻦ )‪.(CnH2n-2‬‬
‫ﺍﳌﻌﻠﻮﻣﺔ ﺍﻹﺿﺎﻓﻴﺔ ﺍﳌﻄﻠﻮﺑﺔ ﻫﻲ ﻋﺪﺩ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﺍﳌﻮﺟﻮﺩﺓ ﰲ‬ ‫‪‬‬
‫ﺍﻷﻟﻜﲔ؛ ﺇﺫ ﲢﺘﺎﺝ ﻛﻞ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﺇﱃ ‪ 1mol‬ﻣﻦ ﻏﺎﺯ ﺍﳍﻴﺪﺭﻭﺟﲔ‬
‫ﻟﻜﻞ ﻣﻮﻝ ﻣﻦ ﺍﻷﻟﻜﲔ ﺣﺘﻰ ﻳﺘﻢ ﲢﻮﻳﻠﻪ‪ .‬‬

‫‪147‬‬
 ‫‪83‬‬

‫‪CH3CH — CHCHCH2CHCH3‬‬ ‫‪‬‬

‫‪‬‬
‫‪Heptene parent chain‬‬ ‫‪‬‬ ‫اﻟﺮﻳﺎﺿﻴﺎت ﻓﻲ اﻟﻜﻴﻤﻴﺎء‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫ﺳﻢ ﺍﻷﻟﻜﲔ ﺍﳌﺠﺎﻭﺭ‪.‬‬
‫ﱢ‬

‫ﻣﺘﻔﺮﻋﺔ ﲢﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﻭﺍﺣﺪﺓ ﻭﳎﻤﻮﻋﺘﻲ ﺃﻟﻜﻴﻞ‪ .‬ﺍﺗﺒﻊ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ ﻟﺘﺴﻤﻴﺔ‬
‫‪ 1‬ﺗﺤﻠﻴﻞ اﻟﻤﺴﺄﻟﺔ‬
‫ﹸ‬ ‫‪    ‬ﻣﺎ ﻋﺪﺩ ﻣﻮﻻﺕ ﻏﺎﺯ ﺍﳍﻴﺪﺭﻭﺟﲔ ﺍﻟﺘﻲ ﻳﺘﻄﻠﺐ ﺇﺿﺎﻓﺘﻬﺎ‬
‫ﻟﻘﺪ ﺃﻋﻄﻴﺖ ﺃﻟﻜﻴﻨﹰﺎ ﺫﺍ ﺳﻠﺴﻠﺔ ﱢ‬
‫‪C22-068C-828378-08-A‬‬ ‫ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ‪.‬‬ ‫ﺇﱃ ‪ 1 mol‬ﻣﻦ ﺃﻟﻜﲔ ﳛﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺘﲔ ﺛﻨﺎﺋﻴﺘﲔ ﻟﺘﺤﻮﻳﻠﻪ ﻛﺎﻣ ﹰ‬
‫ﻼ‬
‫ﺣﺴﺎب اﻟﻤﻄﻠﻮب‬ ‫‪2‬‬

‫ﺍﳋﻄﻮﺓ ‪ .1‬ﲢﺘﻮﻱ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﻣﺘﺼﻠﺔ ﺗﻮﺟﺪ ﻓﻴﻬﺎ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ ﻋﲆ ﺳﺒﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ‪ .‬ﻭﻳﺴﻤﻰ ﺍﻷﻟﻜﺎﻥ ﺫﻭ‬ ‫ﺇﱃ ﺃﻟﻜﺎﻥ؟ ‪ 2 mol‬‬
‫ﻳﺘﻐﲑ ﺍﻻﺳﻢ ﺇﱃ ﻫﺒﺘﲔ ﺑﺴﺒﺐ ﻭﺟﻮﺩ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ‪.‬‬
‫ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴﺒﻊ "ﻫﺒﺘﺎﻥ"‪ ،‬ﻭﻟﻜﻦ ﹼ‬
‫‪‬‬ ‫‪ CH3CH — CHCHCH2CHCH3‬‬
‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪‬‬
‫ﺍﳋﻄﻮﺓ ‪ .2‬ﺭ ﹼﻗﻢ ﺍﻟﺴﻠﺴﻠﺔ ﻋﲆ ﺃﻥ ﺗﻌﻄﻲ ﺃﺻﻐﺮ ﺭﻗﻢ ﻟﻠﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ‪.‬‬

‫ﺳﻢ ﺍﻷﻟﻜﲔ ﺍﳌﺒﲔ ﰲ ﺍﻟﺼﻮﺭﺓ ﺃﺩﻧﺎﻩ‪.‬‬

‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫‪5‬‬ ‫‪6‬‬ ‫‪7‬‬

‫‪ ‬ﱢ‬
‫‪–2‬‬ ‫‪‬‬ ‫‪CH3CH — CHCHCH2CHCH3‬‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫ﺍﳋﻄﻮﺓ ‪ .3‬ﱢ‬
‫ﺳﻢ ﻛﻞ ﳎﻤﻮﻋﺔ ﺑﺪﻳﻠﺔ‪.‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬ ‫‪5‬‬ ‫‪6‬‬ ‫‪7‬‬ ‫‪CH 3‬‬
‫‪‬‬ ‫‪‬‬ ‫‪CH3CH— CHCHCH2CHCH3‬‬ ‫‪2-Heptene parent chain‬‬

‫‪CH 3‬‬ ‫‪CH 3‬‬

‫↑‬ ‫↑‬ ‫‪CH 3CH — CHCHCHCH‬‬ ‫‪3‬‬
‫‪‬‬
‫ﺍﳋﻄﻮﺓ ‪ .4‬ﺣﺪﹼ ﺩ ﻋﺪﺩ ﻛﻞ ﳎﻤﻮﻋﺔ ﺑﺪﻳﻠﺔ‪ ،‬ﻭﻋﲔ ﺍﻟﺒﺎﺩﺋﺔ ﺍﻟﺼﺤﻴﺤﺔ ﻟﺘﻤﺜﻴﻞ ﻫﺬﺍ ﺍﻟﻌﺪﺩ‪ ،‬ﱠ‬
‫ﺛﻢ ﺃﺩﺧﻞ ﺃﺭﻗﺎﻡ ﺍﳌﻮﺍﻗﻊ ﻟﺘﺤﺼﻞ ﻋﲆ‬ ‫‪CH 3‬‬
‫‪C22-068C-828378-08-C‬‬
‫ﺍﻟﺒﺎﺩﺋﺔ ﻛﺎﻣﻠ ﹰﺔ‪.‬‬
‫‪ –2 ‬‬
‫‪64‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3 4 5‬‬ ‫‪6 7‬‬
‫‪CH3CH — CHCHCH2CHCH3‬‬ ‫‪2-Heptene parent chain‬‬ ‫‪‬‬
‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪Two methyl groups at Positions 4 and 6‬‬

‫‪ -5،4‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ–‪–2‬ﻫﻜﺴﲔ‪.‬‬
‫‪Prefix is 4,6-dimethyl‬‬
‫‪–6،4‬‬
‫ﺍﳋﻄﻮﺓ ‪ .5‬ﻟﻴﺲ ﻫﻨﺎﻙ ﺣﺎﺟﺔ ﺇﱃ ﻛﺘﺎﺑﺔ ﺃﺳﲈﺀ ﺍﻟﺘﻔﺮﻋﺎﺕ ﺑﺎﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ؛ ﻷﳖﺎ ﻣﺘﲈﺛﻠﺔ‪ .‬ﻟﺬﺍ ﺃﺩﺧﻞ ﺍﻟﺒﺎﺩﺋﺔ ﺍﻟﻜﺎﻣﻠﺔ ﺇﱃ ﺍﺳﻢ‬
‫ﺳﻠﺴﻠﺔ ﺍﻷﻟﻜﲔ ﺍﻟﺮﺋﻴﺴﺔ‪ ،‬ﻭﺍﺳﺘﺨﺪﻡ ﺍﻟﻔﻮﺍﺻﻞ ﺑﲔ ﺍﻷﺭﻗﺎﻡ‪ ،‬ﻭﺍﻟﴩﻃﺎﺕ ﺑﲔ ﺍﻷﺭﻗﺎﻡ ﻭﺍﻟﻜﻠﲈﺕ‪ ،‬ﺛﻢ ﺍﻛﺘﺐ ﺍﻻﺳﻢ‪:‬‬
‫‪-‬ﻫﺒﺘﲔ‪.‬‬‫‪ –6،4‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ–‪2‬‬
‫‪C22-068C-828378-08-D‬‬
‫ﺗﻘﻮﻳﻢ اﺟﺎﺑﺔ‬
‫اﺳﺘﺨﺪام اﻟﻤﻔﺮدات اﻟﻌﻠﻤﻴﺔ‬
‫‪3‬‬

‫ﲢﺘﻮﻱ ﺃﻃﻮﻝ ﺳﻠﺴﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﻋﲆ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ‪ ،‬ﻭﻣﻮﻗﻊ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ ﻟﻪ ﺃﺻﻐﺮ ﺭﻗﻢ ﳑﻜﻦ‪ .‬ﻭﺍﺳﺘﻌﻤﻠﺖ ﺍﻟﺒﺎﺩﺋﺎﺕ‬
‫ﺍﻟﺼﺤﻴﺤﺔ ﻭﺃﺳﲈﺀ ﳎﻤﻮﻋﺎﺕ ﺍﻷﻟﻜﻴﻞ ﻟﺘﻌﻴﲔ ﺍﻟﺘﻔﺮﻋﺎﺕ‪.‬‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻛﺘﺎﺑﺔ ﻋﺒﺎﺭﺍﺕ ﻳﻮﺿﺤﻮﺍ ﻓﻴﻬﺎ ﻣﻌﻨﻰ‬

‫ﺍﳌﺼﻄﻠﺤﲔ‪ :‬ﺃﻟﻜﲔ ﻭﺃﻟﻜﺎﻳﻦ‪ .‬‬

‫ﺗﻄﻮﻳﺮ اﻟﻤﻔﻬﻮم‬
‫‪ ‬ﺗﺄﻛﺪ ﻣﻦ ﺍﺳـﺘﻴﻌﺎﺏ ﺍﻟﻄﻼﺏ ﺃﻥ ﺍﻟﺼﻴـﻎ ﺍﻟﻌﺎﻣﺔ‬
‫ﻟﻸﻟﻜﻴﻨـﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺗﻨﻄﺒﻖ ﻓﻘـﻂ ﻋﲆ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﺘﻲ ﲢﺘﻮﻱ‬
‫ﻋـﲆ ﺭﺍﺑﻄﺔ ﻏﲑ ﻣﺸـﺒﻌﺔ ﻭﺍﺣﺪﺓ ﻓﻘـﻂ‪ .‬ﻭﻻ ﺗﻨﻄﺒﻖ ﻋﲆ ﺍﻷﻟﻜﻴﻨﺎﺕ‬
‫‪ ‬ﺳﻴﺘﻤﻜﻦ ﺑﻌﺾ ﺍﻟﻄﻼﺏ ﻣﻦ ﻓﻬﻢ ﺍﻟﻔﺮﻭﻕ ﺑﲔ ﺍﻷﻟﻜﺎﻧﺎﺕ‬ ‫ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺍﳊﻠﻘﻴﺔ‪  .‬‬
‫ﻭﺍﻷﻟﻜﻴﻨـﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨـﺎﺕ ﺑﺼـﻮﺭﺓ ﺃﻓﻀـﻞ‪ ،‬ﺇﺫﺍ ﲤﻜﻨـﻮﺍ ﻣـﻦ ﻣﻘﺎﺭﻧﺘﻬـﺎ‬
‫ﺑﺎﺳـﺘﺨﺪﺍﻡ ﺍﻟﻨـﲈﺫﺝ‪ .‬ﻟـﺬﺍ ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻋﻤـﻞ ﻧـﲈﺫﺝ ﻟـﻜﻞ ﻣـﻦ‬
‫ﺍﻹﻳﺜـﺎﻥ ﻭﺍﻹﻳﺜـﲔ ﻭﺍﻹﻳﺜﺎﻳﻦ‪ ،‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﻋﻤﻞ ﻗﺎﺋﻤﺔ ﺑﻨﻘﺎﻁ ﺍﻟﺘﺸـﺎﺑﻪ‬
‫ﻭﺍﻻﺧﺘـﻼﻑ ﺍﻟﻈﺎﻫـﺮﺓ ﰲ ﺍﻟﻨﲈﺫﺝ‪ .‬ﻭﻋﻠﻴﻬـﻢ ﺃﻥ ﻳﻜﺘﺸـﻔﻮﺍ ﹰ‬
‫ﺃﻳﻀﺎ ﺃﻥ ﺫﺭﰐ‬
‫ﺍﻟﻜﺮﺑـﻮﻥ ﰲ ﺍﻹﻳﺜـﲔ ﻏﲑ ﻗﺎﺩﺭﺗﲔ ﻋـﲆ ﺍﻟﺪﻭﺭﺍﻥ ﺑﺴـﻬﻮﻟﺔ ﺑﻌﻀﻬﲈ ﺣﻮﻝ‬
‫ﺑﻌﺾ‪ ،‬ﰲ ﺣﲔ ﺗﺴﺘﻄﻴﻊ ﺫﺭﺍﺕ ﺍﻹﻳﺜﺎﻥ ﺫﻟﻚ‪ .‬ﻛﺬﻟﻚ ﻓﺈﻥ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‬
‫ﻧﺴﺒﻴﺎ‬
‫ﰲ ﺍﻹﻳﺜﺎﻳﻦ ﻏﲑ ﻗﺎﺩﺭﺓ ﻋﲆ ﺍﻟﺪﻭﺭﺍﻥ‪ ،‬ﻭﻟﻜﻦ ﻫﺬﻩ ﺍﳋﺎﺻﻴﺔ ﻏﲑ ﻣﻬﻤﺔ ﹼﹰ‬
‫ﰲ ﺍﻷﻟﻜﺎﻳﻨﺎﺕ‪ .‬‬

‫‪148‬‬
 ‫‪‬‬
‫‪ .17‬ﺍﺳﺘﺨﺪﻡ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ ﻟﺘﺴﻤﻴﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ‪ IUPAC‬ﺍﻵﺗﻴﺔ‪:‬‬
‫‪‬‬ ‫‪CH3‬‬ ‫‪.b‬‬ ‫‪— CHCHCH3‬‬
‫— ‪CH3CH‬‬ ‫‪.a‬‬

‫—‬

‫—‬
‫‪CH2‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬

‫—‬
‫‪ -4 .a .17‬ﻣﻴﺜﻴﻞ‪ -2-‬ﺑﻨﺘﲔ‬

‫—‬
‫‪— CHCCH3‬‬
‫— ‪CH3CHCH2CH‬‬

‫—‬
‫‪CH3‬‬

‫‪ -6،2.2 .b‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ–‪ -3‬ﺃﻭﻛﺘﲔ‬ ‫ﻟﻠﺠﺰﻱﺀ ‪ –3،1‬ﺑﻨﺘﺎﺩﺍﻳﲔ‪.‬‬ ‫‪  .18‬ﺍﺭﺳﻢ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‬
‫‪C22-069C-828378-08‬‬

‫‪CH3CH=CHCH=CH2 .18‬‬
‫— ‪ ‬ﺍﻟﺸـﻜﻞ ‪ 8-14‬ﻳﻤﻜﻦ ﻗﻄـﻒ ﺍﳌﻨﺘﺞ ﺍﻟﺰﺭﺍﻋﻲ‪،‬‬
‫ﻭﻧﻘﻠـﻪ ﺇﱃ ﺍﻟﺴـﻮﻕ‪ ،‬ﻭﺑﻴﻌـﻪ ﻛﻠـﻪ ﰲ ﺍﻟﻮﻗـﺖ ﻧﻔﺴـﻪ‪ ،‬ﳑـﺎ ﻳﺰﻳﺪ ﻣﻦ‬
‫ﺍﻷﺭﺑﺎﺡ‪.‬‬
‫اﻟﺨﻠﻔﻴﺔ اﻟﻨﻈﺮﻳﺔ ﻟﻠﻤﺤﺘﻮى‬
‫‪ ‬ﺗﻢ ﻭﺻﻒ ﺍﻹﻳﺜﺎﻳﻦ‪ ،‬ﺃﻭ ﺍﻷﺳﺘﻴﻠﲔ ﺃﻭﻝ ﻣﺮﺓ‬
‫ﻋﲆ ﻳﺪ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ ﺍﻟﻔﺮﻧـﴘ ﺑﲑﺛﻮﻟﻮﺕ ‪ P.E.M. Berthelot‬ﰲ‬
‫ﻋـﺎﻡ ‪1862‬ﻡ‪ ،‬ﻭﺗـﻢ ﲢﻀـﲑﻩ ﺃﻭﻝ ﻣﺮﺓ ﻋﲆ ﻧﻄﺎﻕ ﻭﺍﺳـﻊ ﰲ ﺍﻟﻌﻘﺪ‬
‫‪    ‬‬
‫ﺍﻟﺘﺎﺳﻊ ﻣﻦ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳﻊ ﻋﴩ‪.‬‬
‫‪             ‬‬
‫ﻻ‪ ،‬ﹸﻳ ﹶﺴ ﱠـﺨﻦ ﺍﳊﺠﺮ ﺍﳉـﲑﻱ ‪ CaCO3‬ﻟﻌﻤﻞ ﺍﳉـﲑ ﺍﳊﻲ‪ ،‬ﻭﻫﻮ‬ ‫ﺃﻭ ﹰ‬
‫‪C22-070C-828378-08‬‬
‫‪ ‬ﺍﻷﻟﻜﻴﻨﺎﺕ‪ ،‬ﻣﺜﻞ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻣﻮﺍﺩ ﻏﲑ ﻗﻄﺒﻴﺔ‪،‬‬
‫ﻟﺬﺍ ﻓﺈﻥ ﺫﺍﺋﺒﻴﺘﻬﺎ ﻗﻠﻴﻠﺔ ﰲ ﺍﳌﺎﺀ‪ ،‬ﻭﺗﻜﻮﻥ ﺩﺭﺟﺎﺕ ﺍﻧﺼﻬﺎﺭﻫﺎ ﻭﻏﻠﻴﺎﳖﺎ ﻣﻨﺨﻔﻀﺔ‪ .‬ﻟﻜﻦ‬
‫ﺍﻷﻟﻜﻴﻨﺎﺕ ﺃﻛﺜﺮ ﹰ‬
‫ﻧﺸﺎﻃﺎ ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ؛ ﺣﻴﺚ ﺇﻥ ﺍﻟﺮﺍﺑﻄﺔ ﺍﳌﺸﱰﻛﺔ ﺍﻟﺜﺎﻧﻴﺔ ﺗﺰﻳﺪ ﻣﻦ ﺍﻟﻜﺜﺎﻓﺔ‬
‫ﻣﻮﻗﻌﺎ ﺟﻴﺪﹰ ﺍ ﻟﻠﻨﺸﺎﻁ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‪ .‬ﻭﻫﺬﺍ ﳚﻌﻞ‬
‫ﹰ‬ ‫ﺑﺬﻟﻚ‬ ‫ﹰ‬
‫ﺔ‬ ‫ﻣﻬﻴﺌ‬ ‫ﺍﻟﻜﺮﺑﻮﻥ‪،‬‬ ‫ﺫﺭﰐ‬ ‫ﺍﻹﻟﻜﱰﻭﻧﻴﺔ ﺑﲔ‬
‫ﺍﳌﻮﺍﺩ ﺍﳌﺘﻔﺎﻋﻠﺔ ﻗﺎﺩﺭﺓ ﻋﲆ ﺟﺬﺏ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﻋﲆ ﺳﺤﺐ ﺇﻟﻜﱰﻭﻧﺎﺕ ﺍﻟﺮﺍﺑﻄﺔ ﺑﺎﻱ ﺑﻌﻴﺪﹰ ﺍ‬
‫ﻋﻦ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ‪.‬‬
‫ﻳﻨﺘﺞ ﺍﻟﻌﺪﻳﺪ ﻣﻦ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺑﺼﻮﺭﺓ ﻃﺒﻴﻌﻴﺔ ﰲ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ‪ .‬ﻓﺎﻹﻳﺜﲔ‪ ،‬ﻋﲆ ﺳﺒﻴﻞ‬
‫ﺍﳌﺜﺎﻝ‪ ،‬ﻫﺮﻣﻮﻥ ﺗﹸﻨﺘﺠﻪ ﺍﻟﻨﺒﺎﺗﺎﺕ ﻋﲆ ﻧﺤﻮ ﻃﺒﻴﻌﻲ‪ ،‬ﻭﻫﻮ ﺍﳌﺴﺆﻭﻝ ﻋﻦ ﻋﻤﻠﻴﺔ ﺍﻟﻨﻀﺞ ﰲ‬
‫ﺩﻭﺭﺍ ﰲ ﻋﻤﻠﻴﺔ ﺗﺴﺎﻗﻂ ﺃﻭﺭﺍﻕ ﺍﻷﺷﺠﺎﺭ ﺇﻳﺬﺍ ﹰﻧﺎ ﺑﺪﺧﻮﻝ ﻓﺼﻞ ﺍﻟﺸﺘﺎﺀ‪.‬‬
‫ﺍﻟﻔﻮﺍﻛﻪ‪ ،‬ﻭﻳﺆﺩﻱ ﹰ‬
‫ﺗﻨﻀﺞ ﺍﻟﻔﻮﺍﻛﻪ ﺍﻟﻈﺎﻫﺮﺓ ﰲ ﺍﻟﺸﻜﻞ ‪ 8-14‬ﻭﻏﲑﻫﺎ ﻣﻦ ﺍﳌﻨﺘﺠﺎﺕ ﺍﻟﺘﻲ ﺗﹸﺒﺎﻉ ﰲ ﳏﻼﺕ‬
‫ﺻﻨﺎﻋﻴﺎ ﻋﻨﺪ ﺗﻌﺮﻳﻀﻬﺎ ﻟﻺﻳﺜﲔ‪ .‬ﻭ ﹸﻳﻌﺪ ﺍﻹﻳﺜﲔ ﻣﻦ ﺍﳌﻮﺍﺩ ﺍﻷﻭﻟﻴﺔ ﺍﳌﺴﺘﺨﺪﻣﺔ ﰲ‬
‫ﹼﹰ‬ ‫ﺍﻟﺒﻘﺎﻟﺔ‬
‫ﺗﺼﻨﻴﻊ ﻣﺎﺩﺓ ﺑﻮﱄ ﺇﻳﺜﻴﻠﲔ ﺍﻟﺒﻼﺳﺘﻴﻜﻴﺔ ﺍﳌﺴﺘﺨﺪﻣﺔ ﰲ ﺻﻨﺎﻋﺔ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﻨﺘﺠﺎﺕ‪ ،‬ﻭﻣﻨﻬﺎ‬
‫ﺍﳊﻘﺎﺋﺐ ﺍﻟﺒﻼﺳﺘﻴﻜﻴﺔ ﻭﺍﳊﺒﺎﻝ ﻭﻋﻠﺐ ﺍﳊﻠﻴﺐ‪ .‬ﻭﻫﻨﺎﻙ ﺃﻟﻜﻴﻨﺎﺕ ﺃﺧﺮ￯ ﻣﺴﺆﻭﻟﺔ ﻋﻦ‬
‫ﺭﻭﺍﺋﺢ ﺍﻟﻠﻴﻤﻮﻥ ﺍﻷﺻﻔﺮ‪ ،‬ﻭﺍﻟﻠﻴﻤﻮﻥ ﺍﻷﺧﴬ‪ ،‬ﻭﺃﺷﺠﺎﺭ ﺍﻟﺼﻨﻮﺑﺮ‪.‬‬
‫‪  8-14 ‬‬
‫‪‬‬
‫‪‬‬

‫ﻳﺘﻜﻮﻥ ﰲ ﻣﻌﻈﻤﻪ ﻣﻦ ﺃﻛﺴﻴﺪ ﺍﻟﻜﺎﻟﺴﻴﻮﻡ ‪.CaO‬‬

‫‪CaCO3 → CaO + CO2‬‬

‫ﺛﻢ ﻳﺘﻢ ﺗﺴـﺨﲔ ﺃﻛﺴـﻴﺪ ﺍﻟﻜﺎﻟﺴـﻴﻮﻡ ﺑﻌﺪ ﺫﻟﻚ ﰲ ﻓﺮﻥ ﻣﻊ ﻛﺮﺑﻮﻥ‬

‫ﻋﲆ ﻫﻴﺌﺔ ﻓﺤﻢ ﺍﻟﻜﻮﻙ؛ ﻓﺘﻨﺘﺞ ﻣﺎﺩﺓ ﻛﺮﺑﻴﺪ ﺍﻟﻜﺎﻟﺴـﻴﻮﻡ ﻣﻦ ﺗﺴﺨﲔ‬
‫ﺍﻟﻔﺤﻢ ﰲ ﻏﻴﺎﺏ ﺍﻷﻛﺴﺠﲔ‪ ،‬ﻭﻳﻨﺘﺞ ﺃﻭﻝ ﺃﻛﺴﻴﺪ ﺍﻟﻜﺮﺑﻮﻥ ﺑﻮﺻﻔﻪ‬
‫ﻣﺎﺩﺓ ﺛﺎﻧﻮﻳﺔ )ﺟﺎﻧﺒﻴﺔ(‪.‬‬
‫‪CaO + 3C → CaC2 + CO‬‬

‫ﺛﻢ ﻳﺘﻔﺎﻋﻞ ﻛﺮﺑﻴﺪ ﺍﻟﻜﺎﻟﺴﻴﻮﻡ ﻣﻊ ﺍﳌﺎﺀ ﻟﺘﻜﻮﻳﻦ ﺍﻷﺳﺘﻴﻠﲔ‪.‬‬

‫‪CaC2 + 2H2O → C2H2 + Ca(OH) 2‬‬

‫ﺃﻣﺎ ﺍﻟﻴﻮﻡ‪ ،‬ﻓﺘﻨﺘﺞ ﻛﻤﻴﺔ ﺃﻛﱪ ﻣﻦ ﺍﻷﺳﺘﻴﻠﲔ ﺑﻌﻤﻠﻴﺔ ﺍﻷﻛﺴﺪﺓ ﺍﳉﺰﺋﻴﺔ‬

‫ﻟﻠﻤﻴﺜﺎﻥ‪:‬‬
‫‪6CH4 + O2 → 2C2H2 + 2CO + 10H2‬‬

‫‪149‬‬
 ‫ا¶ﻟﻜﺎﻳﻨﺎت ‪Alkynes‬‬
‫ﺗﹸﺴﻤﻰ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﺃﻭ ﺃﻛﺜﺮ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‬
‫ﺍﻷﻟﻜﺎﻳﻨﺎﺕ‪ .‬ﻭﺗﺸﱰﻙ ﰲ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻼﺛﻴﺔ ﺛﻼﺛﺔ ﺃﺯﻭﺍﺝ ﻣﻦ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ‪ .‬ﻭﻳﻌﺪ ﺍﻹﻳﺜﺎﻳﻦ ‪ C2H2‬ﺃﺑﺴﻂ‬
‫ﻭﳛ ﱢﻔﺰ‬
‫‪ ‬ﻟﻠﺮﺍﺑﻄﺔ ﺍﻟﺜﻼﺛﻴﺔ ﻛﺜﺎﻓﺔ ﺇﻟﻜﱰﻭﻧﻴﺔ ﻋﺎﻟﻴﺔ‪ ،‬ﹸ ﹶ‬
‫ﺗﻔﺤﺺ‬
‫ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻭﺃﻛﺜﺮﻫﺎ ﺍﺳﺘﺨﺪﺍ ﹰﻣﺎ‪ ،‬ﻭﻫﻮ ﻣﻌﺮﻭﻑ ﻋﲆ ﻧﻄﺎﻕ ﻭﺍﺳﻊ ﺑﺎﺳﻤﻪ ﺍﻟﺸﺎﺋﻊ‪ ،‬ﺃﺳﻴﺘﻴﻠﲔ‪ .‬ﹼ‬
‫ﻧﲈﺫﺝ ﺍﻹﻳﺜﺎﻳﻦ ﰲ ﺍﻟﺸﻜﻞ ‪.8-15‬‬
‫ﲡﻤـﻊ ﺍﻹﻟﻜﱰﻭﻧـﺎﺕ ﻓﻴﻬـﺎ ﺗﻜﻮﻳـﻦ ﺃﻗﻄـﺎﺏ ﰲ ﺍﳉﺰﻳﺌـﺎﺕ‬
‫‪  ‬ﺗﹸﺴﻤﻰ ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺍﳌﺴﺘﻘﻴﻤﺔ ﻭﺍﳌﺘﻔﺮﻋﺔ ﺑﻄﺮﻳﻘﺔ ﳑﺎﺛﻠﺔ ﻟﻸﻟﻜﻴﻨﺎﺕ‪ .‬ﻭﺍﻟﻔﺮﻕ‬
‫ﺍﻟﻮﺣﻴﺪ ﻫﻮ ﺃﻥ ﺍﺳﻢ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻳﻨﺘﻬﻲ ﺑـ )ﺍﻳﻦ( ﺑﺪ ﹰ‬
‫ﺍﳌﺠـﺎﻭﺭﺓ‪ ،‬ﺑﺤﻴﺚ ﲡﻌـﻞ ﺍﳉﺰﻳﺌﺎﺕ ﺍﳌﺠﺎﻭﺭﺓ ﻏﲑ ﻣﺘﺴـﺎﻭﻳﺔ‬
‫ﻻ ﻣﻦ )ﻳﻦ(‪ .‬ﻛﲈ ﻳﻈﻬﺮ ﰲ ﺃﻣﺜﻠﺔ ﺍﳉﺪﻭﻝ ‪.8-6‬‬
‫ﹰ‬
‫ﹸﺸﻜﻞ ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺍﳌﺤﺘﻮﻳﺔ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﺳﻠﺴﻠﺔ ﻣﺘﲈﺛﻠﺔ ﳍﺎ ﺍﻟﺼﻴﻐﺔ ﺍﻟﻌﺎﻣﺔ ‪.Cn H2n – 2‬‬ ‫ﻭﺗ ﱢ‬ ‫ﺍﻟﺸﺤﻨﺔ ﻭﺫﺍﺕ ﻧﺸﺎﻁ ﻛﻴﻤﻴﺎﺋﻲ ﹴ‬
‫ﻋﺎﻝ‪.‬‬
‫‪   ‬ﺍﻋﺘﲈ ﹰﺩﺍ ﻋﲆ ﻃﺒﻴﻌﺔ ﺭﻭﺍﺑﻂ ﺍﻹﻳﺜﺎﻳﻦ‪ ،‬ﳌﺎﺫﺍ ﻳﺘﻔﺎﻋﻞ ﺑﴪﻋﺔ ﻋﺎﻟﻴﺔ ﻣﻊ‬
‫ﺍﻷﻛﺴﺠﲔ؟‬

‫‪ ‬‬ ‫‪8-15‬‬

‫— ‪H —C‬‬
‫‪—C —H‬‬

‫‪‬‬

‫‪‬‬ ‫‪86‬‬

‫‪‬‬ ‫‪‬‬ ‫‪‬‬ ‫‪‬‬

‫‪CH — CH‬‬ ‫‪H‬‬ ‫—‪C‬‬

‫‪—C‬‬ ‫‪H‬‬ ‫‪C2H2‬‬ ‫ﺇﻳﺜﺎﻳﻦ‬

‫‪H‬‬ ‫‪C23H24‬‬
‫—‬

‫— ‪CH‬‬
‫‪— CCH3‬‬ ‫—‪H—C‬‬
‫‪—C—C—H‬‬ ‫‪C34H46‬‬ ‫ﺑﺮﻭﺑﺎﻳﻦ‬
‫—‬

‫‪H‬‬ ‫‪C2H2‬‬
‫‪C4H6‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪C3H4‬‬
‫‪C‬‬
‫‪C24H‬‬
‫—‬

‫—‬

‫‪H26‬‬
‫— ‪CH‬‬
‫‪— CCH2CH3‬‬ ‫‪H—C—C—C—C—H‬‬ ‫‪C4H6‬‬ ‫‪ – 1‬ﺑﻴﻮﺗﺎﻳﻦ‬
‫—‬

‫—‬

‫‪H‬‬ ‫‪H‬‬ ‫‪C3H4‬‬

‫‪C4H6‬‬
‫‪C22-074C-828378-08‬‬
‫‪C4H6‬‬
‫‪H‬‬ ‫‪H‬‬
‫—‬

‫—‬

‫— ‪CH3C‬‬
‫‪— CCH3‬‬ ‫‪H—C—C—C—C—H‬‬
‫‪C22-075C-828378-08‬‬ ‫‪C4H6‬‬ ‫‪ -2‬ﺑﻴﻮﺗﺎﻳﻦ‬
‫—‬

‫—‬

‫‪H‬‬ ‫‪H‬‬

‫‪C22-076C-828378-08‬‬

‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬

‫‪ ‬ﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﻭﺟﻮﺩ ﺍﻷﻟﻜﻴﻨـﺎﺕ ﻋﺎﺩﺓ ﰲ ﺍﻟﻄﺒﻴﻌﺔ‪ ،‬ﺇﻻ‬

‫ﺃﻥ ﻣـﻦ ﺍﻟﺼﻌـﺐ ﺇﳚـﺎﺩ ﺃﻟﻜﺎﻳﻦ ﻃﺒﻴﻌﻲ‪ .‬ﻭﺃﺣـﺪ ﺍﻷﻟﻜﻴﻨـﺎﺕ ﺍﻟﻄﺒﻴﻌﻴﺔ ﻫﻮ‬
‫‪ ،dynemycin A‬ﻭﻫـﻮ ﺗﺮﻛﻴـﺐ ﺑﻨﺎﺋـﻲ ﻣﻌﻘﺪ ﻣﺘﻌـﺪﺩ ﺍﳊﻠﻘﺎﺕ‪ ،‬ﻭﳛﻮﻱ‬
‫ﺗـﻢ ﺍﺧﺘﺒـﺎﺭﻩ ﻟﻜﻮﻧـﻪ ﹰ‬
‫ﻋﺎﻣﻼ‬ ‫ﺭﺍﺑﻄﺘـﻲ ﻛﺮﺑـﻮﻥ– ﻛﺮﺑـﻮﻥ ﺛﻼﺛﻴﺘـﲔ‪ .‬ﻭﻟﻘـﺪ ﹼ‬
‫ﻣﻀـﺎﺩﺍ ﻟﻠﴪﻃﺎﻥ‪ .‬ﻟـﺬﺍ ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤـﺚ ﰲ ﺍﻟﺼﻴﻐﺔ‬
‫ﹼﹰ‬ ‫ﹰ‬
‫ﳏﺘﻤـﻼ‬
‫ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﺮﻛﺐ ‪ dynemycin A‬ﻭﺍﳌﺼﺪﺭ ﺍﻟﻄﺒﻴﻌﻲ ﻟﻪ‪ ،‬ﻭﺗﺴـﺠﻴﻞ ﻫﺬﻩ‬
‫ﺍﳌﻌﻠﻮﻣﺎﺕ ﰲ ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ‪ .‬‬

‫‪150‬‬
 ‫‪ .5‬‬

‫‪‬‬
‫ﺗﺤﻀﻴﺮ اﻳﺜﺎﻳﻦ وﻣﻼﺣﻈﺔ ﺧﺼﺎﺋﺼﻪ‬
‫‪ ‬‬
‫‪‬‬
‫‪ ‬‬ ‫‪ ‬‬
‫‪‬‬ ‫ﺧﻄﻮات اﻟﻌﻤﻞ‬
‫‪A‬‬ ‫‪B‬‬ ‫‪C‬‬ ‫‪D‬‬
‫‪‬‬
‫‪E‬‬ ‫‪F‬‬
‫‪‬‬
‫‪G AH B‬‬ ‫‪AA I ACBBJ BC‬‬ ‫‪DA‬‬
‫‪C K CD‬‬
‫‪.6‬‬
‫‪FDFN FHGEGO GHIF‬‬
‫‪EBD L DFECEM EG‬‬ ‫‪HP HJG‬‬ ‫‪I I IK‬‬‫‪JHJ JK‬‬‫‪L‬‬
‫‪I KMLJL N‬‬
‫‪K‬‬ ‫‪LMM‬‬
‫‪K M‬‬‫‪O‬‬‫‪NNL NPOO‬‬ ‫‪MOPN‬‬
‫‪.P1‬‬ ‫‪PO‬‬ ‫‪P‬‬
‫‪‬‬ ‫‪         .2‬‬
‫‪ 25 ml .7 10cm40cm‬‬
‫‪‬‬ ‫‪‬‬
‫‪CaC2‬‬
‫‪ ‬ﺳﻴﺤﴬ ﺍﻟﻄﻼﺏ ﺍﻹﻳﺜﺎﻳﻦ ﻭﻣﻼﺣﻈﺔ ﺑﻌﺾ ﺧﺼﺎﺋﺼﻪ‪.‬‬
‫‪‬‬
‫‪‬‬ ‫‪150ml120ml .3‬‬
‫اﻟﺘﺤﻠﻴﻞ‬ ‫‪ 5ml‬‬
‫‪CaC2        .4‬‬
‫‪ ‬ﺍﳌﻼﺣﻈـﺔ ﻭﺍﻻﺳـﺘﻨﺘﺎﺝ‪ ،‬ﺍﻟﺘﻮﺍﺻـﻞ‪ ،‬ﺗﻄﺒﻴـﻖ‬ ‫‪  .1‬‬
‫‪‬‬
‫‪CaC2 ‬‬
‫‪‬‬
‫‪   .2‬‬
‫ﺍﳌﻔﺎﻫﻴﻢ‪.‬‬ ‫‪C2H2 ‬‬
‫‪‬‬
‫‪‬‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻻﻃـﻼﻉ ﻋﲆ ﻧﲈﺫﺝ‬ ‫‪ ‬ﻟﻸﻟﻜﺎﻳﻨﺎﺕ ﺧﺼﺎﺋﺺ ﻓﻴﺰﻳﺎﺋﻴﺔ ﻭﻛﻴﻤﻴﺎﺋﻴﺔ ﺷﺒﻴﻬﺔ‬

‫ﺍﻟﺴـﻼﻣﺔ ﰲ ﺍﳌﺨﺘﱪ ﻗﺒﻞ ﺑﺪﺀ ﺍﻟﻌﻤﻞ‪ .‬ﻭﻳﻨﺒﻐﻲ ﺭﺑﻂ ﺍﻟﺸـﻌﺮ ﺍﻟﻄﻮﻳﻞ‬ ‫اﻟﻤﻄﻮﻳﺎت‬
‫ﺑﺎﻷﻟﻜﻴﻨـﺎﺕ‪ .‬ﻭﲣﻀﻊ ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻟﻜﺜﲑ ﻣﻦ ﺍﻟﺘﻔﺎﻋﻼﺕ ﺍﻟﺘـﻲ ﲣﻀﻊ ﳍﺎ ﺍﻷﻟﻜﻴﻨﺎﺕ‪ ،‬ﺇﻻ ﺃﻥ‬
‫ﹰ‬
‫ﻧﺸـﺎﻃﺎ ﻣﻦ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻋﻤﻮ ﹰﻣﺎ؛ ﻭﺫﻟﻚ ﻷﻥ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻼﺛﻴﺔ ﰲ ﺍﻷﻟﻜﺎﻳﻨﺎﺕ‬ ‫ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺃﻛﺜﺮ‬
‫ﺃﺩﺧﻞ ﻣﻌﻠﻮﻣﺎﺕ ﻣﻦ ﻫﺬﺍ ﺍﻟﻘﺴﻢ‬
‫ﺇﱃ ﺍﳋﻠـﻒ‪ ،‬ﻭﲡﻨـﺐ ﳌـﺲ ﺍﻟﻌـﲔ ﻭﺍﳉﻠﺪ ﺑﺴـﺒﺐ ﺍﳌـﺎﺩﺓ ﺍﻟﻜﺎﻭﻳﺔ‬ ‫ﰲ ﻣﻄﻮﻳﺘﻚ‪.‬‬ ‫ﻓﻌـﺎﻝ ﰲ ﲢﻔﻴﺰ ﺗﻜﻮﻳﻦ ﺍﻷﻗﻄﺎﺏ ﰲ ﺍﳉﺰﻳﺌﺎﺕ ﺍﳌﺠﺎﻭﺭﺓ‪ ،‬ﳑﺎ ﳚﻌﻠﻬﺎ ﻏﲑ ﻣﺘﲈﺛﻠﺔ ﺍﻟﺸـﺤﻨﺔ‪ ،‬ﻟﺬﺍ‬
‫ﺗ ﹼ‬
‫ﹸﺸﻜﻞ ﻛﺜﺎﻓﺔ ﺇﻟﻜﱰﻭﻧﻴﺔ ﺃﻛﱪ ﳑﹼﺎ ﰲ ﺭﺍﺑﻄﺔ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺍﻟﺜﻨﺎﺋﻴﺔ‪ .‬ﺇﻥ ﻫﺬﺍ ﺍﻟﺘﺠﻤﻊ ﻣﻦ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ‬
‫ﹼ‬
‫‪ Ca(OH) 2‬ﺍﻟﻨﺎﲡﺔ ﻋﻦ ﺗﻔﺎﻋﻞ ‪ CaC2‬ﻣﻊ ﺍﻟﺮﻃﻮﺑﺔ )ﺍﳌﺎﺀ(‪.‬‬ ‫ﺗﻜﻮﻥ ﺃﻛﺜﺮ ﹰ‬
‫ﻧﺸﺎﻃﺎ‪.‬‬
‫ﺃﻳﻀﺎ ﺑﻜﻤﻴﺎﺕ‬ ‫ﺇﻥ ﺍﻹﻳﺜﺎﻳﻦ– ﺍﳌﻌﺮﻭﻑ ﺑﺎﻷﺳـﻴﺘﻴﻠﲔ–ﻧﺎﺗﺞ ﺛﺎﻧﻮﻱ ﻋﻦ ﺗﻨﻘﻴﺔ ﺍﻟﺒﱰﻭﻝ‪ ،‬ﻭﻳﻨﺘﺞ ﹰ‬
‫ﻛﺒـﲑﺓ ﻋـﻦ ﺗﻔﺎﻋﻞ ﻛﺮﺑﻴﺪ ﺍﻟﻜﺎﻟﺴـﻴﻮﻡ ‪ CaC2‬ﻣـﻊ ﺍﳌﺎﺀ‪ .‬ﻋﻨﺪﻣﺎ ﹼ‬
‫ﻳـﺰﻭﺩ ﺍﻹﻳﺜﺎﻳـﻦ ﺑﻜﻤﻴﺔ ﻛﺎﻓﻴﺔ‬
‫‪ ‬ﺍﺳـﻜﺐ ﳏﻠـﻮﻝ ﺍﻟﺘﻔﺎﻋـﻞ ﰲ ﺍﳌﻐﺴـﻠﺔ‬ ‫ﻣﻨﺘﺠﺎ ﳍ ﹰﺒﺎ ﺫﺍ ﺣﺮﺍﺭﺓ ﻋﺎﻟﻴﺔ ﺟﺪﹼﹰ ﺍ ﻗﺪ ﺗﺼﻞ ﺇﱃ ‪ ،3000 °C‬ﻭﺗﺴـﺘﻌﻤﻞ‬
‫ﻣﻦ ﺍﻷﻛﺴـﺠﲔ ﳛﱰﻕ ﹰ‬
‫ﻣﺸـﺎﻋﻞ ﺍﻷﺳـﻴﺘﻴﻠﲔ ﻋﺎﺩ ﹰﺓ ﻷﻏﺮﺍﺽ ﺍﻟﻠﺤﻢ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸـﻜﻞ ‪ .8-16‬ﻭﻷﻥ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻼﺛﻴﺔ‬
‫ﻣﺼﺤﻮ ﹰﺑـﺎ ﺑﺎﻟﻜﺜـﲑ ﻣﻦ ﺍﳌﺎﺀ‪ .‬ﻭﺩﻉ ‪ CaC2‬ﺍﻟﺮﻃـﺐ ﻳﺘﻔﺎﻋﻞ ﻣﻊ ﺍﳌﺎﺀ‬ ‫ﹰ‬
‫ﻧﺸـﺎﻃﺎ ﻓﺈﻥ ﺍﻷﻟﻜﺎﻳﻨـﺎﺕ ﺍﻟﺒﺴـﻴﻄﺔ ﻛﺎﻹﻳﺜﺎﻳﻦ ﺗﹸﺘﺨﺬ ﻣـﻮﺍ ﹼﺩ ﺃﻭﻟﻴﺔ ﰲ‬ ‫ﲡﻌـﻞ ﺍﻷﻟﻜﺎﻳﻨـﺎﺕ ﺃﻛﺜﺮ‬

‫ﲤﺎ ﹰﻣﺎ ﻗﺒﻞ ﺳﻜﺐ ﺍﳌﺤﻠﻮﻝ‪.‬‬

‫ﺻﻨﺎﻋﺔ ﺍﻟﺒﻼﺳﺘﻴﻚ ﻭﻏﲑﻫﺎ ﻣﻦ ﺍﳌﻮﺍﺩ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﺍﻟﻌﻀﻮﻳﺔ ﺍﳌﺴﺘﺨﺪﻣﺔ ﰲ ﺍﻟﺼﻨﺎﻋﺔ‪.‬‬

‫‪‬‬ ‫‪8-16‬‬
‫‪‬‬ ‫‪2C 2H 2 + 5O 2 → 4CO 2 + 2H 2O‬‬
‫‪‬‬
‫• ﻳﻤﻜـﻦ ﺍﺳـﺘﺨﺪﺍﻡ ﺍﻟﻘﺪﺍﺣﺔ ﺍﻟﻄﻮﻳﻠـﺔ ﺑﺪ ﹰ‬
‫ﻻ ﻣﻦ ﺍﳌﺴـﻄﺮﺓ ﺍﳌﺜﺒﺖ‬
‫ﻋﻠﻴﻬﺎ ﻗﻄﻌﺔ ﺍﳋﺸﺐ‪ .‬ﺗﺄﻛﺪ ﻣﻦ ﺇﻃﻔﺎﺀ ﺍﻟﻄﻼﺏ ﻟﻠﻘﻄﻌﺔ ﺍﳋﺸﺒﻴﺔ‬
‫ﻗﺒﻞ ﺃﻥ ﲢﱰﻕ ﺍﳌﺴﻄﺮﺓ‪.‬‬
‫ﻧﺴـﺒﻴﺎ‪ ،‬ﻟـﺬﺍ ﻟﻦ ﲢﱰﻕ‬
‫ﹼﹰ‬ ‫• ﺳـﻮﻑ ﺗﺘﻜـﻮﻥ ﻓﻘﺎﻗﻴﻊ ﻣـﻦ ﺇﻳﺜﺎﻳﻦ ﻧﻘﻲ‬ ‫اﻟﺘﻘﻮﻳﻢ‬
‫ﺍﻧﻔﺠﺎﺭﺍ ﻋﻨﺪﻣﺎ ﻳﺘﻢ ﺇﺷـﻌﺎﳍﺎ‪ ،‬ﻛﲈ ﻟـﻮ ﻛﺎﻧﺖ ﲢﺘﻮﻱ ﻋﲆ‬
‫ﹰ‬ ‫ﻣﺴـﺒﺒﺔ‬
‫ﺧﻠﻴﻂ ﻣﻦ ﺍﳍﻮﺍﺀ ﻭﺍﻹﻳﺜﺎﻳﻦ‪.‬‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﻟﺒﺤـﺚ ﰲ ﺳـﺒﺐ ﺗﺴـﻤﻴﺔ ﻛﺮﺑﻴـﺪ‬
‫‪‬‬ ‫ﺍﻟﻜﺎﻟﺴـﻴﻮﻡ ﰲ ﺑﻌـﺾ ﺍﻷﺣﻴـﺎﻥ ﺑﻀﻮﺀ ﻋـﲈﻝ ﺍﳌﻨﺎﺟـﻢ )‪miner`s‬‬
‫ﻳﻄﻠـﻖ ﺍﻹﻳﺜﺎﻳﻦ ﻋﻨﺪ ﺇﺷـﻌﺎﻟﻪ ﺻﻮﺕ ﻓﺮﻗﻌﺔ )‪ ،(pop‬ﻭﳛﱰﻕ ﻋﲆ‬ ‫‪ .(lamp‬‬
‫ﻫﻴﺌﺔ ﻛﺮﺓ ﺻﻔﺮﺍﺀ ﺑﺮﺗﻘﺎﻟﻴﺔ ﺍﻟﻠﻮﻥ ﺗﺮﺗﻔﻊ ﻣﻦ ﺍﻟﻜﺄﺱ‪ .‬ﻭﻗﺪ ﻳﱰﺳـﺐ‬
‫ﺳـﻨﺎﺝ ﻋـﲆ ﺟﻮﺍﻧﺐ ﺍﻟـﻜﺄﺱ ﻧﺘﻴﺠﺔ ﺍﻻﺣـﱰﺍﻕ ﻏـﲑ ﺍﻟﻜﺎﻣﻞ‪ .‬ﺇﻥ‬ ‫‪‬‬
‫ﺍﻹﻳﺜﺎﻳﻦ ﺫﺍ ﺍﻟﻜﺘﻠﺔ ﺍﳌﻮﻟﻴﺔ ‪ ،26 g/mol‬ﺃﻗﻞ ﻛﺜﺎﻓﺔ ﻣﻦ ﺍﳍﻮﺍﺀ ﺍﻟﺬﻱ‬ ‫ﺍﻟﻜﺜﺎﻓﺔ ﺃﻗﻞ ﻣﻦ ﺍﳍﻮﺍﺀ ﻗﻠﻴ ﹰ‬
‫ﻼ‪.‬‬ ‫‪.1‬‬
‫ﻳﺴﺎﻭﻱ ﻣﺘﻮﺳﻂ ﻛﺘﻠﺘﻪ ﺍﳌﻮﻟﻴﺔ ‪ 29‬ﺗﻘﺮﻳ ﹰﺒﺎ‪.‬‬
‫ﳚـﺐ ﺃﻥ ﻳـﺪﺭﻙ ﺍﻟﻄﻼﺏ ﰲ ﺿـﻮﺀ ﺗﻐﲑ ﺍﻟﻠﻮﻥ ﺃﻥ ﻣـﺎﺩﺓ ﺫﺍﺕ ﺗﺄﺛﲑ‬ ‫‪.2‬‬
‫ﻭﻗـﺪ ﺗﻄﻔﻮ ﺍﻟﻔﻘﺎﻗﻴـﻊ ﺑﺒﻂﺀ ﺇﱃ ﺃﻋـﲆ‪ ،‬ﻷﻥ ﻛﺜﺎﻓﺘﻬﺎ ﺃﻗـﻞ ﻣﻦ ﻛﺜﺎﻓﺔ‬
‫ﻗﺎﻋﺪﻱ ﻗﺪ ﻧﺘﺠـﺖ‪ .‬ﺃﺧﱪﻫﻢ ﺃﻥ ﺍﻷﻳﻮﻥ ﺍﳌﻮﺟﺐ ‪ Ca2+‬ﻣﻮﺟﻮﺩ ﰲ‬
‫ﺍﳍﻮﺍﺀ‪.‬‬
‫ﺍﳌﺤﻠﻮﻝ‪ ،‬ﻓﻘﺪ ﻳﺴﺘﻨﺘﺠﻮﻥ ﺃﻥ ﺍﳌﺎﺩﺓ ﻏﲑ ﺍﻟﺬﺍﺋﺒﺔ ﻫﻲ ‪.Ca(OH) 2‬‬
‫ﺗﻜﻮﻥ‬
‫ﻛـﲈ ﻳﺘﺤـﻮﻝ ﻟﻮﻥ ﺍﻟﻔﻴﻨـﻮﻝ ﻓﺜﺎﻟﲔ ﺇﱃ ﺍﻟﻠـﻮﻥ ﺍﻟﺰﻫﺮﻱ ﻋﻨـﺪ ﹼ‬ ‫‪CaC 2 +2H 2O → C 2H 2 + Ca(OH) 2‬‬
‫‪.Ca(OH) 2‬‬

‫‪151‬‬
 ‫اﻟﺘﻘﻮﻳﻢ ‪8-3‬‬
‫‪ .19‬اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺻـﻒ ﻛﻴﻒ ﲣﺘﻠﻒ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻸﻟﻜﻴﻨـﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻋﻦ‬ ‫اﻟﺨﻼﺻﺔ‬ ‫‪ .3‬اﻟﺘﻘﻮﻳﻢ‬
‫ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻸﻟﻜﺎﻧﺎﺕ‪.‬‬
‫ﺍﻷﻟــﻜــﻴــﻨــﺎﺕ ﻭﺍﻷﻟــﻜــﺎﻳــﻨــﺎﺕ‬
‫‪ .20‬ﺣـﺪﹼ ﺩ ﻛﻴﻒ ﲣﺘﻠﻒ ﺍﳋﺼﺎﺋﺺ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﻟﻸﻟﻜﻴﻨـﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﹼ‬
‫ﻋﲈ ﺗﺘﺼﻒ ﺑﻪ‬ ‫ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲢﻮﻱ ﻋﲆ ﺍﻷﻗﻞ‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ‪.‬‬
‫ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ‪،‬‬
‫اﻟﺘﺤﻘﻖ ﻣﻦ اﻟﻔﻬﻢ‬
‫ﺳﻢ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺃﺩﻧﺎﻩ ﻣﺴﺘﺨﺪ ﹰﻣﺎ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻡ ﺍﻷﻳﻮﺑﺎﻙ‪.‬‬
‫‪ .21‬ﱢ‬ ‫ﻋﲆ ﺍﻟﺘﻮﺍﱄ‪.‬‬
‫‪CH3‬‬
‫‪.b‬‬
‫‪CH3‬‬
‫‪.a‬‬ ‫ﺗﹸﻌﺪ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻣﺮﻛﺒﺎﺕ‬ ‫ﻗﺼـﲑﺍ ﻟﻠﻄـﻼﺏ ﳌﻌﺮﻓﺔ ﻣـﺎ ﺇﺫﺍ ﻛﺎﻧﻮﺍ ﻳﺴـﺘﻄﻴﻌﻮﻥ‬
‫ﹰ‬ ‫ﺍﺧﺘﺒـﺎﺭﺍ‬
‫ﹰ‬ ‫ﺃﺟـ ﹺﺮ‬
‫ﻏـﲑ ﻗﻄﺒﻴﺔ ﺫﺍﺕ ﻧﺸـﺎﻁ ﻛﻴﻤﻴﺎﺋﻲ ﺃﻋﲆ‬

‫—‬
‫—‬

‫‪CH3CH2CHCH — CHCH2CH3‬‬ ‫‪CH — CCH2‬‬

‫ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻭﳍﺎ ﺧﺼﺎﺋﺺ ﺃﺧﺮ￯‬ ‫ﺗﺴﻤﻴﺔ ﺍﻷﻟﻜﻴﻨﺎﺕ ﺫﺍﺕ ﺍﻟﺴﻼﺳﻞ ﺍﳌﺴﺘﻘﻴﻤﺔ ﻭﺍﳌﺘﻔﺮﻋﺔ ﻣﻦ ﺧﻼﻝ‬
‫‪ .22‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟـ ‪-4‬ﻣﻴﺜﻴﻞ‪ -1،3-‬ﺑﻨﺘﺎﺩﺍﻳﻦ ﻭ ‪ -3،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ‪-2-‬‬ ‫ﻣﺸﺎﲠﺔ ﳋﺼﺎﺋﺺ ﺍﻷﻟﻜﺎﻧﺎﺕ‪.‬‬
‫ﺑﻴﻮﺗﲔ‪.‬‬ ‫ﻧﲈﺫﺟﻬﺎ‪  .‬‬
‫ﺍﻷﻟﻜﺎﻳﻨﺎﺕ‬ ‫‪C22-078C-828378-08‬‬
‫ﺩﺭﺟـﺎﺕ ﺍﻻﻧﺼﻬـﺎﺭ ﻭﺍﻟﺘﺠﻤﺪ ﻟﻜﻞ ﻣـﻦ‬
‫‪C22-080C-828378-08‬‬ ‫‪ .23‬ﺍﺳـﺘﻨﺘﺞ ﻛﻴـﻒ ﺗﹸﻘﺎﺭﻥ ﺑﲔ‬
‫ﻭﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻧﻔﺴﻬﺎ‪ .‬ﻓﴪ ﺇﺟﺎﺑﺘﻚ‪.‬‬
‫‪ .24‬ﺗﻮﻗـﻊ ﻣـﺎ ﺍﻟﱰﺗﻴﺒـﺎﺕ ﺍﳍﻨﺪﺳـﻴﺔ ﺍﻟﺘـﻲ ﺗﺘﻮﻗـﻊ ﺃﻥ ﺗﻜﻮﳖـﺎ ﺍﻟﺮﻭﺍﺑﻂ ﺍﳌﺤﻴﻄـﺔ ﺑﺬﺭﺓ‬
‫ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻭﺍﻷﻟﻜﻴﻨﺎﺕ‪ ،‬ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ؟‬
‫إﻋﺎدة اﻟﺘﺪرﻳﺲ‬
‫ﺍﺳـﻤﺢ ﻟﻠﻄـﻼﺏ ﺑﺎﻟﻌﻤـﻞ ﰲ ﳎﻤﻮﻋـﺎﺕ ﻟﺒﻨﺎﺀ ﻧـﲈﺫﺝ ﻷﻟﻜﻴﻨﺎﺕ‬
‫ﻣﺘﻔﺮﻋﺔ‪ .‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺗﺴﻤﻴﺔ ﻫﺬﻩ ﺍﻟﻨﲈﺫﺝ ﺛﻢ ﺗﺒﺎﺩﳍﺎ ﻣﻊ ﳎﻤﻮﻋﺎﺕ‬
‫ﺃﻳﻀﺎ‪  .‬‬ ‫ﺃﺧﺮ￯ ﳌﺤﺎﻭﻟﺔ ﺗﺴﻤﻴﺘﻬﺎ ﹰ‬

‫اﻟﺘﻮﺳﻊ‬
‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺑﻨﺎﺀ ﻧﲈﺫﺝ ﻟﻺﻳﺜﲔ ﻭﻭﺻﻒ ﺷـﻜﻞ ﺍﳉﺰﻱﺀ‪.‬‬
‫ﻭﻳﺘﻌـﲔ ﻋﻠﻴﻬﻢ ﺇﺛﺒﺎﺕ ﻭﺇﺩﺭﺍﻙ ﺃﻥ ﺍﳉﺰﻱﺀ ﻣﺴـﺘ ﹴﻮ‪ .‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ‬
‫ﺑﻌـﺪ ﺫﻟﻚ ﺇﺿﺎﻓﺔ ﳎﻤﻮﻋﺘﻲ ﻣﻴﺜﻴﻞ ﻟﻄـﺮﰲ ﺍﳉﺰﻱﺀ ﻹﻧﺘﺎﺝ ﺟﺰﻱﺀ‬
‫ﹴ‬
‫ﻭﻋﻨﺪﺋﺬ‬ ‫‪ -2‬ﺑﻴﻮﺗﲔ‪ .‬ﻭﻋﻠﻴﻬﻢ ﻭﺻﻒ ﺍﻟﺸﻜﻞ ﺍﳍﻨﺪﳼ ﻣﺮﺓ ﺃﺧﺮ￯‪.‬‬
‫ﺳﻴﻜﺘﺸـﻒ ﺑﻌﻀﻬـﻢ ﻭﺟـﻮﺩ ﺻﻮﺭﺗـﲔ )‪(conformations‬‬
‫ﳐﺘﻠﻔﺘﲔ ﻟﻠﺠﺰﻱﺀ‪ .‬‬

‫اﻟﺘﻘﻮﻳﻢ ‪8-3‬‬
‫‪ .22‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟـﺪﺭﺱ ﻭﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ ،‬ﺃﻭ ﺇﱃ ﺩﻟﻴﻞ ﺣﻠﻮﻝ‬ ‫‪ .19‬ﲢﺘـﻮﻱ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﻋـﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳـﺔ ﰲ ﺑﻨﺎﺋﻬـﺎ‪ .‬ﻭﲢﺘﻮﻱ‬
‫ﺍﳌﺴﺎﺋﻞ ﺹ ‪80‬‬ ‫ﺍﻷﻟﻜﻴﻨـﺎﺕ ﻋـﲆ ﺭﺍﺑﻄـﺔ ﺛﻨﺎﺋﻴـﺔ ﻭﺍﺣـﺪﺓ ﻋﲆ ﺍﻷﻗـﻞ‪ .‬ﰲ ﺣﲔ‬
‫‪ .23‬ﻷﻥ ﺍﻷﻟﻜﺎﻳﻨـﺎﺕ ﺃﻛﺜﺮ ﻗﻄﺒﻴﺔ ﹰ‬
‫ﻗﻠﻴـﻼ ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻟﺬﺍ ﺗﻜﻮﻥ‬ ‫ﲢﺘـﻮﻱ ﺍﻷﻟﻜﺎﻳﻨـﺎﺕ ﻋﲆ ﺭﺍﺑﻄـﺔ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﻋـﲆ ﺍﻷﻗﻞ ﰲ‬
‫ﺩﺭﺟـﺎﺕ ﺍﻧﺼﻬﺎﺭﻫـﺎ ﻭﻏﻠﻴﺎﳖـﺎ ﺃﻋـﲆ‪ .‬ﺗﺪﻋـﻢ ﺍﻟﺒﻴﺎﻧـﺎﺕ ﻫﺬﻩ‬ ‫ﺑﻨﺎﺋﻬﺎ‪.‬‬
‫ﺍﻟﻔﺮﺿﻴﺔ‪.‬‬ ‫‪ .20‬ﺗﻌـﺪ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨـﺎﺕ ﻋﲆ ﺩﺭﺟﺔ ﻋﺎﻟﻴﺔ ﻣﻦ ﺍﻟﻨﺸـﺎﻁ‬
‫‪ .24‬ﺗﺘﻮﻗﻊ ﻓﺮﺿﻴﺔ ‪ VSEPR‬ﺑﺎﻷﺷـﻜﺎﻝ ﺍﳍﻨﺪﺳﻴﺔ ﺍﻟﺘﺎﻟﻴﺔ ﻟﻠﺮﻭﺍﺑﻂ‪.‬‬ ‫ﻣﻘﺎﺭﻧـﺔ ﺑﺎﻷﻟﻜﺎﻧـﺎﺕ؛ ﻭﺫﻟـﻚ ﻷﳖـﺎ ﲢﺘـﻮﻱ ﻋـﲆ ﻣﻨﺎﻃﻖ ﻣﻦ‬
‫ﺃﻟـﻜﺎﻥ‪ :‬ﺷـﻜﻞ ﺭﺑﺎﻋﻲ ﺍﻷﻭﺟﻪ؛ ﺃﻟﻜﲔ‪ :‬ﺷـﻜﻞ ﻣﺜﻠﺚ ﻣﺴـﺘ ﹴﻮ‬ ‫ﺍﻟﻜﺜﺎﻓـﺔ ﺍﻹﻟﻜﱰﻭﻧﻴﺔ ﺍﳌﺮﻛﺰﺓ ﺍﻟﺘـﻲ ﲡﺬﺏ ﺍﳌﻮﺍﺩ ﺍﳌﺘﻔﺎﻋﻠﺔ ﺫﺍﺕ‬
‫)ﻣﺜﻠﺚ ﻣﺴﻄﺢ(؛ ﺃﻟﻜﺎﻳﻦ‪ :‬ﺷﻜﻞ ﺧﻄﻲ‪.‬‬ ‫ﺍﻟﺸﺤﻨﺔ ﺍﳌﻌﺎﻛﺴﺔ‪.‬‬
‫‪ -1 .a .21‬ﺑﻴﻮﺗﺎﻳﻦ‬
‫‪ -5‬ﻣﻴﺜﻴﻞ‪ -3-‬ﻫﺒﺘﲔ‬ ‫‪.b‬‬

‫‪152‬‬
 ‫‪8-4‬‬ ‫ﻣﺘﺸﻜﻼت اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت‬
‫‪8-4‬‬
‫اﻫﺪاف‬
‫‪ ‬ﺑـﲔ ﺍﻟﻔﺌﺘـﲔ ﺍﻟﺮﺋﻴﺴـﺘﲔ‬
‫‪Hydrocarbon Isomers‬‬
‫‪ .1‬اﻟﺘﺮﻛﻴﺰ‬
‫ﻟﻠﻤﺘﺸﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻭﺍﻟﻔﺮﺍﻏﻴﺔ‪.‬‬
‫‪ ‬ﺑﲔ ﺍﳌﺘﺸﻜﻼﺕ ﺍﳍﻨﺪﺳﻴﺔ اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ‪‬‬ ‫‪ ‬‬
‫ﺫﺍﺕ ﺍﻟﺒﺎﺩﺋـﺔ ﺳـﻴﺲ ﻭﺍﻟﺒﺎﺩﺋـﺔ ‪‬‬
‫‪‬‬ ‫‪ ‬ﻫﻞ ﻗﺎﺑﻠﺖ ﻳﻮ ﹰﻣﺎ ﺗﻮﺃﻣﲔ ﻣﺘﲈﺛﻠﲔ؟ ﻟﻠﺘﻮﺃﻣﲔ ﺍﳌﺘﲈﺛﻠﲔ ﺍﻟﺘﻜﻮﻳﻦ ﺍﳉﻴﻨﻲ‬
‫ﹼ‬
‫ﺗﺮﺍﻧﺲ‪.‬‬
‫ﻭﺍﳌﺘﺸﻜﻼﺕ ﺷﺒﻴﻬﺔ ﺑﺎﻟﺘﻮﺍﺋﻢ؛ ﺇ ﹾﺫ‬ ‫‪  ‬ﺍﻻﺧـﺘـﻼﻑ ﺍﻟﺒـﻨﺎﺋﻲ ﻧﻔﺴﻪ‪ ،‬ﻭﻣﻊ ﺫﻟﻚ ﻓﻬﲈ ﻓﺮﺩﺍﻥ ﻣﺴﺘﻘﻼﻥ ﻟﻜﻞ ﻣﻨﻬﲈ ﺷﺨﺼﻴﺘﻪ‪.‬‬
‫ﻗﺒﻞ ﺑﺪﺀ ﺍﻟـﺪﺭﺱ‪ ،‬ﺍﻋﺮﺽ ﻋﲆ ﺍﻟﻄﻼﺏ ﴍﳛـﺔ ﺍﻟﱰﻛﻴﺰ ﺭﻗﻢ‬ ‫ﰲ ﺍﳉﺰﻳﺌـﺎﺕ ﺍﻟﺘـﻲ ﺗﻨﺘﺞ ﻋﻦ ﳍﺎ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴﻬﺎ‪ ،‬ﻭﻟﻜﻨﻬﺎ ﲣﺘﻠﻒ ﰲ ﺷﻜﻠﻬﺎ ﺍﻟﺒﻨﺎﺋﻲ ﻭﺧﺼﺎﺋﺼﻬﺎ‪.‬‬
‫ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﻀﻮﺋﻴﺔ‪.‬‬
‫)‪ (30‬ﺍﻟـﻮﺍﺭﺩﺓ ﰲ ﻣﺼﺎﺩﺭ ﺍﻟﺘﻌﻠﻢ ﻟﻠﻔﺼﻮﻝ )‪ ،(5-8‬ﻭﻳﻤﻜﻨﻚ‬ ‫اﻟﻤﺘﺸﻜﻼت اﻟﺒﻨﺎﺋﻴﺔ ‪Structural Isomers‬‬
‫ﻣﺮاﺟﻌﺔ اﻟﻤﻔﺮدات‬
‫ﺗﻔﺤـﺺ ﻧﲈﺫﺝ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﻟﺜﻼﺛﺔ ﰲ ﺍﻟﺸـﻜﻞ ‪ 8-17‬ﻟﺘﺤﺪﻳﺪ ﺃﻭﺟﻪ ﺍﻟﺘﺸـﺎﺑﻪ ﻭﺍﻻﺧﺘﻼﻑ؛ ﺇﺫ‬
‫ﻋﺮﺿﻬﺎ ﻣﻠﻮﻧﺔ ﻣﻦ ﺧﻼﻝ ﺍﻟﺮﺟﻮﻉ ﺇﱃ ﺍﳌﻮﻗﻊ ﺍﻹﻟﻜﱰﻭﲏ‪ :‬‬ ‫ﳛﺘﻮﻱ ﻛﻞ ﻣﻦ ﺍﻟﻨﲈﺫﺝ ﺍﻟﺜﻼﺛﺔ ﻋﲆ ‪ 5‬ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﻭ‪ 12‬ﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ‪ ،‬ﻟﺬﺍ ﻓﺈﻥ ﳍﺎ ﺍﻟﺼﻴﻐﺔ‬ ‫‪‬‬ ‫‪‬‬
‫ﺃﻣﻮﺍﺝ ﻣﺴﺘﻌﺮﺿﺔ ﲢﻤﻞ ﺍﻟﻄﺎﻗﺔ‬
‫ﺍﳉﺰﻳﺌﻴـﺔ‪ .C5H12‬ﻭﻣﻊ ﺫﻟﻚ ﲤﺜﻞ ﻫـﺬﻩ ﺍﻟﻨﲈﺫﺝ ﺛﻼﺛﺔ ﺗﺮﻛﻴﺒﺎﺕ )ﺗﺮﺗﻴﺒﺎﺕ( ﳐﺘﻠﻔﺔ ﻣﻦ ﺍﻟﺬﺭﺍﺕ‪،‬‬
‫ﺧﻼﻝ ﺍﻟﻔﺮﺍﻍ‪.‬‬
‫‪www.obeikaneducation.com‬‬ ‫ﻭﺛﻼﺛـﺔ ﻣﺮﻛﺒـﺎﺕ ﳐﺘﻠﻔـﺔ‪ :‬ﺑﻨﺘﺎﻥ‪ ،‬ﻭ ‪ -2‬ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗـﺎﻥ‪ ،‬ﻭ ‪ -2،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴـﻞ ﺑﺮﻭﺑﺎﻥ‪ .‬ﺇﻥ ﻫﺬﻩ‬
‫اﻟﻤﻔﺮدات اﻟﺠﺪﻳﺪة‬
‫ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﺜﻼﺛﺔ ﻫﻲ ﻣﺘﺸـﻜﻼﺕ )ﺃﻳﺰﻭﻣﲑﺍﺕ‪ .(isomers ،‬ﻭﺍﳌﺘﺸـﻜﻼﺕ ﺍﺛﻨﺎﻥ ﺃﻭ ﺃﻛﺜﺮ ﻣﻦ‬
‫ﺍﳌﺘﺸﻜﻼﺕ‬
‫ﺍﳌﺮﻛﺒـﺎﺕ‪ ،‬ﳍـﺎ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴـﻬﺎ‪ ،‬ﺇﻻ ﺃﳖﺎ ﲣﺘﻠﻒ ﰲ ﺻﻴﻐﻬﺎ ﺍﻟﺒﻨﺎﺋﻴـﺔ‪ .‬ﻻﺣﻆ ﺃﻥ ﺍﻟﺒﻨﺘﺎﻥ‬
‫اﻟﺮﺋﻴﺴﺔ‬ ‫اﻟﻔﻜﺮة‬ ‫ﺍﳊﻠﻘﻲ ﻭﺍﻟﺒﻨﺘﺎﻥ ﺍﻟﻌﺎﺩﻱ ﻟﻴﺴﺎ ﻣﺘﺸﻜﻠﲔ؛ ﻷﻥ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻟﻸﻭﻝ ﻫﻲ ‪.C5H10‬‬ ‫ﺍﻟﺒﻨﺎﺋﻲ‬ ‫ﺍﳌﺘﺸﻜﻞ‬

‫ﻫﻨـﺎﻙ ﻓﺌﺘـﺎﻥ ﺭﺋﻴﺴـﺘﺎﻥ ﻣـﻦ ﺍﳌﺘﺸـﻜﻼﺕ‪ .‬ﻭ ﹸﻳﺒـﲔ ﺍﻟﺸـﻜﻞ ‪ 8-17‬ﻣﺮﻛﺒـﺎﺕ ﺗﻌـﺪﹼ ﺃﻣﺜﻠـﺔ ﻋﲆ‬ ‫ﺍﳌﺘﺸﻜﻞ ﺍﻟﻔﺮﺍﻏﻲ‬
‫‪ ‬ﺍﺳـﺘﺨﺪﻡ ﳎﻤﻮﻋـﺔ ﺍﻟﻨـﲈﺫﺝ ﺍﳉﺰﻳﺌﻴـﺔ )ﺍﻟﻜـﺮﺍﺕ‬ ‫ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﻭﻟﻠﻤﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴـﻬﺎ‪ ،‬ﺇﻻ ﺃﻥ ﻣﻮﺍﻗﻊ )ﺗﺮﺗﻴﺐ(‬ ‫ﺍﳌﺘﺸﻜﻞ ﺍﳍﻨﺪﳼ‬
‫ﺍﻟﻜﲑﺍﻟﻴﺔ‬
‫ﻭﺍﻟﻮﺻﻼﺕ( ﻟﺒﻨﺎﺀ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﻈﺎﻫﺮﺓ ﰲ ﺍﻟﺸﻜﻞ ‪.8-16‬‬
‫ﺍﻟﺬﺭﺍﺕ ﻓﻴﻬﺎ ﲣﺘﻠﻒ‪ .‬ﻭﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺍﺷـﱰﺍﻙ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﰲ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴﻬﺎ‬
‫ﺇﻻ ﺃﳖـﺎ ﲣﺘﻠﻒ ﰲ ﺧﺼﺎﺋﺼﻬـﺎ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﻭﺍﻟﻔﻴﺰﻳﺎﺋﻴﺔ‪ .‬ﻭﺗﺪﻋﻢ ﻫﺬﻩ ﺍﳌﻼﺣﻈﺔ ﺃﺣﺪ ﺃﻫﻢ ﻣﺒﺎﺩﺉ‬ ‫ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﻏﲑ ﺍﳌﺘﲈﺛﻠﺔ‬

‫ﻭﺍﻋﺮﺽ ﺍﻟﻨﲈﺫﺝ ﻋﲆ ﺍﻟﻄﻼﺏ ﺣﺘﻰ ﻳﺘﻤﻜﻨﻮﺍ ﻣﻦ ﺭﺅﻳﺘﻬﺎ‪ .‬ﻭﺍﻃﻠﺐ‬ ‫ﺍﻟﻜﻴﻤﻴـﺎﺀ ﺍﻟـﺬﻱ ﻳﻨﺺ ﻋﲆ ﺃﻥ "ﺑﻨﺎﺀ ﺍﳌﺎﺩﺓ ﳛﺪﺩ ﺧﺼﺎﺋﺼﻬﺎ"‪ .‬ﻛﻴـﻒ ﻳﺮﺗﺒﻂ ﻧﻤﻂ ﺗﻐﲑ ﺩﺭﺟﺎﺕ‬
‫ﻏﻠﻴﺎﻥ ﻣﺘﺸﻜﻼﺕ ‪ C5H12‬ﺑﺼﻴﻐﻬﺎ ﺍﻟﺒﻨﺎﺋﻴﺔ؟‬
‫ﺍﳌﺘﺸﻜﻞ ﺍﻟﻀﻮﺋﻲ‬
‫ﺍﻟﺪﻭﺭﺍﻥ ﺍﻟﻀﻮﺋﻲ‬
‫ﺇﱃ ﺃﺣـﺪ ﺍﻟﻄـﻼﺏ ﺇﻋﻄـﺎﺀ ﺍﻟﺼﻴﻐـﺔ ﺍﳉﺰﻳﺌﻴـﺔ ﻟـﻜﻞ ﺻﻴﻐـﺔ ﺑﻨﺎﺋﻴﺔ‬ ‫ﻛﻠﲈ ﺯﺍﺩ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﺯﺩﺍﺩ ﻋﺪﺩ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﺤﺘﻤﻠﺔ‪ .‬ﻓﻌﲆ‬
‫ﺳﺒﻴﻞ ﺍﳌﺜﺎﻝ‪ ،‬ﻫﻨﺎﻙ ‪ 9‬ﺃﻟﻜﺎﻧﺎﺕ ﺫﺍﺕ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ‪ .C7H16‬ﻭﻫﻨﺎﻙ ﺃﻛﺜﺮ ﻣﻦ ‪300،000‬‬

‫‪ .C5H12‬ﺛﻢ ﺍﺳﺄﻝ‪ :‬ﻛﻴﻒ ﺗﺘﺸﺎﺑﻪ ﺍﻟﺼﻴﻎ ﺍﳉﺰﻳﺌﻴﺔ؟ ﺍﻟﺼﻴﻎ ﺍﳉﺰﻳﺌﻴﺔ‬ ‫ﻣﺘﺸﻜﻞ ﺑﻨﺎﺋﻲ ﳛﻤﻞ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ‪.C20H42‬‬

‫ﻫـﻲ ﻧﻔﺴـﻬﺎ ﻟﻠﺠﺰﻳﺌـﺎﺕ ﺍﻟﺜﻼﺛـﺔ‪ .‬ﺍﻃﻠﺐ ﺇﱃ ﻃﺎﻟـﺐ ﺁﺧﺮ ﻭﺻﻒ‬ ‫‪ 8-17‬‬

‫ﻛﻴـﻒ ﲣﺘﻠﻒ ﺍﳉﺰﻳﺌﺎﺕ‪ .‬ﺗﺮﺗﺒﻂ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ ﺑﻄﺮﺍﺋﻖ ﳐﺘﻠﻔﺔ‪.‬‬

‫‪   ‬‬
‫‪‬‬

‫ﻭﻭﺿﺢ ﻟﻠﻄﻼﺏ ﺃﻥ ﻫﺬﻩ ﺍﻟﻨﲈﺫﺝ ﲤﺜﻞ ﻣﺘﺸﻜﻼﺕ ﺑﻨﺎﺋﻴﺔ‪ .‬‬ ‫‪22‬‬ ‫‪2‬‬ ‫‪‬‬
‫‪‬‬

‫‪9°C‬‬ ‫‪28°C‬‬ ‫‪36°C‬‬

‫— ‪ ‬ﻗﺪ ﻳﺴـﺘﻨﺘﺞ ﺍﻟﻄـﻼﺏ ﺃﻥ ﺩﺭﺟﺔ ﺍﻟﻐﻠﻴﺎﻥ‬

‫ﻗﻞ ﺍﻟﺘﻔـﺮﻉ ﰲ ﺍﳉـﺰﻱﺀ ﻭﺃﺻﺒـﺢ ﺃﻗﺮﺏ ﺇﱃ ﺍﻟﺸـﻜﻞ‬ ‫ﺗـﺰﺩﺍﺩ ﻛﻠـﲈ ﹼ‬ ‫‪C22-010C-828378-08‬‬

‫ﺍﳋﻄﻲ‪.‬‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻛﺘﺎﺑـﺔ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﲨﻴﻌﻬﺎ‬

‫ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺫﻱ ﺍﻟﺼﻴﻐﺔ ‪ .C7H16‬ﻫﻨﺎﻙ ﺗﺴـﻌﺔ ﻣﺘﺸﻜﻼﺕ ﺑﻨﺎﺋﻴﺔ ﻫﻲ‪:‬‬
‫ﻫﺒﺘﺎﻥ؛ ‪ -2‬ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ؛ ‪ –3‬ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ؛ ‪ -3،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ؛‬
‫‪ -4،2‬ﺛﻨﺎﺋـﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘـﺎﻥ؛ ‪ -2،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘـﺎﻥ؛ ‪ -3،3‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ‬
‫ﺑﻨﺘﺎﻥ؛ ‪ -3‬ﺇﻳﺜﻴﻞ ﺑﻨﺘﺎﻥ؛ ‪ -3،2،2‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗﺎﻥ‪ .‬‬

‫‪153‬‬
 ‫‪‬‬ ‫‪‬‬ ‫‪      8-18‬‬

‫‪‬‬
‫‪  ‬‬
‫‪‬‬
‫‪ .2‬اﻟﺘﺪرﻳﺲ‬
‫‪‬‬
‫‪‬‬
‫‪   ‬‬
‫‪‬‬
‫‪‬‬ ‫‪   ‬‬
‫ﺑﻨﺎء ﻧﻤﻮذج‬
‫‪‬‬ ‫‪‬‬

‫‪C22110C82837808‬‬ ‫‪ "" ""‬ﺍﻃﻠﺐ ﺇﱃ ﻛﻞ ﳎﻤﻮﻋﺔ ﻣﺆﻟﻔﺔ ﻣﻦ‬

‫اﻟﻤﺘﺸﻜﻼت اﻟﻔﺮاﻏﻴﺔ ‪Stereoisomers‬‬
‫ﲣﺘﻠﻒ ﺍﻟﻔﺌﺔ ﺍﻟﺜﺎﻧﻴﺔ ﻣﻦ ﺍﳌﺘﺸﻜﻼﺕ ﺑﻔﺎﺭﻕ ﺧﻔﻲ ﻭﺩﻗﻴﻖ ﺟﺪﹼﹰ ﺍ ﰲ ﺍﻟﺮﻭﺍﺑﻂ؛ ﻓﺎﳌﺘﺸﻜﻼﺕ ﺍﻟﻔﺮﺍﻏﻴﺔ‬ ‫ﻃﺎﻟﺒﲔ ﺃﻭ ﺛﻼﺛﺔ ﺑﻨﺎﺀ ﻧﲈﺫﺝ ﻟﻜﻞ ﻣﻦ‪ :‬ﺳﻴﺲ‪ -2-‬ﺑﻴﻮﺗﲔ‪ ،‬ﺗﺮﺍﻧﺲ‪-‬‬
‫ﻣﺘﺸﻜﻼﺕ ﺗﺮﺗﺒﻂ ﻓﻴﻬﺎ ﺍﻟﺬﺭﺍﺕ ﺑﺎﻟﱰﺗﻴﺐ ﻧﻔﺴﻪ‪ ،‬ﻭﻟﻜﻨﻬﺎ ﲣﺘﻠﻒ ﰲ ﺗﺮﺗﻴﺒﻬﺎ ﺍﻟﻔﺮﺍﻏﻲ )ﺍﻻﲡﺎﻫﺎﺕ ﰲ‬
‫ﺍﻟﻔﺮﺍﻍ(‪ .‬ﻭﻫﻨﺎﻙ ﻧﻮﻋﺎﻥ ﻣﻦ ﺍﳌﺘﺸﻜﻼﺕ‪ :‬ﺃﺣﺪﳘﺎ ﰲ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ‪،‬‬
‫‪ -2‬ﺑﻴﻮﺗﲔ‪ .‬ﺛﻢ ﺍﲨﻊ ﺍﻟﻨﲈﺫﺝ ﲨﻴﻌﻬﺎ‪ ،‬ﻭﺍﺳـﺘﺨﺪﻣﻬﺎ ﻟﺘﻮﺿﻴﺢ ﻛﻴﻒ‬
‫ﺣﻴﺚ ﺗﻜﻮﻥ ﺫﺭﺗﺎ ﺍﻟﻜﺮﺑﻮﻥ ﺍﳌﺮﺗﺒﻄﺘﺎﻥ ﺑﺮﺍﺑﻄﺔ ﺃﺣﺎﺩﻳﺔ ﻗﺎﺩﺭﺗﲔ ﻋﲆ ﺍﻟﺪﻭﺭﺍﻥ ﺑﺴﻬﻮﻟﺔ ﺇﺣﺪﺍﳘﺎ ﺣﻮﻝ‬
‫ﺍﻷﺧﺮ￯‪ .‬ﻭﺍﻟﺜﺎﻧﻴﺔ ﰲ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻋﻨﺪ ﻭﺟﻮﺩ ﺭﺍﺑﻄﺔ ﺗﺴﺎﳘﻴﺔ ﺛﻨﺎﺋﻴﺔ‪ ،‬ﺣﻴﺚ ﻻ ﻳﺴﻤﺢ ﻟﻠﺬﺭﺍﺕ ﺑﺎﻟﺪﻭﺭﺍﻥ‪،‬‬
‫ﺗﺆﺛﺮ ﺍﻻﺧﺘﻼﻓﺎﺕ ﰲ ﻗﺪﺭﺓ ﺍﳉﺰﻳﺌﺎﺕ ﻋﲆ ﺍﻟﱰﺍﺹ ﰲ ﺧﺼﺎﺋﺼﻬﺎ‪.‬‬
‫ﻭﺗﺒﻘﻰ ﺛﺎﺑﺘﺔ ﰲ ﻣﻜﺎﳖﺎ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪.8-18‬‬ ‫‪‬‬
‫ﻟــ ‪ -2‬ﺑﻴﻮﺗـﲔ ﰲ ﺍﻟﺸـﻜﻞ ‪ .8-19‬ﺇﻥ ﺍﻟﱰﻛﻴﺐ ﺍﻟﺬﻱ‬ ‫ﻗـﺎﺭﻥ ﺑـﲔ ﺍﻟﺼﻴﻐﺘـﲔ ﺍﻟﺒﻨﺎﺋﻴﺘـﲔ ﺍﳌﺤﺘﻤﻠﺘﲔ ﹺ‬
‫ﺗﻜﻮﻥ ﻓﻴﻪ ﳎﻤﻮﻋﺘﺎ ﺍﳌﻴﺜﻴﻞ ﰲ ﺍﳉﻬﺔ ﻧﻔﺴـﻬﺎ ﻣﻦ ﺍﳉﺰﻱﺀ ﻳﺸـﺎﺭ ﺇﻟﻴﻪ ﺑﺎﻟﺒﺎﺩﺋﺔ )ﺳـﻴﺲ(‪ ،‬ﰲ ﺣﲔ ﹸﻳﺸـﺎﺭ‬
‫ﺇﱃ ﺍﻟﱰﻛﻴـﺐ ﺍﻟﺬﻱ ﺗﻜـﻮﻥ ﻓﻴﻪ ﳎﻤﻮﻋﺘﺎ ﺍﻷﻟﻜﻴﻞ ﰲ ﺟﻬﺘﲔ ﻣﺘﻘﺎﺑﻠﺘﲔ ﻣﻦ ﺍﳉﺰﻱﺀ ﺑﺎﻟﺒﺎﺩﺋﺔ )ﺗﺮﺍﻧﺲ(‪.‬‬
‫— ‪ ‬ﺍﻟﺸـﻜﻞ ‪ 8-18‬ﺇﻥ ﳎﻤﻮﻋﺎﺕ ﺍﻟﺬﺭﺍﺕ ﺍﳌﺮﺗﺒﻄﺔ‬
‫ﻭﻫﺬﻩ ﺍﳌﺼﻄﻠﺤﺎﺕ ﻣﺸـﺘﻘﺔ ﻣﻦ ﺍﻟﻠﻐﺔ ﺍﻟﻼﺗﻴﻨﻴﺔ‪) :‬ﺳﻴﺲ( ﺗﻌﻨﻲ ﺍﳉﻬﺔ ﻧﻔﺴﻬﺎ‪ ،‬ﻭ)ﺗﺮﺍﻧﺲ( ﺗﻌﻨﻲ ﺍﳉﻬﺔ‬ ‫ﻣـﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﺣﺎﺩﻳﺔ ﺍﻟﺮﺑﻂ ﻏﲑ ﺛﺎﺑﺘﺔ ﰲ ﺍﻟﻔﺮﺍﻍ؛ ﺣﻴﺚ ﺗﺪﻭﺭ‬
‫ﺍﻷﺧـﺮ￯‪ .‬ﻭﻷﻥ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ ﺍﻟﺜﻨﺎﺋﻴـﺔ ﺍﻟﺮﺑـﻂ ﻏﲑ ﻗﺎﺩﺭﺓ ﻋﲆ ﺍﻟـﺪﻭﺭﺍﻥ ﻓﺈﻥ ﺍﻟﱰﻛﻴﺐ ﺳـﻴﺲ ﻻ‬
‫ﻳﺴﺘﻄﻴﻊ ﺍﻟﺘﺤﻮﻝ ﺑﺴﻬﻮﻟﺔ ﺇﱃ ﺍﻟﱰﻛﻴﺐ ﺗﺮﺍﻧﺲ‪.‬‬ ‫ﺃﻥ ﳎﻤﻮﻋﺎﺕ ﺍﻟﺬﺭﺍﺕ ﺍﳌﺮﺗﺒﻄﺔ ﻣﻊ ﺫﺭﺍﺕ‬ ‫ﻻ ﹼ‬‫ﻣﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪ .‬ﺇ ﹼ‬
‫ﺍﻟﻜﺮﺑـﻮﻥ ﺛﻨﺎﺋﻴـﺔ ﺍﻟﺮﺑﻂ ﺛﺎﺑﺘﺔ ﰲ ﺍﻟﻔﺮﺍﻍ ﺑﺎﻟﻨﺴـﺒﺔ ﺇﱃ ﺑﻌﻀﻬﺎ ﹰ‬
‫ﺑﻌﻀﺎ؛‬
‫‪ 2  8-19‬‬
‫‪‬‬ ‫ﻷﻥ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ ﲤﻨﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻣﻦ ﺍﻟﺪﻭﺭﺍﻥ‪.‬‬

‫اﻟﺘﻘﻮﻳﻢ‬
‫‪H‬‬ ‫‪H‬‬
‫‪H‬‬ ‫‪H H‬‬ ‫‪H‬‬
‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪H‬‬
‫‪H‬‬ ‫‪C—C‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪C—C‬‬ ‫‪H‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪C‬‬
‫‪H‬‬ ‫‪H‬‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﻟﺘﻤﻴﻴـﺰ ﺑـﲔ ﺍﳌﺼﻄﻠﺤـﲔ‪ :‬ﻧﻈﲑ‬

‫‪C4H82‬‬
‫‪106°C‬‬ ‫‪C4H82‬‬
‫‪0.8°C‬‬ ‫‪139°C‬‬
‫‪3.7°C‬‬

‫‪C22-092C-828378-08‬‬
‫‪C22-093C-828378-08‬‬
‫)‪ (isotope‬ﻭﻣﺘﺸﻜﻞ )‪ .(isomer‬ﺍﻟﻨﻈﺎﺋﺮ ﻫﻲ ﻋﻨﺎﴏ ﳍﺎ ﺍﻟﻌﺪﺩ‬
‫ﺍﻟﺬﺭﻱ ﻧﻔﺴـﻪ ﻭﻟﻜﻨﻬـﺎ ﲣﺘﻠﻒ ﰲ ﻋﺪﺩﻫﺎ ﺍﻟﻜﺘﲇ‪ .‬ﺃﻣﺎ ﺍﳌﺘﺸـﻜﻼﺕ‬
‫ﻓﻬـﻲ ﻣﺮﻛﺒـﺎﺕ ﳍـﺎ ﺍﻟﺼﻴﻐـﺔ ﺍﳉﺰﻳﺌﻴـﺔ ﻧﻔﺴـﻬﺎ ﻭﻟﻜﻨﻬـﺎ ﲣﺘﻠﻒ ﰲ‬
‫ﺃﺷﻜﺎﳍﺎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬‬
‫‪ ‬ﻟﻠﻤﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺍﻟﺼﻴﻐـﺔ ﺍﻟﻜﻴﻤﻴﺎﺋﻴـﺔ‬
‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬
‫ﻧﻔﺴـﻬﺎ‪ ،‬ﻭﻟﻜـﻦ ﺫﺭﺍﲥـﺎ ﻣﺮﺗﺒﻄـﺔ ﺑﱰﺗﻴﺒـﺎﺕ ﳐﺘﻠﻔـﺔ‪ .‬ﺃﻣـﺎ‬
‫ﺍﳌﺘﺸـﻜﻼﺕ ﺍﳍﻨﺪﺳـﻴﺔ ﻓﻬﻲ ﻣﺘﺸـﻜﻼﺕ ﺑﻨﺎﺋﻴﺔ ﳍـﺎ ﺗﺮﺗﻴﺒﺎﺕ‬
‫‪ LouisPasteur‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﻟﺒﺤـﺚ ﰲ‬ ‫ﳐﺘﻠﻔﺔ ﻟﻠﻤﺠﻤﻮﻋﺎﺕ ﺣﻮﻝ ﺍﻟﺮﺍﺑﻄﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ‪.‬‬
‫ﺣﻘﻮﻝ ﺩﺭﺍﺳﺎﺕ ﻭﺃﺑﺤﺎﺙ ﻟﻮﻳﺲ ﺑﺎﺳﺘﻮﺭ‪ ،‬ﻭﻛﺘﺎﺑﺔ ﻣﺎ ﻳﺘﻌﻠﻖ ﺑﺄﻋﲈﻟﻪ ﺑﺈﳚﺎﺯ‬
‫ﰲ ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ‪ .‬‬

‫‪154‬‬
 ‫واﻗﻊ اﻟﻜﻴﻤﻴﺎء ﻓﻲ اﻟﺤﻴﺎة‬ ‫‪ 8-20 ‬‬
‫اﻟﺘﻘﻮﻳﻢ‬ ‫‪‬‬ ‫‪‬‬
‫‪‬‬ ‫‪‬‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﺴﻤﻴﺔ ﻣﺎ ﺃﻣﻜﻦ ﻣﻦ ﺍﻷﺷﻴﺎﺀ ﺍﳌﻌﺮﻭﻓﺔ‬ ‫ﻭﺗﹸﺴـﻤﻰ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﻨﺎﲡـﺔ ﻋﻦ ﺍﺧﺘﻼﻑ ﺗﺮﺗﻴـﺐ ﺍﳌﺠﻤﻮﻋـﺎﺕ ﻭﺍﲡﺎﻫﻬﺎ ﺣﻮﻝ‬

‫ﺯﻭﺟﺎ ﻣﻦ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﻀﻮﺋﻴﺔ‪ .‬ﻗﺪ ﺗﺸﻤﻞ ﺍﻹﺟﺎﺑﺎﺕ‬ ‫ﺍﻟﺘﻲ ﲢﺎﻛﻲ ﹰ‬

‫ﺍﻟﺮﺍﺑﻄـﺔ ﺍﻟﺜﻨﺎﺋﻴـﺔ ﺑﺎﳌﺘﺸـﻜﻼﺕ ﺍﳍﻨﺪﺳـﻴﺔ‪ .‬ﻻﺣـﻆ ﺃﻥ ﺍﺧﺘﻼﻑ ﺍﻟﱰﺗﻴـﺐ ﺍﳍﻨﺪﳼ‬
‫ﻳﺆﺛﺮ ﰲ ﺧﺼﺎﺋﺺ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﻔﻴﺰﻳﺎﺋﻴـﺔ‪ ،‬ﻭﻣﻨﻬﺎ ﺩﺭﺟﺎﺕ ﺍﻻﻧﺼﻬـﺎﺭ ﻭﺍﻟﻐﻠﻴﺎﻥ‪.‬‬

‫ﺃﻧﻮﺍﻋـﺎ ﳐﺘﻠﻔﺔ ﻣﻦ ﺍﻟﻘﻔﺎﺯﺍﺕ‪ ،‬ﻭﺍﻷﺣﺬﻳـﺔ‪ ،‬ﻭﺍﳌﻀﺎﺭﺏ ﻭﺍﳉﻮﻟﻒ‪،‬‬

‫ﹰ‬ ‫ﺃﻳﻀﺎ ﰲ ﺑﻌﺾ ﺧﺼﺎﺋﺼﻬـﺎ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ‪ .‬ﻭﺇﺫﺍ ﻛﺎﻥ‬ ‫ﻭﲣﺘﻠﻒ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﳍﻨﺪﺳـﻴﺔ ﹰ‬
‫ﺑﻴﻮﻟﻮﺟﻴﺎ‪ ،‬ﻛﲈ ﻫﻮ ﺍﳊﺎﻝ ﰲ ﻣﺮﻛﺒﺎﺕ ﺍﻷﺩﻭﻳﺔ‪ ،‬ﻛﺎﻥ ﳌﺘﺸﻜﻼﺕ ﺳﻴﺲ‬
‫ﹼﹰ‬ ‫ﺍﳌﺮﻛﺐ ﹰ‬
‫ﻧﺸﻄﺎ‬

‫ﻭﻏﲑﻫـﺎ ﻣـﻦ ﺍﻷﺩﻭﺍﺕ ﺍﻟﺮﻳﺎﺿﻴـﺔ‪ .‬ﻭﻗـﺪ ﻳﺘﻤﻜـﻦ ﺍﻟﻄﺎﻟـﺐ ﺍﻟﺬﻱ‬ ‫‪‬ﺗﺴﻤﻰ ﺍﻟﺪﻫﻮﻥ‬
‫ﻭ ﺗﺮﺍﻧﺲ ﻋﺎﺩ ﹰﺓ ﺗﺄﺛﲑﺍﺕ ﳐﺘﻠﻔﺔ ﻭﻭﺍﺿﺤﺔ ﺟﺪﹼﹰ ﺍ‪.‬‬
‫‪‬ﻛﻴﻒﲣﺘﻠﻒﺍﳌﺘﺸﻜﻼﺕﺍﻟﺒﻨﺎﺋﻴﺔﻋﻦﺍﳌﺘﺸﻜﻼﺕﺍﳍﻨﺪﺳﻴﺔ؟‬
‫‪ ‬‬
‫ﺫﺍﺕ ﻣﺘﺸﻜﻼﺕ ﺗﺮﺍﻧﺲ ﺑﺪﻫﻮﻥ ﺗﺮﺍﻧﺲ‪.‬‬
‫ﻳﺴـﺘﺨﺪﻡ ﺍﻟﻴﺪ ﺍﻟﻴﴪ￯ ﻣﻦ ﺇﻋﻄﺎﺀ ﺃﻣﺜﻠﺔ – ﻣﺜﻞ ﺍﳌﻘﺺ ﻭﻏﲑﻩ ﻣﻦ‬ ‫ﻭﲢـﴬ ﺍﻟﻜﺜـﲑ ﻣـﻦ ﺍﻷﻃﻌﻤـﺔ ﺍﳌﻐ ﹼﻠﻔـﺔ‬ ‫اﻟﻜﻴﺮاﻟﻴﺔ ‪Chirality‬‬

‫ﺍﻷﺩﻭﺍﺕ– ﻻ ﺗﻜـﻮﻥ ﻣﺄﻟﻮﻓـﺔ ﻟـﺪ￯ ﺍﻟﻄﻼﺏ ﺍﻟﺬﻳﻦ ﻳﺴـﺘﺨﺪﻣﻮﻥ‬ ‫ﺑﺎﺳـﺘﺨﺪﺍﻡ ﺩﻫـﻮﻥ ﺗﺮﺍﻧـﺲ؛ ﻷﻥ ﳍﺎ ﻓﱰﺓ‬
‫ﺣﻔـﻆ ﺃﻃـﻮﻝ‪ .‬ﻭﺗﺸـﲑ ﺍﻟﺪﻻﺋـﻞ ﺇﱃ ﺃﻥ‬
‫ﺃﻋﻠﻦ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ ﺍﻟﻔﺮﻧﴘ ﺍﻟﺸﺎﺏ‬ ‫‪   ‬ﰲ ﻋﺎﻡ ‪1848‬ﻡ‪ ،‬‬
‫ﻟﻮﻳﺲ ﺑﺎﺳﺘﻮﺭ )‪ (1822-1895‬ﻋﻦ ﺍﻛﺘﺸﺎﻓﻪ ﻭﺟﻮﺩ ﺑﻠﻮﺭﺍﺕ ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ‬
‫‪‬‬

‫ﺃﻳﺪﳞﻢ ﺍﻟﻴﻤﻨﻰ‪ .‬‬ ‫ﻫﺬﻩ ﺍﻟﺪﻫﻮﻥ ﺗﺰﻳﺪ ﻣﻦ ﻧﻮﻉ ﺍﻟﻜﻮﻟﺴﱰﻭﻝ‬

‫ﺍﻟﻀـﺎﺭ‪ ،‬ﻭﺗﻘﻠﻞ ﻣﻦ ﺍﻟﻨﻮﻉ ﺍﻟﻨﺎﻓﻊ‪ ،‬ﳑﺎ ﻳﺰﻳﺪ‬
‫ﲪﺾ ﺍﻟﻄﺮﻃﺮﻳﻚ‪ ،‬ﰲ ﺻﻮﺭﺗﲔ‪ ،‬ﺍﻟﻌﻼﻗﺔ ﺑﻴﻨﻬﲈ ﻛﻌﻼﻗﺔ ﺟﺴﻢ ﻭﺻﻮﺭﺗﻪ ﰲ ﺍﳌﺮﺁﺓ‪.‬‬
‫ﻭﻷﻥ ﻳﺪﻱ ﺍﻹﻧﺴﺎﻥ ﻛﻞ ﻣﻨﻬﲈ ﺻﻮﺭﺓ ﻟﻸﺧﺮ￯ ﰲ ﺍﳌﺮﺁﺓ‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸﻜﻞ ‪،8-20‬‬
‫ﻣﻦ ﺍﺣﺘﲈﻟﻴﺔ ﺍﻹﺻﺎﺑﺔ ﺑﺄﻣﺮﺍﺽ ﺍﻟﻘﻠﺐ‪.‬‬ ‫ﻟﺬﺍ ﹸﺳﻤﻴﺖ ﺃﺷﻜﺎﻝ ﺍﻟﺒﻠﻮﺭﺍﺕ ﺍﳌﺸﺎﲠﺔ ﻟﺼﻮﺭﺓ ﺍﻟﻴﺪ ﺍﻟﻴﻤﻨﻰ ﻭﺍﳌﺸﺎﲠﺔ ﻟﺼﻮﺭﺓ ﺍﻟﻴﺪ‬
‫ﺍﻟﻴﴪ￯‪ .‬ﻭﻟﺸﻜﲇ ﲪﺾ ﺍﻟﻄﺮﻃﺮﻳﻚ ﺍﳋﺼﺎﺋﺺ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﻧﻔﺴﻬﺎ‪ ،‬ﻭﻛﺬﻟﻚ ﳍﲈ‬
‫ﺩﺭﺟﺔ ﺍﻻﻧﺼﻬﺎﺭ‪ ،‬ﻭﺍﻟﻜﺜﺎﻓﺔ‪ ،‬ﻭﺍﻟﺬﺍﺋﺒﻴﺔ ﰲ ﺍﳌﺎﺀ ﻧﻔﺴﻬﺎ‪ ،‬ﻏﲑ ﺃﻥ ﺷﻜﻞ ﺍﻟﻴﺪ ﺍﻟﻴﴪ￯‬
‫ﻋﺮض ﺳﺮﻳﻊ‬ ‫ﻧﺘﺞ ﻋﻦ ﻋﻤﻠﻴﺔ ﺍﻟﺘﺨﻤﲑ‪ ،‬ﻭﻳﺴﺒﺐ ﺗﻜﺎﺛﺮ ﺍﻟﺒﻜﺘﲑﻳﺎ ﺑﻌﺪ ﺗﻐﺬﳞﺎ ﻋﻠﻴﻪ‪.‬‬
‫ﻳﻈﻬﺮ ﺍﻟﺸﻜﻼﻥ ﺍﻟﺒﻠﻮﺭﻳﺎﻥ ﳊﻤﺾ ﺍﻟﻄﺮﻃﺮﻳﻚ ﰲ ﺍﻟﱰﻛﻴﺒﲔ ﰲ ﺍﻟﺸﻜﻞ ‪.8-21‬‬
‫ﻭ ﹸﻳﻄﻠﻖ ﺍﻟﻴﻮﻡ ﻋﲆ ﻫﺬﻳﻦ ﺍﻟﺸﻜﻠﲔ ‪ – D‬ﲪﺾ ﺍﻟﻄﺮﻃﺮﻳﻚ‪ ،‬ﻭ ‪ -L‬ﲪﺾ‬
‫ﻟﺰﻭﺝ ﻣﻦ ﺍﳌﺘﺸـﻜﻼﺕ‬‫ﹴ‬ ‫‪ ‬ﺍﻋﻤﻞ ﻧـﲈﺫﺝ‬ ‫ﺍﻟﻄﺮﻃﺮﻳﻚ‪ .‬ﻭﻳﺮﻣﺰ ﺍﳊﺮﻓﺎﻥ ‪ D‬ﻭ‪ L‬ﺇﱃ ﺍﻟﺒﺎﺩﺋﺘﲔ ﺍﻟﻼﺗﻴﻨﻴﺘﲔ)‪ (dextro‬ﻭﺗﻌﻨﻲ‬

‫ﺍﻟﻀﻮﺋﻴـﺔ ﳉـﺰﻱﺀ ﻛـﲑﺍﱄ )ﻻ ﻳﺘﻄﺎﺑﻖ ﻣـﻊ ﺻﻮﺭﺗـﻪ ﰲ ﺍﳌﺮﺁﺓ(‬

‫ﺑﺴـﻴﻂ ﻣﺜﻞ ﺑﺮﻭﻣﻮﻛﻠﻮﺭﻓﻠﻮﺭﻭﻣﻴﺜﺎﻥ‪ ،‬ﻭﺃﻣﺴـﻚ ﺑﺄﺣﺪ ﺍﻟﻨﲈﺫﺝ‬ ‫‪        8-21 ‬‬
‫‪D‬‬

‫ﻋﺎﻟ ﹰﻴـﺎ ﺃﻣـﺎﻡ ﻣـﺮﺁﺓ ﻋﲆ ﺃﻥ ﻳﺘﻤﻜـﻦ ﺍﻟﻄﻼﺏ ﻣـﻦ ﺭﺅﻳﺔ ﻛﻞ ﻣﻦ‬ ‫‪L    ‬‬
‫‪     ‬‬
‫‪‬‬
‫ﺛـﻢ ﺑـﲔ ﺃﻥ ﺻـﻮﺭﺓ ﺍﳌـﺮﺁﺓ ﳍـﺎ‬
‫ﺍﳉـﺰﻱﺀ ﻭﺻﻮﺭﺗـﻪ ﰲ ﺍﳌـﺮﺁﺓ‪ .‬ﹼ‬ ‫‪L‬‬ ‫‪D‬‬

‫ﻣﻈﻬﺮ ﻧﻤﻮﺫﺝ ﺍﳌﺘﺸـﻜﻞ ﺍﻵﺧﺮ ﻧﻔﺴـﻪ ﻭﻫﻴﺌﺘـﻪ‪ .‬ﺛﻢ ﹼﺑﲔ ﺃﻥ ﻛﻼ‬

‫ﺍﻟﻨﻤﻮﺫﺟـﲔ ﻻ ﻳﻤﻜـﻦ ﺗﺪﻭﻳﺮﳘـﺎ ﺑﺄﻱ ﻃﺮﻳﻘﺔ ﳑﻜﻨـﺔ ﻟﻴﺼﺒﺤﺎ‬
‫ﻣﺘﲈﺛﻠـﲔ ﺃﻭ ﻳﻨﻄﺒـﻖ ﺃﺣﺪﳘـﺎ ﻋـﲆ ﺍﻵﺧـﺮ‪ .‬ﻭﻷﻥ ﺍﻟﻄﻼﺏ ﱂ‬
‫ﻳﺪﺭﺳـﻮﺍ ﻫﺎﻟﻴﺪﺍﺕ ﺍﻷﻟﻜﻴﻞ ﺑﻌﺪ‪ ،‬ﻟﺬﺍ ﺍﻋﺮﺽ ﺍﳉﺰﻱﺀ ﻋﲆ ﺃﻧﻪ‬
‫ﺟـﺰﻱﺀ ﳛﺘﻮﻱ ﻋﲆ ﺃﺭﺑﻊ ﳎﻤﻮﻋﺎﺕ ﳐﺘﻠﻔﺔ ﳑﺜﻠﺔ ﺑﺄﺭﺑﻊ ﻛﺮﺍﺕ‬
‫ﺫﺍﺕ ﺃﻟﻮﺍﻥ ﳐﺘﻠﻔﺔ‪.‬‬
‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤﺚ ﻋﻦ ﺃﳘﻴﺔ ﺍﳉﺰﻳﺌﺎﺕ ﺍﻟﻜﲑﺍﻟﻴﺔ‬
‫ﺍﳌﺴـﺘﻌﻤﻠﺔ ﰲ ﺍﳌـﻮﺍﺩ ﺍﻟﺪﻭﺍﺋﻴـﺔ ﻭﺍﺳـﺘﻘﺼﺎﺋﻬﺎ‪ .‬ﺗﻌﺪ ﺍﻟﻜﲑﺍﻟﻴـﺔ ﻣﻬﻤﺔ ﺟﺪﹼﹰ ﺍ؛‬
‫ﻓﻘﺪ ﻳﻜﻮﻥ ﻹﺣﺪ￯ ﺃﺯﻭﺍﺝ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﻀﻮﺋﻴﺔ ﺗﺄﺛﲑ ﻋﻼﺟﻲ‪ ،‬ﻭﻟﻶﺧﺮ‬
‫ﺗﺄﺛـﲑﺍﺕ ﺟﺎﻧﺒﻴـﺔ ﺿـﺎﺭﺓ ﺟﺪﹼﹰ ﺍ‪ .‬ﻟﻘـﺪ ﺗﻢ ﺍﻟﻜﺸـﻒ ﻋﻦ ﻫﺬﺍ ﺍﳌﺠـﺎﻝ ﻷﻭﻝ‬
‫ﻣـﺮﺓ ﻋﻨﺪﻣـﺎ ﻧﺠـﻢ ﻋـﻦ ﺃﺣـﺪ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﻀﻮﺋﻴـﺔ ﻟـﺪﻭﺍﺀ ﺛﺎﻟﻴﺪﻭﻣﺎﻳﺪ‬
‫)‪ (thalidomide‬ﻋﻴﻮﺏ ﺧﻠﻘﻴﺔ ﺧﻄﲑﺓ ﻟﺪ￯ ﺍﻷﻃﻔﺎﻝ‪ .‬‬

‫‪155‬‬
‫ﹸﺴﻤﻰ ﺍﳋﺎﺻﻴﺔ ﺍﻟﺘﻲ ﻳﻮﺟﺪ ﻓﻴﻬﺎ‬
‫ﺟﻬﺔ ﺍﻟﻴﻤﲔ‪ ،‬ﻭ )‪ (levo‬ﻭﺗﻌﻨﻲ ﺟﻬﺔ ﺍﻟﻴﺴﺎﺭ‪ .‬ﻭﺗ ﹼ‬
‫ﺍﳉﺰﻱﺀ ﰲ ﺻﻮﺭﺗﲔ ﺇﺣﺪﺍﳘﺎ ﺗﺸﺒﻪ ﺻﻮﺭﺓ ﺍﻟﻴﺪ ﺍﻟﻴﻤﻨﻰ ﻭﺍﻷﺧﺮ￯ ﺗﺸﺒﻪ ﺻﻮﺭﺓ ﺍﻟﻴﺪ‬
‫ﺍﻟﻴﴪ￯ ﺍﻟﻜﲑﺍﻟﻴﺔ‪ .‬ﻭﺗﺘﻤﺘﻊ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﻮﺍﺩ ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ ـ ﻭﻣﻨﻬﺎ‬ ‫اﻟﺘﻘﻮﻳﻢ‬
‫ﺍﳌﻜﻮﻧﺔ ﻟﻠﱪﻭﺗﻴﻨﺎﺕ ـ ﲠﺬﻩ ﺍﻟﻜﲑﺍﻟﻴﺔ‪.‬‬
‫ﺍﳊﻤﻮﺽ ﺍﻷﻣﻴﻨﻴﺔ ﱢ‬
‫ﻭﺗﺴﺘﻔﻴﺪ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ ﻋﻤﻮ ﹰﻣﺎ ﻣﻦ ﺗﺮﻛﻴﺐ ﻛﲑﺍﱄ ﻭﺍﺣﺪ ﻓﻘﻂ ﻣﻦ ﺍﳌﺎﺩﺓ؛ ﻷﻥ‬
‫ﻫﺬﺍ ﺍﻟﺸﻜﻞ ﻭﺣﺪﻩ ﻳﺘﻼﺀﻡ ﻣﻊ ﺍﳌﻮﻗﻊ ﺍﻟﻨﺸﻂ ﰲ ﺍﻹﻧﺰﻳﻢ‪.‬‬

‫اﻟﻤﺘﺸﻜﻼت اﻟﻀﻮﺋﻴﺔ ‪Optical Isomers‬‬ ‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻋﻤﻞ ﻧﲈﺫﺝ ﺍﻟﻜﺮﺓ ﻭﺍﻟﻌﺼﺎ ﻟﻜﻞ ﻣﻦ‪:‬‬
‫ﺃﺩﺭﻙ ﺍﻟﻜﻴﻤﻴﺎﺋﻴـﻮﻥ ﰲ ﺍﻟﻌﻘﺪ ﺍﻟﺴـﺎﺩﺱ ﻣﻦ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳـﻊ ﻋﴩ ‪1860‬ﻡ ﻭﺟﻮﺩ‬ ‫ﺳﻴﺲ‪ -2-‬ﺑﻨﺘﲔ‪ ،‬ﻭﺗﺮﺍﻧﺲ‪ -2-‬ﺑﻨﺘﲔ ﻭﺍﳌﻘﺎﺭﻧﺔ ﺑﻴﻨﻬﺎ؟ ‪‬‬
‫ﺧﺎﺻﻴـﺔ ﺍﻟﻜﲑﺍﻟﻴـﺔ ﰲ ﺍﳌﺮﻛـﺐ ﺍﻟـﺬﻱ ﳛﺘﻮﻱ ﻋـﲆ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﻏـﲑ ﻣﺘﲈﺛﻠﺔ‪ .‬ﻭﺫﺭﺓ‬
‫ﺍﻟﻜﺮﺑﻮﻥ ﻏﲑ ﺍﳌﺘﲈﺛﻠﺔ ﻫﻲ ﺗﻠﻚ ﺍﻟﺘﻲ ﺗﺮﺗﺒﻂ ﺑﺄﺭﺑﻊ ﺫﺭﺍﺕ ﺃﻭ ﳎﻤﻮﻋﺎﺕ ﺫﺭﺍﺕ ﳐﺘﻠﻔﺔ‪.‬‬
‫ﻼ‪ ،‬ﺍﻓﱰﺽ ﺃﻥ‬ ‫ﺩﺍﺋﲈ ﺗﺮﺗﻴﺐ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻷﺭﺑﻊ ﺑﻄﺮﻳﻘﺘﲔ ﳐﺘﻠﻔﺘﲔ‪ .‬ﻓﻤﺜ ﹰ‬
‫ﺇﺫ ﻳﻤﻜـﻦ ﹰ‬
‫ﺍﳌﺠﻤﻮﻋﺎﺕ ‪ W‬ﻭ ‪ X‬ﻭ ‪Y‬ﻭ‪ Z‬ﻣﺮﺗﺒﻄﺔ ﻣﻊ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﻧﻔﺴﻬﺎ ﰲ ﺍﻟﱰﻛﻴﺒﲔ ﺍﳌﺒﻴﻨﲔ‬ ‫اﻟﻤﻄﻮﻳﺎت‬

‫ﺃﺩﺧﻞ ﻣﻌﻠﻮﻣﺎﺕ ﻣﻦ ﻫﺬﺍ ﺍﻟﻘﺴﻢ ﰲ‬

‫ﰲ ﺍﻟﺸﻜﻞ ‪ ،8-22‬ﻓﺴﺘﻼﺣﻆ ﺃﻥ ﺳﺒﺐ ﺍﻻﺧﺘﻼﻑ ﺑﲔ ﺍﻟﱰﻛﻴﺒﲔ ﻫﻮ ﺗﺒﺪﻳﻞ ﻣﻮﺍﻗﻊ‬
‫ﻣﻄﻮﻳﺘﻚ‪.‬‬
‫ﺍﳌﺠﻤﻮﻋﺘﲔ ‪ X‬ﻭ‪ .Y‬ﻭﻻ ﺗﺴـﺘﻄﻴﻊ ﺗﺪﻭﻳﺮ ﺍﻟﺸـﻜﻠﲔ ﺑﺄﻱ ﻃﺮﻳﻘﺔ ﻟﻴﺼﺒﺤﺎ ﻣﺘﻄﺎﺑﻘﲔ‬
‫ﲤﺎ ﹰﻣﺎ‪.‬‬
‫ﻭﺍﻵﻥ ﺍﻓﱰﺽ ﺃﻧﻚ ﺑﻨﻴﺖ ﻧﲈﺫﺝ ﳍﺬﻳﻦ ﺍﻟﺸـﻜﻠﲔ‪ ،‬ﻓﻬﻞ ﺗﻮﺟﺪ ﺃﻱ ﻃﺮﻳﻘﺔ ﺗﺴـﺘﻄﻴﻊ‬
‫ﲠـﺎ ﲢﻮﻳﻞ ﺃﺣﺪ ﻫﺬﻳﻦ ﺍﻟﺸـﻜﻠﲔ ﻟﻴﺒﺪﻭ ﻣﺜﻞ ﺍﻵﺧﺮ ﲤﺎ ﹰﻣـﺎ؟ )ﺑﻐﺾ ﺍﻟﻨﻈﺮ ﻋﻦ ﺑﺮﻭﺯ‬
‫ﺍﻷﺣـﺮﻑ ﺇﱃ ﺍﻷﻣـﺎﻡ ﺃﻭ ﺍﳋﻠﻒ(‪ .‬ﺳﺘﻜﺘﺸـﻒ ﺃﻧﻪ ﻟﻴﺲ ﻫﻨـﺎﻙ ﻃﺮﻳﻘﺔ ﻹﻧﺠﺎﺯ ﻫﺬﻩ‬
‫ﺍﳌﻬﻤـﺔ ﺩﻭﻥ ﺇﺯﺍﻟـﺔ ‪ X‬ﻭ‪ Y‬ﻣـﻦ ﺫﺭﺓ ﺍﻟﻜﺮﺑـﻮﻥ ﻭﺗﺒﺪﻳﻞ ﻣﻮﻗﻌﻴﻬﲈ‪ .‬ﻟـﺬﺍ ﻓﺈﻥ ﺍﳉﺰﻳﺌﲔ‬
‫ﲑﺍ‪.‬‬
‫ﳐﺘﻠﻔﺎﻥ ﺣﺘﻰ ﻟﻮ ﻛﺎﻧﺎ ﻳﺒﺪﻭﺍﻥ ﻣﺘﺸﺎﲠﲔ ﻛﺜ ﹰ‬
‫ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﻀﻮﺋﻴﺔ ﻣﺘﺸﻜﻼﺕ ﻓﺮﺍﻏﻴﺔ ﻧﺎﲡﺔ ﻋﻦ ﺍﻟﱰﺗﻴﺒﺎﺕ ﺍﳌﺨﺘﻠﻔﺔ ﻟﻠﻤﺠﻤﻮﻋﺎﺕ‬
‫ﺍﻷﺭﺑـﻊ ﺍﳌﺨﺘﻠﻔـﺔ ﻭﺍﳌﻮﺟـﻮﺩﺓ ﻋـﲆ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﻧﻔﺴـﻬﺎ ﳍـﺎ ﺍﳋﺼﺎﺋـﺺ ﺍﻟﻔﻴﺰﻳﺎﺋﻴﺔ‬
‫ﻻ ﺃﻥﹼ ﺗﻔﺎﻋﻼﲥـﺎ ﺍﻟﻜﻴﻤﻴﺎﺋﻴـﺔ ﺗﻌﺘﻤـﺪ ﻋـﲆ ﺍﻟﻜﲑﺍﻟﻴـﺔ‪ .‬ﻣـﺎ ﻋﺪﺍ‬‫ﻭﺍﻟﻜﻴﻤﻴﺎﺋﻴـﺔ ﻧﻔﺴـﻬﺎ ﺍ ﹼ‬
‫ﺍﻟﺘﻔﺎﻋـﻼﺕ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﺍﻟﺘﻲ ﺗﻜﻮﻥ ﻓﻴﻬـﺎ ﺍﻟﻜﲑﺍﻟﻴﺔ ﻣﻬﻤﺔ‪ ،‬ﻭﻣﻨﻬﺎ ﺍﻟﺘﻔﺎﻋﻼﺕ ﺍﳌﺤ ﱠﻔﺰﹶ ﺓ‬

‫‪    8-22 ‬‬

‫‪W‬‬ ‫‪W‬‬ ‫‪W‬‬
‫‪X‬‬ ‫‪W‬‬ ‫‪Y‬‬ ‫‪  ‬‬
‫—‬

‫—‬

‫‪Z—C—X‬‬ ‫‪Z—C—Y‬‬ ‫‪‬‬

‫—‬

‫‪Z‬‬
‫—‬

‫‪Y‬‬ ‫‪Y‬‬ ‫‪Z‬‬ ‫‪X‬‬ ‫‪YX‬‬

‫‪X‬‬

‫‪C22-082C-828378-08‬‬ ‫‪C22-083C-828378-08‬‬

‫ﻣﺸﺮوع اﻟﻜﻴﻤﻴﺎء‬

‫‪ ‬ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﻟﺒﺤﺚ ﰲ‬

‫‪‬‬
‫ﻭﺧﺼﻮﺻـﺎ ﺍﻟﺬﻱ ﻳﻨﺘﺞ ﻋﻦ ﺍﺧﺘﻼﻓـﺎﺕ ﺍﻟﻜﻴﻤﻴﺎﺀ‬
‫ﹰ‬ ‫ﺃﳘﻴـﺔ ﺍﻟﺸـﻜﻞ ﺍﳉﺰﻳﺌﻲ‪،‬‬
‫ﺍﻟﻔﺮﺍﻏﻴﺔ‪ ،‬ﻋﲆ ﺣﺎﺳـﺔ ﺍﻟﺸﻢ ﻋﻨﺪ ﺍﻹﻧﺴﺎﻥ‪ .‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﹰ‬
‫ﺃﻳﻀﺎ ﻛﺘﺎﺑﺔ ﺗﻘﺮﻳﺮ‬
‫ﻋﻦ ﻫﺬﺍ ﺍﳌﻮﺿﻮﻉ ﻭﻋﺮﺿﻪ ﻋﲆ ﺍﻟﺼﻒ‪ .‬‬

‫‪156‬‬
 ‫‪  8-23 ‬‬ ‫‪‬‬ ‫‪‬‬

‫‪ .3‬اﻟﺘﻘﻮﻳﻢ‬
‫‪‬‬ ‫‪‬‬
‫‪   ‬‬
‫‪   ‬‬ ‫‪‬‬
‫‪‬‬ ‫‪‬‬
‫‪‬‬ ‫‪‬‬

‫اﻟﺘﺤﻘﻖ ﻣﻦ اﻟﻔﻬﻢ‬ ‫‪‬‬

‫‪‬‬
‫‪ ‬‬ ‫‪‬‬
‫‪ ‬‬ ‫‪‬‬
‫ﺍﻛﺘﺐ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻷﺯﻭﺍﺝ ﺍﳉﺰﻳﺌﺎﺕ ﺍﻵﺗﻴﺔ ﻋﲆ ﺍﻟﺴـﺒﻮﺭﺓ‪ .‬ﺛﻢ‬ ‫‪‬‬ ‫‪L‬‬

‫ﺯﻭﺟﺎ ﻣﻦ‬
‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﲢﺪﻳﺪ ﻣـﺎ ﺇﺫﺍ ﻛﺎﻥ ﻛﻞ ﻣﻨﻬﺎ ﻳﻤﺜـﻞ ﹰ‬ ‫‪D‬‬

‫ﺍﳌﺘﺸـﻜﻼﺕ ﺃﻡ ﻻ‪ ،‬ﻭﺇﺫﺍ ﻛﺎﻧﺖ ﻛﺬﻟﻚ‪ ،‬ﻓﺄﻱ ﻧﻮﻉ ﻣﻦ ﺍﳌﺘﺸـﻜﻼﺕ‬

‫ﺗﻨﺘﻤﻲ ﺇﻟﻴﻪ؟‬ ‫ﻼ ﺗﺴـﻤﺢ ﺑﺪﺧـﻮﻝ ﺍﳊﻤﻮﺽ ﺍﻷﻣﻴﻨﻴﺔ‬ ‫ﺑﺎﻹﻧﺰﻳـﲈﺕ ﰲ ﺍﻷﻧﻈﻤﺔ ﺍﻟﺒﻴﻮﻟﻮﺟﻴﺔ‪ .‬ﻓﺎﳋﻼﻳﺎ ﺍﻟﺒﴩﻳﺔ ﻣﺜ ﹰ‬
‫ﻣﻦ ﻧﻮﻉ )‪ (L‬ﻓﻘﻂ ﰲ ﺑﻨﺎﺀ ﺍﻟﱪﻭﺗﻴﻨﺎﺕ‪ .‬ﻛﲈ ﺃﻥ ﺍﻟﻨﻮﻉ )‪ (L‬ﻣﻦ ﲪﺾ ﺍﻹﺳـﻜﻮﺭﺑﻴﻚ ﻓﻌﺎﻝ ﺑﻮﺻﻔﻪ‬
‫‪ .a‬ﺑﻨﺘﺎﻥ ﻭ ‪ -2‬ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗﺎﻥ‪ .‬ﻧﻌﻢ‪ ،‬ﻣﺘﺸﻜﻼﺕ ﺑﻨﺎﺋﻴﺔ‪.‬‬ ‫ﺃﻳﻀﺎ‪ .‬ﻓﻤﺜ ﹰ‬
‫ﻼ ﻳﻜﻮﻥ ﻣﺘﺸـﻜﻞ ﻭﺍﺣﺪ ﻓﻘﻂ ﰲ‬ ‫ﻓﻴﺘﺎﻣـﲔ ‪ .C‬ﻭﺗﻌـﺪ ﺍﻟﻜﲑﺍﻟﻴﺔ ﰲ ﺟﺰﻱﺀ ﺍﻟﺪﻭﺍﺀ ﻣﻬﻤﺔ ﹰ‬
‫ﺿﺎﺭﺍ‪.‬‬
‫ﻻ ﰲ ﺣﲔ ﻗﺪ ﻳﻜﻮﻥ ﺍﻵﺧﺮ ﹼﹰ‬ ‫ﺑﻌﺾ ﺍﻷﺩﻭﻳﺔ ﻓﻌﺎ ﹰ‬
‫‪ .b‬ﺳﻴﺲ ‪ -2-‬ﺑﻴﻮﺗﲔ ﻭﺗﺮﺍﻧﺲ‪ -2-‬ﺑﻴﻮﺗﲔ‪.‬‬ ‫‪ ‬ﺇﻥ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﺘﻲ ﻳﻜﻮﻥ ﻛﻞ ﻣﻨﻬﺎ ﺻﻮﺭﺓ ﻣﺮﺁﺓ ﻟﻶﺧﺮ ﺗﹸﺴﻤﻰ ﺍﳌﺘﺸﻜﻼﺕ‬
‫ﺍﻟﻀﻮﺋﻴـﺔ؛ ﻷﳖﺎ ﺗﺆﺛﺮ ﰲ ﺍﻟﻀﻮﺀ ﺍﳌﺎﺭ ﺧﻼﳍﺎ‪ .‬ﻋـﺎﺩ ﹰﺓ ﺗﺘﺤﺮﻙ ﺍﻷﻣﻮﺍﺝ ﺍﻟﻀﻮﺋﻴﺔ ﰲ ﺣﺰﻣﺔ ﺍﻟﻀﻮﺀ‬
‫ﻧﻌﻢ‪ ،‬ﻣﺘﺸﻜﻼﺕ ﻫﻨﺪﺳﻴﺔ‬ ‫ﺍﻟﺼﺎﺩﺭﺓ ﻋﻦ ﺍﻟﺸﻤﺲ ﺃﻭ ﺍﳌﺼﺒﺎﺡ ﰲ ﺍﳌﺴﺘﻮﻳﺎﺕ ﺍﳌﺤﺘﻤﻠﺔ ﲨﻴﻌﻬﺎ‪ .‬ﻭﻟﻜﻦ ﻳﻤﻜﻦ ﺗﺼﻔﻴﺔ ﺍﻟﻀﻮﺀ‬
‫ﺃﻭ ﻋﻜﺴﻪ ﺑﻄﺮﻳﻘﺔ ﲡﻌﻞ ﺍﻷﻣﻮﺍﺝ ﺍﻟﻨﺎﲡﺔ ﲨﻴﻌﻬﺎ ﺗﻘﻊ ﰲ ﺍﳌﺴﺘﻮ￯ ﻧﻔﺴﻪ‪ .‬ﻭ ﹸﻳﺴﻤﻰ ﻫﺬﺍ ﺍﻟﻨﻮﻉ ﻣﻦ‬
‫‪ .c‬ﺑﻴﻮﺗﺎﻥ ﻭ ﺑﻴﻮﺗﺎﻥ ﺣﻠﻘﻲ‪.‬ﻻ‬ ‫ﺍﻟﻀﻮﺀ ﺍﻟﻨﺎﺗﺞ ﺍﻟﻀﻮﺀ ﺍﳌﺴﺘﻘﻄﺐ‪.‬‬
‫ﻋﻨﺪﻣـﺎ ﻳﻤـﺮ ﺍﻟﻀـﻮﺀ ﺍﳌﺴـﺘﻘﻄﺐ ﺧـﻼﻝ ﳏﻠـﻮﻝ ﳛﺘـﻮﻱ ﻋـﲆ ﻣﺘﺸـﻜﻞ ﺿﻮﺋﻲ ﻓﺈﻥ ﻣﺴـﺘﻮ￯‬
‫‪ .d‬ﺑﻴﻮﺗﺎﻥ ﺣﻠﻘﻲ ﻭ ‪ -1‬ﺑﻴﻮﺗﲔ‪ .‬ﻧﻌﻢ‪ ،‬ﻣﺘﺸﻜﻼﺕ ﺑﻨﺎﺋﻴﺔ‪ .‬‬ ‫ﺍﻻﺳـﺘﻘﻄﺎﺏ ﻳـﺪﻭﺭ ﺇﱃ ﺍﻟﻴﻤـﲔ )ﻣﻊ ﻋﻘﺎﺭﺏ ﺍﻟﺴـﺎﻋﺔ‪ ،‬ﻋﻨﺪﻣﺎ ﺗﻨﻈﺮ ﺇﱃ ﻣﺼـﺪﺭ ﺍﻟﻀﻮﺀ( ﺑﺘﺄﺛﲑ‬
‫ﻨﺘﺠﺎ ﺍﻟﺘﺄﺛـﲑ ﺍ ﹸﳌ ﹼ‬
‫ﺴﻤﻰ‬ ‫ﻣﺘﺸـﻜﻞ ‪ ،D‬ﺃﻭ ﺇﱃ ﺍﻟﻴﺴـﺎﺭ )ﻋﻜﺲ ﻋﻘﺎﺭﺏ ﺍﻟﺴﺎﻋﺔ( ﺑﺘﺄﺛﲑ ﻣﺘﺸﻜﻞ ‪ ،L‬ﹸﻣ ﹰ‬
‫ﺍﻟﺪﻭﺭﺍﻥ ﺍﻟﻀﻮﺋﻲ‪ .‬ﻭﻳﻈﻬﺮ ﻫﺬﺍ ﺍﻟﺘﺄﺛﲑ ﰲ ﺍﻟﺸﻜﻞ ‪.8-23‬‬
‫إﻋﺎدة اﻟﺘﺪرﻳﺲ‬ ‫ﻗﺪ ﻳﻜﻮﻥ ‪ – L‬ﻣﻴﻨﺜﻮﻝ ﺃﺣﺪ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﻀﻮﺋﻴﺔ ﺍﻟﺘﻲ ﺗﺴـﺘﺨﺪﻣﻬﺎ ﰲ ﺣﻴﺎﺗﻚ‪ .‬ﻭﳍﺬﺍ ﺍﳌﺘﺸﻜﻞ‬
‫ﺍﻟﻄﺒﻴﻌـﻲ ﻧﻜﻬﺔ ﺍﻟﻨﻌﻨﺎﻉ ﺍﳊﺎﺩﺓ‪ ،‬ﻭﻟـﻪ ﺗﺄﺛﲑ ﻣﻨﻌﺶ ﹰ‬
‫ﺃﻳﻀﺎ‪ .‬ﺃ ﹼﻣﺎ ﺍﳌﺘﺸـﻜﻞ ﺍﻵﺧﺮ )ﺻﺎﺣﺐ ﺻﻮﺭﺓ‬
‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺭﺳـﻢ ﺧﺮﻳﻄـﺔ ﻣﻔﺎﻫﻴﻢ ﺗﻮﺿـﺢ ﺍﻟﻌﻼﻗﺔ ﺑﲔ‬ ‫ﺍﳌﺮﺁﺓ( ‪ -D‬ﻣﻴﻨﺜﻮﻝ ﻓﻠﻴﺲ ﻟﻪ ﺍﻟﺘﺄﺛﲑ ﺍﳌﻨﻌﺶ ﺍﳋﺎﺹ ﺑـ ‪ -L‬ﻣﻴﻨﺜﻮﻝ ﻧﻔﺴﻪ‪.‬‬

‫ﺍﳌﺼﻄﻠﺤﺎﺕ ﺍﻵﺗﻴﺔ‪ :‬ﻣﺘﺸـﻜﻞ‪ ،‬ﻣﺘﺸـﻜﻞ ﺑﻨﺎﺋﻲ‪ ،‬ﻣﺘﺸﻜﻞ ﻓﺮﺍﻏﻲ‪،‬‬

‫ﻣﺘﺸﻜﻞ ﻫﻨﺪﳼ‪ ،‬ﻭﻣﺘﺸﻜﻞ ﺿﻮﺋﻲ‪ .‬‬

‫اﻟﺘﻮﺳﻊ‬
‫ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤﺚ ﻋﻦ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻜﻞ ﻣﻦ ﻣﺘﺸﻜﻞ ‪L‬‬
‫ﻭ ‪ D‬ﻣﻦ ﲪﺾ ﺍﻷﺳﻜﻮﺭﺑﻴﻚ )ﻓﻴﺘﺎﻣﲔ ‪ .(C‬‬

‫‪157‬‬
 ‫اﻟﺘﻘﻮﻳﻢ ‪8-4‬‬
‫‪ .25‬اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺍﻛﺘﺐ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﺤﺘﻤﻠﺔ ﻟﻸﻟﻜﺎﻥ ﺫﻱ ﺍﻟﺼﻴﻐﺔ‬ ‫اﻟﺨﻼﺻﺔ‬ ‫اﻟﺘﻘﻮﻳﻢ‬
‫ﺍﳉﺰﻳﺌﻴﺔ ‪ C6H14‬ﲨﻴﻌﻬﺎ‪ ،‬ﻋﲆ ﺃﻥ ﺗﻈﻬﺮ ﻓﻘﻂ ﺳﻼﺳﻞ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬ ‫ﺍﳌﺘﺸـﻜﻼﺕ ﻣﺮﻛﺒﺎﻥ ﺃﻭ ﺃﻛﺜﺮ ﳍﲈ ﺍﻟﺼﻴﻐﺔ‬
‫ﻓﴪ ﺍﻟﻔﺮﻕ ﺑﲔ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻭﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﻔﺮﺍﻏﻴﺔ‪.‬‬ ‫ﺍﳉﺰﻳﺌﻴـﺔ ﻧﻔﺴـﻬﺎ‪ ،‬ﻭﻟﻜﻨﻬـﺎ ﲣﺘﻠـﻒ ﰲ ‪ .26‬ﱢ‬
‫‪ .27‬ﺍﺭﺳﻢ ﺃﺷﻜﺎﻝ ﻛﻞ ﻣﻦ ﺳﻴﺲ‪-3-‬ﻫﻜﺴﲔ ﻭﺗﺮﺍﻧﺲ‪-3-‬ﻫﻜﺴﲔ‪.‬‬ ‫ﺻﻴﻐﻬﺎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫ﲣﺘﻠﻒ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﰲ ﺍﻟﱰﺗﻴﺐ ‪ .28‬ﺍﺳﺘﻨﺘﺞ ﳌﺎﺫﺍ ﺗﺴﺘﻔﻴﺪ ﺍﳌﺨﻠﻮﻗﺎﺕ ﺍﳊﻴﺔ ﻣﻦ ﺷﻜﻞ ﻛﲑﺍﱄ ﻭﺍﺣﺪ ﻓﻘﻂ ﻣﻦ‬ ‫ﻧﻤﻮﺫﺟﺎ ﳌﺮﻛﺐ‬
‫ﹰ‬ ‫‪ ‬ﺃﻋـﻂ ﻛﻞ ﳎﻤﻮﻋﺔ ﻣﻦ ﻃﺎﻟﺒـﲔ ﺃﻭ ﺛﻼﺛـﺔ‬
‫ﺍﳌﺎﺩﺓ؟‬ ‫ﻣﻌﺎ‪.‬‬
‫ﺍﻟﺬﻱ ﺗﺮﺗﺒﻂ ﺑﻪ ﺍﻟﺬﺭﺍﺕ ﹰ‬
‫ﻗﻮﻡ ﹸﻳﻨﺘﺞ ﺗﻔﺎﻋﻞ ﻣﻌﲔ ‪ 80%‬ﺗﺮﺍﻧﺲ‪-2-‬ﺑﻨﺘﲔ ﻭ ‪ 20%‬ﺳﻴﺲ‪ -2-‬ﺑﻨﺘﲔ‪.‬‬ ‫‪ .29‬ﹼ‬ ‫ﺍﳌﺘﺸـﻜﻼﺕ‬ ‫ﰲ‬ ‫ﺗﺮﺗﺒـﻂ ﺍﻟـﺬﺭﺍﺕ ﲨﻴﻌﻬﺎ‬ ‫ﻛـﲑﺍﱄ ﺑﺴـﻴﻂ‪ .‬ﻭﺍﻃﻠـﺐ ﺇﱃ ﻛﻞ ﻣﻨﻬﺎ ﺑﻨﺎﺀ ﻧﻤﻮﺫﺝ ﻳﻤﺜﻞ ﺍﳌﺘﺸـﻜﻞ‬
‫ﺍﻟﻀﻮﺋﻲ ﻟﻠﻤﺮﻛﺐ ﺍ ﹸﳌﻌﻄﻰ‪ .‬‬
‫ﻭﻛﻮﻥ ﻓﺮﺿﻴﺔ ﻟﺘﻔﺴﲑ ﺳﺒﺐ‬ ‫ﱢ‬ ‫ﺍﳍﻨﺪﺳﻴﲔ‪،‬‬ ‫ﺍﳌﺘﺸﻜﻠﲔ‬ ‫ﻫﺬﻳﻦ‬ ‫ﺷﻜﻞ‬ ‫ﺍﺭﺳﻢ‬ ‫ﲣﺘﻠﻒ‬ ‫ﻭﻟﻜﻨﻬﺎ‬ ‫ﻧﻔﺴﻪ‪،‬‬ ‫ﺍﻟﻔﺮﺍﻏﻴﺔ ﺑﺎﻟﱰﺗﻴﺐ‬
‫ﺗﻜﻮﻥ ﺍﳌﺘﺸﻜﻠﲔ ﲠﺬﻩ ﺍﻟﻨﺴﺒﺔ‪.‬‬ ‫ﰲ ﺗﺮﻛﻴﺒﻬـﺎ ﺍﻟﻔﺮﺍﻏـﻲ )ﺍﻻﲡﺎﻫـﺎﺕ ﰲ‬
‫‪ .30‬ﺍﻋﻤﻞ ﻧﲈﺫﺝ ﺍﺑﺘﺪﺍ ﹰﺀ ﺑﺬﺭﺓ ﻛﺮﺑﻮﻥ ﻭﺍﺣﺪﺓ‪ ،‬ﺍﺭﺳﻢ ﻣﺘﺸﻜﻠﲔ ﺿﻮﺋﻴﲔ ﺑﺮﺑﻂ‬ ‫ﺍﻟﻔﺮﺍﻍ(‪.‬‬
‫ﺍﻟﺬﺭﺍﺕ ﺃﻭ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺘﺎﻟﻴﺔ ﻣﻊ ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ‪:‬‬
‫‪–H, –CH 3; –CH 2CH 3; –CH 2CH 2CH 3.‬‬

‫اﻟﺘﻘﻮﻳﻢ ‪8-4‬‬
‫‪ .28‬ﺗﺴـﺘﻔﻴﺪ ﺍﳌﺨﻠﻮﻗـﺎﺕ ﺍﳊﻴـﺔ ﻋﻤﻮ ﹰﻣﺎ ﻣﻦ ﺗﺮﻛﻴﺐ ﻛـﲑﺍﱄ ﻭﺍﺣﺪ‬ ‫‪ .25‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﺳﺘﻤﺜﻞ ﺍﻹﺟﺎﺑﺎﺕ ‪5‬‬
‫ﻓﻘـﻂ ﰲ ﺍﳌـﺎﺩﺓ؛ ﻷﻥ ﻫـﺬﺍ ﺍﻟﱰﻛﻴﺐ ﻭﺣـﺪﻩ ﻳﺘﻼﺀﻡ ﻣـﻊ ﺍﳌﻮﻗﻊ‬ ‫ﻣﺘﺸـﻜﻼﺕ ﺑﻨﺎﺋﻴﺔ ﻫﻲ‪ –2 :‬ﻣﻴﺜﻴﻞ ﺑﻨﺘـﺎﻥ‪ ،‬ﻭ ‪ -3‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‪،‬‬
‫ﺍﻟﻨﺸﻂ ﰲ ﺍﻹﻧﺰﻳﻢ‪.‬‬ ‫ﻭ ‪ -3 ،2‬ﺛﻨﺎﺋـﻲ ﻣﻴﺜﻴـﻞ ﺑﻴﻮﺗﺎﻥ‪ ،‬ﻭ‪ -2 ،2‬ﺛﻨﺎﺋـﻲ ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗﺎﻥ‪،‬‬
‫‪ .29‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﻳﻨﺘﺞ ﻣﺘﺸﻜﻞ ﺗﺮﺍﻧﺲ‬ ‫ﻭﻫﻜﺴﺎﻥ‪.‬‬
‫ﺑﻨﺴـﺒﺔ ﺃﻋـﲆ؛ ﻷﻥ ﺑﻨـﺎﺀﻩ ﻳﺴـﻤﺢ ﳌﺠﻤﻮﻋﺘﻲ ﺍﳌﻴﺜﻴـﻞ ﻭﺍﻹﻳﺜﻴﻞ‬ ‫‪ .26‬ﲣﺘﻠـﻒ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺑﻌﻀﻬـﺎ ﻋﻦ ﺑﻌـﺾ ﰲ ﺍﻟﱰﺗﻴﺐ‬
‫ﺍﻟﻜﺒﲑﺗﲔ ﺑﺎﻟﺘﺒﺎﻋﺪ ﺑﻌﻀﻬﲈ ﻋﻦ ﺑﻌﺾ ﺃﻛﺜﺮ ﻣﻦ ﺗﺮﻛﻴﺐ ﺳﻴﺲ‪.‬‬ ‫ﻣﻌـﺎ‪ ،‬ﻓﻔﻲ ﺍﻟﻮﻗـﺖ ﺍﻟﺬﻱ ﺗﻜـﻮﻥ ﻓﻴﻪ‬
‫ﺍﻟـﺬﻱ ﺗﺮﺗﺒـﻂ ﺑـﻪ ﺫﺭﺍﲥﺎ ﹰ‬
‫‪ .30‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﳚﺐ ﺃﻥ ﹸﺗﻈﻬﺮ ﺍﻟﺼﻴﻎ‬ ‫ﺍﻟﺬﺭﺍﺕ ﰲ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﻔﺮﺍﻏﻴﺔ ﻣﺮﺗﺒﻄﺔ ﺑﺎﻟﱰﺗﻴﺐ ﻧﻔﺴﻪ ﻓﺈﳖﺎ‬
‫ﺍﳌﺠﻤﻮﻋـﺎﺕ ﺍﳌﻌﻄﺎﺓ ﻣﺮﺗﺒﻄﺔ ﻣﻊ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﻭﺍﺣﺪﺓ‪ .‬ﻛﲈ ﳚﺐ‬ ‫ﺗﻜﻮﻥ ﳐﺘﻠﻔﺔ ﰲ ﺗﺮﺗﻴﺒﻬﺎ ﺍﻟﻔﺮﺍﻏﻲ )ﺍﻻﲡﺎﻫﺎﺕ ﰲ ﺍﻟﻔﺮﺍﻍ(‪.‬‬
‫ﺃﻥ ﲣﺘﻠـﻒ ﰲ ﻛﻮﻥ ﺍﺛﻨﺘﲔ ﻣـﻦ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﳌﺮﺗﺒﻄﺔ ﰲ ﺍﻟﻔﺮﺍﻍ‬ ‫‪ .27‬ﺍﺭﺟـﻊ ﺇﱃ ﺍﻟـﺪﺭﺱ ﻟﻜﺘﺎﺑـﺔ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴـﺔ‪ .‬ﺗﻘـﻊ ﺫﺭﺍﺕ‬
‫ﻗﺪ ﻋﻜﺲ ﻣﻜﺎﻥ ﱟ‬
‫ﻛﻞ ﻣﻨﻬﲈ‪.‬‬ ‫ﺍﳍﻴﺪﺭﻭﺟـﲔ ﺍﳌﺮﺗﺒﻄـﺔ ﻣـﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺜﻨﺎﺋﻴـﺔ ﺍﻟﺮﺑﻂ ﰲ‬
‫ﺳﻴﺲ‪-3-‬ﻫﻜﺴﲔ ﻋﲆ ﺍﳉﻬﺔ ﻧﻔﺴﻬﺎ ﻣﻦ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﻜﺮﺑﻮﻧﻴﺔ‪.‬‬
‫ﺃﻣـﺎ ﰲ ﺗﺮﻛﻴﺐ ﺗﺮﺍﻧـﺲ ﻓﺘﻘـﻊ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﻋﲆ ﺟﻬﺎﺕ‬
‫ﻣﺘﻌﺎﻛﺴﺔ ﻣﻦ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﻜﺮﺑﻮﻧﻴﺔ‪.‬‬

‫‪158‬‬
 ‫‪8-5‬‬ ‫اﻟﻬﻴﺪروﻛﺮﺑﻮﻧﺎت ا“روﻣﺎﺗﻴﺔ‬
‫‪8-5‬‬
‫اﻫﺪاف‬
‫‪  ‬ﺑـــﲔ ﺧـــﻮﺍﺹ‬
‫‪Aromatic Hydrocarbons‬‬
‫‪ .1‬اﻟﺘﺮﻛﻴﺰ‬ ‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ‪‬‬
‫ﺍﳍﻴـﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺭﻭﻣﺎﺗـﻴـﺔ‬
‫ﻭﺍﻷﻟﻴﻔﺎﺗﻴﺔ‪.‬‬
‫‪‬‬ ‫‪  ‬ﺍﳌــﻘــﺼــﻮﺩ ﺑــﺎﳌــﺎﺩﺓ‬
‫‪‬‬ ‫‪ ‬ﻣﺎ ﺍﻟﴚﺀ ﺍﳌﺸﱰﻙ ﺑﲔ ﺍﻷﻧﺴﺠﺔ ﺫﺍﺕ ﺍﻷﻟﻮﺍﻥ ﺍﻟﺰﺍﻫﻴﺔ ﻭﺍﻟﺰﻳﻮﺕ ﺍﻟﻌﻄﺮﻳﺔ‬ ‫ﺍﳌﴪﻃﻨﺔ ﻭﺗﺬﻛﺮ ﺑﻌﺾ ﺍﻷﻣﺜﻠﺔ‬
‫)ﺍﻟﻄﻴﺎﺭﺓ( ﺍﳌﺴﺘﺨﺪﻣﺔ ﰲ ﺍﻟﻌﻄﻮﺭ؟ ﻛﻞ ﻣﻨﻬﲈ ﳛﺘﻮﻱ ﻋﲆ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺃﺭﻭﻣﺎﺗﻴﺔ‪.‬‬ ‫ﻋﻠﻴﻬﺎ‪.‬‬
‫ﻗﺒﻞ ﺑﺪﺀ ﺍﻟـﺪﺭﺱ‪ ،‬ﺍﻋﺮﺽ ﻋﲆ ﺍﻟﻄﻼﺏ ﴍﳛـﺔ ﺍﻟﱰﻛﻴﺰ ﺭﻗﻢ‬ ‫اﻟﺼﻴﻐﺔ اﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﺒﻨﺰﻳﻦ ‪The Structure of Benzene‬‬ ‫‪  ‬ﺍﳌـــﺮﻛـــﺒـــﺎﺕ‬
‫)‪ (31‬ﺍﻟـﻮﺍﺭﺩﺓ ﰲ ﻣﺼﺎﺩﺭ ﺍﻟﺘﻌﻠﻢ ﻟﻠﻔﺼﻮﻝ )‪ ،(5-8‬ﻭﻳﻤﻜﻨﻚ‬ ‫ﺇﻥ ﺍﻷﺻﺒـﺎﻍ ﺍﻟﻄﺒﻴﻌﻴـﺔ ـ ﻭﻣﻨﻬـﺎ ﺗﻠﻚ ﺍﳌﻮﺟـﻮﺩﺓ ﰲ ﺍﻷﻧﺴـﺠﺔ ﺍﻟﻈﺎﻫﺮﺓ ﰲ ﺍﻟﺸـﻜﻞ ‪ 8-24‬ـ‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﻴﺔ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ‪.‬‬
‫ﻭﺍﻟﺰﻳـﻮﺕ ﺍﻟﻌﻄﺮﻳﺔ‪ ،‬ﲢﺘﻮﻱ ﻋﲆ ﺻﻴﻎ ﺑﻨﺎﺋﻴﺔ ﺫﺍﺕ ﺣﻠﻘﺔ ﻛﺮﺑﻮﻥ ﺳﺪﺍﺳـﻴﺔ‪ .‬ﻭﻗﺪ ﻋﺮﻓﺖ ﻫﺬﻩ‬ ‫ﻣﺮاﺟﻌﺔ اﻟﻤﻔﺮدات‬
‫ﻋﺮﺿﻬﺎ ﻣﻠﻮﻧﺔ ﻣﻦ ﺧﻼﻝ ﺍﻟﺮﺟﻮﻉ ﺇﱃ ﺍﳌﻮﻗﻊ ﺍﻹﻟﻜﱰﻭﲏ‪ :‬‬ ‫ﺍﳌﺮﻛﺒﺎﺕ ﻭﺍﺳـﺘﺨﺪﻣﺖ ﻣﻨـﺬ ﻗﺮﻭﻥ‪ .‬ﻓﻘﺪ ﻛﺎﻥ ﻟـﺪ￯ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﲔ ﰲ ﻣﻨﺘﺼﻒ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳـﻊ‬ ‫‪  ‬ﺩﻣــﺞ‬
‫ﻋـﴩ ﻣﻌﺮﻓﺔ ﻭﺩﺭﺍﻳـﺔ ﺃﺳﺎﺳـﻴﺔ ﺑﺄﺷـﻜﺎﻝ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺫﺍﺕ ﺍﻟﺮﻭﺍﺑﻂ ﺍﳌﺸـﱰﻛﺔ‬ ‫ﺍﳌﺠﺎﻻﺕ ﺍﻹﻟﻜﱰﻭﻧﻴﺔ ﺍﳌﺨﺘﻠﻔﺔ‬
‫‪www.obeikaneducation.com‬‬ ‫ﺍﻷﺣﺎﺩﻳﺔ ﻭﺍﻟﺜﻨﺎﺋﻴﺔ ﻭﺍﻟﺜﻼﺛﻴﺔ‪ .‬ﻭﻣﻊ ﺫﻟﻚ ﺑﻘﻴﺖ ﺑﻌﺾ ﺍﻟﱰﺍﻛﻴﺐ ﺍﳊﻠﻘﻴﺔ ﻏﺎﻣﻀﺔ‪.‬‬ ‫ﰲ ﺍﻟﺸﻜﻞ ﻭﺍﻟﻄﺎﻗﺔ ﻟﻠﺤﺼﻮﻝ‬
‫ﺇﻥ ﺃﺑﺴـﻂ ﻣﺜـﺎﻝ ﻋﲆ ﻫﺬﻩ ﺍﻟﻔﺌﺔ ﻣـﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻫﻮ ﺍﻟﺒﻨﺰﻳﻦ‪ ،‬ﺍﻟـﺬﻱ ﹸﻋﺰﻝ ﺃﻭﻝ ﻣﺮﺓ ﻋﺎﻡ‬ ‫ﻋﲆ ﳎﺎﻻﺕ ﺇﻟﻜﱰﻭﻧﻴﺔ ﻣﺘﲈﺛﻠﺔ‬
‫‪1825‬ﻡ ﻋﲆ ﻳﺪ ﺍﻟﻔﻴﺰﻳﺎﺋﻲ ﺍﻟﱪﻳﻄﺎﲏ ﻣﺎﻳﻜﻞ ﻓﺎﺭﺍﺩﺍﻱ ‪1791-1867) Michael Faraday‬ﻡ(‬ ‫ﺍﻟﺸﻜﻞ ﻭﺍﻟﻄﺎﻗﺔ‪.‬‬
‫اﻟﺮﺋﻴﺴﺔ‬ ‫اﻟﻔﻜﺮة‬ ‫ﻣﻦ ﺍﻟﻐﺎﺯﺍﺕ ﺍﳌﻨﺒﻌﺜﺔ ﻋﻨﺪ ﺗﺴﺨﲔ ﺯﻳﻮﺕ ﺍﳊﻴﺘﺎﻥ ﺃﻭ ﺍﻟﻔﺤﻢ‪ .‬ﻭﺭﻏﻢ ﻗﻴﺎﻡ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﲔ ﺑﺘﺤﺪﻳﺪ‬ ‫اﻟﻤﻔﺮدات اﻟﺠﺪﻳﺪة‬
‫ﺻﻴﻐﺔ ﺍﻟﺒﻨﺰﻳﻦ ﺍﳉﺰﻳﺌﻴﺔ ﺑـ ‪ C6H6‬ﺇﻻ ﺃﻧﻪ ﻛﺎﻥ ﻣﻦ ﺍﻟﺼﻌﺐ ﻋﻠﻴﻬﻢ ﲢﺪﻳﺪ ﺍﻟﺒﻨﺎﺀ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﲏ‬
‫‪ ‬ﺍﻛﺘـﺐ ﻋـﲆ ﺍﻟﺴـﺒﻮﺭﺓ ﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﻟﻠﺒﻨﺰﻳـﻦ ﺍﻟﺘﻲ‬ ‫ﺍﻟـﺬﻱ ﻳﻌﻄﻲ ﻫـﺬﻩ ﺍﻟﺼﻴﻐﺔ‪ .‬ﻓﺼﻴﻐﺔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳌﺸـﺒﻊ ﺫﻱ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴـﺖ ﻫﻲ‬
‫ﺍﳌﺮﻛﺐ ﺍﻷﺭﻭﻣﺎﰐ‬
‫ﺍﳌﺮﻛﺐ ﺍﻷﻟﻴﻔﺎﰐ‬
‫ﺍﻗﱰﺣﻬـﺎ ﻛﻴﻜﻮﱄ‪ ،‬ﻭﺍﺳـﺄﻝ‪ :‬ﻣﺎ ﻧﻮﻉ ﺍﻟﺮﻭﺍﺑـﻂ ﺍﻟﻜﺮﺑﻮﻧﻴﺔ ﺍﳌﻮﺟﻮﺩﺓ‬ ‫‪ .C6H14‬ﻭﻷﻥ ﺟﺰﻱﺀ ﺍﻟﺒﻨﺰﻳﻦ ﻳﻨﻘﺼﻪ ﺍﻟﻘﻠﻴﻞ ﻣﻦ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ‪ ،‬ﻓﻘﺪ ﺍﺳﺘﻨﺘﺞ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ‬
‫ﺃﻥ ﻣﻦ ﺍﻟﴬﻭﺭﻱ ﺃﻥ ﻳﻜﻮﻥ ﻏﲑ ﻣﺸﺒﻊ؛ ﻭﻫﺬﺍ ﻳﻌﻨﻲ ﺃﻥ ﻟﺪﻳﻪ ﺑﻌﺾ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﺃﻭ ﺍﻟﺜﻼﺛﻴﺔ‬

‫ﰲ ﻫـﺬﻩ ﺍﻟﺼﻴﻐﺔ؟ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ ﻭﺛﻨﺎﺋﻴﺔ ﻣﺘﻨﺎﻭﺑﺔ‪ .‬ﺍﴍﺡ ﻟﻠﻄﻼﺏ‬ ‫ﻣﻌﺎ‪ .‬ﻭﺍﻗﱰﺣﻮﺍ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﺨﺘﻠﻔﺔ‪ ،‬ﻭﻣﻨﻬﺎ ﺍﻟﺼﻴﻐﺔ ﺃﺩﻧﺎﻩ ﺍﻟﺘﻲ ﺍﻗﱰﺣﺖ‬
‫ﺃﻭ ﻛﻠﺘﻴﻬﲈ ﹰ‬
‫ﻋﺎﻡ ‪1860‬ﻡ‪.‬‬

‫ﺃﻥ ﻫـﺬﺍ ﻣﺎ ﺍﻋﺘﻘﺪﻩ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﺑﺎﻟﻨﺴـﺒﺔ ﻟﻠﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﺒﻨﺰﻳﻦ‪.‬‬ ‫‪CH2 — C — CH — CH — C — CH2‬‬

‫ﻭﺍﺭﺳﻢ ﺍﻟﻨﻤﻮﺫﺝ ﺍﳊﺎﱄ ﻟﻠﺒﻨﺰﻳﻦ ﻋﲆ ﺍﻟﺴﺒﻮﺭﺓ‪ ،‬ﺛﻢ ﺍﺳﺄﻝ‪ :‬ﻣﺎ ﺃﻧﻮﺍﻉ‬ ‫‪      8-24 ‬‬
‫ﺍﻟﺮﻭﺍﺑﻂ ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﻫﺬﻩ ﺍﻟﺼﻴﻐﺔ؟ ﺍﻗﺒﻞ ﲨﻴﻊ ﺍﻹﺟﺎﺑﺎﺕ ﺍﳌﻨﻄﻘﻴﺔ‪.‬‬ ‫‪‬‬
‫‪‬‬ ‫‪‬‬
‫ﺃﺧـﱪ ﺍﻟﻄـﻼﺏ ﺃﻥ ﺍﻟﻜﻴﻤﻴﺎﺋﻴـﲔ ﺍﻟﻴـﻮﻡ ﻳﻌﻠﻤـﻮﻥ ﺃﻥ ﺇﻟﻜﱰﻭﻧـﺎﺕ‬ ‫‪    ‬‬
‫‪‬‬
‫ﺍﻟﺒﻨﺰﻳـﻦ ﲨﻴﻌﻬـﺎ ﺗﺘـﻮﺯﻉ ﻋﲆ ﻧـﻮ￯ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴـﺖ ﺍﳌﻮﺟﻮﺩﺓ ﰲ‬
‫ﻭﲤﺜـﻞ ﺑﺤﻠﻘﺔ ﰲ ﻣﻨﺘﺼـﻒ ﺍﻟﻨﻤـﻮﺫﺝ‪ .‬ﻭﺃﺧﱪ ﺍﻟﻄﻼﺏ‬ ‫ﺍﳉـﺰﻱﺀ‪ ،‬ﹸ ﹶ‬
‫ﹼ‬
‫ﺃﻥ ﺗﺸـﺎﺭﻙ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﻭﺗﻮﺯﹼ ﻋﻬﺎ ﳚﻌﻼﻥ ﺍﻟﺒﻨﺰﻳﻦ ﺷﺪﻳﺪ ﺍﻟﺜﺒﺎﺕ‬
‫ﻭﻗﻠﻴﻞ ﺍﻟﻨﺸﺎﻁ ﰲ ﺍﻟﺘﻔﺎﻋﻼﺕ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ‪ .‬‬

‫— ‪ ‬ﺍﻟﺸـﻜﻞ ‪ 8-24‬ﲢﺘﻮﻱ ﻋﲆ ﺻﻴـﻎ ﺑﻨﺎﺋﻴﺔ ﺫﺍﺕ‬

‫ﺣﻠﻘﺔ ﺳﺪﺍﺳﻴﺔ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬ ‫‪ ‬ﻗـﺪ ﻳﺴـﺘﻮﻋﺐ ﺍﻟﻄـﻼﺏ ﻣﻔﻬـﻮﻡ ﺗﻮﺯﻳـﻊ ﺍﻹﻟﻜﱰﻭﻧـﺎﺕ‬
‫ﻭﺗﺸﺎﺭﻛﻬﺎ ﰲ ﺍﻟﺒﻨﺰﻳﻦ ﺇﺫﺍ ﺑﻨﻮﺍ ﺍﻟﻨﻤﻮﺫﺝ ﺑﺄﻧﻔﺴﻬﻢ‪ .‬ﻟﺬﺍ ﺍﻃﻠﺐ ﺇﱃ ﺳﺘﺔ ﻃﻼﺏ‬
‫ﻻ ‪ -5، 3، 1‬ﺣﻠﻘﻲ ﻫﺴـﻜﺎ ﺗﺮﺍﻳﲔ‬ ‫ﺗﺸـﻜﻴﻞ ﺣﻠﻘـﺔ ﺑﴩﻳﺔ ﻳﻤﺜﻠﻮﻥ ﻓﻴﻬـﺎ ﺃﻭ ﹰ‬
‫ﻭﺫﻛﺮﻫـﻢ ﺑﺄﻥ ﻛﻞ ﺫﺭﺓ‬ ‫)ﻧﻤـﻮﺫﺝ ﻛﻴﻮﻛﻮﱄ ﺍﻷﺻﲇ ﻟﻠﺒﻨﺰﻳـﻦ( ﺛﻢ ﺍﻟﺒﻨﺰﻳﻦ‪ .‬ﹼ‬
‫ﻛﺮﺑﻮﻥ )ﻛﻞ ﺷﺨﺺ( ﻟﻪ ﺃﺭﺑﻌﺔ ﺇﻟﻜﱰﻭﻧﺎﺕ ﺗﻜﺎﻓﺆ‪ ،‬ﻣﻨﻬﺎ ﺍﺛﻨﺎﻥ ﹸﻣﺴﺘﺨﺪﹶ ﻣﺎﻥ‬
‫ﰲ ﺭﻭﺍﺑـﻂ )ﺭﺍﺑﻄـﺔ ﺳـﻴﺠﲈ( ﻣـﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ ﺍﳌﺠـﺎﻭﺭﺓ‪ .‬ﻭﺇﻟﻜﱰﻭﻥ‬
‫ﺃﻳﻀﺎ( ﻣـﻊ ﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ‪ .‬ﻟﺬﺍ‬ ‫ﺁﺧﺮ ﹸﻣﺴـﺘﺨﺪﹶ ﻡ ﰲ ﺭﺍﺑﻄﺔ )ﺭﺍﺑﻄﺔ ﺳـﻴﺠﲈ ﹰ‬
‫ﻓـﺈﻥ ﻫـﺬﺍ ﺍﻟﺘﻮﺯﻳﻊ ﻳﱰﻙ ﺇﻟﻜﱰﻭ ﹰﻧـﺎ ﻭﺍﺣﺪﹰ ﺍ ﻟﻜﻞ ﺫﺭﺓ ﻛﺮﺑﻮﻥ‪ .‬ﻭﺳـﻴﻤﺜﻞ ﰲ‬
‫ﹺ‬
‫ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﰲ‬ ‫ﺍﻟﻨﻤـﻮﺫﺝ ﺍﻷﻭﻝ ﺛﻼﺛﺔ ﺃﺯﻭﺍﺝ ﻣﻦ ﺍﻟﻄـﻼﺏ ﺍﳌﺘﺠﺎﻭﺭﻳﻦ‬
‫ﺛﻼﺙ ﺭﻭﺍﺑﻂ ﺛﺎﺑﺘﺔ ﻏﲑ ﻗﺎﺑﻠﺔ ﻟﻠﺘﻨﻘﻞ )ﺭﻭﺍﺑﻂ ﺑﺎﻱ( ﺑﺮﻓﻊ ﻛﻠﺘﺎ ﺍﻟﻴﺪﻳﻦ ﻋﺎﻟ ﹰﻴﺎ‬
‫ﺳـﻴﻤﺮﺭ ﺍﻟﻄﻼﺏ ﺍﻟﺴـﺘﺔ ﲨﻴﻌﻬﻢ‬ ‫ﹼ‬ ‫ﻣﻌـﺎ‪ .‬ﰲ ﺣﲔ‬ ‫ﻭﺍﻹﻣﺴـﺎﻙ ﺑﻜـﺮﰐ ﺗﻨﺲ ﹰ‬
‫ﻛﺮﺍﺕ ﺍﻟﺘﻨﺲ ﺑﺎﺳﺘﻤﺮﺍﺭ ﺣﻮﻝ ﺍﳊﻠﻘﺔ ﰲ ﺍﻟﻨﻤﻮﺫﺝ ﺍﻟﺜﺎﲏ‪ .‬‬

‫‪159‬‬
‫ﻭﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺃﻥ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﳍﺬﻩ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻫﻲ ‪ C6H6‬ﻓﺈﻥ ﻣﺜﻞ ﻫﺬﺍ‬

‫‪ .2‬اﻟﺘﺪرﻳﺲ‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻏﲑ ﻣﺴﺘﻘﺮ ﻭﺷﺪﻳﺪ ﺍﻟﺘﻔﺎﻋﻞ؛ ﻟﻮﺟﻮﺩ ﺍﻟﻌﺪﻳﺪ ﻣﻦ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ‪،‬‬
‫ﻛﻴﻤﻴﺎﺋﻴﺎ‪ ،‬ﻭﻻ ﺗﺘﻔﺎﻋﻞ ﺑﺎﻟﻄﺮﺍﺋﻖ ﺍﻟﺘﻲ ﺗﺘﻔﺎﻋﻞ ﲠﺎ‬
‫ﹼﹰ‬ ‫ﺇﻻ ﺃﻥ ﺍﻟﺒﻨﺰﻳﻦ ﻣﺎﺩﺓ ﻏﲑ ﻧﺸﻄﺔ‬
‫ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻋﺎﺩﺓ‪ .‬ﻭﳍﺬﺍ ﺍﻟﺴﺒﺐ ﺍﺳﺘﻨﺘﺞ ﺍﻟﻌﻠﲈﺀ ﺃﻥ ﻣﺜﻞ ﻫﺬﻩ ﺍﻟﺼﻴﻐﺔ‬
‫ﺍﻟﺒﻨﺎﺋﻴﺔ ﻏﲑ ﺻﺤﻴﺤﺔ‪.‬‬
‫اﻟﺘﻘﻮﻳﻢ‬
‫‪ ‬ﰲ ﻋﺎﻡ ‪1865‬ﻡ ﺍﻗﱰﺡ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ ﺍﻷﳌﺎﲏ ﻓﺮﻳﺪﺭﻳﻚ ﺃﻭﺟﺴﺖ ﻛﻴﻜﻮﱄ‬ ‫‪ 8-25‬‬
‫‪1829-1896) Friedric August Kekulé‬ﻡ( ﺻﻴﻐ ﹰﺔ ﺑﻨﺎﺋﻴ ﹰﺔ ﳐﺘﻠﻔ ﹰﺔ ﻟﻠﺒﻨﺰﻳﻦ‪-‬‬ ‫‪C22-013C-828378-08‬‬
‫‪‬‬ ‫‪   ‬‬
‫ﻭﻫﻲ ﺷﻜﻞ ﺳﺪﺍﳼ ﻳﺘﻜﻮﻥ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺗﺘﻨﺎﻭﺏ ﻓﻴﻪ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻷﺣﺎﺩﻳﺔ‬ ‫‪      ‬‬
‫ﹸﻘﺎﺭ ﹸﻥ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﳍﺬﺍ ﺍﻟﺸﻜﻞ ﺑﺎﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻟﻠﺒﻨﺰﻳﻦ؟‬
‫ﻭﺍﻟﺜﻨﺎﺋﻴﺔ‪ .‬ﻓﻜﻴﻒ ﺗ ﹶ‬ ‫‪‬‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺃﻥ ﻳﻜﺘﺒـﻮﺍ ﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺍﻟﺘﻲ‬
‫‪H‬‬
‫‪H‬‬ ‫‪H‬‬
‫‪‬‬ ‫ﺍﻗﱰﺣﻬـﺎ ﻛﻴﻜـﻮﱄ‪ ،‬ﻭﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺍﳊﺎﻟﻴـﺔ ﻟﻠﺒﻨﺰﻳﻦ ﻭﺗﻔﺴـﲑ‬
‫‪H‬‬ ‫‪H‬‬
‫‪H‬‬
‫‪‬‬
‫‪‬‬
‫ﺍﻻﺧﺘﻼﻑ ﺑﻴﻨﻬﲈ‪ .‬‬
‫ﹼﺍﺩﻋـﻰ ﻛﻴﻜﻮﱄ ﺃﻧﻪ ﺭﺃ￯ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﺒﻨﺰﻳـﻦ ﰲ ﺍﳌﻨﺎﻡ ﻋﻨﺪﻣﺎ ﻏﻠﺒﻪ ﺍﻟﻨﻌﺎﺱ ﺃﻣﺎﻡ‬
‫— ‪ ‬ﻛﻠﺘـﺎ ﺍﻟﺼﻴﻐﺘﲔ ﺍﳉﺰﻳﺌﻴﺘـﲔ ﻣﺘﻄﺎﺑﻘﺘﺎﻥ‪،‬‬
‫ﺃﺭﻭﻣﺎﰐ )‪(Aromatic‬‬
‫ﺍﳌﻮﻗﺪ ﰲ ﻣﺪﻳﻨﺔ "ﺟﻨﺖ"‪ ،‬ﺑﺒﻠﺠﻴﻜﺎ‪ ،‬ﺇﺫ ﻗﺎﻝ ﺇﻧﻪ ﺣﻠﻢ ﺑـ"ﺃﻭﺭﻭﺑﻮﺭﻭﺱ‪Ouroboros،‬‬ ‫ﺍﻻﺳـﺘﻌﲈﻝ ﺍﻟﻌﻠﻤﻲ‪ :‬ﻣﺮﻛـﺐ ﻋﻀﻮﻱ ﺛﺎﺑﺖ‬
‫"‪ ،‬ﻭﻫـﻮ ﺷـﻌﺎﺭ ﻣـﴫﻱ ﻗﺪﻳﻢ ﺗﻈﻬﺮ ﻓﻴﻪ ﺃﻓﻌﻰ ﺗﻔﱰﺱ ﺫﻳﻠﻬـﺎ‪ ،‬ﳑﺎ ﺟﻌﻠﻪ ﻳﻔﻜﺮ ﰲ‬ ‫ﺍﻟﱰﻛﻴﺐ ﺑﺴـﺒﺐ ﻋﺪﻡ ﺑﻘﺎﺀ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﰲ‬
‫ﺍﻟﺸـﻜﻞ ﺍﳊﻠﻘﻲ‪ .‬ﻭﻳﻔﴪ ﺍﻟﺸـﻜﻞ ﺍﻟﺴﺪﺍﳼ ﺍ ﹸﳌﺴـﻄﺢ ﺍﻟﺬﻱ ﺍﻗﱰﺣﻪ ﻛﻴﻜﻮﱄ ﺑﻌﺾ‬ ‫ﻣﻜﺎﻥ ﻭﺍﺣﺪ‪.‬‬ ‫‪.C6H6‬‬
‫ﺧﺼﺎﺋﺺ ﺍﻟﺒﻨﺰﻳﻦ‪ ،‬ﻭﻟﻜﻨﻪ ﻻ ﻳﻔﴪ ﺿﻌﻒ ﻧﺸﺎﻃﻪ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‪.‬‬ ‫ﻼ‪ :‬ﺍﻟﺒﻨﺰﻳﻦ ﻣﺮﻛﺐ ﺃﺭﻭﻣﺎﰐ‬ ‫ﻛﺄﻥ ﻧﻘﻮﻝ ﻣﺜ ﹰ‬
‫ﺍﻻﺳﺘﻌﲈﻝ ﺍﻟﺸﺎﺋﻊ‪ :‬ﳍﺎ ﺭﺍﺋﺤﺔ ﻗﻮﻳﺔ‪.‬‬
‫‪ ‬ﺃﻛﺪﺕ ﺍﻷﺑﺤﺎﺙ ﻣﻨﺬ ﺍﻗﱰﺍﺡ ﻛﻴﻜﻮﱄ ﺃﻥ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‬
‫ﻼ‪ :‬ﻫﺬﺍ ﺍﻟﻌﻄﺮ ﺫﻭ ﺭﺍﺋﺤﺔ ﻗﻮﻳﺔ‪.‬‬ ‫ﻛﺄﻥ ﻧﻘﻮﻝ ﻣﺜ ﹰ‬
‫ﻼ ﺍﻟﺸﻜﻞ ﺍﻟﺴﺪﺍﳼ‪ .‬ﻭﻋﲆ ﺍﻟﺮﻏﻢ ﻣﻦ ﺫﻟﻚ ﱂ ﹸﻳﻔﴪ ﺿﻌﻒ ﺍﻟﻨﺸﺎﻁ‬ ‫ﻟﻠﺒﻨﺰﻳﻦ ﻫﻲ ﻓﻌ ﹰ‬
‫ﺍﻟﻜﻴﻤﻴﺎﺋـﻲ ﻟﻠﺒﻨﺰﻳﻦ ﺣﺘﻰ ‪1930‬ﻡ‪ ،‬ﻋﻨﺪﻣﺎ ﺍﻗﱰﺡ ﻟﻴﻨﻮﺱ ﺑﺎﻭﻟﻴﻨﺞ ﻧﻈﺮﻳﺔ ﺍﳌﺠﺎﻻﺕ‬ ‫ﻋﺮض ﺳﺮﻳﻊ‬
‫ﺍﳌﻬﺠﻨـﺔ‪ .‬ﻭﻋﻨﺪ ﺗﻄﺒﻴﻘﻬﺎ ﻋﲆ ﺍﻟﺒﻨﺰﻳﻦ ﺗﻨﺒﺄﺕ ﻫـﺬﻩ ﺍﻟﻨﻈﺮﻳﺔ ﺃﻥ ﺃﺯﻭﺍﺝ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ‬
‫ﺍﳌﻜﻮﻧﺔ ﻟﺮﻭﺍﺑﻂ ﺍﻟﺒﻨﺰﻳﻦ ﺍﻟﺜﻨﺎﺋﻴﺔ ﻻ ﺗﺘﺠﻤﻊ ﺑﲔ ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﳏﺪﹼ ﺩﺗﲔ ﻛﲈ ﻫﻮ ﺍﳊﺎﻝ ﰲ‬
‫ﺗﻜﻮﻥ ﺃﺯﻭﺍﺝ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﻏﲑ ﻣﺘﻤﺮﻛﺰﺓ )ﻣﺘﺤﺮﻛﺔ(‬ ‫ﻭﻋﻮﺿﺎ ﻋﻦ ﺫﻟﻚ ﹸ‬
‫ﹰ‬ ‫ﺍﻷﻟﻜﻴﻨﺎﺕ‪.‬‬
‫‪ ،delocalized‬ﳑﺎ ﻳﻌﻨﻲ ﺃﳖﺎ ﺗﺸﱰﻙ ﰲ ﲨﻴﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴﺖ ﰲ ﺍﳊﻠﻘﺔ‪.‬‬
‫‪A‬‬ ‫‪B‬‬ ‫‪C‬‬ ‫‪D‬‬ ‫‪E‬‬ ‫‪AF‬‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ‪BAG ACB‬‬
‫‪H BD‬‬ ‫ﺍﺣـﱰﺍﻕ‬
‫‪C I CEDJ DFEK‬‬ ‫ﺇﻥ‪EGF L F‬‬
‫‪HGM‬‬
‫‪GHIN HJO‬‬
‫‪I‬‬ ‫‪IKJP JLK KML‬‬ ‫‪N‬‬
‫‪LM‬‬ ‫‪ON‬‬
‫‪M‬‬
‫ﻭﺍﻟﺸـﻜﻞ ‪ 8-25‬ﹸﻳﻮﺿـﺢ ﺃﻥ ﻋـﺪﻡ ﺍﻟﺘﻤﺮﻛـﺰ ﻫـﺬﺍ ﳚﻌـﻞ ﺟـﺰﻱﺀ ﺍﻟﺒﻨﺰﻳـﻦ ﺛﺎﺑﺘﹰـﺎ‬

‫ﺍﻷﻟﻴﻔﺎﺗﻴـﺔ ﰲ ﺍﳍـﻮﺍﺀ ﻋﻤﻮ ﹰﻣـﺎ ﺃﻧﻈـﻒ ﻣـﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ‬

‫ﻛﻴﻤﻴﺎﺋﻴﺎ؛ ﻷﻥ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺍﳌﺸـﱰﻛﺔ ﻣﻊ ﺳﺖ ﻧﻮ￯ ﻛﺮﺑﻮﻥ ﻳﺼﻌﺐ ﺳﺤﺒﻬﺎ ﺑﻌﻴﺪﹰ ﺍ‬
‫ﹼﹰ‬
‫ﻣﻘﺎﺭﻧـﺔ ﺑﺎﻹﻟﻜﱰﻭﻧـﺎﺕ ﺍﻟﺜﺎﺑﺘﺔ ﺣﻮﻝ ﻧﻮﺍﺗﲔ ﻓﻘﻂ‪ .‬ﻭﻻ ﺗﹸﻜﺘﹶـﺐ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ‬
‫ﺍﻟﺴـﺖ ﻋﺎﺩ ﹰﺓ ﰲ ﺍﻟﺸـﻜﻞ‪ ،‬ﻭﻟﻜﻦ ﻣﻦ ﺍﻟﴬﻭﺭﻱ ﺃﻥ ﺗﺘﺬﻛﺮ ﺃﳖـﺎ ﻣﻮﺟﻮﺩﺓ‪ .‬ﻭﰲ ﻫﺬﺍ‬
‫ﺍﻟﺘﻤﺜﻴﻞ ﺗﺮﻣﺰ ﺍﻟﺪﺍﺋﺮﺓ ﰲ ﻣﻨﺘﺼﻒ ﺍﻟﺸـﻜﻞ ﺍﻟﺴـﺪﺍﳼ ﺇﱃ ﺍﻟﻐﻴﻤﺔ ﺍﳌﻜﻮﻧﺔ ﻣﻦ ﺃﺯﻭﺍﺝ‬
‫ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ؛ ﺇﺫ ﻳﻨﺒﻌـﺚ ﻣﻦ ﺍﺣﱰﺍﻕ ﺍﻷﺧﲑﺓ ﹺﺳـﻨﺎﺝ ﺃﺳـﻮﺩ‪.‬‬
‫ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺍﻟﺜﻼﺛﺔ‪.‬‬
‫ﻭﺿـﺢ ﻫـﺬﺍ ﺍﻟﻔﺮﻕ ﺑﺎﺳـﺘﺨﺪﺍﻡ ﺍﺧﺘﺒـﺎﺭ ﺍﻟﻠﻬﺐ ﺍﻟـﺬﻱ ﻳﻤﻜﻨﻪ‬‫ﱢ‬
‫ﺍﻟﺘﻤﻴﻴـﺰ ﺑـﲔ ﺍﳌﺮﻛﺒـﺎﺕ ﺍﻷﻟﻴﻔﺎﺗﻴـﺔ ﻭﺍﻷﺭﻭﻣﺎﺗﻴـﺔ‪ .‬ﻭﻣﻦ ﺃﺟﻞ‬
‫ﺍﻟﺴـﻼﻣﺔ ﻭﻃﻠ ﹰﺒـﺎ ﻟﻠﻔﺎﺋـﺪﺓ‪ ،‬ﺍﺳـﺘﺨﺪﻡ ﻣﺒﻠﻤـﺮﺍﺕ ﺃﻟﻴﻔﺎﺗﻴـﺔ‬
‫ﻭﺃﺭﻭﻣﺎﺗﻴـﺔ ﰲ ﻫـﺬﺍ ﺍﻟﻌـﺮﺽ ﺑـﺪ ﹰ‬
‫ﻻ ﻣـﻦ ﺍﳌﺮﻛﺒـﺎﺕ ﺍﻟﺴـﺎﺋﻠﺔ‪.‬‬
‫‪C22-14C-828378-08-A‬‬
‫ﺃﻣﺴـﻚ ﺑﻘﻄﻌﺔ ﻣﻦ ﺑﻼﺳـﺘﻴﻚ ﺃﻟﻔـﺎﰐ )‪ ،LDPE، HDPE‬ﺃﻭ‬
‫‪ (PP‬ﺑﺎﳌﻠﻘﻂ ﻭﻋﺮﺿﻬﺎ ﻟﻠﻬﺐ ﺇﱃ ﺃﻥ ﺗﺸﺘﻌﻞ‪ .‬ﺛﻢ ﺍﺭﻓﻊ ﺍﻟﻘﻄﻌﺔ‬
‫ﺍﳌﺤﱰﻗـﺔ‪ ،‬ﻭﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻣﻼﺣﻈﺔ ﻣـﺎ ﳛﺪﺙ‪ .‬ﺩﺧﺎﻥ‪،‬‬
‫ﻣﺸﺮوع اﻟﻜﻴﻤﻴﺎء‬ ‫ﻭﻟﻜـﻦ ﻻ ﻳﻨﺒﻌﺚ ﻣﻌﻪ ﺳـﻨﺎﺝ‪ ،‬ﺃﻭ ﻗﺪ ﻳﻨﺒﻌﺚ ﻣﻌﻪ ﺳـﻨﺎﺝ ﻗﻠﻴﻞ‬
‫ﺟﺪﹼﹰ ﺍ‪ .‬ﺃﻋﺪ ﺍﻟﺘﺠﺮﺑﺔ ﺑﺎﺳـﺘﺨﺪﺍﻡ ﺑﻼﺳﺘﻴﻚ ﺃﺭﻭﻣﺎﰐ )‪ PETE‬ﺃﻭ‬
‫‪   ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺍﻟﺒﺤـﺚ ﰲ ﺍﻟﺰﻳﻮﺕ‬
‫‪ .(PS‬ﻳﺘﺼﺎﻋﺪ ﺩﺧﺎﻥ )ﺃﺳﻮﺩ(‪ ،‬ﻭﻳﻨﺒﻌﺚ ﻣﻌﻪ ﺳﻨﺎﺝ‪ .‬‬
‫ﺍﻟﻌﻄﺮﻳـﺔ ﻭﻛﻴﻔﻴﺔ ﺍﳊﺼﻮﻝ ﻋﻠﻴﻬﺎ ﰲ ﺍﻟﻌﺼﻮﺭ ﺍﻟﻘﺪﻳﻤﺔ‪ .‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﹰ‬
‫ﺃﻳﻀﺎ‬
‫ﻛﺘﺎﺑﺔ ﺗﻘﺮﻳﺮ ﻗﺼﲑ ﻳﻔﴪﻭﻥ ﻓﻴﻪ ﻛﻴﻒ ﹸﺗﻌﺎﻟﺞ ﻫﺬﻩ ﺍﻟﺰﻳﻮﺕ ﻭﻛﻴﻒ ﺗﺴﺘﺨﺪﻡ؟‬
‫ﻭﻣﺎ ﺍﻟﺘﻐﲑ ﺍﻟﺬﻱ ﻃﺮﺃ ﻋﲆ ﺻﻨﺎﻋﺔ ﺍﻟﻌﻄﻮﺭ ﰲ ﻭﻗﺘﻨﺎ ﺍﳊﺎﴐ؟‬
‫‪    ‬‬

‫‪160‬‬
 ‫اﻟﺘﻌﺰﻳﺰ‬
‫‪‬‬

‫‪ ‬ﺍﻋﺮﺽ ﻋﲆ ﺍﻟﻄﻼﺏ ﹰ‬
‫ﺻﻴﻐﺎ ﺑﻨﺎﺋﻴﺔ ﺃﻭ ﻧﲈﺫﺝ‬
‫ﻟﻠﻤﺮﻛﺒـﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﺍﻵﺗﻴﺔ ﺍﻟﺘـﻲ ﲢﺘﻮﻱ ﻋﲆ ﺣﻠﻘـﺔ ﺑﻨﺰﻳﻦ ﻣﻊ‬ ‫‪‬‬
‫‪‬‬
‫‪‬‬
‫‪C22-15C-828378-08‬‬
‫‪‬‬
‫ﳎﻤﻮﻋـﺔ ﺃﻟﻜﻴـﻞ ﺑﺪﻳﻠـﺔ ﻭﺍﺣﺪﺓ ﺃﻭ ﺃﻛﺜـﺮ‪ ،‬ﺛﻢ ﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﺗﺴـﻤﻴﺔ‬ ‫‪CH3‬‬

‫ﺍﻷﺷـﻜﺎﻝ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﻭﺭﺍﺟﻊ ﻛﻴﻔﻴﺔ ﺗﺴـﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ ﺫﺍﺕ‬ ‫‪C22-14C-828378-08‬‬

‫ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ ﺇﻥ ﺩﻋﺖ ﺍﳊﺎﺟﺔ ﺇﱃ ﺫﻟﻚ‪.‬‬

‫‪CH3‬‬
‫‪(p-Xylene)‬‬
‫)‪( -4,1‬‬

‫ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ )ﺗﻮﻟﻮﻭﻳﻦ(‬ ‫‪.1‬‬ ‫‪‬‬

‫‪‬‬
‫‪ –2،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ )ﺃﻭﺭﺛﻮ– ﺯﺍﻳﻠﲔ(‬
‫‪‬‬
‫‪.2‬‬ ‫‪‬‬

‫‪ –3،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ )ﻣﻴﺘﺎ– ﺯﺍﻳﻠﲔ(‬ ‫‪         8-26‬‬ ‫اﻟﻤﺮﻛﺒﺎت ا¶روﻣﺎﺗﻴﺔ ‪Aromatic Compounds‬‬
‫‪.3‬‬ ‫ﺍﳌﺮﻛﺒـﺎﺕ ﺍﻟﻌﻀﻮﻳـﺔ ﺍﻟﺘﻲ ﲢﺘﻮﻱ ﻋـﲆ ﺣﻠﻘﺎﺕ ﺍﻟﺒﻨﺰﻳـﻦ ﺟﺰ ﹰﺀﺍ ﻣﻦ ﺑﻨﺎﺋﻬـﺎ ﹼ‬
‫ﺍﳌﺮﻛﺒﺎﺕ‬ ‫ﹸﺴـﻤﻰ ﹼ‬
‫‪  ‬‬ ‫ﺗ ﹼ‬
‫ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ‪ .‬ﺍﺳـﺘﺨﺪﻡ ﺍﳌﺼﻄﻠـﺢ ﺃﺭﻭﻣـﺎﰐ )‪ (aromatic‬ﰲ ﺍﻷﺻـﻞ ﻷﻥ ﺍﻟﻜﺜـﲑ ﻣـﻦ‬
‫‪–4،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ )ﺑﺎﺭﺍ– ﺯﺍﻳﻠﲔ(‬
‫‪‬‬
‫‪.4‬‬ ‫‪   ‬‬ ‫ﺍﳌﺮﻛﺒـﺎﺕ ﺍﳌﺮﺗﺒﻄﺔ ﻣﻊ ﺍﻟﺒﻨﺰﻳﻦ ﻭﺍﳌﻌﺮﻭﻓﺔ ﰲ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳـﻊ ﻋﴩ‪ ،‬ﹸﻭﺟﺪﺕ ﰲ ﺍﻟﺰﻳﻮﺕ ﺫﺍﺕ‬
‫ﺍﻟﺮﺍﺋﺤـﺔ ﺍﻟﻄﻴﺒـﺔ ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﻟﺒﻬـﺎﺭﺍﺕ‪ ،‬ﻭﺍﻟﻔﻮﺍﻛﻪ‪ ،‬ﻭﻏﲑﻫﺎ ﻣﻦ ﺃﺟﺰﺍﺀ ﺍﻟﻨﺒﺎﺗﺎﺕ‪ .‬ﻭﺗﺴـﻤﻰ‬
‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻛﺘﺎﺑﺔ ﺻﻴﻎ ﺑﻨﺎﺋﻴﺔ ﺃﻭ ﻋﻤـﻞ ﻧﲈﺫﺝ ﻟﻠﻤﺮﻛﺒﺎﺕ‬
‫‪‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﺜﻞ ﺍﻷﻟﻜﺎﻧـﺎﺕ‪ ،‬ﻭﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﻟﻴﻔﺎﺗﻴﺔ ﻟﺘﻤﻴﺰﻫﺎ‬
‫ﻋـﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ‪ .‬ﻭﻛﻠﻤﺔ ﺃﻟﻴﻔـﺎﰐ )‪ (aliphatic‬ﻳﻮﻧﺎﻧﻴﺔ ﺍﻷﺻـﻞ‪ ،‬ﺗﻌﻨﻲ ﺍﻟﺪﱡ ﻫﻦ‪.‬‬
‫ﺍﻵﺗﻴﺔ‪:‬‬ ‫ﻭﺫﻟﻚ ﺃﻥ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﲔ ﺍﻟﻘﺪﺍﻣﻰ ﺣﺼﻠﻮﺍ ﻋﲆ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﻟﻴﻔﺎﺗﻴﺔ ﺑﺘﺴﺨﲔ ﺩﻫﻮﻥ ﺍﳊﻴﻮﺍﻧﺎﺕ‬
‫ﻭﺷﺤﻮﻣﻬﺎ‪ .‬ﻣﺎ ﺑﻌﺾ ﺍﻷﻣﺜﻠﺔ ﻋﲆ ﺍﻟﺪﻫﻮﻥ ﺍﳊﻴﻮﺍﻧﻴﺔ ﺍﻟﺘﻲ ﻗﺪ ﲢﺘﻮﻱ ﻋﲆ ﻣﺮﻛﺒﺎﺕ ﺃﻟﻴﻔﺎﺗﻴﺔ؟‬
‫ﺇﻳﺜﻴﻞ ﺑﻨﺰﻳﻦ‬ ‫‪.1‬‬ ‫ﺍﺳﺘﻤﺮ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﰲ ﺍﺳﺘﺨﺪﺍﻡ ﻣﺼﻄﻠﺤﻲ ﺍﳌﺮﻛﺒﺎﺕ‬
‫ﹼ‬ ‫‪‬ﳌﺎﺫﺍ‬
‫ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﻭﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﻟﻴﻔﺎﺗﻴﺔ ﺇﱃ ﺍﻵﻥ؟‬
‫ﺃﻳﺰﻭﺑﺮﻭﺑﻴﻞ ﺑﻨﺰﻳﻦ‬ ‫‪.2‬‬ ‫ﺗﻈﻬﺮ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﺒﻌﺾ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﰲ ﺍﻟﺸﻜﻞ ‪ .8-26‬ﻻﺣﻆ ﺃﻥ ﺍﻟﺼﻴﻐﺔ‬
‫ﻻ ﻋﲆ‬‫ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻨﻔﺜﺎﻟﲔ ﺗﺒﺪﻭ ﻛﺤﻠﻘﺘﻲ ﺑﻨﺰﻳﻦ ﻣﺘﻼﺻﻘﺘﲔ ﺟﻨ ﹰﺒﺎ ﺇﱃ ﺟﻨﺐ‪ .‬ﻭﻳﻌﺪ ﺍﻟﻨﻔﺜﺎﻟﲔ ﻣﺜﺎ ﹰ‬
‫‪ -4، 1 .3‬ﺛﻨﺎﺋﻲ ﺇﻳﺜﻴﻞ ﺑﻨﺰﻳﻦ ‪‬‬ ‫ﻧﻈﺎﻡ ﺍﳊﻠﻘﺎﺕ ﺍﳌﻠﺘﺤﻤﺔ )‪ ،(fused‬ﺑﺤﻴﺚ ﳛﺘﻮﻱ ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ ﻋﲆ ﺣﻠﻘﺘﲔ ﺃﻭ ﺃﻛﺜﺮ‬
‫ﺍﳌﻜﻮﻧﺔ ﻟﻠﺤﻠﻘﺎﺕ ﺑﺎﻹﻟﻜﱰﻭﻧﺎﺕ ﻛﲈ‬‫ﺗﺸﱰﻛﺎﻥ ﰲ ﺍﻟﻀﻠﻊ ﻧﻔﺴﻪ‪ .‬ﻭﺗﺘﺸﺎﺭﻙ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﱢ‬
‫ﰲ ﺍﻟﺒﻨﺰﻳﻦ‪.‬‬

‫— ‪ ‬ﺍﻟﺪﻫـﻦ ﺍﻟﺒﻘﺮﻱ‪ ،‬ﺩﻫـﻦ ﺍﳋﺮﻭﻑ‪ ،‬ﺩﻫﻦ‬

‫ﺍﻟﺪﺟﺎﺝ‪.‬‬
‫‪ ‬ﺍﺳـﺘﺨﺪﻣﺖ ﻫﺬﻩ ﺍﳌﺼﻄﻠﺤﺎﺕ ﺑﺎﺳﺘﻤﺮﺍﺭ ﻋﲆ‬
‫ﻣﺮ ﺍﻟﺴﻨﲔ‪ ،‬ﻭﺃﺻﺒﺤﺖ ﺟﺰ ﹰﺀﺍ ﻣﻦ ﺍﻟﻠﻐﺔ‪.‬‬

‫دﻓﺘﺮ اﻟﻜﻴﻤﻴﺎء‬

‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﺍﻟﺘﻔﻜﲑ ﰲ ﺳـﺒﺐ‬

‫ﺗﺴـﻤﻴﺔ ﻫﺬﻩ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ ﺑﺎﻷﺭﻭﻣﺎﺗﻴـﺔ‪ ،‬ﻭﺍﻃﻠﺐ ﺇﻟﻴﻬﻢ ﻛﺘﺎﺑﺔ‬
‫ﺗﻢ ﻋـﺰﻝ ﻫﺬﻩ ﺍﳌﺮﻛﺒﺎﺕ ﻭﻓﺼﻠﻬﺎ ﻷﻭﻝ‬ ‫ﺍﻹﺟﺎﺑـﺔ ﰲ ﺩﻓﱰ ﺍﻟﻜﻴﻤﻴﺎﺀ‪ .‬ﻋﻨﺪﻣﺎ ﹼ‬
‫ﻣﺮﺓ ﰲ ﺍﻟﻌﻘﺪ ﺍﻟﺴـﺎﺩﺱ ﻣﻦ ﺍﻟﻘﺮﻥ ﺍﻟﺘﺎﺳـﻊ ﻋﴩ‪ ،‬ﲤﻜﻦ ﺍﻟﻌﻠﲈﺀ ﻣﻦ ﺍﻟﺘﻤﻴﻴﺰ‬
‫ﺑﻴﻨﻬﺎ ﻣﻦ ﺧﻼﻝ ﺭﻭﺍﺋﺤﻬﺎ‪ .‬‬

‫‪161‬‬
‫‪ ‬ﻟﻠﻤﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﺍﻟﻘﺪﺭﺓ ﻋﲆ ﺍﻣﺘﻼﻙ‬
‫ﳎﻤﻮﻋﺎﺕ ﳐﺘﻠﻔﺔ ﻣﺮﺗﺒﻄﺔ ﻣﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻓﻴﻬﺎ ﻛﺒﻘﻴﺔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪ .‬ﻓﻤﺜ ﹰ‬
‫ﻼ‪ ،‬ﻳﺘﺄﻟﻒ‬
‫ﻣﻴﺜﻴـﻞ ﺍﻟﺒﻨﺰﻳﻦ‪ ،‬ﺍﳌﻌﺮﻭﻑ ﹰ‬
‫ﺃﻳﻀﺎ ﺑــ )ﺍﻟﺘﻮﻟﻮﻳﻦ ‪ ،( toluene‬ﻣﻦ ﳎﻤﻮﻋﺔ ﻣﻴﺜﻴﻞ ﻣﺮﺗﺒﻄﺔ ﻣﻊ‬
‫ﺣﻠﻘﺔ ﺍﻟﺒﻨﺰﻳﻦ ﺑﺪ ﹰ‬
‫ﺗﻄﺒﻴﻘﺎت اﻟﻜﻴﻤﻴﺎء‬
‫ﻻ ﻣﻦ ﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ ﻭﺍﺣﺪﺓ‪ .‬ﻭﻣﺘﻰ ﻭﺟﺪﺕ ﳎﻤﻮﻋﺔ ﺑﺪﻳﻠﺔ ﻣﺮﺗﺒﻄﺔ ﻣﻊ‬
‫ﺗﺬﻛﺮ ﺃﻥ ﺫﺭﺓ ﺍﳍﻴﺪﺭﻭﺟﲔ ﱂ ﺗﻌﺪ ﻫﻨﺎﻙ‪.‬‬‫ﺣﻠﻘﺔ ﺍﻟﺒﻨﺰﻳﻦ ﹼ‬
‫ﻭﺗﺴـﻤﻰ ﻣﺮﻛﺒﺎﺕ ﺍﻟﺒﻨﺰﻳﻦ ﺫﺍﺕ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ ﺑﻄﺮﻳﻘﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ ﻧﻔﺴـﻬﺎ‪.‬‬ ‫‪ ‬ﻫﻨﺎﻙ ﺛﻼﺛﺔ ﻣﺘﺸﻜﻼﺕ ﳐﺘﻠﻔﺔ ﻟﺜﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ‬
‫ﺍﳌﻜﻮﻧﺔ ﻣﻦ ﺫﺭﰐ ﻛﺮﺑﻮﻥ ﻣﺘﺼﻠﺔ‬
‫ﻓﻌﲆ ﺳﺒﻴﻞ ﺍﳌﺜﺎﻝ‪ ،‬ﳛﺘﻮﻱ ﺇﻳﺜﻴﻞ ﺑﻨﺰﻳﻦ ﻋﲆ ﳎﻤﻮﻋﺔ ﺇﻳﺜﻴﻞ‪ ،‬ﹼ‬
‫ﺑﺎﳊﻠﻘـﺔ‪ ،‬ﻭﳛﺘـﻮﻱ ‪ -4،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳـﻦ‪ ،para - xylene ،‬ﻋـﲆ ﳎﻤﻮﻋﺘﻲ ﻣﻴﺜﻴﻞ‬ ‫ﺑﻨﺰﻳﻦ‪ ،‬ﻭﻳﺸـﺎﺭ ﺇﻟﻴﻬﺎ ﺑـ ‪-‬ﺃﻭﺭﺛﻮ‪ ،‬ﻭﻣﻴﺘﺎ‪ ،‬ﻭﺑﺎﺭﺍ ‪ -‬ﺯﺍﻳﻠﲔ‪ .‬ﻭﻳﺴـﻤﻰ‬
‫ﻣﺘﺼﻠﺘﲔ ﺑﺎﳌﻮﻗﻌﲔ ‪ 1‬ﻭ ‪.4‬‬
‫ﺃﻭﺭﺛﻮ‪ -‬ﺯﺍﻳﻠﲔ ﻭﻓﻖ ﻧﻈﺎﻡ ﺃﻳﻮﺑﺎﻙ‪:‬‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫‪CH2CH3‬‬
‫‪ -2،1‬ﺛﻨﺎﺋـﻲ ﻣﻴﺜﻴـﻞ ﺑﻨﺰﻳﻦ ﻭﻳﺴـﻤﻰ ﻣﻴﺘﺎ‪ -‬ﺯﺍﻳﻠـﲔ‪ -3،1 :‬ﺛﻨﺎﺋﻲ‬
‫‪CH3‬‬ ‫‪‬‬
‫‪‬‬
‫ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ ﻭﻳﺴـﻤﻰ ﺑـﺎﺭﺍ‪ -‬ﺯﺍﻳﻠﲔ ‪ -4،1 :‬ﺛﻨﺎﺋـﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬
‫ﻭ ﹸﻳﺴﺘﺨﺪﻡ ﺍﻟﺰﺍﻳﻠﲔ ﻣﺬﻳ ﹰﺒﺎ ﰲ ﺍﻟﺼﻨﺎﻋﺎﺕ ﺍﻵﺗﻴﺔ‪ :‬ﺍﻟﺪﻫﺎﻥ‪ ،‬ﺍﻟﻄﺒﺎﻋﺔ‪،‬‬
‫‪‬‬
‫‪41‬‬

‫ﻭﺗﹸﺮ ﱠﻗـﻢ ﺣﻠﻘـﺎﺕ ﺍﻟﺒﻨﺰﻳﻦ ﺍﳌﺘﻔﺮﻋﺔ ﲤﺎ ﹰﻣـﺎ ﻣﺜﻞ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﺍﳊﻠﻘﻴﺔ ﺍﳌﺘﻔﺮﻋـﺔ ﺑﻄﺮﻳﻘﺔ ﺗﻌﻄﻲ‬ ‫ﻼ ﻟﻠﺪﻫﻮﻥ ﻭﻣﻨﻈ ﹰﻔﺎ‬‫ﺃﻳﻀﺎ ﻣﺰﻳ ﹰ‬
‫ﺍﳌﻄﺎﻁ‪ ،‬ﺍﻟﻐﺮﺍﺀ‪ ،‬ﻭﺍﳉﻠﻮﺩ‪ .‬ﻭﻳﺴﺘﺨﺪﻡ ﹰ‬
‫ﺃﺻﻐـﺮ ﺃﺭﻗﺎﻡ ﳑﻜﻨﺔ ﳌﻮﺍﻗﻊ ﺍﳌﺠﻤﻮﻋـﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ ﺃﻭ )ﺍﻟﺘﻔﺮﻋﺎﺕ(‪ ،‬ﻛﲈ ﰲ ﺍﻟﺸـﻜﻞ ‪.8-27‬‬
‫ﺇﻥ ﺗﺮﻗﻴـﻢ ﺍﳊﻠﻘـﺔ ـ ﻛﲈ ﻫﻮ ﻣﺒﲔ ـ ﻳﻌﻄـﻲ ﺍﻷﺭﻗﺎﻡ ‪ ،2، 1‬ﻭ‪ 4‬ﳌﻮﺍﻗـﻊ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ‪.‬‬ ‫ﻟﻠﺸـﺤﻮﻡ؛ ﻭﻳﺪﺧـﻞ ﰲ ﺗﻜﻮﻳـﻦ ﻭﻗـﻮﺩ ﺍﻟﺴـﻴﺎﺭﺍﺕ ﻭﺍﻟﻄﺎﺋـﺮﺍﺕ‪.‬‬
‫ﻻ ﻋﲆ ﺍﻟﺼﻮﺭﺓ‪:‬‬‫ﻭﻷﻥ ﻛﻠﻤﺔ ﺇﻳﺜﻴﻞ ﺗﺄﰐ ﻗﺒﻞ ﻣﻴﺜﻴﻞ ﰲ ﺍﻟﱰﺗﻴﺐ ﺍﳍﺠﺎﺋﻲ‪ ،‬ﻟﺬﺍ ﻓﺈﳖﺎ ﺗﻜﺘﺐ ﺃﻭ ﹰ‬
‫‪-2‬ﺇﻳﺜﻴﻞ–‪ –4،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬ ‫ﻭﻳﺴـﺘﺨﺪﻡ ﰲ ﺗﺼﻨﻴﻊ ﺑﻌﺾ ﺍﻟﻌﻄﻮﺭ ﻭﺍﳌﻮﺍﺩ ﺍﻟﻄﺎﺭﺩﺓ ﻟﻠﺤﴩﺍﺕ‪.‬‬
‫‪‬ﻣﺎﺫﺍ ﺗﻌﻨﻲ ﺍﻟﺪﺍﺋﺮﺓ ﺩﺍﺧﻞ ﺍﳊﻠﻘـﺔ ﺍﻟﺴـﺪﺍﺳﻴـﺔ ﺍﻟﻈﺎﻫﺮﺓ ﰲ‬
‫‪   ‬‬
‫ﺍﻟﺸﻜﻞ ‪8-27‬؟‬ ‫ﻭﺗﺸـﻤﻞ ﺗﺄﺛﲑﺍﺗـﻪ ﺍﻟﺼﺤﻴﺔ ﺇﳊـﺎﻕ ﺍﻟـﴬﺭ ﺑﺎﻟﻌﲔ‪ ،‬ﻭﺗﺜﺒﻴـﻂ ﺃﺩﺍﺀ‬
‫ﺍﳉﻬﺎﺯ ﺍﻟﻌﺼﺒﻲ ﺍﳌﺮﻛﺰﻱ‪ ،‬ﻭﺿﻌﻒ ﻋﻤﻞ ﺍﻟﻜﻠﻴﺔ ﻭﺍﻟﻜﺒﺪ‪.‬‬
‫‪CH3‬‬ ‫‪    8-27 ‬‬
‫‪4‬‬
‫‪    ‬‬
‫‪5‬‬

‫‪6‬‬
‫‪3‬‬
‫‪2‬‬ ‫‪‬‬ ‫اﻟﺘﻘﻮﻳﻢ‬
‫‪CH2CH3‬‬
‫‪1‬‬
‫‪CH3‬‬

‫‪412‬‬
‫‪ ‬ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﻋﻤﻞ ﻗﺎﺋﻤﺔ ﺑﺎﺳـﺘﺨﺪﺍﻣﺎﺕ ﻛﻞ ﻣﻦ‬
‫ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪ .a‬ﺑﺎﺭﺍ‪ -‬ﺯﺍﻳﻠﲔ ﲢﻀﲑ ﺍﻟﺒﻮﻟﻴﺴﱰ‪.‬‬
‫‪ .b‬ﻧﻔﺜﺎﻟﲔ ﻃﺎﺭﺩ ﻟﻠﻌﺚ‪.‬‬
‫‪ .c‬ﺇﻧﺜﺮﺍﺳﲔ ﺻﻨﺎﻋﺔ ﺍﻷﺻﺒﺎﻍ‪ .‬‬

‫‪ ‬ﹸﺗﺸـﺎﺭﻙ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴﺖ‬

‫ﰲ ﺍﳊﻠﻘﺔ ﲨﻴﻌﻬﺎ‪.‬‬

‫‪162‬‬
 ‫‪84‬‬

‫‪‬‬ ‫‪CH2CH2CH3‬‬ ‫ﺳﻢ ﹼ‬

‫ﺍﳌﺮﻛﺐ ﺍﻷﺭﻭﻣﺎﰐ ﺍﻟﺘﺎﱄ‪.‬‬ ‫‪ ‬ﱢ‬

‫‪CH2CH2CH3‬‬ ‫‪ 1‬ﺗﺤﻠﻴﻞ اﻟﻤﺴﺄﻟﺔ‬

‫ﺳﻢ ﺍﳌﺮﻛﺐ ﺍﻷﺭﻭﻣﺎﰐ ﺍﻵﰐ‪.‬‬
‫‪ ‬ﱢ‬ ‫ﺃﺭﻭﻣﺎﺗﻴﺎ‪ ،‬ﺍﺗﺒﻊ ﺍﻟﻘﻮﺍﻋﺪ ﻟﺘﺴﻤﻴﺘﻪ‪.‬‬
‫ﹼﹰ‬ ‫ﻟﻘﺪ ﹸﺃﻋﻄﻴﺖ ﻣﺮﻛ ﹰﺒﺎ‬

‫ﺣﺴﺎب اﻟﻤﻄﻠﻮب‬ ‫‪2‬‬

‫‪CH 2CH 3‬‬ ‫ﺍﳋﻄﻮﺓ ‪ .1‬ﺭ ﹼﻗﻢ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﻹﻋﻄﺎﺀ ﺃﺻﻐﺮ ﺃﺭﻗﺎﻡ ﳑﻜﻨﺔ‪.‬‬
‫‪CH2CH2CH3‬‬ ‫‪CH2CH2CH3‬‬
‫‪1‬‬ ‫‪5‬‬
‫‪2‬‬ ‫‪4‬‬

‫‪3‬‬ ‫‪1‬‬
‫‪3‬‬ ‫‪CH2CH2CH3‬‬ ‫‪CH2CH2CH3‬‬
‫‪CH 2CH 3‬‬ ‫‪2‬‬

‫ﺇﻥ ﺍﻟﺮﻗﻤﲔ ‪ 1‬ﻭ ‪ 3‬ﻛﲈ ﺗﺮ￯ ﺃﺻﻐﺮ ﻣﻦ ﺍﻟﺮﻗﻤﲔ ‪ 1‬ﻭ ‪.5‬‬

‫‪CH 2CH 2CH 3‬‬
‫ﻟﺬﺍ ﻓﺈﻥ ﺍﻷﺭﻗﺎﻡ ﺍﻟﺘﻲ ﳚﺐ ﺍﺳﺘﺨﺪﺍﻣﻬﺎ ﻟﱰﻗﻴﻢ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻫﻲ ‪ 1‬ﻭ ‪.3‬‬
‫ﺍﳋﻄﻮﺓ ‪ .2‬ﺣﺪﹼ ﺩ ﺃﺳﲈﺀ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ‪ .‬ﺇﺫﺍ ﺗﻜﺮﺭﺕ ﺍﳌﺠﻤﻮﻋﺔ ﻧﻔﺴﻬﺎ ﺃﻛﺜﺮ ﻣﻦ ﻣﺮﺓ ﻓﺄﺿﻒ ﺍﻟﺒﺎﺩﺋﺔ ﺍﻟﺪﺍﻟﺔ ﻋﲆ ﻋﺪﺩ ﺍﳌﺠﻤﻮﻋﺎﺕ‬
‫‪‬‬ ‫ﺍﳌﻮﺟﻮﺩﺓ‪.‬‬
‫ﻫﺠﺎﺋﻴﺎ‪ ،‬ﻣﺴﺘﺨﺪ ﹰﻣﺎ ﺍﻟﻔﻮﺍﺻﻞ ﺑﲔ ﺍﻷﺭﻗﺎﻡ ﻭﺍﻟﴩﻃﺎﺕ ﺑﲔ ﺍﻷﺭﻗﺎﻡ ﻭﺍﻟﻜﻠﲈﺕ‪،‬‬
‫ﹼﹰ‬ ‫ﲨﻊ ﺍﻻﺳﻢ‪ ،‬ﻭﺭﺗﺐ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ‬ ‫ﺍﳋﻄﻮﺓ ‪ .3‬ﹼ‬
‫‪ –3،1‬ﺛﻨﺎﺋﻲ ﺇﻳﺜﻴﻞ–‪ –4‬ﺑﺮﻭﺑﻴﻞ ﺑﻨﺰﻳﻦ‬ ‫ﺛﻢ ﺍﻛﺘﺐ ﺍﻻﺳﻢ ﻋﲆ ﺍﻟﺼﻮﺭﺓ ‪ -3،1‬ﺛﻨﺎﺋﻲ ﺑﺮﻭﺑﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬

‫ﺗﻘﻮﻳﻢ اﺟﺎﺑﺔ‬ ‫‪3‬‬

‫ﹸﺭ ﹼﻗﻤﺖ ﺣﻠﻘﺔ ﺍﻟﺒﻨﺰﻳﻦ ﻟﺘﻌﻄﻲ ﺍﻟﺘﻔﺮﻋﺎﺕ ﺃﺻﻐﺮ ﳎﻤﻮﻋﺔ ﳑﻜﻨﺔ ﻣﻦ ﺍﻷﺭﻗﺎﻡ‪ ،‬ﹸ‬
‫ﻭﺣﺪﹼ ﺩﺕ ﺃﺳﲈﺀ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻟﺒﺪﻳﻠﺔ ﻋﲆ ﻧﺤ ﹴﻮ ﺻﺤﻴﺢ‪.‬‬
‫‪‬‬

‫‪‬‬ ‫ﺳﻢ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﺘﺎﻟﻴﺔ‪:‬‬

‫‪ .31‬ﹼ‬
‫‪CH3‬‬ ‫‪.c‬‬ ‫‪CH3‬‬ ‫‪.b‬‬ ‫‪CH2CH2CH3 .a‬‬
‫‪CH3‬‬ ‫‪CH2CH3‬‬

‫‪ .a .31‬ﺑﺮﻭﺑﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬ ‫‪CH2CH3‬‬

‫‪ –1‬ﺇﻳﺜﻴﻞ–‪ –2‬ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬ ‫‪.b‬‬ ‫‪  .32‬ﺍﺭﺳﻢ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﺮﻛﺐ ‪ -4،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬

‫‪ –1‬ﺇﻳﺜﻴﻞ– ‪ –3 ،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬ ‫‪.c‬‬

‫‪.32‬‬
‫‪CH 3‬‬

‫‪CH 3‬‬

‫‪‬ﺍﻃﻠﺐ ﺇﱃ ﻃﺎﻟﺒﲔ ﺃﺣﺪﳘﺎ ﺿﻤﻦ ﺍﳌﺴـﺘﻮ￯‪ ،‬ﻭﺍﻵﺧﺮ ﺩﻭﻥ‬

‫ﻣﻌﺎ‪ ،‬ﻭﺩﻉ ﺍﻟﻄﺎﻟﺐ ﺍﻷﻭﻝ ﻳﴩﺡ ﻟﺰﻣﻴﻠﻪ ﻛﻴﻔﻴﺔ ﺗﺴـﻤﻴﺔ‬‫ﺍﳌﺴـﺘﻮ￯ ﺃﻥ ﻳﻌﻤﻼ ﹰ‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﺧﻄﻮﺓ ﺧﻄﻮﺓ ﻣﺴـﺘﺨﺪ ﹰﻣﺎ ﺍﳌﺜـﺎﻝ ‪ ،8-4‬ﺛﻢ‬
‫ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﺎﻟﺐ ﺫﻱ ﺍﳌﺴـﺘﻮ￯ ﺍﳌﺘﺪﲏ ﺃﻥ ﻳـﴩﺡ ﻟﻠﻄﺎﻟﺐ ﺍﻟﺬﻱ ﺿﻤﻦ‬
‫ﺍﳌﺴﺘﻮ￯ ﺗﺴﻤﻴﺔ ﺍﳌﺮﻛﺐ ﺍﳌﻮﺟﻮﺩ ﲢﺖ ﻋﻨﻮﺍﻥ "ﻣﺜﺎﻝ ﰲ ﺍﻟﺼﻒ"‪ .‬‬

‫‪163‬‬
 ‫‪ .3‬اﻟﺘﻘﻮﻳﻢ‬
‫اﻟﺘﺤﻘﻖ ﻣﻦ اﻟﻔﻬﻢ‬
‫ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺇﻋﺪﺍﺩ ﻗﺎﺋﻤﺔ ﺑﺎﳋﺼﺎﺋـﺺ ﺍﻟﺘﻲ ﲤﻴﺰ ﺍﳌﺮﻛﺒﺎﺕ‬
‫‪‬‬

‫‪ ‬ﺷﺎﻉ ﺳﺎﺑ ﹰﻘﺎ ﺍﺳﺘﺨﺪﺍﻡ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ‪ ،‬ﻭﺑﺨﺎﺻﺔ ﺍﻟﺒﻨﺰﻳﻦ‬ ‫‪  8-28 ‬‬ ‫ﺍﻟﻌﻀﻮﻳـﺔ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﻋـﻦ ﺍﻷﻟﻴﻔﺎﺗﻴـﺔ ﻏـﲑ ﺍﳌﺸـﺒﻌﺔ‪ .‬ﺍﳌﺮﻛﺒـﺎﺕ‬
‫ﻭﺍﻟﺘﻮﻟﻮﻭﻳﻦ ﻭﺍﻹﻛﺰﺍﻳﻠﲔ‪ ،‬ﺑﻮﺻﻔﻬﺎ ﻣﺬﻳﺒﺎﺕ ﺻﻨﺎﻋﻴﺔ ﻭﳐﺘﱪﻳﺔ‪ ،‬ﺇﻻ ﺃﻥ ﺍﻻﺧﺘﺒﺎﺭﺍﺕ ﺃﻇﻬﺮﺕ‬ ‫‪‬‬
‫ﹴ‬
‫ﻋـﺎﻝ‬ ‫ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﻫـﻲ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺣﻠﻘﻴـﺔ ﺫﺍﺕ ﺛﺒـﺎﺕ‬
‫ﺍﳌﻌﺮﺿﲔ ﳍﺎ‬‫ﴐﻭﺭﺓ ﺍﳊﺪ ﻣﻦ ﺍﺳﺘﺨﺪﺍﻡ ﻫﺬﻩ ﺍﳌﺮﻛﺒﺎﺕ؛ ﻷﳖﺎ ﺗﺆﺛﺮ ﰲ ﺻﺤﺔ ﺍﻷﺷﺨﺎﺹ ﹼ‬ ‫‪ ‬‬
‫ﺑﺼﻮﺭﺓ ﻣﺘﻜﺮﺭﺓ‪ .‬ﻭﺗﺸﻤﻞ ﺍﳌﺨﺎﻃﺮ ﺍﻟﺼﺤﻴﺔ ﺍﳌﺮﺗﺒﻄﺔ ﻣﻊ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﺃﻣﺮﺍﺽ‬
‫ﺍﳉﻬﺎﺯ ﺍﻟﺘﻨﻔﴘ‪ ،‬ﻭﺍﳌﺸﺎﻛﻞ ﺍﳌﺘﻌﻠﻘﺔ ﺑﺎﻟﻜﺒﺪ‪ ،‬ﻭﺗﻠﻒ ﺍﳉﻬﺎﺯ ﺍﻟﻌﺼﺒﻲ‪ .‬ﻭﺑﺎﻹﺿﺎﻓﺔ ﺇﱃ ﻫﺬﻩ‬
‫‪‬‬
‫ﻭﻧﺸـﺎﻁ ﻛﻴﻤﻴﺎﺋﻲ ﺃﻗﻞ ﻣـﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﻟﻴﻔﺎﺗﻴﺔ ﻏﲑ ﺍﳌﺸـﺒﻌﺔ؛ ﻷﻥ‬
‫ﺍﳌﺨﺎﻃﺮ ﻓﺈﻥ ﺑﻌﺾ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﻣﻮﺍﺩ ﻣﴪﻃﻨﺔ‪ ،‬ﺃﻱ ﺗﺴﺒﺐ ﻣﺮﺽ ﺍﻟﴪﻃﺎﻥ‪.‬‬ ‫ﻋـﺪﻡ ﺍﻹﺷـﺒﺎﻉ ﰲ ﺍﳌﺮﻛﺒـﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﻳﺘﻀﻤـﻦ ﳎﻤﻮﻋـﺔ ﻣـﻦ‬
‫ﺗﻌﺮﻓﻬﺎ ﻫﻲ ﻣﺎﺩﺓ ﺃﺭﻭﻣﺎﺗﻴﺔ ﺍﻛﺘﺸﻔﺖ ﰲ ﺍﻟﻘﺮﻥ ﺍﻟﻌﴩﻳﻦ ﰲ‬
‫ﺗﻢ ﹼ‬‫ﺃﻭﻝ ﻣﺎﺩﺓ ﻣﴪﻃﻨﺔ ﹼ‬ ‫ﺇﻥ‬
‫ﺍﻹﻟﻜﱰﻭﻧـﺎﺕ ﺍﳊﺮﺓ ﺍﳊﺮﻛـﺔ ﹰ‬
‫ﻋﻮﺿﺎ ﻋـﻦ ﺭﻭﺍﺑﻂ ﺛﻨﺎﺋﻴـﺔ ﻣﻨﻔﺼﻠﺔ‬
‫‪80-873828-C810-22C‬‬
‫ﹺﺳﻨﺎﺝ ﺍﳌﺪﺍﺧﻦ‪ .‬ﻭﻗﺪ ﹸﻋﺮﻑ ﻣﻨﻈﻔﻮ ﺍﳌﺪﺍﺧﻦ ﰲ ﺑﺮﻳﻄﺎﻧﻴﺎ ﺑﺈﺻﺎﺑﺘﻬﻢ ﺑﺎﻟﴪﻃﺎﻥ ﺑﻤﻌﺪﻻﺕ‬
‫اﻟﻤﻄﻮﻳﺎت‬

‫ﺃﺩﺧﻞ ﻣﻌﻠﻮﻣﺎﺕ ﻣﻦ ﻫﺬﺍ ﺍﻟﻘﺴﻢ‬

‫ﻋﺎﻟﻴﺔ ﺟﺪﹼﹰ ﺍ‪ .‬ﻭﺍﻛﺘﺸﻒ ﺍﻟﻌﻠﲈﺀ ﺃﻥ ﺍﻟﺴﺒﺐ ﰲ ﺫﻟﻚ ﻳﻌﻮﺩ ﺇﱃ ﺍﳌﺮﻛﺐ ﺍﻷﺭﻭﻣﺎﰐ ﺑﻨﺰﻭﺑﺎﻳﺮﻳﻦ‬
‫ﺍﻟﻈﺎﻫﺮ ﰲ ﺍﻟﺸﻜﻞ ‪ ،8-28‬ﻭﻫﻮ ﻧﺎﺗﺞ ﺛﺎﻧﻮﻱ ﻋﻦ ﺍﺣﱰﺍﻕ ﺍﳌﺨﺎﻟﻴﻂ ﺍﳌﻌﻘﺪﺓ ﻣﻦ ﺍﳌﻮﺍﺩ‬
‫ﰲ ﻣﻄﻮﻳﺘﻚ‪.‬‬ ‫ﺗﺘﺠﻤﻊ ﻓﻴﻬﺎ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ‪ .‬‬
‫ﻭﻋﺮﻓﺖ ﹰ‬
‫ﺃﻳﻀﺎ ﺑﻌﺾ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﺍﳌﻮﺟﻮﺩﺓ‬ ‫ﺍﻟﻌﻀﻮﻳﺔ‪ ،‬ﻭﻣﻨﻬﺎ ﺍﳋﺸﺐ ﻭﺍﻟﻔﺤﻢ‪ .‬ﹸ‬
‫ﰲ ﺍﳉﺎﺯﻭﻟﲔ ﻋﲆ ﺃﳖﺎ ﻣﴪﻃﻨﺔ‪.‬‬
‫إﻋﺎدة اﻟﺘﺪرﻳﺲ‬
‫اﻟﺘﻘﻮﻳﻢ ‪8-5‬‬
‫ﻓﴪ ﺍﻟﺸﻜﻞ ﺍﻟﺒﻨﺎﺋﻲ ﻟﻠﺒﻨﺰﻳﻦ‪ ،‬ﻭﻛﻴﻒ ﳚﻌﻠﻪ ﻋﺎﱄ ﺍﻻﺳﺘﻘﺮﺍﺭ ﺃﻭ ﺍﻟﺜﺒﺎﺕ؟‬
‫اﻟﺮﺋﻴﺴﺔ ﹼ‬ ‫‪ .33‬اﻟﻔﻜﺮة‬ ‫اﻟﺨﻼﺻﺔ‬ ‫ﺍﺭﺳـﻢ ﻧﻤﻮﺫﺝ ﻛﻴﻜـﻮﱄ ﻟﻠﺒﻨﺰﻳﻦ ﻭﺍﻟﻨﻤﻮﺫﺝ ﺍﳊـﺎﱄ ﺟﻨ ﹰﺒﺎ ﺇﱃ ﺟﻨﺐ‬
‫ﻓﴪ ﻛﻴﻒ ﲣﺘﻠﻒ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﻋﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﻟﻴﻔﺎﺗﻴﺔ؟‬ ‫ﲢﺘــــﻮﻱ ﺍﳍﻴــﺪﺭﻭﻛـﺮﺑﻮﻧــﺎﺕ ‪ .34‬ﹼ‬
‫ﺍﻷﺭﻭﻣـﺎﺗـﻴـﺔ ﻋﲆ ﺣﻠﻘـﺎﺕ ﺑﻨﺰﻳﻦ ‪ .35‬ﺻﻒ ﺧﻮﺍﺹ ﺍﻟﺒﻨﺰﻳﻦ ﺍﻟﺘﻲ ﺟﻌﻠﺖ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﲔ ﻳﻨﻔﻮﻥ ﺍﺣﺘﲈﻟﻴﺔ ﻛﻮﻧﻪ ﺃﻟﻜﻴﻨﹰﺎ ﺫﺍ ﺭﻭﺍﺑﻂ ﺛﻨﺎﺋﻴﺔ‬ ‫ﻋﲆ ﺍﻟﺴـﺒﻮﺭﺓ‪ .‬ﺛﻢ ﺍﺳـﺄﻝ‪ :‬ﺃﻱ ﺍﻟﺸـﻜﻠﲔ ﻫﻮ ﲤﺜﻴﻞ ﺃﻓﻀﻞ ﻟﻠﺸﻜﻞ‬
‫ﻣﺘﻌﺪﺩﺓ‪.‬‬
‫ﺳﻢ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﺘﺎﻟﻴﺔ‪:‬‬
‫‪ .36‬ﱢ‬
‫ﺑﻮﺻـﻔﻬـﺎ ﺟـــﺰ ﹰﺀﺍ ﻣــﻦ ﺻﻴـﻐﻬﺎ‬
‫ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫ﺍﻟﻮﺍﻗﻌـﻲ ﻭﺍﳊﻘﻴﻘـﻲ ﻟﻠﺒﻨﺰﻳـﻦ؟ ﻭﳌـﺎﺫﺍ؟ ﺇﻥ ﺍﻟﻨﻤـﻮﺫﺝ ﺍﳊـﺎﱄ ﻫﻮ‬
‫ﺍﻷﻓﻀـﻞ؛ ﻷﻧﻪ ﻳﻤﺜـﻞ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺍﳊﺮﺓ ﺍﳊﺮﻛﺔ ﺍﳌﺘﺸـﺎﺭﻛﺔ ﺑﲔ‬
‫‪CH2CH2CH3 .b‬‬ ‫‪.a‬‬ ‫ﺗـــﺘـــﻮﺯﻉ ﺍﻹﻟـــﻜـــﱰﻭﻧـــﺎﺕ ﰲ‬
‫‪CH3‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﻋﲆ‬

‫‪CH3CH2‬‬ ‫‪CH3‬‬
‫ﺍﳊﻠﻘﺔ ﻛﺎﻣﻠﺔ ﺑﺎﻟﺘﺴﺎﻭﻱ‪.‬‬
‫ﲨﻴﻊ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴـﺖ ﰲ ﺍﳊﻠﻘﺔ‪ .‬ﻛﲈ ﻳﻤﻜﻦ ﺍﺳﺘﺨﺪﺍﻡ ﻫﺬﺍ‬
‫‪CH2CH3‬‬
‫ﻓﴪ ﳌﺎﺫﺍ ﻛﺎﻧﺖ ﺍﻟﻌﻼﻗﺔ ﺑﲔ ﺍﻟﺒﻨﺰﻭﺑﺎﻳﺮﻳﻦ‪ ،‬ﻭﺍﻟﴪﻃﺎﻥ ﻭﻃﻴﺪﺓ؟‬
‫‪ .37‬ﹼ‬ ‫ﺍﻟﻨﻤﻮﺫﺝ ﻟﺘﻔﺴﲑ ﺍﻟﺜﺒﺎﺕ ﺍﻟﻌﺎﱄ ﻟﻠﺒﻨﺰﻳﻦ ﺑﻄﺮﻳﻘﺔ ﺃﻓﻀﻞ ﻣﻦ ﻧﻤﻮﺫﺝ‬
‫ﻛﻴﻜﻮﱄ‪ .‬‬

‫اﻟﺘﻘﻮﻳﻢ ‪8-5‬‬ ‫اﻟﺘﻮﺳﻊ‬

‫‪ .33‬ﺗﺘﻮﺯﻉ ﺃﺯﻭﺍﺝ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﰲ ﺍﻟﺒﻨﺰﻳﻦ ﻭﺗﺘﺸـﺎﺭﻙ ﰲ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‬ ‫ﻛ ﱢﻠـﻒ ﺍﻟﻄـﻼﺏ ﺑﺎﻟﺒﺤﺚ ﻭﺗﻔﺴـﲑ ﻋـﺪﻡ ﺍﻋﺘﺒﺎﺭ ﻧﻤـﻮﺫﺝ ﻛﻴﻜﻮﱄ‬
‫ﻛﻴﻤﻴﺎﺋﻴﺎ ﻷﻧﻪ‬
‫ﹼﹰ‬ ‫ﺍﻟﺴﺖ ﲨﻴﻌﻬﺎ ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﳊﻠﻘﺔ‪ .‬ﺇﻥ ﺍﻟﺒﻨﺰﻳﻦ ﻏﲑ ﻧﺸﻂ‬ ‫ﻣﺜﺎﻟﻴﺎ ﻟﻨﻤـﻂ ﺍﻟﱰﺍﺑﻂ ﺍﳊﻘﻴﻘـﻲ ﰲ ﺍﻟﺒﻨﺰﻳﻦ‪ .‬ﺭﻭﺍﺑﻂ‬
‫ﻼ ﹼﹰ‬ ‫ﻟﻠﺒﻨﺰﻳـﻦ ﲤﺜﻴ ﹰ‬
‫ﻣﻦ ﺍﻟﺼﻌﺐ ﺳﺤﺐ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺑﻌﻴﺪﹰ ﺍ ﻋﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﺴﺖ‪.‬‬ ‫ﻛﺮﺑـﻮﻥ – ﻛﺮﺑـﻮﻥ ﰲ ﻧﻤﻮﺫﺝ ﻛﻴﻜـﻮﱄ ﳍﺎ ﺃﻃﻮﺍﻝ ﻭﻗـﻮ￯ ﳐﺘﻠﻔﺔ‪،‬‬
‫‪ .34‬ﲢﺘـﻮﻱ ﺍﳌﺮﻛﺒـﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﻋـﲆ ﺣﻠﻘـﺎﺕ ﰲ ﺑﻨﺎﺋﻬـﺎ‪ ،‬ﻭﲢﺘـﻮﻱ‬ ‫ﺣﻴﺚ ﺗﻜﻮﻥ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﺃﻗﴫ ﻭﺃﻗﻮ￯ ﻣﻦ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻷﺣﺎﺩﻳﺔ‪.‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﻟﻴﻔﺎﺗﻴﺔ ﻋﲆ ﺳﻼﺳﻞ ﻣﺴﺘﻘﻴﻤﺔ ﺃﻭ ﻣﺘﻔﺮﻋﺔ‪.‬‬ ‫ﻭﻫـﺬﺍ ﻻ ﻳﺪﻋﻤﻪ ﺍﻟﺪﻟﻴﻞ ﺍﳌﺨﺘﱪﻱ ﺍﻟﺬﻱ ﻳﺒـﲔ ﺃﻥ ﺍﻟﺮﻭﺍﺑﻂ ﲨﻴﻌﻬﺎ‬
‫ﲑﺍ ﻣﻨـﻪ ﻟﻸﻟﻜﻴﻨﺎﺕ ﺫﺍﺕ ﺍﻟﺮﻭﺍﺑﻂ‬ ‫ﻣﺘﺴﺎﻭﻳﺔ ﺍﻟﺘﻮﺯﻳﻊ ﺍﻹﻟﻜﱰﻭﲏ‪ .‬‬
‫‪ .35‬ﺍﻟﻨﺸـﺎﻁ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ ﻟﻠﺒﻨﺰﻳﻦ ﺃﻗﻞ ﻛﺜ ﹰ‬
‫ﻛﻴﻤﻴﺎﺋﻴﺎ‪.‬‬
‫ﹼﹰ‬ ‫ﺍﻟﺜﻨﺎﺋﻴﺔ ﺍﳌﺘﻌﺪﺩﺓ‪ ،‬ﻭﺍﻟﺘﻲ ﺗﻜﻮﻥ ﻋﺎﺩﺓ ﻏﲑ ﺛﺎﺑﺘﺔ‬
‫‪-1 .a .36‬ﺇﻳﺜﻴﻞ–‪ -5،3‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬
‫‪–1‬ﺇﻳﺜﻴﻞ–‪-4‬ﺑﺮﻭﺑﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬ ‫‪.b‬‬

‫‪ .37‬ﻛﺎﻥ ﺍﻟﺒﻨﺰﻭﺑﺎﻳﺮﻳـﻦ ﺃﻭﻝ ﻣـﺎﺩﺓ ﻣﴪﻃﻨـﺔ ﻣﻌﺮﻭﻓـﺔ‪ ،‬ﻭﻛﺎﻥ ﺍﻟﺘﻌﺮﺽ ﳍﺎ‬

‫ﻣﺮﺗﺒﻄـﺎ ﻣﻊ ﻧﻮﻉ ﺍﳌﻬﻨﺔ‪ .‬ﻭﺑﻌﺪ ﺃﻥ ﺍﻛﺘﺸـﻒ ﺃﳖﺎ ﻣـﺎﺩﺓ ﻣﴪﻃﻨﺔ ﹸﺃ ﹺﺧﺬﺕ‬
‫ﹰ‬
‫ﺍﻻﺣﺘﻴﺎﻃـﺎﺕ ﻭﺍﻹﺟﺮﺍﺀﺍﺕ ﳊﲈﻳﺔ ﺍﻟﻌﲈﻝ‪ .‬ﻭﻗﺪ ﺩﻓﻊ ﻫﺬﺍ ﺍﻻﻛﺘﺸـﺎﻑ‬
‫ﺍﻟﻌﻠـﲈﺀ ﻭﺍﳌﺨﺘﺼـﲔ ﰲ ﳎـﺎﻝ ﺍﻟﻄﺐ ﺇﱃ ﺍﻟﺒﺤﺚ ﻋﻦ ﻣـﻮﺍﺩ ﺃﺧﺮ￯ ﻗﺪ‬
‫ﺗﻜﻮﻥ ﺫﺍﺕ ﺃﺧﻄﺎﺭ ﳏﺘﻤﻠﺔ ﻋﲆ ﺍﻟﻌﲈﻝ‪.‬‬
‫‪164‬‬
 ‫ ﻛﻴﻒ ﻳﻌﻤﻞ ﺟﻬﺎز ﻫﻀﻢ اﻟﻤﻴﺜﺎن؟‬:‫ﺗﺤﻮﻳﻞ اﻟﻤﺨﻠﻔﺎت إﻟﻰ ﻃﺎﻗﺔ‬
‫ﻳﺄﻣﻞ ﺍﳌﺘﺨﺼﺼﻮﻥ ﺃﻥ ﻳﺴﺎﻫﻢ ﻣﺮﰊ ﺍﳊﻴﻮﺍﻧﺎﺕ ﺍﻷﻟﻴﻔﺔ ﰲ ﺗﻘﺪﻳﻢ ﺍﳌﺨﻠﻔﺎﺕ‬
‫ﳛﻮﻝ ﺍﳌﻮﺍﺩ ﺍﻟﻌﻀﻮﻳﺔ ﺇﱃ ﻃﺎﻗﺔ ﻣﻔﻴﺪﺓ؛ ﺇﺫ‬
‫ﺍﻟﻌﻀﻮﻳﺔ ﳊﻴﻮﺍﻧﺎﲥﻢ ﳌﴩﻭﻉ ﲡﺮﻳﺒﻲ ﹼ‬
-(‫ﳛﻮﻝ ﺟﻬﺎﺯ ﻫﻀﻢ ﺍﳌﻴﺜﺎﻥ ﺍﳌﺨﻠﻔﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﺇﱃ ﻏﺎﺯ ﺑﻴﻮﻟﻮﺟﻲ )ﺣﻴﻮﻱ‬
‫اﻟﻬﺪف‬ ‫ﻳﺰﻭﺩ ﺑﺎﻟﻄﺎﻗﺔ‬
‫ ﻭﺣﺮﻕ ﺍﳌﻴﺜﺎﻥ ﹼ‬،‫ﻭﻫﻮ ﺧﻠﻴﻂ ﻣﻦ ﺍﳌﻴﺜﺎﻥ ﻭﺛﺎﲏ ﺃﻛﺴﻴﺪ ﺍﻟﻜﺮﺑﻮﻥ‬
.‫ﺍﻟﻼﺯﻣﺔ‬

‫ﻭﻳﻘﻮﻣـﻮﻥ ﺍﻟﺘﺄﺛـﲑ ﺍﻟﺒﻴﺌـﻲ ﻹﻧﺘـﺎﺝ‬

‫ ﹼ‬،‫ﺳـﻴﺼﻒ ﺍﻟﻄـﻼﺏ ﺍﻟﻌﻤﻠﻴـﺔ‬    4

‫ ﺑﲈ ﰲ ﺫﻟﻚ‬،‫ﺍﻟﻐـﺎﺯ ﺍﳊﻴﻮﻱ ﻣـﻦ ﺗﻔﻜﻴﻚ ﺍﳌﻮﺍﺩ ﺍﻟﻌﻀﻮﻳـﺔ ﻭﲢﻠﻴﻠﻬﺎ‬

         
 


.‫ﺍﳌﺨﻠﻔﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﺍﻟﺘﻲ ﲣﻠﻔﻬﺎ ﺍﳊﻴﻮﺍﻧﺎﺕ ﺍﻷﻟﻴﻔﺔ‬      1
 
 
         

‫اﻟﺨﻠﻔﻴﺔ‬
      
         
       
      
 

‫ﺃ ﹼﺩ￯ ﺍﺭﺗﻔـﺎﻉ ﺗﻜﺎﻟﻴﻒ ﺍﻟﻄﺎﻗﺔ ﻭﺍﻧﺨﻔﺎﺽ ﳐﺰﻭﳖﺎ ﺍﻟﺪﻭﺭﻱ ﺇﱃ ﺩﻓﻊ‬ 

‫ﺍﳊﻜﻮﻣـﺎﺕ ﺇﱃ ﺩﺭﺍﺳـﺔ ﻣﺼـﺎﺩﺭ ﺍﻟﻄﺎﻗـﺔ ﺍﻟﺒﺪﻳﻠﺔ ﺑـﲈ ﰲ ﺫﻟﻚ ﻏﺎﺯ‬


.‫ﺍﳌﻴﺜﺎﻥ‬




‫ ﻣﻨﺘﺠﺔ ﻏﺎﺯ ﺍﳌﻴﺜﺎﻥ ﺃﺣﺪ ﻏﺎﺯﺍﺕ‬،‫ﲢﻠﻞ ﺍﻟﺒﻜﺘﲑﻳـﺎ ﺭﻭﺙ ﺍﳊﻴﻮﺍﻧﺎﺕ‬ 



‫ ﻭﻳﺴـﻤﺢ ﺟﻬﺎﺯ ﻫﻀـﻢ ﺍﳌﻴﺜﺎﻥ ﺑﺈﻧﺘﺎﺝ‬.‫ﺍﻟﺪﻓﻴﺌـﺔ ﺇﱃ ﺍﻟﻐﻼﻑ ﺍﳉﻮﻱ‬ 

        2

.‫ ﻭﲨﻌﻪ ﻭﺍﺳﺘﺨﺪﺍﻣﻪ‬،‫ﺍﳌﻴﺜﺎﻥ‬            3
    %100    
  

     
    
      
   37 °C35 °C 
    

‫اﺳﺘﺮاﺗﻴﺠﻴﺎت اﻟﺘﺪرﻳﺲ‬
     
 
‫ﺍﺑﺤﺚ ﺍﻋﻤﻞ ﻛﺘﻴ ﹰﺒﺎ ﺗﺒﲔ ﻓﻴﻪ ﻛﻴﻔﻴﺔ ﺇﻧﺘﺎﺝ ﺍﻟﻐﺎﺯ ﻣﻦ ﺍﳌﺨﻠﻔﺎﺕ‬
.‫ﺍﻟﻌﻀﻮﻳﺔ‬
‫• ﺍﺳـﺘﺨﺪﻡ ﺍﳌﺨﻄﻂ ﻟﺘﺤﺪﻳـﺪ ﺃﳘﻴﺔ ﻛﻞ ﺣﺎﻟـﺔ ﻓﻴﺰﻳﺎﺋﻴﺔ ﰲ ﻋﻤﻠﻴﺔ‬
.‫ﺇﻧﺘﺎﺝ ﺍﻟﻐﺎﺯ ﺍﳊﻴﻮﻱ‬
‫• ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﺒﺎﺩﻝ ﺍﻷﻓﻜﺎﺭ ﺣﻮﻝ ﻣﺰﺍﻳﺎ ﺍﺳـﺘﺨﺪﺍﻡ ﺟﻬﺎﺯ‬
.‫ﻫﻀﻢ ﺍﳌﻴﺜﺎﻥ ﻋﲆ ﺃﻧﻪ ﻣﺼﺪﺭ ﻟﻠﻄﺎﻗﺔ‬



‫ ﳚـﺐ ﺃﻥ ﺗﱪﺯ ﻧـﴩﺍﺕ ﺍﻟﻄـﻼﺏ ﺍﻟﺴـﲈﺕ ﺍﻹﳚﺎﺑﻴﺔ‬

.‫ﻣﺼﺪﺭﺍ ﻟﻠﻄﺎﻗﺔ‬
‫ﹰ‬ ‫ﻹﻧﺘﺎﺝ ﺍﻟﻐﺎﺯ ﺍﳊﻴﻮﻱ ﻭﺍﺳﺘﺨﺪﺍﻣﻪ ﺑﻮﺻﻔﻪ‬

165
 ‫‪‬‬
‫‪‬‬
‫‪ ‬ﺩﻋـﺖ ﺍﳊﺎﺟـﺔ ﺇﱃ ﺗﻐﻴﲑ ﺃﺣـﺪ ﺻﲈﻣﺎﺕ‬
‫‪‬‬
‫ﳏﴬ ﺍﳌﺨﺘﱪ ﺇﻥ ﺍﻟﻐﺎﺯ ﺍﳌﺴـﺘﻌﻤﻞ ﻫﻮ ﻏﺎﺯ‬ ‫ﺍﻟﻐﺎﺯ ﰲ ﺍﳌﺨﺘﱪ‪ .‬ﻓﻘﺎﻝ ﱢ‬
‫ﺍﻟﱪﻭﺑـﺎﻥ‪ ،‬ﻋـﲆ ﺣﲔ ﻗﺎﻝ ﺍﳌﻌﻠـﻢ ﺇﻥ ﺍﻟﻐﺎﺯ ﻫﻮ ﺍﻟﻐـﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﺃﻭ‬
‫ﻏﺎﺯ ﺍﳌﻴﺜﺎﻥ‪ .‬ﺍﺳﺘﻌﻤﻞ ﺍﻟﻄﺮﺍﺋﻖ ﺍﻟﻌﻠﻤﻴﺔ ﻟﻠﻔﺼﻞ ﺑﻴﻨﻬﲈ‪.‬‬
‫‪‬‬
‫‪ ‬ﺃﻱ ﻧـﻮﻉ ﻣـﻦ ﻏـﺎﺯﺍﺕ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﻳﺴـﺘﻌﻤﻞ ﰲ ﳐﺘﱪ‬
‫ﺍﻟﻌﻠﻮﻡ؟‬
‫‪‬ﺣﺼﺔ ﻭﺍﺣﺪﺓ‬
‫‪‬‬
‫• ﻗﺎﺭﻭﺭﺓ ﲨﻊ ﺍﻟﻐﺎﺯﺍﺕ ﲢﺖ‬ ‫• ﺑﺎﺭﻭﻣﻴﱰ‬ ‫‪‬ﺍﳊﺼﻮﻝ ﻋـﲆ ﺍﳌﻌﻠﻮﻣﺎﺕ ﻭﲢﻠﻴﻠﻬﺎ‪ ،‬ﺗﻄﺒﻴﻖ‬
‫ﺍﻟﺴﻮﺍﺋﻞ‪.‬‬
‫‪ .8‬ﺳﺠﻞ ﻛﺘﻠﺔ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺍﳌﻤﻠﻮﺀﺓ ﺑﺎﻟﻐﺎﺯ‪.‬‬
‫‪ .9‬ﺿـﻊ ﺍﻟﻘـﺎﺭﻭﺭﺓ ﺩﺍﺧﻞ ﺻﻨـﺪﻭﻕ ﺳـﺤﺐ ﺍﻟﻐـﺎﺯﺍﺕ ﻭﺍﻧﺰﻉ‬
‫• ﻣﻘﻴﺎﺱ ﺣﺮﺍﺭﺓ )ﺛﲑﻣﻮﻣﱰ(‬
‫• ﻗــﺎﺭﻭﺭﺓ ﻣﴩﻭﺑﺎﺕ ﻏﺎﺯﻳﺔ • ﳐﺒﺎﺭ ﻣﺪﺭﺝ ﺳﻌﺔ ‪100 ml‬‬ ‫ﺍﳌﻔﺎﻫﻴﻢ‪ ،‬ﺍﻟﻘﻴﺎﺱ‪ ،‬ﺍﺳﺘﺨﺪﺍﻡ ﺍﻷﻋﺪﺍﺩ‪ ،‬ﺍﻟﺘﺤﻠﻴﻞ ﻭﺍﻻﺳﺘﻨﺘﺎﺝ‪.‬‬
‫ﺍﻟﻐﻄـﺎﺀ ﻭﺃﺧـﺮﺝ ﺍﻟﻐـﺎﺯ ﲨﻴﻌـﻪ ﺑﺎﻟﻀﻐـﻂ ﻋـﲆ ﺟﻮﺍﻧـﺐ‬ ‫ﺳﻌﺘﻬﺎ ‪ ،1 L‬ﻭﺃﺧﺮ￯ ﺳﻌﺘﻬﺎ • ﻣﻴﺰﺍﻥ )‪(0.01g‬‬
‫ﺍﻟﻘـﺎﺭﻭﺭﺓ‪ .‬ﺛﻢ ﺍﻣﻸ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺑﺎﳌﺎﺀ ﻭﺳـﺠﻞ ﺣﺠﻤﻪ ﺑﻮﺿﻌﻪ‬ ‫• ﳏﺎﺭﻡ ﻭﺭﻗﻴﺔ‬ ‫‪ 2 L‬ﺑﻐﻄﺎﺀ‪.‬‬ ‫‪‬ﻭﺍﻓﻖ ﻋﲆ ﻧﲈﺫﺝ ﺍﻟﺴﻼﻣﺔ ﰲ ﺍﳌﺨﺘﱪ ﻗﺒﻞ‬
‫ﰲ ﺍﳌﺨﺒﺎﺭ ﺍﳌﺪﺭﺝ‪.‬‬ ‫• ﺃﻧﺎﺑﻴﺐ ﻣﻄﺎﻃﻴﺔ‬
‫ﻧﻈﻒ ﻣـﻜﺎﻥ ﺍﻟﻌﻤﻞ‬ ‫‪ .10‬ﺍﻟﻨﻈﺎﻓـﺔ ﻭﺍﻟﺘﺨﻠـﺺ ﻣـﻦ ﺍﻟﻨﻔﺎﻳـﺎﺕ ﹼ‬ ‫‪‬‬ ‫ﻭﺫﻛـﺮ ﺍﻟﻄﻼﺏ ﺑﴬﻭﺭﺓ ﺇﻗﻔـﺎﻝ ﺍﻟﺼﲈﻣﺎﺕ ﺑﻌﺪ‬ ‫ﺑـﺪﺀ ﺍﻟﻌﻤﻞ‪ .‬ﹼ‬
‫ﺍﻻﺭﺷﺎﺩﺍﺕ‪F A G .‬‬
‫ﺑﺤﺴﺐ‪BAH ACB I BD‬‬ ‫ﺍﻟﺴﻮﺍﺋﻞ‬
‫ﲨﻊ ﺍﻟﻐﺎﺯ ﻭﺗﻨﻈﻴﻒ ﺍﻧﺴﻜﺎﺑﺎﺕ ﺍﳌﺎﺀ‪.‬‬
‫‪A‬‬ ‫‪B‬‬ ‫‪C‬‬ ‫‪D‬‬ ‫‪E‬‬ ‫‪CJ CE‬‬‫‪ADK DF‬‬
‫‪BEL EC‬‬
‫‪G‬‬‫ﺍﺣﻔﻆ‪FM FHDGN‬‬‫ﻟﻼﺷﺘﻌﺎﻝ‪IO ،‬‬
‫‪GEH‬‬ ‫‪HJFPI IK‬‬‫ﻗﺎﺑﻠﺔ ‪GJ‬‬
‫‪K‬ﻣﺎﺩﺓ‪JHLK‬‬
‫ﺍﻟﻜﺤﻮﻻﺕ‪MIL‬‬
‫‪N‬‬
‫‪LJM M‬‬ ‫‪K‬‬
‫‪ON‬‬ ‫‪NPOL OM‬‬
‫‪P‬‬ ‫‪PN‬‬ ‫‪O‬‬ ‫‪P‬‬
‫‪‬‬ ‫ﻭﺍﻷﺑﺨﺮﺓ ﺑﻌﻴﺪﺍ ﻋﻦ ﻣﺼﺎﺩﺭ ﺍﻟﻠﻬﺐ ﻭﺍﻟﴩﺭ‪.‬‬
‫‪ .1‬ﺟﺪ ﻗﻴﻤﺔ ﻛﺜﺎﻓﺔ ﺍﳍﻮﺍﺀ ﲢﺖ ‪ 1 atm‬ﻭﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ‪20 oC‬‬ ‫‪‬‬
‫ﺗﺴﺎﻭﻱ ‪ .1.205 g/L‬ﻭﺍﺳﺘﻌﻤﻞ ﺣﺠﻢ ﺍﻟﻘﺎﺭﻭﺭﺓ ﳊﺴﺎﺏ‬
‫ﻛﺘﻠﺔ ﺍﳍﻮﺍﺀ ﰲ ﺍﻟﺰﺟﺎﺟﺔ‪.‬‬
‫‪ .1‬ﺍﻗﺮﺃ ﻧﻤﻮﺫﺝ ﺍﻟﺴﻼﻣﺔ ﻛﺎﻣ ﹰ‬
‫ﻼ‪.‬‬
‫‪ .2‬ﺻﻞ ﺃﻧﺒﻮﺏ ﲨﻊ ﺍﻟﻐﺎﺯ ﺑﻤﺼﺪﺭ ﺍﻟﻐﺎﺯ ﰲ ﺍﳌﺨﺘﱪ ﻭﻗﺎﺭﻭﺭﺓ‬
‫‪‬‬
‫ﻻ ﻳﻤﻜﻦ ﲡﻨﺐ ﺑﻘﺎﺀ ﺑﻌﺾ ﺍﳌﺎﺀ ﻋﲆ ﺟﻮﺍﻧﺐ ﺍﻟﻘﺎﺭﻭﺭﺓ‪ ،‬ﻟﺬﺍ ﺍﻃﻠﺐ‬
‫‪ .2‬ﺍﺣﺴﺐ ﻛﺘﻠﺔ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺍﻟﻔﺎﺭﻏﺔ‪ ،‬ﻭﻛﺘﻠﺔ ﺍﻟﻐﺎﺯ ﻓﻴﻬﺎ‪ ،‬ﻭﺍﺳﺘﻌﻤﻞ‬ ‫ﲨﻊ ﺍﻟﻐﺎﺯﺍﺕ‪ .‬ﺛﻢ ﺍﻣﻸ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺑﺎﳌﺎﺀ ﻭﺍﻓﺘﺢ ﺻﲈﻡ ﺍﻟﻐﺎﺯ‬
‫ﺣﺠﻢ ﺍﻟﻐﺎﺯ ﻭﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ﺍﳌﺎﺀ ﻭﺍﻟﻀﻐﻂ ﺍﳉﻮﻱ ﻭﻗﺎﻧﻮﻥ‬ ‫ﺑﺮﻓﻖ‪ ،‬ﻭﺩﻉ ﺍﻟﻐﺎﺯ ﳛﻞ ﳏﻞ ﺍﳌﺎﺀ ﰲ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺑﻌﺪ ﺍﺧﺮﺍﺝ‬
‫ﻫﺰ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺑﻘﻮﺓ ﻹﺧﺮﺍﺝ ﻣﺎ ﺑﺪﺍﺧﻠﻬﺎ ﻣﻦ ﺍﳌﺎﺀ‪.‬‬
‫ﺇﱃ ﺍﻟﻄﻼﺏ ﹾ‬
‫ﺍﻟﻐﺎﺯ ﺍﳌﺜﺎﱄ ﰲ ﺣﺴﺎﺏ ﻋﺪﺩ ﻣﻮﻻﺕ ﺍﻟﻐﺎﺯ ﺍﻟﺬﻱ ﺗﻢ ﲨﻌﻪ‪.‬‬ ‫ﺍﳍﻮﺍﺀ ﻣﻦ ﺍﻷﻧﺒﻮﺏ‪.‬‬
‫ﺃﻳﻀﺎ ﻛﺘﻠﺔ ﺍﻟﻐﺎﺯ ﻭﻋﺪﺩ ﺍﳌﻮﻻﺕ ﰲ ﺣﺴﺎﺏ ﺍﻟﻜﺘﻠﺔ‬ ‫ﻭﺍﺳﺘﻌﻤﻞ ﹰ‬
‫‪ .3‬ﺳﺠﻞ ﻛﺘﻠﺔ ﻗﺎﺭﻭﺭﺓ ﺍﳌﴩﻭﺑﺎﺕ ﺍﻟﻐﺎﺯﻳﺔ ﺍﳉﺎﻓﺔ ﻣﻊ ﺍﻟﻐﻄﺎﺀ‪،‬‬
‫ﺍﳌﻮﻟﻴﺔ ﻟﻠﻐﺎﺯ‪.‬‬
‫‪ ‬ﻳﺘﻜﻮﻥ ﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ ﰲ ﺍﻟﻮﻻﻳﺎﺕ ﺍﳌﺘﺤﺪﺓ‬
‫ﻭﺳﺠﻞ ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ ﻭﺍﻟﻀﻐﻂ‪.‬‬
‫‪ .3‬ﺍﺳﺘﻨﺘﺞ ﻛﻴﻒ ﺗﻘﺎﺭﻥ ﺑﲔ ﺍﻟﻜﺘﻠﺔ ﺍﳌﻮﻟﻴﺔ ﺍﳌﺤﺴﻮﺑﺔ ﻭﺍﻟﻜﺘﻠﺔ‬
‫‪ .4‬ﺍﻣﻸ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺑﺎﳌﺎﺀ ﻭﺃﻏﻠﻘﻬﺎ ﺑﺈﺣﻜﺎﻡ ﳌﻨﻊ ﺩﺧﻮﻝ ﺍﳍﻮﺍﺀ‪.‬‬
‫ﺍﳌﻮﻟﻴﺔ ﻟﻠﻤﻴﺜﺎﻥ‪ ،‬ﺍﻹﻳﺜﺎﻥ‪ ،‬ﻭﺍﻟﱪﻭﺑﺎﻥ؟ ﺍﺳﺘﻨﺘﺞ ﻧﻮﻉ ﺍﻟﻐﺎﺯ ﰲ‬
‫ﺍﻷﻣﺮﻳﻜﻴـﺔ ﻣـﻦ‪ 85% :‬ﻣﻴﺜـﺎﻥ‪ 9% ،‬ﺇﻳﺜـﺎﻥ‪ 3% ،‬ﺑﺮﻭﺑﺎﻥ‪3% ،‬‬
‫ﺍﻟﻘﺎﺭﻭﺭﺓ‪.‬‬ ‫‪ .5‬ﺿﻊ ﻣﻘﻴﺎﺱ ﺍﳊﺮﺍﺭﺓ )ﺛﲑﻣﻮﻣﱰ( ﰲ ﻣﺎﺀ ﻭﻋﺎﺀ ﺟﺎﻣﻊ ﺍﻟﻐﺎﺯﺍﺕ‪،‬‬
‫ﻭﺿﻊ ﺍﻟﻘﺎﺭﻭﺭﺓ ﻓﻮﻗﻪ ﺛﻢ ﺍﻧﺰﻉ ﺍﻟﻐﻄﺎﺀ ﻣﻊ ﺇﺑﻘﺎﺀ ﺍﻟﻔﺘﺤﺔ ﲢﺖ‬
‫‪ .4‬ﲢﻠﻴﻞ ﺍﳋﻄﺄ‪ .‬ﺍﻗﱰﺡ ﻣﺼﺎﺩﺭ ﻟﻸﺧﻄﺎﺀ ﰲ ﻫﺬﻩ ﺍﻟﺘﺠﺮﺑﺔ‪.‬‬

‫‪‬‬
‫ﺍﳌﺎﺀ‪ ،‬ﻭﺿﻊ ﻓﻮﻫﺔ ﺍﻟﻘﺎﺭﻭﺭﺓ ﻓﻮﻕ ﺃﻧﺒﻮﺏ ﺍﻟﻐﺎﺯ ﻣﺒﺎﴍﺓ‪.‬‬
‫‪ .6‬ﺍﻓﺘﺢ ﺻﻨﺒﻮﺭ ﺍﻟﻐﺎﺯ ﺑﺒﻂﺀ ﻭﺩﻋﻪ ﻳﻤﻸ ﺍﻟﻘﺎﺭﻭﺭﺓ‪ ،‬ﺛﻢ ﺃﻏﻠﻖ‬
‫ﻧﻴﱰﻭﺟﲔ ﻭﺑﻴﻮﺗﺎﻥ ﻭﻫﻴﻠﻴﻮﻡ‪.‬‬
‫ﺻﻤـﻢ ﲡﺮﺑـﺔ ﻻﺧﺘﺒـﺎﺭ ﺗﺄﺛـﲑ ﻣﺘﻐـﲑ ﻭﺍﺣﺪ ﻣﺜـﻞ ﺩﺭﺟﺔ‬ ‫ﹼ‬ ‫ﺍﻟﺼﲈﻡ ﻭﺳﺠﻞ ﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ﺍﳌﺎﺀ‪.‬‬
‫ﺍﳊﺮﺍﺭﺓ ﺃﻭ ﺍﻟﻀﻐﻂ ﺍﳉﻮﻱ ﰲ ﻧﺘﺎﺋﺞ ﲡﺮﺑﺘﻚ‪.‬‬ ‫ﺛـﻢ‬ ‫ﻣﻘﻠـﻮﺏ‪،‬‬ ‫ﻭﺿـﻊ‬ ‫ﰲ‬ ‫‪ .7‬ﺍﻏﻠـﻖ ﺍﻟﻘـﺎﺭﻭﺭﺓ ﺑﺎﻟﻐﻄـﺎﺀ ﻭﻫـﻲ‬
‫ﺃﺧﺮﺟﻬﺎ ﻣﻦ ﺍﳌﺎﺀ ﻭﺟﻔﻔﻬﺎ ﰲ ﺍﳋﺎﺭﺝ‪.‬‬
‫‪ ‬‬
‫‪ .1‬ﻛﺘﻠﺔ ﺍﳍﻮﺍﺀ = ﺍﻟﻜﺜﺎﻓﺔ × ﺍﳊﺠﻢ‬
‫ﺍﺭﺟﻊ ﺇﱃ ﺟﺪﻭﻝ ﺍﻟﺒﻴﺎﻧﺎﺕ‪.‬‬
‫‪ .2‬ﺍﺭﺟﻊ ﺇﱃ ﺟﺪﻭﻝ ﺍﻟﺒﻴﺎﻧﺎﺕ‪ .‬ﻋﻨﺪ ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ ‪ ،25 °C‬ﺗﻘﺮﻳ ﹰﺒﺎ‬
‫‪ 30%‬ﻣﻦ ﺣﺠﻢ ﺍﻟﻘﺎﺭﻭﺭﺓ ﻳﻜﻮﻥ ﺑﺨﺎﺭ ﺍﳌﺎﺀ ﻷﻧﻪ ﺗﻢ ﲨﻊ ﺍﻟﻐﺎﺯ‬
‫ﻓﻮﻕ ﺍﳌـﺎﺀ‪ .‬ﻭﻳﻤﻜﻦ ﺇﳘﺎﻝ ﺣﺠﻢ ﺑﺨﺎﺭ ﺍﳌـﺎﺀ ﰲ ﻣﺜﻞ ﺩﻗﺔ ﻫﺬﻩ‬
‫ﺍﳊﺠﻢ‬ ‫ﺑﻴﺎﻧﺎﺕ ﻛﺘﻠﺔ ﻭﺣﺠﻢ ﻋﻴﻨﺔ‬ ‫ﺍﻟﺘﺠﺮﺑـﺔ‪ .‬ﻟﺬﺍ ﻳﻌـﻮﺽ ﺍﻟﻄﻼﺏ ﺍﻟﻘﻴﻢ ﰲ ﻣﻌﺎﺩﻟـﺔ ﺍﻟﻐﺎﺯ ﺍﳌﺜﺎﱄ‬
‫‪30.49 g‬‬ ‫ﻛﺘﻠﺔ ﺍﻟﻘﺎﺭﻭﺭﺓ ﻭﺍﳍﻮﺍﺀ‬ ‫ﻹﳚﺎﺩ ﻗﻴﻤﺔ ‪ .n‬ﻭﺳﻴﺤﺴﺐ ﺍﻟﻄﻼﺏ ﻣﺎ ﻳﺄﰐ‪:‬‬
‫‪0.82 g‬‬ ‫ﻛﺘﻠﺔ ﺍﳍﻮﺍﺀ‬ ‫ﺍﻟﻜﺘﻠﺔ ﺍﳌﻮﻟﻴﺔ = ﻛﺘﻠﺔ ﺍﻟﻐﺎﺯ‪ /‬ﻋﺪﺩ ﻣﻮﻻﺕ ﺍﻟﻐﺎﺯ‪.‬‬
‫‪29.67 g‬‬ ‫ﻛﺘﻠﺔ ﺍﻟﻘﺎﺭﻭﺭﺓ ﺍﻟﻔﺎﺭﻏﺔ‬ ‫‪ .3‬ﺳﺘﻌﺘﻤﺪ ﺍﻟﻨﺘﺎﺋﺞ ﻋﲆ ﺗﺮﻛﻴﺐ ﺍﻟﻐﺎﺯ‪.‬‬
‫‪30.30 g‬‬ ‫ﻛﺘﻠﺔ ﺍﻟﻐﺎﺯ‬ ‫‪ .4‬ﺗﺘﻀﻤﻦ ﺍﻻﺣﺘﲈﻻﺕ ﺍﳌﺎﺀ ﺍﻟﺰﺍﺋﺪ ﺍﳌﺤﺼﻮﺭ ﰲ ﺍﻟﻘﺎﺭﻭﺭﺓ‪،‬‬
‫‪0.63 g‬‬ ‫ﻛﺘﻠﺔ ﺍﻟﻘﺎﺭﻭﺭﺓ ﻭﺍﻟﻐﺎﺯ‬ ‫ﺗﻘﻨﻴـﺎﺕ ﺍﻟﻘﻴـﺎﺱ ﺍﻟﻀﻌﻴﻔـﺔ ﺃﻭ ﻏـﲑ ﺍﻟﺼﺤﻴﺤـﺔ‪ ،‬ﺍﻷﺧﻄـﺎﺀ‬
‫‪1.01 atm‬‬ ‫ﺍﻟﻀﻐﻂ‬ ‫ﺍﳊﺴـﺎﺑﻴﺔ‪ .‬ﻗـﺪ ﻳﻨﺘﺞ ﺍﳌﺨﻠـﻮﻁ ﻛﺘﻠـﺔ ﻣﻮﻟﻴﺔ ﻻ ﺗﺴـﺎﻭﻱ ﺃ ﱟﻳﺎ ﻣﻦ‬
‫‪24 °C‬‬ ‫ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ‬ ‫ﳌﻜﻮﻧﺎﺕ ﺍﳌﺨﻠﻮﻁ‪.‬‬‫ﺍﻟﻜﺘﻞ ﺍﳌﻮﻟﻴﺔ ﹼ‬
‫‪297 k‬‬ ‫ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ‬
‫‪0.630 L‬‬ ‫ﺣﺠﻢ ﺍﻟﻐﺎﺯ‬ ‫‪‬‬
‫ﺳـﻴﺠﺪ ﺍﻟﻄﻼﺏ ﺃﻥ ﺍﻟﻀﻐﻂ ﻭﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ ﻳﺘﻐﲑﺍﻥ ﹰ‬
‫ﻗﻠﻴﻼ ﰲ‬
‫ﺍﳌﺨﺘـﱪ ﻣـﻦ ﻳﻮﻡ ﺇﱃ ﺁﺧـﺮ ﻏﲑ ﺃﻥ ﺫﻟﻚ ﻟﻦ ﻳﺆﺛـﺮ ﰲ ﻧﺘﺎﺋﺞ ﻣﺜﻞ‬
‫ﻫﺬﻩ ﺍﻟﺘﺠﺮﺑﺔ‪ .‬ﻓﺎﻟﻘﻴﺎﺳﺎﺕ ﻟﻴﺴﺖ ﺩﻗﻴﻘﺔ ﺑﺪﺭﺟﺔ ﻛﺎﻓﻴﺔ ﻹﻇﻬﺎﺭ‬
‫ﺍﻟﻔـﺮﻕ‪ .‬ﻭﻋـﲆ ﺃﻳﺔ ﺣـﺎﻝ‪ ،‬ﺇﺫﺍ ﻻﺣـﻆ ﺍﻟﻄﻼﺏ ﺗﻐـﲑ ﺩﺭﺟﺎﺕ‬
‫ﺍﳊﺮﺍﺭﺓ ﻭﺍﻟﻀﻐﻂ‪ ،‬ﻳﻜﻮﻥ ﺑﻤﻘﺪﺭﻭﻫﻢ ﺗﺒﻴﺎﻥ ﺍﻟﻔﺮﻕ ﰲ ﻧﺘﺎﺋﺠﻬﻢ‪.‬‬
‫‪166‬‬
 ‫ﲣﺘﻠﻒ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪ ،‬ﻭﻫﻲ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻳﺔ‪ ،‬ﺑﺎﺧﺘﻼﻑ ﺃﻧﻮﺍﻉ ﺍﻟﺮﻭﺍﺑﻂ ﻓﻴﻬﺎ‪.‬‬ ‫اﻟﻌﺎﻣﺔ‬ ‫اﻟﻔﻜﺮة‬

‫دﻟﻴﻞ ﻣﺮاﺟﻌﺔ اﻟﻔﺼﻞ‬
‫‪‬‬
‫ﺍﻃﻠﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻛﺘﺎﺑﺔ ﲨﻠﺔ ﻭﺍﺣﺪﺓ ﻟﻜﻞ ﻣﺼﻄﻠﺢ ﰲ ﺍﻟﻔﺼﻞ‪،‬‬
‫ﻭﺫﻟﻚ ﻟﺘﻌﺰﻳﺰ ﻣﻌﺮﻓﺘﻬﻢ ﺑﺎﳌﻔﺮﺩﺍﺕ‪ .‬‬
‫‪‬‬
‫‪81‬‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﺮﻛﺒﺎﺕ ‪‬‬
‫ﲢﺘﻮﻱ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﻋﲆ ﺍﻟﻜﺮﺑﻮﻥ؛ ﺇﺫ ﻳﻤﻜﻨﻪ ﺗﻜﻮﻳﻦ ﺳﻼﺳﻞ ﻣﺴﺘﻘﻴﻤﺔ‬
‫ﻭﺃﺧﺮ￯ ﻣﺘﻔﺮﻋﺔ‪.‬‬
‫ﻋﻀﻮﻳﺔ ﲢﺘﻮﻱ ﻋﲆ ﻋﻨﴫ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺗﻌﺪ •‬
‫ﻣﺼﺪﺭﺍ ﻟﻠﻄﺎﻗﺔ ﻭﺍﳌﻮﺍﺩ ﺍﳋﺎﻡ‪.‬‬
‫ﹰ‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻣﻮﺍﺩ ﻋﻀﻮﻳﺔ ﺗﺘﺄﻟﻒ ﻣﻦ ﺍﻟﻜﺮﺑﻮﻥ ﻭﺍﳍﻴﺪﺭﻭﺟﲔ‪.‬‬ ‫•‬ ‫‪‬‬
‫ﺍﳌﺼﺪﺭﺍﻥ ﺍﻟﺮﺋﻴﺴﺎﻥ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﳘﺎ ﺍﻟﻨﻔﻂ ﻭﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ‪.‬‬ ‫•‬
‫ﻳﻤﻜﻦ ﻓﺼﻞ ﺍﻟﻨﻔﻂ ﺇﱃ ﻣﻜﻮﻧﺎﺗﻪ ﻋﻦ ﻃﺮﻳﻖ ﻋﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ‪.‬‬ ‫•‬
‫• ﺍﳌﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ‬
‫• ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳌﺸﺒﻊ‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻏﲑ ﺍﳌﺸﺒﻊ‬ ‫•‬
‫ﺍﻟﺘﻜﺴﲑ ﺍﳊﺮﺍﺭﻱ‬ ‫•‬
‫ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ‬ ‫•‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ‬ ‫•‬
‫‪82‬‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ‪‬‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ‬

‫• ﲢﺘﻮﻱ ﺍﻷﻟﻜﺎﻧﺎﺕ ﻋﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ ﻓﻘﻂ ﺑﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬ ‫ﲢﺘﻮﻱ ﻓﻘﻂ ﻋﲆ ﺭﻭﺍﺑﻂ ﺃﺣﺎﺩﻳﺔ‪.‬‬
‫• ﺗﻌﺪ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺃﻓﻀﻞ ﲤﺜﻴﻞ ﻟﻸﻟﻜﺎﻧﺎﺕ ﻭﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﺍﻷﺧﺮ￯‪ .‬ﻭﻳﻤﻜﻦ‬ ‫‪‬‬
‫• ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄﻼﺏ ﺗﻠﺨﻴـﺺ ﻧﻘﺎﻁ ﺍﻟﺘﺸـﺎﺑﻪ ﻭﺍﻻﺧﺘﻼﻑ ﺑﲔ‬ ‫ﺗﺴﻤﻴﺔ ﻫﺬﻩ ﺍﳌﺮﻛﺒﺎﺕ ﺑﺎﺳﺘﺨﺪﺍﻡ ﻗﻮﺍﻋﺪ ﻧﻈﺎﻣﻴﺔ ﹸﺣﺪﱢ ﺩﺕ ﻣﻦ ﺍﻻﲢﺎﺩ ﺍﻟﺪﻭﱄ ﻟﻠﻜﻴﻤﻴﺎﺀ‬ ‫ﺍﻟﺴﻠﺴﻠﺔ ﺍﳌﺘﲈﺛﻠﺔ‬ ‫•‬
‫ﺍﻟﺒﺤﺘﺔ ﻭﺍﻟﺘﻄﺒﻴﻘﻴﺔ )ﺃﻳﻮﺑﺎﻙ ‪.(IUPAC‬‬ ‫ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ‬ ‫•‬
‫ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻭﺍﻷﻟﻜﻴﻨﺎﺕ‪ ،‬ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ‪ .‬‬ ‫• ﺗﺴﻤﻰ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳌﺤﺘﻮﻳﺔ ﻋﲆ ﺣﻠﻘﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﻴﺔ ﺑﺎﻷﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ‪.‬‬ ‫ﺍﳌﺠﻤﻮﻋﺔ ﺍﻟﺒﺪﻳﻠﺔ‬ ‫•‬
‫ﺍﻷﻟﻜﺎﻥ‬ ‫•‬
‫• ﺍﻃﻠـﺐ ﺇﱃ ﺍﻟﻄـﻼﺏ ﻋﻤـﻞ ﻗﺎﺋﻤـﺔ ﺑﺄﺳـﲈﺀ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ‬ ‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﳊﻠﻘﻲ‬ ‫•‬
‫ﺍﻷﻟﻜﺎﻥ ﺍﳊﻠﻘﻲ‬ ‫•‬
‫ﻭﺃﺷﻜﺎﳍﺎ‪ .‬‬ ‫‪83‬‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ‪‬‬
‫• ﻳﻤﻜﻦ ﺍﺳﺘﺨﺪﺍﻡ ﺃﺳﺌﻠﺔ ﺍﻟﻔﺼﻞ ﺃﻭ ﳎﻤﻮﻋﺎﺕ ﺍﻷﺳﺌﻠﺔ ﺍﻹﺿﺎﻓﻴﺔ‬ ‫ﲢﺘﻮﻱ ﻋﲆ ﺍﻷﻗــﻞ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ • ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲢﺘﻮﻱ ﻋﲆ ﺍﻷﻗﻞ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﺃﻭ‬
‫ﻭﺍﺣــــﺪﺓ‪ ،‬ﻭﺃﻣـــﺎ ﺍﻷﻟــﻜــﺎﻳــﻨــﺎﺕ ﻓﻬﻲ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ‪ ،‬ﻋﲆ ﺍﻟﺘﻮﺍﱄ‪.‬‬
‫ﰲ ﻣﺮﺍﺟﻌﺔ ﺍﻟﻔﺼﻞ‪ .‬‬ ‫ﻫﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﲢﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ • ﺗﹸﻌﺪ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻣﺮﻛﺒﺎﺕ ﻋﻀﻮﻳﺔ ﻏﲑ ﻗﻄﺒﻴﺔ ﺫﺍﺕ ﻧﺸﺎﻁ ﻛﻴﻤﻴﺎﺋﻲ‬
‫ﺃﻋﲆ ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻭﳍﺎ ﺧﺼﺎﺋﺺ ﺃﺧﺮ￯ ﻣﺸﺎﲠﺔ ﳋﺼﺎﺋﺺ ﺍﻷﻟﻜﺎﻧﺎﺕ‪.‬‬ ‫ﻭﺍﺣﺪﺓ ﻋﲆ ﺍﻷﻗﻞ‪.‬‬
‫‪‬‬
‫• ﺍﻷﻟﻜﺎﻳﻦ‬
‫• ﺍﻷﻟﻜﲔ‬

‫‪167‬‬
 ‫‪84‬‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﻟﺒﻌﺾ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ‪‬‬
‫ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴﻬﺎ‪ ،‬ﻟﻜﻨﻬﺎ ﲣﺘﻠﻒ ﰲ • ﺍﳌﺘﺸﻜﻼﺕ ﻣﺮﻛﺒﺎﻥ ﺃﻭ ﺃﻛﺜﺮ ﳍﺎ ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻔﺴﻬﺎ‪ ،‬ﻭﻟﻜﻨﻬﺎ ﲣﺘﻠﻒ ﰲ ﺻﻴﻐﻬﺎ‬
‫ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬ ‫ﺻﻴﻐﻬﺎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫ﻣﻌﺎ‪.‬‬
‫• ﲣﺘﻠﻒ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﰲ ﺍﻟﱰﺗﻴﺐ ﺍﻟﺬﻱ ﺗﺮﺗﺒﻂ ﺑﻪ ﺍﻟﺬﺭﺍﺕ ﹰ‬ ‫‪‬‬
‫• ﺗﺮﺗﺒﻂ ﺍﻟﺬﺭﺍﺕ ﲨﻴﻌﻬﺎ ﰲ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﻔﺮﺍﻏﻴﺔ ﺑﺎﻟﱰﺗﻴﺐ ﻧﻔﺴﻪ‪ ،‬ﻭﻟﻜﻨﻬﺎ ﲣﺘﻠﻒ ﰲ‬ ‫• ﺍﳌﺘﺸﻜﻞ ﺍﻟﻀﻮﺋﻲ‬
‫ﺗﺮﺗﻴﺒﻬﺎ ﺍﻟﻔﺮﺍﻏﻲ )ﺍﻻﲡﺎﻫﺎﺕ ﰲ ﺍﻟﻔﺮﺍﻍ(‪.‬‬ ‫• ﺍﻟﺪﻭﺭﺍﻥ ﺍﻟﻀﻮﺋﻲ‬ ‫‪‬‬
‫ﺍﳌﺘﺸﻜﻞ ﺍﻟﻔﺮﺍﻏﻲ‬ ‫•‬
‫ﺍﳌﺘﺸﻜﻞ ﺍﻟﺒﻨﺎﺋﻲ‬ ‫•‬ ‫‪www.obeikaneducation.com‬‬
‫ﺫﺭﺓ ﺍﻟﻜﺮﺑﻮﻥ ﻏﲑ ﺍﳌﺘﲈﺛﻠﺔ‬ ‫•‬
‫ﺍﻟﻜﲑﺍﻟﻴﺔ‬ ‫•‬ ‫‪‬‬
‫ﺍﳌﺘﺸﻜﻞ ﺍﳍﻨﺪﳼ‬ ‫•‬
‫ﺍﳌﺘﺸﻜﻞ‬ ‫•‬ ‫• ‪ ‬‬
‫‪85‬‬
‫اﻟﻔﻜﺮة اﻟﺮﺋﻴﺴﺔ ﺗﺘﺼﻒ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ‪‬‬
‫• ‪ ‬‬
‫ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﺑﺪﺭﺟﺔ ﻋﺎﻟﻴﺔ ﻣﻦ ﺍﻟﺜﺒﺎﺕ‪ ،‬ﺑﺴﺒﺐ • ﲢﺘﻮﻱ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﻋﲆ ﺣﻠﻘﺎﺕ ﺑﻨﺰﻳﻦ ﺑﻮﺻﻔﻬﺎ ﺟﺰ ﹰﺀﺍ ﻣﻦ ﺻﻴﻐﻬﺎ‬
‫ﺑﻨﺎﺋﻬﺎ ﺍﳊﻠﻘﻲ ﺣﻴﺚ ﺗﺘﺸﺎﺭﻙ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫• ‪‬‬
‫• ﺗﺘﻮﺯﻉ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﰲ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﻋﲆ ﺍﳊﻠﻘﺔ ﻛﺎﻣﻠﺔ ﺑﺎﻟﺘﺴﺎﻭﻱ‪.‬‬ ‫ﰲ ﻋﺪﺩ ﻣﻦ ﺍﻟﺬﺭﺍﺕ‪.‬‬
‫‪‬‬
‫• ﺍﳌﺮﻛﺐ ﺍﻷﺭﻭﻣﺎﰐ‬
‫• ﺍﳌﺮﻛﺐ ﺍﻷﻟﻴﻔﺎﰐ‬

‫‪168‬‬
 ‫‪ .46‬ﻳﺒﲔ ﺍﻟﺸﻜﻞ ‪ 8-29‬ﻧﻤﻮﺫﺟﲔ ﻟﻠﻴﻮﺭﻳﺎ‪ ،‬ﻭﻫﻮ ﺟﺰﻱﺀ‬
‫ﹼ‬
‫ﺣﴬﻩ ﻓﺮﻳﺪﺭﻳﻚ ﻓﻮﻫﻠﺮ ﻷﻭﻝ ﻣﺮﺓ ﻋﺎﻡ ‪1828‬ﻡ‪.‬‬
‫‪8-1‬‬
‫‪‬‬ ‫‪‬‬
‫‪ .38‬ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ ﳌﺎﺫﺍ ﺃﺩ￯ ﺍﻛﺘﺸﺎﻑ ﻓﻮﻫﻠﺮ ﺇﱃ ﺗﻄﻮﻳﺮ‬
‫‪O‬‬
‫‪ .44‬ﻣﻴﺜﺎﻥ‪ ،‬ﺑﺮﻭﺑﺎﻥ‪ ،‬ﺑﻴﻮﺗﺎﻥ‪ ،‬ﻫﻜﺴﺎﻥ‪ ،‬ﺃﻭﻛﺘﺎﻥ‬ ‫ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﻌﻀﻮﻳﺔ؟‬

‫—‬
‫‪C‬‬
‫‪H2N‬‬ ‫‪NH2‬‬
‫‪ .39‬ﻣﺎ ﺍﳋﺎﺻﻴﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻟﻠﻤﺮﻛﺐ ﺍﻟﻌﻀﻮﻱ؟‬
‫‪ 2 .a .45‬ﺇﻟﻜﱰﻭﻥ‬ ‫ﺍﻟﺸﻜﻞ ‪8-29‬‬
‫‪ .40‬ﻣﺎ ﺧﺎﺻﻴﺔ ﺍﻟﻜﺮﺑﻮﻥ ﺍﳌﺴﺆﻭﻟﺔ ﻋﻦ ﺍﻟﺘﻨﻮﻉ ﺍﳍﺎﺋﻞ ﰲ ﺍﳌﺮﻛﺒﺎﺕ‬
‫ﺍﻟﻌﻀﻮﻳﺔ؟‬
‫‪ 4‬ﺇﻟﻜﱰﻭﻧﺎﺕ‬ ‫‪.b‬‬
‫‪ .a‬ﺣﺪﹼ ﺩ ﻧﻮﻉ ﻛﻞ ﻣﻦ ﺍﻟﻨﻤﻮﺫﺟﲔ‪.‬‬
‫‪ .b‬ﻫﻞ ﺍﻟﻴﻮﺭﻳﺎ ﻣﺮﻛﺐ ﻋﻀﻮﻱ ﺃﻡ ﻏﲑ ﻋﻀﻮﻱ؟ ﻓﴪ‬
‫ﺳﻢ ﻣﺼﺪﺭﻳﻦ ﻃﺒﻴﻌﻴﲔ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪.‬‬
‫‪ .41‬ﹼ‬
‫ﺇﺟﺎﺑﺘﻚ‪.‬‬ ‫‪ .42‬ﻓﴪ ﺍﳋﺼﺎﺋﺺ ﺍﻟﻔﻴﺰﻳﺎﺋﻴﺔ ﳌﺮﻛﺒﺎﺕ ﺍﻟﻨﻔﻂ ﺍﻟﺘﻲ ﺗﺴﺘﻌﻤﻞ‬
‫‪ 6‬ﺇﻟﻜﱰﻭﻧﺎﺕ‬ ‫‪.c‬‬ ‫‪ .47‬ﹸﲤﺜﱠـﻞ ﺍﳉﺰﻳﺌـﺎﺕ ﺑﺎﺳـﺘﺨﺪﺍﻡ ﺍﻟﺼﻴـﻎ ﺍﳉﺰﻳﺌﻴـﺔ‪ ،‬ﻭﺍﻟﺼﻴـﻎ‬
‫ﻟﻔﺼﻠﻬﺎ ﰲ ﺃﺛﻨﺎﺀ ﻋﻤﻠﻴﺔ ﺍﻟﺘﻘﻄﲑ ﺍﻟﺘﺠﺰﻳﺌﻲ‪.‬‬
‫ﺍﻟﺒﻨﺎﺋﻴﺔ‪ ،‬ﻭﻧﻤﻮﺫﺝ ﺍﻟﻜﺮﺓ ﻭﺍﻟﻌﺼـﺎ‪ ،‬ﻭﺍﻟﻨﻤﻮﺫﺝ ﺍﻟﻔﺮﺍﻏﻲ‪ .‬ﻣﺎ‬ ‫ﻓﴪ ﺍﻟﻔﺮﻕ ﺑﲔ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸﺒﻌﺔ ﻭﻏﲑ ﺍﳌﺸﺒﻌﺔ‪.‬‬
‫‪ .43‬ﹼ‬
‫‪ .a .46‬ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻭﺍﻟﻨﻤﻮﺫﺝ ﺍﻟﻔﺮﺍﻏﻲ‪.‬‬ ‫ﻣﺰﺍﻳﺎ ﻭﻣﺴﺎﻭﺉ ﻛﻞ ﻧﻤﻮﺫﺝ؟‬
‫‪‬‬
‫ﺗﻌـﺪ ﺍﻟﻴﻮﺭﻳـﺎ ﻣﺮﻛ ﹰﺒﺎ ﻋﻀﻮ ﹼﹰﻳـﺎ ﻷﳖﺎ ﲢﺘﻮﻱ ﻋـﲆ ﺍﻟﻜﺮﺑﻮﻥ‬ ‫‪.b‬‬ ‫‪8-2‬‬ ‫‪ .44‬ﺍﻟﺘﻘﻄﲑ ﺭﺗﺐ ﺍﳌﺮﻛﺒﺎﺕ ﺍﳌﺪﺭﺟﺔ ﰲ ﺍﳉﺪﻭﻝ ‪ 8-7‬ﺣﺴﺐ‬
‫ﺍﻟﱰﺗﻴﺐ ﺍﻟﺬﻱ ﲣﺮﺝ ﺑﻪ ﺧﻼﻝ ﺗﻘﻄﲑﻫﺎ ﻣﻦ ﺍﳋﻠﻴﻂ‪.‬‬

‫ﻭﻫـﻲ ﻟﻴﺴـﺖ ﻣـﻦ ﺍﳌﺠﻤﻮﻋـﺎﺕ ﺍ ﹸﳌﺴـﺘﺜﻨﺎﺓ – ﺃﻛﺴـﻴﺪ‬

‫‪‬‬
‫‪ .48‬ﺻﻒ ﺧﺼﺎﺋﺺ ﺍﻟﺴﻼﺳﻞ ﺍ ﹸﳌﺘﲈﺛﻠﺔ ﻟﻠﻬﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ‪.‬‬ ‫‪87‬‬

‫ﺍﻟﻜﺮﺑﻮﻥ‪ ،‬ﻛﺮﺑﻴﺪﺍﺕ‪ ،‬ﺃﻭ ﻛﺮﺑﻮﻧﺎﺕ‪.‬‬ ‫‪ .49‬ﺍﻟﻮﻗﻮﺩ ﱢ‬

‫ﺳﻢ ﺛﻼﺛﺔ ﺃﻟﻜﺎﻧﺎﺕ ﺗﹸﺘﺨﺬ ﻭﻗﻮﺩﹰﺍ‪ ،‬ﺛﻢ ﺍﺫﻛﺮ ﺍﺳﺘﺨﺪﺍ ﹰﻣﺎ‬ ‫‪°C‬‬ ‫‪‬‬
‫ﺁﺧﺮ ﻟﻜﻞ ﻣﻨﻬﺎ‪.‬‬ ‫‪68.7‬‬ ‫ﺍﳍﻜﺴﺎﻥ‬

‫‪ .47‬ﺗﻮﺿـﺢ ﺍﻟﻨﲈﺫﺝ ﺍﳉﺰﻳﺌﻴﺔ ﻧﻮﻉ ﺍﻟﺬﺭﺍﺕ ﰲ ﺍﳉﺰﻱﺀ‪ ،‬ﻭﻟﻜﻨﻬﺎ ﻻ‬ ‫‪ .50‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻜﻞ ﳑﺎ ﻳﺄﰐ‪:‬‬
‫‪ .c‬ﺍﻟﱪﻭﺑﺎﻥ‬ ‫‪ .a‬ﺍﻹﻳﺜﺎﻥ‬
‫‪- 161.7‬‬ ‫ﺍﳌﻴﺜﺎﻥ‬
‫ﺍﻷﻭﻛﺘﺎﻥ‬
‫ﹸﺗﻈﻬﺮ ﻫﻨﺪﺳـﺔ ﺍﳉـﺰﻱﺀ‪ .‬ﻭﺗﺒﲔ ﺍﻟﻨﲈﺫﺝ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﻧﻮﻉ ﺍﻟﺬﺭﺍﺕ‬
‫‪125.7‬‬
‫‪ .d‬ﺍﳍﺒﺘﺎﻥ‬ ‫‪ .b‬ﺍﳍﻜﺴﺎﻥ‬
‫‪ .51‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﻜﺜﻔﺔ ﻟﻜﻞ ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ ﰲ ﺍﻟﺴﺆﺍﻝ‬ ‫‪- 0.5‬‬ ‫ﺍﻟﺒﻴﻮﺗﺎﻥ‬

‫ﰲ ﺍﳉـﺰﻱﺀ‪ ،‬ﻭﺍﻟﱰﺗﻴﺐ ﺍﻟﻌﺎﻡ ﻟﻠﺬﺭﺍﺕ‪ ،‬ﻭﻟﻜﻦ ﻟﻴﺲ ﺍﻟﺸـﻜﻞ‬ ‫ﺍﻟﺴﺎﺑﻖ‪.‬‬ ‫‪- 42.1‬‬ ‫ﺍﻟﱪﻭﺑﺎﻥ‬
‫‪ .45‬ﻣﺎ ﻋﺪﺩ ﺍﻹﻟﻜﱰﻭﻧﺎﺕ ﺍﳌﺸﱰﻛﺔ ﺑﲔ ﺫﺭﰐ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﻛﻞ ‪ .52‬ﺍﻛﺘﺐ ﳎﻤﻮﻋﺔ ﺍﻷﻟﻜﻴﻞ ﺍﳌﻘﺎﺑﻠﺔ ﻟﻜﻞ ﻣﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﻵﺗﻴﺔ‪،‬‬
‫ﺍﳍﻨﺪﳼ ﺍﻟﺪﻗﻴﻖ‪ .‬ﻭﻳﺒﲔ ﻧﻤـﻮﺫﺝ ﺍﻟﻜﺮﺓ ﻭﺍﻟﻌﺼﺎ ﻧﻮﻉ ﺍﻟﺬﺭﺍﺕ‬ ‫ﻭﺍﻛﺘﺐ ﺍﺳﻤﻬﺎ‪:‬‬ ‫ﻣﻦ ﺭﻭﺍﺑﻂ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻵﺗﻴﺔ؟‬
‫‪ .a‬ﺍﳌﻴﺜﺎﻥ‬
‫ﰲ ﺍﳉـﺰﻱﺀ‪ ،‬ﻭﺍﻟﱰﺗﻴـﺐ ﺍﻟﻌـﺎﻡ‪ ،‬ﻭﻟﻜـﻦ ﻻ ﻳﻮﺿـﺢ ﺍﻟﺸـﻜﻞ‬ ‫‪ .b‬ﺍﻟﺒﻴﻮﺗﺎﻥ‬
‫‪ .a‬ﺭﺍﺑﻄﺔ ﺃﺣﺎﺩﻳﺔ‬
‫‪ .b‬ﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ‬
‫‪ .c‬ﺍﻷﻭﻛﺘﺎﻥ‬ ‫‪ .c‬ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ‬
‫ﺍﳍﻨـﺪﳼ ﺍﻟﺪﻗﻴﻖ‪ .‬ﻭ ﹸﻳﺒﲔ ﺍﻟﺸـﻜﻞ ﺍﻟﻔﺮﺍﻏﻲ ﺻﻮﺭﺓ ﻭﺍﻗﻌﻴﺔ ﻋﻦ‬
‫ﺍﳉﺰﻱﺀ‪ ،‬ﻭﻟﻜﻦ ﻣﻦ ﺍﻟﺼﻌﺐ ﲢﺪﻳﺪ ﻧﻮﻉ ﺍﻟﺮﻭﺍﺑﻂ ﰲ ﺍﳉﺰﻱﺀ‪.‬‬
‫ﺿﺨﲈ‪ ،‬ﻓﺴـﻴﻜﻮﻥ ﻣﻦ ﺍﻟﺼﻌﺐ ﺭﺅﻳﺔ ﲨﻴﻊ‬ ‫ﹰ‬ ‫ﻭﺇﺫﺍ ﻛﺎﻥ ﺍﳉـﺰﻱﺀ‬
‫ﺍﻟﺬﺭﺍﺕ ﰲ ﺍﳉﺰﻱﺀ‪.‬‬

‫‪8–2‬‬ ‫‪8–1‬‬
‫‪‬‬
‫‪‬‬
‫‪ .48‬ﻫـﻲ ﺳﻠﺴـﻠﺔ ﻣـﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﺘـﻲ ﳜﺘﻠﻒ ﺑﻌﻀﻬـﺎ ﻋﻦ ﺑﻌﺾ‬
‫‪ .38‬ﺃﺩﺭﻙ ﺍﻟﻜﻴﻤﻴﺎﺋﻴـﻮﻥ ﺃﻥ ﺑﺎﻹﻣـﻜﺎﻥ ﲢﻀﲑ ﺍﳌﺮﻛﺒـﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﺩﻭﻥ ﻗﻮﺓ‬
‫ﰲ ﻋـﺪﺩ ﻭﺣـﺪﺍﺕ ﺍﻟﺒﻨﺎﺀ‪ ،‬ﻭﳍـﺎ ﻋﻼﻗﺔ ﺭﻗﻤﻴﺔ ﺛﺎﺑﺘـﺔ ﺑﲔ ﺃﻋﺪﺍﺩ‬
‫ﺣﻴﻮﻳﺔ‪.‬‬
‫ﺍﻟﺬﺭﺍﺕ‪.‬‬
‫‪ .39‬ﲢﺘﻮﻱ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻌﻀﻮﻳﺔ ﻋﲆ ﻋﻨﴫ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬
‫‪ .49‬ﻣﻴﺜـﺎﻥ‪ :‬ﻭﻗـﻮﺩ ﻟﻠﻄﺒـﺦ ﻭﺍﻟﺘﺪﻓﺌـﺔ؛ ﺑﺮﻭﺑـﺎﻥ‪ :‬ﻭﻗـﻮﺩ ﻟﻠﻄﺒـﺦ‬
‫ﺍﻟﻮﻻﻋﺎﺕ ﺍﻟﺼﻐﲑﺓ ﻭﺑﻌﺾ ﺍﳌﺸﺎﻋﻞ‪.‬‬ ‫ﻭﺍﻟﺘﺪﻓﺌﺔ؛ ﺑﻴﻮﺗﺎﻥ‪ :‬ﰲ ﹼ‬ ‫‪ .40‬ﺗﺴـﺘﻄﻴﻊ ﺫﺭﺓ ﺍﻟﻜﺮﺑـﻮﻥ ﺗﻜﻮﻳﻦ ﺃﺭﺑﻊ ﺭﻭﺍﺑﻂ ﻣﺸـﱰﻛﺔ ﻗﻮﻳﺔ‪ ،‬ﺑﲈ ﰲ ﺫﻟﻚ‬
‫ﺍﻟﺮﻭﺍﺑﻂ ﻣﻊ ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ ﺃﺧﺮ￯‪.‬‬
‫‪ .50‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫‪ .41‬ﺍﻟﻨﻔﻂ ﻭﺍﻟﻐﺎﺯ ﺍﻟﻄﺒﻴﻌﻲ‬
‫‪CH3CH2CH3 .c‬‬ ‫‪CH3CH3 .a .51‬‬
‫‪CH3(CH2) 5CH3 .d CH3(CH2) 4CH3 .b‬‬ ‫‪ .42‬ﺍﻻﺧﺘﻼﻑ ﰲ ﺩﺭﺟﺔ ﺍﻟﻐﻠﻴﺎﻥ‬
‫‪ .43‬ﲢﺘﻮﻱ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﳌﺸـﺒﻌﺔ ﻋﲆ ﺭﻭﺍﺑـﻂ ﻛﺮﺑﻮﻥ – ﻛﺮﺑﻮﻥ ﺃﺣﺎﺩﻳﺔ‬
‫‪ .52‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫ﻓﻘـﻂ‪ .‬ﰲ ﺣﲔ ﲢﺘﻮﻱ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸـﺒﻌﺔ ﻋﲆ ﺭﺍﺑﻄﺔ ﻛﺮﺑﻮﻥ‬
‫ﻣﻴﺜﺎﻥ‪ ،‬ﻣﻴﺜﻴﻞ‪.‬‬ ‫‪.a‬‬
‫– ﻛﺮﺑﻮﻥ ﺛﻨﺎﺋﻴﺔ ﺃﻭ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﺃﻭﺃﻛﺜﺮ‪.‬‬
‫ﺑﻴﻮﺗﺎﻥ‪ ،‬ﺑﻴﻮﺗﻴﻞ‪.‬‬ ‫‪.b‬‬

‫ﺃﻭﻛﺘﺎﻥ‪ ،‬ﺃﻭﻛﺘﻴﻞ‪.‬‬ ‫‪.c‬‬

‫‪169‬‬
 ‫ﺳﻢ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﺘﻲ ﳍﺎ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪ .53‬ﻛﻴـﻒ ﳜﺘﻠـﻒ ﺑﻨﺎﺀ ﺍﻷﻟـﻜﺎﻥ ﺍﳊﻠﻘﻲ ﻋـﻦ ﺑﻨـﺎﺀ ﺍﻷﻟﻜﺎﻧﺎﺕ ‪ .58‬ﹼ‬
‫‪CH2CH2CH3‬‬ ‫‪.c‬‬ ‫‪CH3 .a‬‬ ‫ﺍﳌﺴﺘﻘﻴﻤﺔ ﺃﻭ ﺍﳌﺘﻔﺮﻋﺔ؟‬ ‫‪ .53‬ﳛﺘﻮﻱ ﺍﻷﻟﻜﺎﻥ ﺍﳊﻠﻘﻲ ﻋﲆ ﺣﻠﻘﺔ ﻣﻦ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬
‫‪ .54‬ﺩﺭﺟـﺎﺕ ﺍﻟﺘﺠﻤﺪ ﻭﺍﻟﻐﻠﻴﺎﻥ ﺍﺳـﺘﺨﺪﻡ ﺍﳌﺎﺀ ﻭﺍﳌﻴﺜﺎﻥ ﻟﺘﻔﺴـﲑ‬
‫‪CH3‬‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫ﻛﻴـﻒ ﺗﺆﺛﺮ ﻗـﻮ￯ ﺍﻟﺘﺠﺎﺫﺏ ﺑـﲔ ﺍﳉﺰﻳﺌﻴـﺔ ﰲ ﺩﺭﺟﺔ ﻏﻠﻴﺎﻥ‬ ‫ﻜﻮﻥ ﺭﻭﺍﺑﻂ ﻫﻴﺪﺭﻭﺟﻴﻨﻴﺔ ﻣﻊ‬ ‫‪ .54‬ﺟﺰﻳﺌﺎﺕ ﺍﳌﻴﺜﺎﻥ ﻏﲑ ﻗﻄﺒﻴﺔ ﻭﻻ ﹸﺗ ﱢ‬
‫ﻭﺩﺭﺟﺔ ﲡﻤﺪ ﺍﳌﺎﺩﺓ‪.‬‬
‫‪.d‬‬ ‫‪.b‬‬ ‫ﻜﻮﻥ ﺭﻭﺍﺑﻂ‬‫ﺟﺰﻳﺌـﺎﺕ ﻣﻴﺜﺎﻥ ﺃﺧﺮ￯‪ .‬ﺟﺰﻳﺌﺎﺕ ﺍﳌـﺎﺀ ﻗﻄﺒﻴﺔ ﻭ ﹸﺗ ﱢ‬
‫‪CH3‬‬
‫‪CH3‬‬
‫‪CH3‬‬ ‫‪C22-130C-828378-08‬‬ ‫‪‬‬
‫ﻫﻴﺪﺭﻭﺟﻴﻨﻴـﺔ ﻣﻊ ﺟﺰﻳﺌﺎﺕ ﻣﺎﺀ ﺃﺧﺮ￯‪ .‬ﻭﺑﺴـﺒﺐ ﻗﻮﺓ ﺍﻟﺮﺍﺑﻄﺔ‬
‫‪C22-132C-828378-08‬‬
‫‪CH3‬‬ ‫‪CH2CH3‬‬ ‫ﺳﻢ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﺘﻲ ﳍﺎ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﺘﺎﻟﻴﺔ‪:‬‬
‫‪ .55‬ﱢ‬
‫‪CH3CH2‬‬ ‫‪CH3CH2CH2CH2CH3 .a‬‬

‫‪C22-133C-828378-08‬‬ ‫‪CH3‬‬ ‫‪.b‬‬ ‫ﺍﳍﻴﺪﺭﻭﺟﻴﻨﻴـﺔ ﺑـﲔ ﺟﺰﻳﺌﺎﺕ ﺍﳌـﺎﺀ‪ ،‬ﻓﺈﻥ ﻟﻠـﲈﺀ ﺩﺭﺟﺘﻲ ﻏﻠﻴﺎﻥ‬
‫‪8-3‬‬
‫‪C22-131C-828378-08‬‬ ‫‪CH3CH2CHCH2CH3‬‬
‫ﻭﺍﻧﺼﻬﺎﺭ ﺃﻋﲆ ﻣﻦ ﺍﳌﻴﺜﺎﻥ‪.‬‬
‫‪‬‬ ‫‪.c‬‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫ﻓﴪ ﻛﻴﻒ ﲣﺘﻠﻒ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻋﻦ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻭﻛﻴﻒ ﲣﺘﻠﻒ‬
‫‪ .59‬ﹼ‬
‫‪‬‬
‫‪H‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪H‬‬
‫ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻋﻦ ﱟ‬
‫ﻛﻞ ﻣﻦ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻧﺎﺕ؟‬
‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪H‬‬
‫‪ .60‬ﹸﻳﺒﻨﻰ ﺍﺳﻢ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﻋﲆ ﺃﺳﺎﺱ ﺍﺳﻢ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ‪.‬‬ ‫‪H‬‬ ‫‪C‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪C‬‬ ‫‪H‬‬
‫ﻓﴪ ﻛﻴﻒ ﲣﺘﻠﻒ ﻃﺮﻳﻘﺔ ﲢﺪﻳﺪ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻋﻨﺪ ﺗﺴﻤﻴﺔ‬‫ﱢ‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪ .a .55‬ﺑﻨﺘﺎﻥ‪.‬‬
‫ﺍﻷﻟﻜﻴﻨﺎﺕ ﻋﻨﻬﺎ ﻋﻨﺪ ﺗﺴﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ؟‬
‫‪CH3‬‬ ‫‪.d‬‬
‫‪‬‬ ‫‪CHCH3‬‬ ‫‪ - 3‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‬ ‫‪.b‬‬
‫ﺳﻢ ﺍﳌﺮﻛﺒﺎﺕ ﺍ ﹸﳌ ﹶﻤﺜﱠﻠﺔ ﺑﺎﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﻜﺜﻔﺔ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪ .61‬ﹼ‬ ‫‪CHCH3‬‬
‫‪CH3‬‬
‫‪.c‬‬ ‫‪CH3‬‬ ‫‪.‬‬‫‪a‬‬
‫‪CH3‬‬ ‫‪ – 5 ،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ‪.‬‬ ‫‪.c‬‬
‫—‬

‫—‪C‬‬
‫‪— CHCH3‬‬
‫‪ .56‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﻜﺎﻣﻠﺔ ﻟﻠﻤﺮﻛﺒﺎﺕ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪ - 3 ،2‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗﺎﻥ‪.‬‬
‫—‬

‫‪CH3 .d‬‬
‫‪CH3‬‬
‫‪.b‬‬
‫‪ .a‬ﻫﺒﺘﺎﻥ‬ ‫‪.d‬‬
‫‪CH3CH2‬‬ ‫‪ -2 .b‬ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ‬
‫‪ .56‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫—‬

‫‪C22-136C-828378-08‬‬ ‫‪C — CH2‬‬ ‫—‬ ‫‪ -3،2 .c‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‬

‫‪-2،2 .d‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﺮﻭﺑﺎﻥ‬
‫—‬

‫‪C22-134C-828378-08‬‬
‫‪CH CH‬‬ ‫‪3‬‬ ‫‪2‬‬

‫‪ .62‬ﺍﻛﺘﺐ ﺻﻴﻐﹰ ﺎ ﺑﻨﺎﺋﻴﺔ ﻣﻜﺜﻔﺔ ﻟﻠﻤﺮﻛﺒﺎﺕ ﺍﻵﺗﻴﺔ‪:‬‬ ‫‪ .57‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﻜﺜﻔﺔ ﻟﻠﻤﺮﻛﺒﺎﺕ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪ -2،1 .a‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﺮﻭﺑﺎﻥ ﺣﻠﻘﻲ‬
‫‪ .57‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫‪ –4،1 .a‬ﺛﻨﺎﺋﻲ ﺇﻳﺜﻴﻞ ﻫﻜﺴﲔ ﺣﻠﻘﻲ‬
‫‪C22-137C-828378-08‬‬ ‫‪ -1،1 .b‬ﺛﻨﺎﺋﻲ ﺇﻳﺜﻴﻞ‪-2-‬ﻣﻴﺜﻴﻞ ﺣﻠﻘﻲ ﺑﻨﺘﺎﻥ‪.‬‬
‫ﻣﻴﺜﻴﻞ‪-1-‬ﺃﻭﻛﺘﲔ‬ ‫‪ –4،2 .b‬ﺛﻨﺎﺋﻲ‬
‫‪C22-135C-828378-08‬‬
‫‪–2،2 .c‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ‪-3-‬ﻫﻜﺴﺎﻳﻦ‬ ‫‪ -4 ،2 ،1 .a .58‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﺎﻥ ﺣﻠﻘﻲ‪.‬‬
‫‪ –1‬ﺇﻳﺜﻴﻞ–‪ –3‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ ﺣﻠﻘﻲ‪.‬‬ ‫‪.b‬‬

‫‪ –1‬ﺑﺮﻭﺑﻴﻞ–‪ –3‬ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗﺎﻥ ﺣﻠﻘﻲ‪.‬‬ ‫‪.c‬‬

‫‪ -6‬ﺇﻳﺜﻴﻞ–‪–3،2،1‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﺃﻭﻛﺘﺎﻥ ﺣﻠﻘﻲ‪.‬‬ ‫‪.d‬‬

‫‪‬‬
‫‪ –2 .a .61‬ﻣﻴﺜﻴﻞ–‪ –2‬ﺑﻴﻮﺗﲔ‪.‬‬
‫‪–2‬ﺇﻳﺜﻴﻞ–‪ –1‬ﺑﻴﻮﺗﲔ‪.‬‬
‫‪ –1‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﲔ ﺣﻠﻘﻲ‪.‬‬
‫‪ –3‬ﻣﻴﺜﻴﻞ ﺑﻴﻮﺗﲔ ﺣﻠﻘﻲ‪.‬‬
‫‪ .62‬ﺍﺭﺟـﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ ،‬ﺃﻭ ﺇﱃ‬
‫ﺩﻟﻴﻞ ﺣﻠﻮﻝ ﺍﳌﺴﺎﺋﻞ ﺹ ‪.86‬‬
‫‪8–3‬‬
‫‪‬‬
‫‪ .59‬ﲢﺘـﻮﻱ ﺍﻷﻟﻜﺎﻧـﺎﺕ ﻋـﲆ ﺭﻭﺍﺑـﻂ ﺃﺣﺎﺩﻳـﺔ ﻓﻘـﻂ ﺑـﲔ ﺫﺭﺍﺕ‬
‫‪.b‬‬ ‫ﺍﻟﻜﺮﺑـﻮﻥ ﰲ ﺍﳉﺰﻱﺀ‪ .‬ﰲ ﺣﲔ ﲢﺘـﻮﻱ ﺍﻷﻟﻜﻴﻨﺎﺕ ﻋﲆ ﺭﺍﺑﻄﺔ‬
‫‪.c‬‬ ‫ﺛﻨﺎﺋﻴـﺔ ﻭﺍﺣﺪﺓ ﻋـﲆ ﺍﻷﻗﻞ ﺑـﲔ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ ﰲ ﺍﳉﺰﻱﺀ‪.‬‬
‫ﻭﲢﺘﻮﻱ ﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ ﻭﺍﺣﺪﺓ ﻋﲆ ﺍﻷﻗﻞ ﺑﲔ‬
‫‪.d‬‬
‫ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﳉﺰﻱﺀ‪.‬‬
‫‪ .60‬ﻋﻨﺪ ﺗﺴـﻤﻴﺔ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺗﻜﻮﻥ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴـﺔ ﻫﻲ ﺃﻃﻮﻝ‬
‫ﺳﻠﺴـﻠﺔ ﻛﺮﺑﻮﻧﻴـﺔ ﻣﺘﺼﻠـﺔ‪ .‬ﻭﻋﻨﺪ ﺗﺴـﻤﻴﺔ ﺍﻷﻟﻜﻴﻨـﺎﺕ ﺗﻜﻮﻥ‬
‫ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﺮﺋﻴﺴﺔ ﻫﻲ ﺃﻃﻮﻝ ﺳﻠﺴـﻠﺔ ﻛﺮﺑﻮﻧﻴﺔ ﻣﺘﺼﻠﺔ ﺗﺸﻤﻞ‬
‫ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﳌﺮﺗﺒﻄﺔ ﺑﺮﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ‪.‬‬

‫‪170‬‬
 ‫ﻋﲔ ﺯﻭﺝ ﺍﳌﺘﺸﻜﻼﺕ ﺍﳍﻨﺪﺳﻴﺔ ﻣﻦ ﺑﲔ ﺍﻷﺷﻜﺎﻝ ﺍﻵﺗﻴﺔ‪،‬‬ ‫‪ .71‬ﹼ‬ ‫ﺳﻢ ﺍﳌﺮﻛﺐ ﺍ ﹸﳌ ﹶﻤﺜﻞ ﺑﺎﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪ .63‬ﱢ‬
‫ﻓﴪ ﻋﻼﻗﺔ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﺜﺎﻟﺜﺔ‬
‫ﹼ‬ ‫ﺛﻢ‬ ‫ﺍﺧﺘﻴﺎﺭﻙ‪،‬‬ ‫ﺳﺒﺐ‬ ‫ﹰﺎ‬
‫ﻨ‬ ‫ﻣﺒﻴ‬
‫‪ .66‬ﻟﻠﲈﺩﺓ ﺍﻟﻜﲑﺍﻟﻴﺔ ﻣﺘﺸﻜﻼﻥ‪ :‬ﺃﺣﺪﳘﺎ ‪ D‬ﻭﺍﻵﺧﺮ ‪.L‬‬
‫‪CH3‬‬ ‫‪CH2CH2CH3‬‬
‫ﺑﺎﻟﺼﻴﻐﺘﲔ ﺍﻵﺧﺮﻳﻦ‪:‬‬

‫—‬

‫—‬
‫‪C —C‬‬
‫‪.a‬‬

‫—‬

‫—‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫‪ .67‬ﲥﺘـﺰ ﻣﻮﺟﺎﺕ ﺍﻟﻀﻮﺀ ﺍﳌﺴـﺘﻘﻄﺐ ﰲ ﻣﺴـﺘﻮ￯ ﻭﺍﺣـﺪ‪ ،‬ﺃﻣﺎ ﰲ‬
‫‪CH3CH2‬‬ ‫‪CH2CH3‬‬

‫—‬

‫—‬
‫—‪C‬‬
‫‪—C‬‬

‫‪8-4‬‬

‫—‬

‫—‬
‫ﺍﻟﻀﻮﺀ ﺍﻟﻌﺎﺩﻱ ﻓﺘﻬﺘﺰ ﰲ ﲨﻴﻊ ﺍﳌﺴﺘﻮﻳﺎﺕ ﺍﳌﺤﺘﻤﻠﺔ‪.‬‬
‫‪CH3‬‬ ‫‪CH2CH2CH3‬‬

‫‪CH3‬‬ ‫‪CH2CH3‬‬ ‫‪.b‬‬ ‫‪C22-138C-828378-08‬‬

‫‪‬‬

‫—‬

‫—‬
‫‪ .68‬ﺗﺴﺒﺐ ﺩﻭﺭﺍﻥ ﺍﻟﻀﻮﺀ ﺍﳌﺴﺘﻘﻄﺐ‪.‬‬
‫—‪C‬‬
‫‪C22-144C-828378-08‬‬
‫‪—C‬‬
‫ﻓﻴﻢ ﺗﺘﺸﺎﺑﻪ ﺍﳌﺘﺸﻜﻼﺕ؟ ﻭﻓﻴﻢ ﲣﺘﻠﻒ؟‬
‫‪ .64‬ﹶ‬

‫—‬

‫—‬
‫‪CH3CH2‬‬ ‫‪CH3‬‬
‫‪.c‬‬ ‫‪ .65‬ﺻﻒ ﺍﻻﺧﺘﻼﻑ ﺑﲔ ﻣﺘﺸـﻜﻼﺕ ﺳـﻴﺲ ﻭﺗﺮﺍﻧﺲ ﻣﻦ ﺣﻴﺚ‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫ﺍﻟﱰﺗﻴﺐ ﺍﳍﻨﺪﳼ‪.‬‬
‫‪‬‬

‫—‬

‫—‬
‫‪C22-146C-828378-08‬‬
‫—‪C‬‬
‫‪—C‬‬
‫‪ .66‬ﻣﺎ ﺧﺼﺎﺋﺺ ﺍﳌﺎﺩﺓ ﺍﻟﻜﲑﺍﻟﻴﺔ؟‬

‫—‬

‫—‬
‫‪CH3CH2‬‬ ‫‪CH2CH3‬‬
‫‪ .67‬ﺍﻟﻀﻮﺀ ﻛﻴﻒ ﳜﺘﻠﻒ ﺍﻟﻀﻮﺀ ﺍﳌﺴـﺘﻘﻄﺐ ﻋﻦ ﺍﻟﻀﻮﺀ ﺍﻟﻌﺎﺩﻱ‪،‬‬
‫‪ .69‬ﻗﺪ ﺗﺸـﻤﻞ ﺇﺟﺎﺑﺎﺕ ﺍﻟﻄﻼﺏ ﺃﻱ ﺷﻜﻠﲔ ﻣﺎ ﻋﺪﺍ ‪ b‬ﻭ ‪ d‬ﻷﳖﲈ‬ ‫‪ .72‬ﺍﻛﺘﺐ ﻣﺘﺸﻜﻠﲔ ﺳﻴﺲ ﻭﺗﺮﺍﻧﺲ ﻟﻠﺠﺰﻱﺀ ﺍ ﹸﳌ ﹶﻤﺜﻞ ﺑﺎﻟﺼﻴﻐﺔ‬
‫ﻭﻣﻴﺰ ﺑﻴﻨﻬﲈ‪:‬‬
‫ﻭﻣﻦ ﺫﻟﻚ ﺿﻮﺀ ﺍﻟﺸﻤﺲ؟‬
‫ﺍﳌﻜﺜﻔﺔ ﺍﻵﺗﻴﺔ‪ ،‬ﹼ‬
‫‪C22-145C-828378-08‬‬
‫ﻣﺘﲈﺛﻼﻥ )ﻧﻔﺲ ﺍﻟﺸﻜﻞ(‪.‬‬
‫‪ .68‬ﻛﻴﻒ ﺗﺆﺛﺮ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﻀﻮﺋﻴﺔ ﰲ ﺍﻟﻀﻮﺀ ﺍﳌﺴﺘﻘﻄﺐ؟‬
‫‪CH3CH — CHCH2CH3‬‬
‫‪‬‬

‫‪ .70‬ﺍﺭﺟـﻊ ﺇﱃ ﺍﻟـﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﻜﺜﻔـﺔ‪ .‬ﳚﺐ ﺃﻥ‬ ‫ﻋـﲔ ﺯﻭﺝ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﰲ ﳎﻤﻮﻋـﺔ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‬
‫‪ .69‬ﹼ‬
‫‪8-5‬‬ ‫ﺍﳌﻜﺜﻔﺔ ﺍﻵﺗﻴﺔ‪:‬‬

‫ﹸﺗﻈﻬـﺮ ﺇﺟﺎﺑـﺎﺕ ﺍﻟﻄـﻼﺏ ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺍﳌﻜﺜﻔـﺔ ﻟﻜﻞ ﻣﻦ‬ ‫‪‬‬ ‫‪CH3‬‬
‫‪.c‬‬
‫‪CH3‬‬
‫‪.a‬‬

‫—‬

‫—‬
‫‪ .73‬ﻣﺎ ﺍﳋﺎﺻﻴـﺔ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﺍﻟﺘﻲ ﺗﺸﱰﻙ ﻓﻴﻬﺎ ﺍﳍﻴـﺪﺭﻭﻛـﺮﺑﻮﻧﺎﺕ‬
‫ﺑﻴﻮﺗﺎﻥ ﺣﻠﻘﻲ‪ - 1 ،‬ﺑﻴﻮﺗﲔ‪ –2 ،‬ﻣﻴﺜﻴﻞ ﺑﺮﻭﺑﲔ‪.‬‬
‫‪CH3CHCHCH2CH3‬‬ ‫‪CH3CCH2CH2CH3‬‬

‫—‬

‫—‬
‫ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﲨﻴﻌﻬﺎ؟‬ ‫‪CH3‬‬ ‫‪CH3‬‬

‫ﹺ‬ ‫ﹸ‬
‫‪ .74‬ﻣﺎ ﺍﳌﻘﺼﻮﺩ ﺑﺎﳌﻮﺍﺩ ﺍﳌ ﹶﴪﻃﻨﺔ؟‬
‫‪ b .71‬ﻭ ‪ c‬ﻣﺘﺸﻜﻼﻥ ﻫﻨﺪﺳﻴﺎﻥ‪ ،‬ﻳﻤﺜﻼﻥ ﺯﻭﺝ ﻣﺘﺸﻜﻼﺕ ﺳﻴﺲ‪/‬‬ ‫‪‬‬ ‫‪CH3CHCH2CHCH3 .d‬‬
‫‪C22-140C-828378-08‬‬
‫‪CH3 .b‬‬

‫—‬
‫—‬

‫—‬
‫‪C22-142C-828378-08 CH CHCH CH‬‬
‫ﺗﺮﺍﻧﺲ‪ a .‬ﻫﻮ ﻣﺘﺸﻜﻞ ﺑﻨﺎﺋﻲ ﻟﻜﻞ ﻣﻦ ‪ b‬ﻭ ‪.c‬‬ ‫‪ .75‬ﺍﻛﺘﺐ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﹺﻟـ ‪ –2،1‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬
‫‪CH3 CH3‬‬ ‫‪3‬‬ ‫‪2‬‬

‫—‬

‫—‬
‫‪CH3‬‬ ‫‪CH3‬‬
‫ﺳﻢ ﺍﳌﺮﻛﺒﺎﺕ ﺍ ﹸﳌ ﹶﻤﺜﻠﺔ ﺑﺎﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻵﺗﻴﺔ‪:‬‬
‫‪ .76‬ﱢ‬
‫‪ .72‬ﺍﺭﺟـﻊ ﺇﱃ ﺍﻟـﺪﺭﺱ ﻟﻜﺘﺎﺑـﺔ ﺍﳌﺘﺸـﻜﻠﲔ‪ .‬ﺫﺭﺗـﺎ ﺍﳍﻴﺪﺭﻭﺟـﲔ‬ ‫‪.b‬‬ ‫‪.a‬‬ ‫‪ .70‬ﺍﻛﺘﺐ ﺻﻴﻐﹰ ﺎ ﺑﻨﺎﺋﻴﺔ ﻣﻜﺜﻔﺔ ﻷﺭﺑﻌﺔ ﻣﺘﺸﻜﻼﺕ ﳐﺘﻠﻔﺔ ﲢﻤﻞ‬
‫‪C22-143C-828378-08‬‬
‫ﺍﻟﺼﻴﻐﺔ ﺍﳉﺰﻳﺌﻴﺔ ‪.C4H8‬‬
‫ﺍﳌﺮﺗﺒﻄﺘـﺎﻥ ﺑﺬﺭﰐ ﺍﻟﻜﺮﺑـﻮﻥ ﺛﻨﺎﺋﻴﺘﻲ ﺍﻟﺮﺑﻂ ﺗﻘﻌـﺎﻥ ﻋﲆ ﺍﳉﻬﺔ‬ ‫‪CH3‬‬ ‫‪C22-141C-828378-08‬‬

‫ﻧﻔﺴـﻬﺎ ﻣـﻦ ﺍﻟﺴﻠﺴـﻠﺔ ﺍﻟﻜﺮﺑﻮﻧﻴـﺔ ﰲ ﻣﺘﺸـﻜﻞ ﺳـﻴﺲ ﻭﻋﲆ‬

‫‪C22-153C-828378-08C22-151C-828378-08‬‬
‫ﺟﻬﺎﺕ ﻣﺘﻘﺎﺑﻠﺔ ﻣﻦ ﺍﻟﺴﻠﺴﻠﺔ ﺍﻟﻜﺮﺑﻮﻧﻴﺔ ﰲ ﻣﺘﺸﻜﻞ ﺗﺮﺍﻧﺲ‪.‬‬

‫‪8–5‬‬
‫‪‬‬
‫‪ .73‬ﲢﺘﻮﻱ ﲨﻴﻌﻬﺎ ﻋﲆ ﺑﻨﺎﺀ ﺣﻠﻘﻲ ﰲ ﺍﳉﺰﻱﺀ‪.‬‬ ‫‪ – 4 .63‬ﺇﻳﺜﻴﻞ–‪ –3‬ﻣﻴﺜﻴﻞ–‪ -3‬ﻫﺒﺘﲔ‪.‬‬
‫‪ .74‬ﺍﳌﻮﺍﺩ ﺍﳌﴪﻃﻨﺔ ﻫﻲ ﻣﻮﺍﺩ ﻗﺎﺩﺭﺓ ﻋﲆ ﺍﻟﺘﺴﺒﺐ ﰲ ﺍﻟﴪﻃﺎﻥ‪.‬‬ ‫‪8–4‬‬
‫‪‬‬ ‫‪‬‬
‫‪.75‬‬ ‫‪ .64‬ﻟﻠﻤﺘﺸـﻜﻼﺕ ﺍﻟﺼﻴﻐـﺔ ﺍﳉﺰﻳﺌﻴـﺔ ﻧﻔﺴـﻬﺎ ﻭﻟﻜﻨﻬـﺎ ﲣﺘﻠﻒ ﰲ‬
‫‪CH3‬‬ ‫ﺍﻟﺼﻴـﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ .‬ﻗﺪ ﻳﻜـﻮﻥ ﳍﺎ ﺧﺼﺎﺋﺺ ﻛﻴﻤﻴﺎﺋﻴـﺔ ﻭﻓﻴﺰﻳﺎﺋﻴﺔ‬
‫‪CH3‬‬ ‫ﳐﺘﻠﻔﺔ‪.‬‬
‫‪ .65‬ﺗﻘـﻊ ﺃﻛـﱪ ﺍﳌﺠﻤﻮﻋـﺎﺕ ﰲ ﻣﺘﺸـﻜﻼﺕ ﺳـﻴﺲ ﻋـﲆ ﺫﺭﺍﺕ‬
‫ﺍﻟﻜﺮﺑـﻮﻥ ﰲ ﺍﻟﺮﺍﺑﻄـﺔ ﺍﻟﺜﻨﺎﺋﻴﺔ ﻋﲆ ﺍﳉﻬﺔ ﻧﻔﺴـﻬﺎ ﻣﻦ ﺍﻟﺮﺍﺑﻄﺔ؛‬
‫‪ .a .76‬ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ )ﺗﻮﻟﻮﻭﻳﻦ(‪.‬‬ ‫ﰲ ﺣﲔ ﺗﻘﻊ ﰲ ﻣﺘﺸﻜﻼﺕ ﺗﺮﺍﻧﺲ ﻋﲆ ﺍﳉﻬﺎﺕ ﺍﳌﺘﻌﺎﻛﺴﺔ‪.‬‬
‫‪ .b‬ﺃﻧﺜﺮﺍﺳﲔ‪.‬‬
‫‪C22-151C-828378-08‬‬

‫‪171‬‬
‫‪ .84‬ﺃﳞـﲈ ﺗﺘﻮﻗﻊ ﺃﻥ ﻳﻜﻮﻥ ﻟـﻪ ﺧﺼﺎﺋﺺ ﻓﻴﺰﻳﺎﺋﻴﺔ ﻣﺘﺸـﺎﲠﺔ‪ ،‬ﺯﻭﺝ‬ ‫‪‬‬ ‫‪‬‬
‫ﻣـﻦ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺃﻡ ﺯﻭﺝ ﻣﻦ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﻔﺮﺍﻏﻴﺔ؟‬ ‫ﻓﴪ‬
‫‪ .77‬ﻫﻞ ﲤﺜﹼﻞ ﺍﻟﺼﻴﻐﺘﺎﻥ ﺍﻟﺒﻨﺎﺋﻴﺘﺎﻥ ﺍﻵﺗﻴﺘﺎﻥ ﺍﳉﺰﻱﺀ ﻧﻔﺴﻪ؟ ﹼ‬
‫‪‬‬
‫ﻓﴪ ﺍﺳﺘﻨﺘﺎﺟﻚ‪.‬‬
‫ﱢ‬ ‫ﺇﺟﺎﺑﺘﻚ‪.‬‬
‫ﻓـﴪ ﳌـﺎﺫﺍ ﻧﺤﺘـﺎﺝ ﺇﱃ ﺍﻷﺭﻗﺎﻡ ﰲ ﺃﺳـﲈﺀ ﺃﻳﻮﺑـﺎﻙ ﻟﻠﻌﺪﻳﺪ ﻣﻦ‬
‫‪ .85‬ﱢ‬ ‫‪H‬‬ ‫‪CH3 .b‬‬ ‫‪H‬‬ ‫‪H‬‬ ‫‪.a‬‬ ‫‪ .77‬ﻻ‪ ،‬ﳘﺎ ﻣﺘﺸﻜﻼﻥ ﺑﻨﺎﺋﻴﺎﻥ‪.‬‬
‫ﺍﻷﻟﻜﻴﻨﺎﺕ ﻭﺍﻷﻟﻜﺎﻳﻨﺎﺕ ﺍﳌﺴﺘﻘﻴﻤﺔ‪ ،‬ﰲ ﺣﲔ ﺃﻧﻨﺎ ﻟﺴﻨﺎ ﺑﺤﺎﺟﺔ‬

‫—‬

‫—‬
‫—‬

‫—‬
‫‪ 20 .78‬ﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ؛ ‪ 18‬ﺫﺭﺓ ﻫﻴﺪﺭﻭﺟﲔ‪.‬‬
‫‪C—C‬‬ ‫‪C—C‬‬
‫ﺇﱃ ﻛﺘﺎﺑﺘﻬﺎ ﰲ ﺃﺳﲈﺀ ﺍﻷﻟﻜﺎﻧﺎﺕ ﺍﳌﺴﺘﻘﻴﻤﺔ‪.‬‬

‫—‬

‫—‬
‫—‬

‫—‬
‫‪H‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪CH3‬‬
‫ﺍﳌﺮﻛـﺐ ﺍﳌﺤﺘﻮﻱ ﻋـﲆ ﺭﺍﺑﻄﺘـﲔ ﺛﻨﺎﺋﻴﺘـﲔ ﺑﺎﻟﺪﺍﻳﲔ‪،‬‬ ‫ﺴـﻤﻰ ﹼ‬ ‫‪ .78‬ﻣﺎ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﳍﻴﺪﺭﻭﺟﲔ ﰲ ﺟﺰﻱﺀ ﺃﻟﻜﺎﻥ ﳛﺘﻮﻱ ﻋﲆ ﺗﺴﻊ ‪ .86‬ﹸﻳ ﹼ‬
‫ﻭﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﳌﻜﺜﻔﺔ ﺃﺩﻧﺎﻩ ﲤﺜـﻞ ﺍﳌﺮﻛﺐ ‪-4،1‬ﺑﻨﺘﺎﺩﺍﻳﲔ‪.‬‬
‫‪C22-154C-828378-08‬ﰲ ﺃﻟﻜﲔ ﳛﺘﻮﻱ ﻋﲆ ﺗﺴﻊ ﺫﺭﺍﺕ‬
‫ﺫﺭﺍﺕ ﻛﺮﺑﻮﻥ؟ ﻭﻣﺎ ﻋﺪﺩﻫﺎ‬ ‫‪.CnH2n .79‬‬
‫ﺍﺳـﺘﻌﻦ ﺑﻤﻌﺮﻓﺘﻚ ﺑﺄﺳﲈﺀ ﺍﻷﻳﻮﺑﺎﻙ ﻋﲆ ﻛﺘﺎﺑﺔ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‬ ‫‪C22-155C-828378-08‬‬
‫ﻛﺮﺑﻮﻥ ﻭﺭﺍﺑﻄﺔ ﺛﻨﺎﺋﻴﺔ ﻭﺍﺣﺪﺓ؟‬
‫ﻟﻠﻤﺮﻛﺐ ‪ –3،1‬ﺑﻨﺘﺎﺩﺍﻳﲔ‪.‬‬
‫‪ .79‬ﺇﺫﺍ ﻛﺎﻧـﺖ ﺍﻟﺼﻴﻐﺔ ﺍﻟﻌﺎﻣﺔ ﻟﻸﻟﻜﺎﻧـﺎﺕ ﻫﻲ ‪ ،CnH2n+2‬ﻓﺤﺪﺩ‬ ‫‪ .80‬ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﻏﲑ ﺍﳌﺸـﺒﻌﺔ ﳍـﺎ ﺩﺭﺟﺔ ﻋﺎﻟﻴﺔ ﻣﻦ ﺍﻟﻨﺸـﺎﻁ‬
‫ﺍﻟﺼﻴﻐﺔ ﺍﻟﻌﺎﻣﺔ ﻟﻸﻟﻜﺎﻧﺎﺕ ﺍﳊﻠﻘﻴﺔ‪.‬‬
‫ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‪.‬‬
‫‪H2C — CH — CH2 — CH — CH2‬‬

‫‪ .80‬ﺍﻟﺼﻨﺎﻋﺔ ﳌﺎﺫﺍ ﺗﹸﻌﺪﹼ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﻏﲑ ﺍﳌﺸﺒﻌﺔ ﺑﻮﺻﻔﻬﺎ ﻣﻮﺍﺩ‬

‫‪‬‬ ‫ﺃﻛﺜﺮ ﻓﺎﺋﺪﺓ ﰲ ﺍﻟﺼﻨﺎﻋﺔ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﻣﻦ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ‪‬‬‫ﺃﻭﻟﻴﺔ ﹶ‬
‫ﺍﳌﺸﺒﻌﺔ؟‬
‫‪ .81‬ﻻ‪ ،‬ﻟﻠﺒﻨﺘـﺎﻥ ﺍﳊﻠﻘـﻲ )‪ (C5H10‬ﻭﺍﻟﺒﻨﺘـﺎﻥ )‪ (C5H12‬ﺻﻴﻐﺘـﺎﻥ‬
‫‪ .87‬ﺣﺪﱢ ﺩ ﺍﺛﻨﲔ ﻣﻦ ﺍﻷﺳﲈﺀ ﺍﻵﺗﻴﺔ ﻻ ﻳﻤﻜﻦ ﺃﻥ ﻳﻜﻮﻧﺎ ﺻﺤﻴﺤﲔ‪:‬‬
‫‪-2 .a‬ﺇﻳﺜﻴﻞ‪ –2-‬ﺑﻴﻮﺗﲔ‬
‫ﻓﴪ ﺇﺟﺎﺑﺘﻚ‪.‬‬ ‫ﱢ‬ ‫ﻟﻠﺒﻨﺘﺎﻥ؟‬ ‫ﹰ‬
‫ﻣﺘﺸﻜﻼ‬ ‫ﺍﳊﻠﻘﻲ‬ ‫ﺍﻟﺒﻨﺘﺎﻥ‬ ‫‪ .81‬ﻫﻞ ﹸﻳﻌﺪ‬ ‫ﺟﺰﻳﺌﻴﺘﺎﻥ ﳐﺘﻠﻔﺘﺎﻥ‪.‬‬
‫‪ -4،1 .b‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﻫﻜﺴﲔ ﺣﻠﻘﻲ‬ ‫ﹺ‬
‫‪ .82‬ﺣـﺪﹼ ﺩ ﻣﺎ ﺇﺫﺍ ﻛﺎﻥ ﻛﻞ ﻣـﻦ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻵﺗﻴﺔ ﺗﹸﻈﻬﺮ ﺍﻟﱰﻗﻴﻢ‬
‫‪ -5،1 .c‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‬ ‫ﺍﻟﺼﺤﻴـﺢ‪ .‬ﻓـﺈﺫﺍ ﱂ ﻳﻜـﻦ ﻛﺬﻟـﻚ ﻓﺄﻋـﺪ ﻛﺘﺎﺑﺘﻬـﺎ ﺑﺎﻟﱰﻗﻴـﻢ‬
‫ﺍﻟﺼﺤﻴﺢ‪:‬‬
‫‪ .a .82‬ﺍﻟﱰﻗﻴﻢ ﺻﺤﻴﺢ‪.‬‬
‫‪ .88‬ﺍﺳﺘﻨﺘﺞ ﻳﻄﻠﻖ ﺍﻟﺪﻳﻜﺴـﱰﻭﺯ ‪dextrose‬؛ ﰲ ﺑﻌﺾ ﺍﻷﺣﻴﺎﻥ‬
‫ﻋـﲆ ﺳـﻜﺮ ﺍﳉﻠﻮﻛـﻮﺯ؛ ﻷﻥ ﳏﻠـﻮﻝ ﺍﳉﻠﻮﻛـﻮﺯ ﹸﻋـﺮﻑ ﺑﺄﻧـﻪ‬ ‫‪5‬‬
‫‪1‬‬ ‫‪CH3‬‬
‫‪.c‬‬ ‫‪3‬‬ ‫‪2‬‬
‫‪CH3‬‬
‫‪.a‬‬
‫ﻻ‪ ،‬ﳚﺐ ﺗﺮﻗﻴﻤﻪ ﻣﻦ ﺍﻟﻄﺮﻑ ﺍﻵﺧﺮ‪.‬‬ ‫‪.b‬‬
‫‪ .dextrorotatory‬ﺣ ﹼﻠﻞ ﻫﺬﻩ ﺍﻟﻜﻠﻤﺔ‪ ،‬ﻭﺣﺪﺩ ﻣﺎ ﺗﻌﻨﻴﻪ‪.‬‬
‫‪4‬‬

‫‪ .89‬ﺗﻔﺴﲑ ﺍﻟﺘﺼﻮﺭﺍﺕ ﺍﻟﻌﻠﻤﻴﺔ ﺍﺭﺳﻢ ﺑﻨﺎﺀ ﻛﻴﻜﻮﱄ ﻟﻠﺒﻨﺰﻳﻦ‪ ،‬ﹼ‬

‫ﻭﻓﴪ‬ ‫‪CH3‬‬
‫‪3‬‬ ‫‪2‬‬
‫‪4‬‬ ‫‪1‬‬
‫‪CH3‬‬
‫ﺍﻟﱰﻗﻴﻢ ﺻﺤﻴﺢ‪.‬‬ ‫‪.c‬‬
‫ﳌﺎﺫﺍ ﻻ ﻳﻤﺜﹼﻞ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺍﻟﻔﻌﻠﻴﺔ؟‬
‫ﻓﴪ ﺍﻟﺴـﺒﺐ ﻭﺭﺍﺀ ﻛـﻮﻥ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﻣﺜﻞ‬ ‫‪ .90‬ﺍﻟﺴـﺒﺐ ﻭﺍﻟﻨﺘﻴﺠﺔ ﱢ‬ ‫‪5‬‬
‫‪3‬‬
‫‪CH3 .d‬‬
‫‪4‬‬
‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪45‬‬
‫‪.b‬‬ ‫ﺍﻟﱰﻗﻴﻢ ﺻﺤﻴﺢ‪.‬‬ ‫‪.d‬‬
‫— ‪CH3CH2C‬‬
‫‪— CCH3‬‬
‫ﻓﻌﺎﻟﺔ ﰲ ﺇﺫﺍﺑﺔ ﺍﻟﺸﺤﻢ ﺃﻭ ﺍﳌﻮﺍﺩ‬
‫ﹼ‬ ‫ﺍﳊﻠﻘﻲ‪،‬‬ ‫ﻭﺍﳍﻜﺴﺎﻥ‬ ‫ﺍﳍﻜﺴـﺎﻥ‬
‫‪ .83‬ﻻ ﺗﺴﺘﻄﻴﻊ ﺍﻟﺘﻤﻴﻴﺰ ﺑﲔ ﺍﳌﺘﺸﻜﻼﺕ ﻣﻦ ﺧﻼﻝ ﺍﻟﺼﻴﻎ ﺍﳉﺰﻳﺌﻴﺔ‪.‬‬
‫‪C22-158C-828378-08‬‬
‫‪6‬‬ ‫‪2‬‬
‫‪C22-156C-828378-08‬‬
‫ﺍﻟﺪﻫﻨﻴﺔ‪ ،‬ﻋﲆ ﻋﻜﺲ ﺍﳌﺎﺀ‪.‬‬ ‫‪1‬‬
‫‪CH CH‬‬ ‫‪2‬‬ ‫‪3‬‬

‫‪ .83‬ﳌﺎﺫﺍ ﻳﺴﺘﺨﺪﻡ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﻮﻥ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﺮﻛﺒﺎﺕ ‪ .91‬ﹼ‬

‫ﻓـﴪ ﺍﻛﺘﺐ ﻋﺒـﺎﺭﺓ ﺗﻔﴪ ﺍﻟﻌﻼﻗـﺔ ﺑﲔ ﻋـﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ‬
‫ﻭﺩﺭﺟﺔ ﻏﻠﻴﺎﻥ ﺍﻷﻟﻜﺎﻧﺎﺕ‪.‬‬ ‫ﻻ ﻣﻦ ﺍﻟﺼﻴﻎ ﺍﳉﺰﻳﺌﻴﺔ ﻣﺜﻞ ‪C5H12‬؟‬‫ﺍﻟﻌﻀﻮﻳﺔ ﺑﺪ ﹰ‬ ‫‪ .84‬ﻗـﺪ ﲣﺘﻠـﻒ ﺍﳌﺘﺸـﻜﻼﺕ ﺍﻟﺒﻨﺎﺋﻴﺔ ﺇﱃ ﺣﺪ ﻛﺒـﲑ ﰲ ﺧﺼﺎﺋﺼﻬﺎ‬
‫‪C22-159C-828378-08‬‬
‫ﻛﻠﻴﺎ ﻟﻠﻬﻴـﻜﻞ ﺍﻟﻜﺮﺑﻮﲏ‪.‬‬
‫ﺍﻟﻔﻴﺰﻳﺎﺋﻴـﺔ ﻷﻥ ﳍـﺎ ﺗﺮﺗﻴﺒـﺎﺕ ﳐﺘﻠﻔﺔ ﹼﹰ‬
‫ﻟﻠﻤﺘﺸـﻜﻼﺕ ﺍﻟﻔﺮﺍﻏﻴـﺔ )ﺍﳍﻨﺪﺳـﻴﺔ ﻭﺍﻟﻀﻮﺋﻴـﺔ( ﺍﳍﻴـﻜﻞ‬
‫ﺍﻟﻜﺮﺑـﻮﲏ ﻧﻔﺴـﻪ ﻭﻟﻜـﻦ ﺍﲡﺎﻫﺎﲥـﺎ ﳐﺘﻠﻔـﺔ ﰲ ﺍﻟﻔـﺮﺍﻍ‪.‬‬
‫ﻭﻟﻠﻤﺘﺸـﻜﻼﺕ ﺍﳍﻨﺪﺳـﻴﺔ ﺧﺼﺎﺋﺺ ﳐﺘﻠﻔﺔ؛ ﺃﻣﺎ ﺍﳌﺘﺸﻜﻼﺕ‬
‫‪ .88‬ﺍﻟﺒﺎﺩﺋـﺔ ‪" -dextro‬ﺗﻠﻔﻆ ﺩﻳﻜﺴـﱰﻭ" ﺗﻌﻨﻲ ﺇﱃ ﺟﻬﺔ ﺍﻟﻴﻤﲔ‪،‬‬
‫ﺍﻟﻀﻮﺋﻴـﺔ ﻓﺘﺨﺘﻠﻒ ﻓﻘـﻂ ﰲ ﺍﲡﺎﻩ ﺩﻭﺭﺍﻥ ﺍﻟﻀﻮﺀ ﺍﳌﺴـﺘﻘﻄﺐ‬
‫ﻭﺍﻟﻼﺣﻘـﺔ ‪" rotatory‬ﻭﺗﻠﻔﻆ ﺭﻭﺗﺎﺗـﻮﺭﻱ" ﺗﻌﻨﻲ ﻳﺪﻭﺭ‪ .‬ﻟﺬﺍ‬
‫ﻭﰲ ﺍﻟﺘﻔﺎﻋـﻼﺕ ﺍﻟﻜﻴﻤﻴﺎﺋﻴـﺔ ﺍﻟﺘـﻲ ﲤﻴﺰ ﺑﲔ ﺍﳌﺘﺸـﻜﻼﺕ‪ .‬ﻟﺬﺍ‬
‫ﻓﺈﻥ ﺍﻟﺸـﻜﻞ ﺍﻟﻄﺒﻴﻌﻲ ﻣـﻦ ﺍﳉﻠﻮﻛﻮﺯ ﻛﲑﺍﱄ ﻳﺆﺩﻱ ﺇﱃ ﺩﻭﺭﺍﻥ‬
‫ﻟﻠﻤﺘﺸـﻜﻼﺕ ﺍﻟﻀﻮﺋﻴﺔ ﺧﺼﺎﺋﺺ ﻣﺘﺸـﺎﲠﺔ ﺃﻛﺜـﺮ ﻣﻦ ﻏﲑﻫﺎ‬
‫ﻣﺴﺘﻮ￯ ﺍﻟﻀﻮﺀ ﺍﳌﺴﺘﻘﻄﺐ ﺇﱃ ﺍﻟﻴﻤﲔ‪.‬‬
‫ﻣﻦ ﺍﳌﺘﺸﻜﻼﺕ‪.‬‬
‫‪ .89‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﺮﺳـﻢ ﺑﻨﺎﺀ ﻛﻴﻜﻮﱄ ﻟﻠﺒﻨﺰﻳﻦ‪ .‬ﹸﻳﻈﻬﺮ ﺍﻟﺸﻜﻞ‬
‫‪ .85‬ﺍﻷﺭﻗﺎﻡ ﴐﻭﺭﻳﺔ ﻟﺘﺤﺪﻳﺪ ﻣﻮﺍﻗﻊ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﻭﺍﻟﺜﻼﺛﻴﺔ‪.‬‬
‫ﺍﻹﻟﻜﱰﻭﻧـﺎﺕ ﺍﳌﺘﻤﺮﻛﺰﺓ ﺍﳌﻮﺟﻮﺩﺓ ﰲ ﺍﻟﺮﻭﺍﺑﻂ ﺍﻟﺜﻨﺎﺋﻴﺔ ﹰ‬
‫ﻋﻮﺿﺎ‬
‫‪ .86‬ﺍﺭﺟـﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‪ ،‬ﺃﻭ ﺇﱃ ﺩﻟﻴﻞ ﺣﻠﻮﻝ‬
‫ﻋـﻦ ﺍﻹﻟﻜﱰﻭﻧـﺎﺕ ﻏـﲑ ﺍﳌﺘﻤﺮﻛـﺰﺓ ﺍﳌﻮﺯﻋـﺔ ﻋـﲆ ﺍﻟـﺬﺭﺍﺕ‬
‫ﺍﳌﺴﺎﺋﻞ ﺹ ‪.89‬‬
‫)‪.(delocalized‬‬
‫‪ .90‬ﺍﻟﺪﻫﻮﻥ ﻭﺍﻟﺸـﺤﻮﻡ ﻣﻮﺍﺩ ﻏﲑ ﻗﻄﺒﻴﺔ ﻣﺜﻞ ﺍﻷﻟﻜﺎﻧﺎﺕ‪ ،‬ﺃﻣﺎ ﺍﳌﺎﺀ‬ ‫‪‬‬
‫ﻗﻄﺒﻲ‪ .‬ﺍﳌﻮﺍﺩ ﺍﳌﺘﺸﺎﲠﺔ ﻳﺬﻭﺏ ﺑﻌﻀﻬﺎ ﰲ ﺑﻌﺾ‪.‬‬
‫‪ .87‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﻜﺘﺎﺑﺔ ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ‪.‬‬
‫‪ .91‬ﻛﻠـﲈ ﺯﺍﺩ ﻋـﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑـﻮﻥ ﰲ ﺍﻟﺴﻠﺴـﻠﺔ ﺯﺍﺩﺕ ﺩﺭﺟـﺔ‬
‫ﺍﻻﺳﻢ ﺍﻟﺼﺤﻴﺢ ﻫﻮ ‪ –3‬ﻣﻴﺜﻴﻞ – ‪ –2‬ﺑﻨﺘﲔ‪.‬‬ ‫‪.a‬‬
‫ﺍﻟﻐﻠﻴﺎﻥ‪.‬‬
‫ﺍﻻﺳﻢ ﺻﺤﻴﺢ‪.‬‬ ‫‪.b‬‬

‫ﺍﻻﺳﻢ ﺍﻟﺼﺤﻴﺢ ﻫﻮ ‪ -1 ،3‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺰﻳﻦ‪.‬‬ ‫‪.c‬‬

‫‪172‬‬
 ‫‪‬‬
‫‪‬‬ ‫‪ .92‬ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﻜﲑﺍﻟﻴﺔ ﳛﺘﻮﻱ ﺍﻟﻜﺜﲑ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ‬
‫‪‬‬ ‫‪ .96‬ﺍﳉﺎﺯﻭﻟـﲔ ﻛﺎﻥ ﺍﳌﺮﻛﺐ "ﺭﺑﺎﻋﻲ ﺇﻳﺜﻴﻞ ﺍﻟﺮﺻﺎﺹ"ﻟﺴـﻨﻮﺍﺕ‬
‫‪‬‬ ‫ﺍﻟﻌﻀﻮﻳﺔ ﻋﲆ ﺃﻛﺜﺮ ﻣﻦ ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﻛﲑﺍﻟﻴﺔ ﻭﺍﺣﺪﺓ‪ .‬ﻭﻟﻜﻞ‬
‫ﺫﺭﺓ ﻛﺮﺑﻮﻥ ﻛﲑﺍﻟﻴﺔ ﰲ ﺍﳌﺮﻛﺐ ﺯﻭﺝ ﻣﻦ ﺍﳌﺘﺸﻜﻼﺕ ﺍﻟﻔﺮﺍﻏﻴﺔ‪.‬‬
‫ﺃﺳﺎﺳـﻴﺎ ﰲ ﺍﳉﺎﺯﻭﻟـﲔ ﳌﻨﻊ ﺍﻟﻔﺮﻗﻌـﺔ‪ .‬ﺍﺑﺤﺚ‬
‫ﹼﹰ‬ ‫ﻛﺜـﲑﺓ‪ ،‬ﻣﻜﻮﻧﹰـﺎ‬
‫ﺍﳌﺤﺘﻤﻠﺔ ﻟﻠﻤﺮﻛﺐ ﻣﺴﺎ ﹴﻭ ﻟﹺـ‬
‫ﹶ‬ ‫ﻭﺍﳌﺠﻤﻮﻉ ﺍﻟﻜﲇ ﻟﻠﻤﺘﺸﻜﻼﺕ‬
‫ﻋـﻦ ﺍﻟﺼﻴﻐﺔ ﺍﻟﺒﻨﺎﺋﻴـﺔ ﻟﺬﺍ ﺍﳌﺮﻛﺐ ﻭﺗﺎﺭﻳﺦ ﺗﻄﻮﻳﺮﻩ ﻭﺍﺳـﺘﻌﲈﻟﻪ‬
‫‪‬‬ ‫ﻭﺍﻷﺳﺒﺎﺏ ﺍﻟﻜﺎﻣﻨﺔ ﻭﺭﺍﺀ ﺗﻮﻗﻒ ﺍﺳﺘﻌﲈﻟﻪ‪ .‬ﻭﻫﻞ ﻣﺎ ﺯﺍﻝ ﻳﺘﺨﺬ‬
‫‪ ،2n‬ﺣﻴﺚ ﺗﺸﲑ ‪ n‬ﺇﱃ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﻜﲑﺍﻟﻴﺔ‪ .‬ﺍﻛﺘﺐ‬
‫ﻣﺎﺩﺓ ﺗﹸﻀﺎﻑ ﺇﱃ ﺍﻟﺒﻨﺰﻳﻦ ﰲ ﺃﻣﺎﻛﻦ ﻣﻦ ﺍﻟﻌﺎﱂ؟‬ ‫ﺍﻟﺼﻴﻎ ﺍﻟﺒﻨﺎﺋﻴﺔ ﻟﻠﻤﺮﻛﺒﺎﺕ ﺃﺩﻧﺎﻩ‪ ،‬ﻭﺣﺪﹼ ﺩ ﻋﺪﺩ ﺍﳌﺘﺸﻜﻼﺕ‬
‫‪ .96‬ﳚـﺐ ﺃﻥ ﺗﺸـﻤﻞ ﺇﺟﺎﺑـﺎﺕ ﺍﻟﻄـﻼﺏ ﺭﺳـﻢ ﺍﻟﺼﻴﻐـﺔ ﺍﻟﺒﻨﺎﺋﻴﺔ‬ ‫‪ .97‬ﺍﻟﻌﻄﻮﺭ ﻳﺘﻜﻮﻥ ﺍﳌﹺﺴـﻚ ﺍﳌﺴـﺘﻌﻤﻞ ﰲ ﺍﻟﻌﻄـﻮﺭ ﻣﻦ ﺍﻟﻜﺜﲑ ﻣﻦ‬ ‫ﺍﻟﻔﺮﺍﻏﻴﺔ ﺍﳌﻤﻜﻨﺔ ﻟﻜﻞ ﻣﻨﻬﺎ‪.‬‬
‫ﺍﳌﺮﻛﺒـﺎﺕ ﺍﻟﺘـﻲ ﺗﺸـﻤﻞ ﺃﻟﻜﺎﻧـﺎﺕ ﺣﻠﻘﻴﺔ ﻛﺒـﲑﺓ‪ .‬ﺍﺑﺤﺚ ﻋﻦ‬ ‫‪-5،3 .a‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ ﻧﻮﻧﺎﻥ‬
‫ﹰ‬
‫ﻭﻧﻘﺎﺷـﺎ ﺣﻮﻝ‬ ‫ﻟﺮﺑﺎﻋـﻲ ﺇﻳﺜﻴﻞ ﺍﻟﺮﺻـﺎﺹ ‪،Pb(CH2CH3) 4‬‬ ‫ﻣﺼﺎﺩﺭ ﻣﺮﻛﺒﺎﺕ ﺍﳌﹺﺴﻚ ﺍﻟﻄﺒﻴﻌﻲ ﻭﺍﻟﺼﻨﺎﻋﻲ ﰲ ﻫﺬﻩ ﺍﳌﻨﺘﺠﺎﺕ‪،‬‬ ‫‪-7،3 .b‬ﺛﻨﺎﺋﻲ ﻣﻴﺜﻴﻞ‪-5-‬ﺇﻳﺜﻴﻞ ﺩﻳﻜﺎﻥ‪.‬‬
‫ﺗﻘﺮﻳﺮﺍ ﻣﻮﺟﺰﹰ ﺍ ﺣﻮﳍﺎ‪.‬‬
‫ﹰ‬ ‫ﻭﺍﻛﺘﺐ‬
‫ﺑﺪﺍﻳـﺔ ﺍﺳـﺘﺨﺪﺍﻣﻪ‪ ،‬ﻭﺃﺧﻄﺎﺭﻩ ﺍﻟﺼﺤﻴﺔ‪ ،‬ﻭﻗﺎﺋﻤـﺔ ﺑﺒﻌﺾ ﺩﻭﻝ‬ ‫‪‬‬
‫ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴﺔ ﺍﳌﺘﻌﺪﺩﺓ ﺍﳊﻠﻘﺎﺕ‬
‫‪‬‬ ‫‪‬‬

‫ﺍﻟﻌﺎﱂ ﺍﻟﺘﻲ ﻻ ﺗﺰﺍﻝ ﺗﻘﻮﻡ ﺑﺈﺿﺎﻓﺘﻪ ﺇﱃ ﺍﻟﺒﻨﺰﻳﻦ‪.‬‬ ‫‪ (PAH) Polycyclic Aromatic Hydrocarbons‬ﻭﻫـﻲ ﻣﺮﻛﺒﺎﺕ‬
‫ﻃﺒﻴﻌﻴﺔ‪ ،‬ﻭﻟﻜﻦ ﻗﺪ ﻳﺰﻳﺪ ﺍﻟﻨﺸﺎﻁ ﺍﻹﻧﺴﺎﲏ ﻣﻦ ﺗﺮﻛﻴﺰﻫﺎ ﰲ ﺍﻟﺒﻴﺌﺔ‪ .‬ﻭﻟﺪﺭﺍﺳﺔ‬ ‫‪ .93‬ﻣﺎ ﺍﻟﻌﻨﴫ ﺍﻟﺬﻱ ﻟﻪ ﺍﻟﺘﻮﺯﻳﻊ ﺍﻹﻟﻜﱰﻭﲏ ‪[Ar]3d64s2‬‬
‫ﻣﺮﻛﺒﺎﺕ ‪ PAH‬ﹸﲨﻌﺖ ﻋﻴﻨﺎﺕ ﻣﻦ ﺍﻟﱰﺑﺔ‪ ،‬ﻭﺟﺮ￯ ﲢﻠﻴﻠﻬﺎ ﺑﺎﺳﺘﻌﲈﻝ ﻧﻮ￯‬ ‫ﹼ‬
‫ﺍﻷﻗﻞ ﻃﺎﻗﺔ؟‬
‫‪ .97‬ﺍﳌﺼﺪﺭ ﺍﻟﻄﺒﻴﻌﻲ ﻟﻠﻤﺴﻚ ﺍﳌﺴﺘﺨﺪﻡ ﰲ ﺍﻟﻌﻄﻮﺭ ﻫﻮ ﻣﺴﻚ ﺫﻛﺮ‬ ‫ﻣﻜﻮﻥ ﺭﺋﻴﺲ ﻓﻴﻬﺎ‪.‬‬
‫ﺗﺮﺳﺐ ﻛﻞ ﹼ‬ ‫ﻣﺸﻌﺔ ﳌﻌﺮﻓﺔ ﻣﺘﻰ ﹼ‬ ‫ﺍﳌﺘﻜﻮﻥ ﻣﻦ ﺍﳌﺠﻤﻮﻋﺎﺕ ﺍﻵﺗﻴﺔ؟‬
‫ﹼ‬ ‫‪ .94‬ﻣﺎ ﺷﺤﻨﺔ ﺍﻷﻳﻮﻥ‬
‫ﺍﻟﺸـﻜﻞ ‪ 2-29‬ﻳﺒـﲔ ﺗﺮﻛﻴـﺰ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻧـﺎﺕ ﺍﻷﺭﻭﻣﺎﺗﻴـﺔ ﺍﳌﺘﻌﺪﺩﺓ‬
‫‪ .a‬ﺍﻟﻔﻠﺰﺍﺕ ﺍﻟﻘﻠﻮﻳﺔ‪.‬‬
‫ﺍﻟﻐﺰﺍﻝ‪ .‬ﺍﳌﺮﻛﺐ ﺍﻟﻌﻄﺮﻱ ﺍﻟﺮﺋﻴﺲ ﻫﻮ ‪ –3‬ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﺩﻳﻜﺎﻧﻮﻥ‬ ‫ﺍﳊﻠﻘﺎﺕ )‪ (PAH‬ﺍﻟﺘﻲ ﹸﻋﺜﹺﺮ ﻋﻠﻴﻬﺎ ﰲ ﺳﻨﱰﺍﻝ ﺑﺎﺭﻙ ﰲ ﻣﺪﻳﻨﺔ ﻧﻴﻮﻳﻮﺭﻙ‪.‬‬
‫ﺍﻟﺒﻴﺎﻧﺎﺕ ﻣﺄﺧﻮﺫﺓ ﻣﻦ‪:‬‬
‫‪ .b‬ﺍﻟﻔﻠﺰﺍﺕ ﺍﻟﻘﻠﻮﻳﺔ ﺍﻷﺭﺿﻴﺔ‪.‬‬
‫‪ .c‬ﺍﳍﺎﻟﻮﺟﻴﻨﺎﺕ‪.‬‬
‫ﺍﳊﻠﻘﻲ‪ ،‬ﺍﻟﺬﻱ ﻳﺘﻢ ﲢﻀﲑﻩ ﰲ ﺻﻨﺎﻋﺎﺕ ﺍﻟﻌﻄﻮﺭ ﻭﺍﻟﻜﻮﻟﻮﻧﻴﺎ‪.‬‬ ‫‪2005. Environmental science technology 39 (18): 7012 – 7019‬‬

‫‪‬‬
‫‪ .95‬ﺍﻛﺘﺐ ﺍﳌﻌﺎﺩﻻﺕ ﺍﻟﻜﻴﻤﻴﺎﺋﻴﺔ ﻟﺘﻔﺎﻋﻼﺕ ﺍﻻﺣﱰﺍﻕ ﺍﻟﻜﺎﻣﻞ‬
‫‪PAH‬‬
‫ﻟﻺﻳﺜﺎﻥ‪ ،‬ﻭﺍﻹﻳﺜﲔ‪ ،‬ﻭﺍﻹﻳﺜﺎﻳﻦ ﺍﳌﻨﺘﺠﺔ ﻟﻠﲈﺀ ﻭﺛﺎﲏ ﺃﻛﺴﻴﺪ‬

‫‪(µg/g) PAH ‬‬

‫ﺍﻟﻜﺮﺑﻮﻥ‪.‬‬
‫‪‬‬ ‫‪20‬‬

‫‪10‬‬

‫ﺍﻟﺒﻴﺎﻧﺎﺕ ﻣﺄﺧﻮﺫﺓ ﻣﻦ‪:‬‬

‫‪0‬‬
‫‪1880‬‬ ‫‪1900‬‬ ‫‪1920‬‬ ‫‪1940‬‬ ‫‪1960‬‬ ‫‪1980‬‬ ‫‪2000‬‬
‫‪‬‬

‫ﺍﻟﺸﻜﻞ ‪2-29‬‬
‫‪Smith, M. 2004. Science 39: 1021 - 1034‬‬ ‫‪ .98‬ﻗﺎﺭﻥ ﺑﲔ ﻣﻌﺪﻻﺕ ﺗﺮﺍﻛﻴﺰ ‪ PAH‬ﻗﺒﻞ ‪1905‬ﻡ ﻭﺑﻌﺪ ‪1925‬ﻡ‪.‬‬
‫‪ .99‬ﺗﻨﺘﺞ ﺑﻌﺾ ﺍﻟﻨﺒﺎﺗﺎﺕ ﻭﺍﳊﻴﻮﺍﻧﺎﺕ ﻣﺮﻛﺒﺎﺕ ‪ PAH‬ﺑﻜﻤﻴﺎﺕ‬
‫‪ .98‬ﺍﳌﺘﻮﺳﻂ ‪ 3‬ﺗﻘﺮﻳ ﹰﺒﺎ ﻗﺒﻞ ‪1905‬ﻡ ؛ ﻭ ‪ 13‬ﺗﻘﺮﻳ ﹰﺒﺎ ﺑﻌﺪ ‪1925‬ﻡ‪.‬‬ ‫ﻗﻠﻴﻠﺔ‪ ،‬ﻭﻟﻜﻦ ﻣﻌﻈﻤﻬﺎ ﻳﺄﰐ ﻣﻦ ﺍﻟﻨﺸﺎﻃﺎﺕ ﺍﻟﺒﴩﻳﺔ‪ ،‬ﻣﺜﻞ‬
‫ﺣﺮﻕ ﺍﻟﻮﻗﻮﺩ ﺍﻷﺣﻔﻮﺭﻱ‪ .‬ﺍﺳﺘﻨﺘﺞ ﺍﻟﺴﺒﺐ ﻭﺭﺍﺀ ﺍﻻﻧﺨﻔﺎﺽ‬
‫ﺍﻟﻨﺴﺒﻲ ﰲ ﻣﺴﺘﻮﻳﺎﺕ ‪ PAH‬ﰲ ﺍﻟﻌﻘﺪ ﺍﻷﺧﲑ ﻣﻦ ﺍﻟﻘﺮﻥ‬
‫‪ .99‬ﺍﻟﻮﻗـﻮﺩ ﺍﻟﺮﺋﻴـﺲ ﺍﻟـﺬﻱ ﺍﺳـﺘﺨﺪﻣﻪ ﺍﻟﺒـﴩ ﰲ ﻫـﺬﺍ ﺍﻟﻮﻗـﺖ‬ ‫ﺍﻟﺘﺎﺳﻊ ﻋﴩ ﻭﺑﺪﺍﻳﺎﺕ ﺍﻟﻌﻘﺪ ﺍﻷﻭﻝ ﻣﻦ ﺍﻟﻘﺮﻥ ﺍﻟﻌﴩﻳﻦ‪.‬‬

‫ﻫﻮ ﺍﳋﺸـﺐ‪ .‬ﺑﺪﺃﺕ ﻣﺴـﺘﻮﻳﺎﺕ‪ PAH‬ﰲ ﺍﻟﺘﺰﺍﻳـﺪ ﻋﻨﺪﻣﺎ ﹼ‬

‫ﺣﻞ‬
‫ﻣﺼﺪﺭﺍ ﻟﻠﻮﻗﻮﺩ‪.‬‬
‫ﹰ‬ ‫ﺍﻟﻮﻗﻮﺩ ﺍﻷﺣﻔﻮﺭﻱ ﳏﻞ ﺍﳋﺸﺐ ﺑﻮﺻﻔﻪ‬

‫‪‬‬
‫‪ .92‬ﺍﺭﺟﻊ ﺇﱃ ﺍﻟﺪﺭﺱ ﻟﺮﺳﻢ ﺍﻷﺷﻜﺎﻝ‪.‬‬
‫‪ .a‬ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﻜﲑﺍﻟﻴﺔ ﻫﻮ‪2n = 22 = 4 :‬‬

‫‪ .b‬ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﺍﻟﻜﲑﺍﻟﻴﺔ ﻫﻮ‪2n = 23 = 8 :‬‬

‫‪‬‬
‫‪ .93‬ﺣﺪﻳﺪ‬
‫‪1+ .a .94‬‬

‫‪2+ .b‬‬

‫‪1- .c‬‬

‫‪ .95‬ﺇﻳﺜﺎﻥ‪2C2H6 + 7O2 → 4CO2 + 6H2O :‬‬

‫ﺇﻳﺜﲔ‪C2H4 + 3O2 → 2CO2 + 2H2O :‬‬

‫ﺇﻳﺜﺎﻳﻦ‪2C2H2 + 5O2 → 4CO2 + 2H2O :‬‬

‫‪173‬‬
 ‫‪‬‬ ‫‪‬‬
‫ﺍﺳﺘﺨﺪﻡ ﺍﳉﺪﻭﻝ ﺃﺩﻧﺎﻩ ﻟﻺﺟﺎﺑﺔ ﻋﻦ ﺍﻷﺳﺌﻠﺔ ‪ 4‬ﺇﱃ ‪.6‬‬ ‫‪‬‬
‫‪ .1‬ﻳﻮﺟـﺪ ﺍﻷﻧﻴﻠـﲔ‪ ،‬ﻣﺜـﻞ ﲨﻴـﻊ ﺍﻷﲪـﺎﺽ ﺍﻷﻣﻴﻨﻴـﺔ‪ ،‬ﰲ‬
‫أﺳﺌﻠﺔ اﻻﺧﺘﻴﺎر ﻣﻦ ﻣﺘﻌﺪد‬
‫‪‬‬
‫ﺻﻮﺭﺗﲔ‪:‬‬
‫‪‬‬ ‫‪‬‬ ‫‪‬‬
‫‪‬‬ ‫‪COOH‬‬
‫‪‬‬ ‫‪‬‬ ‫‪‬‬ ‫‪‬‬
‫‪C‬‬

‫—‬
‫‪°C‬‬ ‫‪°C‬‬ ‫‪H‬‬ ‫‪C‬‬ ‫‪c .1‬‬
‫‪H2N‬‬ ‫‪H‬‬

‫—‬
‫‪98.5‬‬ ‫‪-90.6‬‬ ‫‪16‬‬ ‫‪7‬‬ ‫ﻫﺒﺘﺎﻥ‬ ‫‪CH3‬‬
‫‪Ú∏«f’CG-L‬‬
‫‪93.6‬‬ ‫‪-119.7‬‬ ‫‪14‬‬ ‫‪7‬‬ ‫‪ -1‬ﻫﺒﺘﲔ‬ ‫‪d .2‬‬
‫‪99.7‬‬ ‫‪-81‬‬ ‫‪12‬‬ ‫‪7‬‬ ‫‪ -1‬ﻫﺒﺘﺎﻳﻦ‬ ‫‪COOH‬‬
‫‪a .3‬‬

‫— —‬
‫‪C‬‬
‫‪125.6‬‬ ‫‪-56.8‬‬ ‫‪18‬‬ ‫‪8‬‬ ‫ﺃﻭﻛﺘﺎﻥ‬ ‫‪C22-182C-828378-08‬‬
‫‪H‬‬ ‫‪NH2‬‬
‫‪CH3‬‬
‫‪121.2‬‬ ‫‪-101.7‬‬ ‫‪16‬‬ ‫‪8‬‬ ‫‪ -1‬ﺃﻭﻛﺘﲔ‬ ‫‪Ú∏«f’CG-D‬‬ ‫‪b .4‬‬
‫‪126.3‬‬ ‫‪-79.3‬‬ ‫‪14‬‬ ‫‪8‬‬ ‫‪ -1‬ﺃﻭﻛﺘﺎﻳﻦ‬ ‫ﺗﻮﺟﺪ ﺍﻷﲪﺎﺽ ﺍﻷﻣﻴﻨﻴﺔ ﲨﻴﻌﻬﺎ ﺗﻘﺮﻳ ﹰﺒﺎ ﻋﲆ ﻫﻴﺌﺔ )‪ .(L‬ﻓﺄﻱ‬
‫ﺍﳌﺼﻄﻠﺤﺎﺕ ﺍﻵﺗﻴﺔ ﻳﺼﻒ ﺑﺪﻗﺔ ‪-L‬ﺃﻧﻴﻠﲔ ﻭ ‪-D‬ﺃﻧﻴﻠﲔ‬ ‫‪d .5‬‬
‫‪ .4‬ﻣﺎ ﻧﻮﻉ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ ﺍﻟﺬﻱ ﻳﺘﺤﻮﻝ ﺇﱃ ﻏﺎﺯ ﻋﻨﺪ ﺃﻗﻞ‬ ‫ﺃﺣﺪﳘﺎ ﺑﺎﻟﻨﺴﺒﺔ ﺇﱃ ﺍﻵﺧﺮ؟‬
‫‪C22-183C-828378-08‬‬
‫ﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ﺑﻨﺎ ﹰﺀ ﻋﲆ ﺍﳌﻌﻠﻮﻣﺎﺕ ﰲ ﺍﳉﺪﻭﻝ ﺍﻟﺴﺎﺑﻖ؟‬ ‫‪ .a‬ﻣﺘﺸﻜﻼﺕ ﺑﻨﺎﺋﻴﺔ‬
‫‪ .a‬ﺃﻟﻜﺎﻥ‬
‫‪a .6‬‬
‫‪ .b‬ﻣﺘﺸﻜﻼﺕ ﻫﻨﺪﺳﻴﺔ‬
‫‪ .b‬ﺃﻟﻜﲔ‬ ‫‪ .c‬ﻣﺘﺸﻜﻼﺕ ﺿﻮﺋﻴﺔ‬
‫‪ .c‬ﺃﻟﻜﺎﻳﻦ‬ ‫‪ .d‬ﻣﺘﺸﻜﻼﺕ ﻓﺮﺍﻏﻴﺔ‬
‫‪ .d‬ﺃﺭﻭﻣﺎﰐ‬
‫ﺃﻱ ﳑﺎ ﻳﺄﰐ ﻻ ﻳﺆﺛﺮ ﰲ ﴎﻋﺔ ﺍﻟﺘﻔﺎﻋﻞ؟‬
‫‪ .2‬ﹼ‬
‫‪ .5‬ﺇﺫﺍ ﹶﺭ ﹶﻣﺰﹶ ‪ n‬ﺇﱃ ﻋﺪﺩ ﺫﺭﺍﺕ ﺍﻟﻜﺮﺑﻮﻥ ﰲ ﺍﳍﻴﺪﺭﻭﻛﺮﺑﻮﻥ‪،‬‬ ‫‪ .a‬ﺍﻟﻌﻮﺍﻣﻞ ﺍﳌﺴﺎﻋﺪﺓ‬
‫ﻓﲈ ﺍﻟﺼﻴﻐﺔ ﺍﻟﻌﺎﻣﺔ ﻟﻸﻟﻜﺎﻳﻦ ﺍﳌﺤﺘﻮﻱ ﻋﲆ ﺭﺍﺑﻄﺔ ﺛﻼﺛﻴﺔ‬ ‫‪ .b‬ﻣﺴﺎﺣﺔ ﺳﻄﺢ ﺍﳌﺘﻔﺎﻋﻼﺕ‬
‫ﻭﺍﺣﺪﺓ؟‬ ‫‪ .c‬ﺗﺮﻛﻴﺰ ﺍﳌﺘﻔﺎﻋﻼﺕ‬
‫‪CnHn+2 .a‬‬ ‫‪ .d‬ﻧﺸﺎﻁ ﺍﻟﻨﻮﺍﺗﺞ ﺍﻟﻜﻴﻤﻴﺎﺋﻲ‬
‫‪CnH2n+2 .b‬‬ ‫‪ .3‬ﻣـﺎ ﻣﻮﻻﻟﻴـﺔ ﳏﻠـﻮﻝ ﳛﺘـﻮﻱ ﻋـﲆ ‪ 0.25 g‬ﻣـﻦ ﺛﻨﺎﺋـﻲ‬
‫‪CnH2n .c‬‬ ‫ﺍﻟﻜﻠﻮﺭﻭﺑﻨﺰﻳﻦ ‪ C6H4Cl2‬ﺍﳌﺬﺍﺏ ﰲ ‪ 10.0 g‬ﻣﻦ ﺍﳍﻜﺴﺎﻥ‬
‫‪CnH2n-2 .d‬‬ ‫ﺍﳊﻠﻘﻲ )‪ (C6H12‬؟‬
‫‪ .6‬ﻧﺘﻮﻗﻊ ﺍﻋﺘﲈﺩﹰﺍ ﻋﲆ ﺍﳉﺪﻭﻝ ﺍﻟﺴﺎﺑﻖ ﺃﻥ ﺗﻜﻮﻥ ﺩﺭﺟﺔ‬
‫‪0.17 mol/kg .a‬‬
‫ﺍﻧﺼﻬﺎﺭ ﺍﻟﻨﻮﻧﺎﻥ‪:‬‬ ‫‪0.00017 mol /kg .b‬‬
‫‪ .a‬ﺃﻋﲆ ﳑﹼﺎ ﻟﻸﻭﻛﺘﺎﻥ‪.‬‬ ‫‪0.025 mol /kg .c‬‬
‫‪ .b‬ﺃﻗﻞ ﳑﹼﺎ ﻟﻠﻬﺒﺘﺎﻥ‪.‬‬ ‫‪0.014 mol/kg .d‬‬
‫‪ .c‬ﺃﻋﲆ ﳑﹼﺎ ﻟﻠﺪﻳﻜﺎﻥ‪.‬‬
‫‪ .d‬ﺃﻗﻞ ﳑﹼﺎ ﻟﻠﻬﻜﺴﺎﻥ‪.‬‬

‫‪174‬‬
 ‫‪‬‬

‫‪‬‬ ‫‪ .7‬ﻋﻨﺪ ﺿﻐﻂ ‪ 1.00 atm‬ﻭﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ‪ ،20 °C‬ﻳﺬﻭﺏ‬

‫‪ 1.72 g CO2‬ﰲ ‪ 1L‬ﻣﺎﺀ‪ .‬ﻓﲈ ﻛﻤﻴﺔ ‪ CO2‬ﺍﻟﺬﺍﺋﺒﺔ ﺇﺫﺍ ﺍﺭﺗﻔﻊ‬
‫ﺍﺳﺘﺨﺪﻡ ﺍﻟﺮﺳﻢ ﺍﻟﺒﻴﺎﲏ ﺍﳌﺒﲔ ﺃﺩﻧﺎﻩ ﻟﻺﺟﺎﺑﺔ ﻋﻦ ﺍﻷﺳﺌﻠﺔ ‪.10 -12‬‬
‫‪a .7‬‬ ‫‪ ‬‬
‫ﺍﻟﻀﻐﻂ ﺇﱃ ‪ 1.35 atm‬ﻣﻊ ﺑﻘﺎﺀ ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ ﻧﻔﺴﻬﺎ؟‬
‫‪16‬‬ ‫‪2.32 g/L‬‬ ‫‪.a‬‬
‫‪a .8‬‬ ‫?‬
‫‪1.27 g/L‬‬ ‫‪.b‬‬

‫‪(atm) ‬‬
‫‪12‬‬ ‫?‬

‫‪8‬‬
‫‪0.785 g/L‬‬ ‫‪.c‬‬
‫‪d .9‬‬ ‫?‬ ‫‪0.431 g/L‬‬ ‫‪.d‬‬
‫‪4‬‬
‫‪ .8‬ﺃﻱ ﺍﻟﻌﺒﺎﺭﺍﺕ ﺍﻵﺗﻴﺔ ﻻ ﻳﺼﻒ ﻣﺎ ﳛﺪﺙ ﻋﻨﺪﻣﺎ ﻳﻐﲇ ﺍﻟﺴﺎﺋﻞ؟‬
‫‪0‬‬

‫أﺳﺌﻠﺔ ا¬ﺟﺎﺑﺎت اﻟﻘﺼﻴﺮة‬

‫‪-100‬‬ ‫‪-80‬‬ ‫‪-60‬‬ ‫‪-40‬‬ ‫‪-20‬‬ ‫‪0‬‬ ‫‪+20‬‬ ‫‪+40‬‬
‫‪(°C) ‬‬ ‫ﺗﺮﺗﻔﻊ ﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ﺍﻟﻨﻈﺎﻡ‪.‬‬ ‫‪.a‬‬
‫ﻳﻤﺘﺺ ﺍﻟﻨﻈﺎﻡ ﺍﻟﻄﺎﻗﺔ‪.‬‬ ‫‪.b‬‬
‫‪ .10‬ﻣﺎ ﺣﺎﻟﺔ ﺍﳌﺎﺩﺓ ﺍﻟﻮﺍﻗﻌﺔ ﻋﻨﺪ ﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ‪ – 80 °C‬ﻭﺿﻐﻂ‬ ‫ﻳﺘﺴﺎﻭ￯ ﺍﻟﻀﻐﻂ ﺍﻟﺒﺨﺎﺭﻱ ﻟﻠﺴﺎﺋﻞ ﻣﻊ ﺍﻟﻀﻐﻂ‬ ‫‪.c‬‬
‫‪ .10‬ﺻﻠﺐ‬ ‫‪10 atm‬؟‬ ‫ﺍﳉﻮﻱ‪.‬‬
‫‪ .11‬ﻣﺎ ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ ﻭﺍﻟﻀﻐﻂ ﻋﻨﺪﻣﺎ ﺗﻜﻮﻥ ﺍﳌﺎﺩﺓ ﻋﻨﺪ ﻧﻘﻄﺘﻬﺎ‬ ‫ﻳﺪﺧﻞ ﺍﻟﺴﺎﺋﻞ ﰲ ﻃﻮﺭ ﺍﻟﻐﺎﺯ‪.‬‬ ‫‪.d‬‬
‫‪ .11‬ﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ ‪ -65° C‬ﻭﺿﻐﻂ ‪ 4.8 atm‬ﺗﻘﺮﻳ ﹰﺒﺎ‪.‬‬ ‫ﺍﻟﺜﻼﺛﻴﺔ؟‬
‫‪C13-19C-828378-08‬‬
‫‪C‬‬
‫‪ .12‬ﺻﻒ ﺍﻟﺘﻐﲑﺍﺕ ﺍﻟﺘﻲ ﲢﺪﺙ ﰲ ﺍﻟﱰﺗﻴﺐ ﺍﳉﺰﻳﺌﻲ ﻋﻨﺪ‬ ‫‪C‬‬ ‫‪C‬‬

‫‪ .12‬ﺗﺘﻐﲑ ﺍﳌﺎﺩﺓ ﻣﻦ ﻏﺎﺯ ﺇﱃ ﺳﺎﺋﻞ ﻛﻠﲈ ﺯﺍﺩ ﺍﻟﻀﻐﻂ؛ ﻋﻨﺪﻣﺎ ﺗﺼﺒﺢ‬ ‫ﺯﻳﺎﺩﺓ ﺍﻟﻀﻐﻂ ﻣﻦ ‪ 8 atm‬ﺇﱃ ‪ ،16 atm‬ﻣﻊ ﺑﻘﺎﺀ ﺩﺭﺟﺔ‬ ‫‪C — C — C— C‬‬ ‫‪C‬‬
‫ﺍﳊﺮﺍﺭﺓ ﺛﺎﺑﺘﺔ ﻋﻨﺪ )‪.(0 °C‬‬ ‫‪C‬‬ ‫‪C‬‬

‫ﺗﺮﺍﺻﺎ ﺗﻔﻘﺪ ﻃﺎﻗﺘﻬﺎ ﺍﳊﺮﻛﻴـﺔ‪ ،‬ﻭﺗﺼﺒﺢ ﺃﻛﺜﺮ‬

‫ﺍﳉﺴـﻴﲈﺕ ﺃﻛﺜـﺮ ﹼﹰ‬ ‫‪‬‬ ‫‪ .9‬ﻣﺎ ﺍﺳﻢ ﺍﳌﺮﻛﺐ ﺫﻱ ﺍﻟﺼﻴﻐﺔ ﺍﳍﻴﻜﻠﻴﺔ ﺍﳌﺒﻴﻨﺔ ﺃﻋﻼﻩ؟‬

‫ﺗﺮﺗﻴ ﹰﺒﺎ ﻭﻗﺮ ﹰﺑﺎ ﺑﻌﻀﻬﺎ ﺇﱃ ﺑﻌﺾ‪.‬‬

‫‪ .13‬ﺇﺫﺍ ﺍﺣﱰﻕ ‪ 5.00 L‬ﻣﻦ ﻏﺎﺯ ﺍﳍﻴﺪﺭﻭﺟﲔ ﻋﻨﺪ ﺩﺭﺟﺔ ﺣﺮﺍﺭﺓ‬
‫‪ - 3 ،2 ،2‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ‪ - 3 -‬ﺇﻳﺜﻴﻞ ﺑﻨﺘﺎﻥ‬ ‫‪.a‬‬
‫‪ 20.0°C‬ﻭﺿﻐﻂ ﻣﻘﺪﺍﺭﻩ ‪ 80.1Kpa‬ﻣﻊ ﻛﻤﻴﺔ ﻓﺎﺋﻀﺔ ﻣﻦ‬
‫‪ - 3‬ﺇﻳﺜﻴﻞ ‪-4 ،4 ،3 -‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‬ ‫‪.b‬‬
‫ﺍﻷﻛﺴﺠﲔ ﻟﺘﻜﻮﻳﻦ ﺍﳌﺎﺀ‪ ،‬ﻓﲈ ﻛﺘﻠﺔ ﺍﻷﻛﺴﺠﲔ ﺍﳌﺴﺘﻬﻠﻚ؟‬ ‫‪ - 2‬ﺑﻴﻮﺗﻴﻞ ‪ - 2 -‬ﺇﻳﺜﻴﻞ ﺑﻴﻮﺗﺎﻥ‪.‬‬ ‫‪.c‬‬
‫أﺳﺌﻠﺔ ا¬ﺟﺎﺑﺎت اﻟﻤﻔﺘﻮﺣﺔ‬ ‫ﺍﻓﱰﺽ ﺃﻥ ﹼﹰ‬
‫ﻛﻼ ﻣﻦ ﺩﺭﺟﺔ ﺍﳊﺮﺍﺭﺓ ﻭﺍﻟﻀﻐﻂ ﺛﺎﺑﺘﺎﻥ‪.‬‬ ‫‪ - 3‬ﺇﻳﺜﻴﻞ ‪ - 3 ،2 ،2 -‬ﺛﻼﺛﻲ ﻣﻴﺜﻴﻞ ﺑﻨﺘﺎﻥ‪.‬‬ ‫‪.d‬‬

‫‪C22-175C-828378-08‬‬
‫‪2.63 g .13‬‬

‫‪175‬‬