Te Mahi me nga Mahi a te Sodium Cyanide i roto i te Whakakotahitanga Organic

Kupu Whakataki

Ko te Konutai Cyanide (NaCN), he totoka tioata mā e wairewa ana i roto i te wai, he turanga kaha, he nucleophile kaha hoki, ā, he mea nui tēnei hei matū i roto i te hanga matū koiora . Ahakoa tōna paitini nui, e hiahiatia ana ngā mahi ārai haumaru i te wā e whakamahia ana, he mea nui te Konutai cyanide i roto i te hanga o ngā matū koiora kanorau, tae atu ki ngā rongoā, ngā matū ahuwhenua, me ngā polymer.

Te Mahi a te Konutai Cyanide i roto i te Whakakotahitanga Organic

Cyanide Ion hei Nucleophile

He tino tauhohe te ion cyanide i roto i te Sodium Cyanide . Nā te utu kino o te ngota waro me te kaha hiko teitei o te ngota hauota, ka taea e ia te whakaeke i ngā pokapū hiko i roto i ngā ngota waro, pērā i ngā rōpū carbonyl, ngā alkyl halides, me ngā epoxides.

Te hanga o nga herenga C - C

Ko tētahi o ngā mahi tino nui a te konutai cyanide i roto i te hanganga rauropi ko te waihanga i ngā here waro-waro hou, e tutukihia ana mā te whakakapinga nucleophilic me ngā tauhohenga tāpiri. Hei tauira, ina tauhohe te alkyl halide ki te konutai cyanide, ka whakakapia te ion cyanide e te ion halide, ka hua ake he nitrile. Mā tēnei tauhohenga ka taea te whakauru i tētahi atu ngota waro ki roto i te ngota. Muri iho, ka taea te huri i te rōpū nitrile ki ētahi atu rōpū mahi pērā i ngā waikawa carboxylic, ngā amine, ngā aldehydes rānei mā roto i ngā tukanga matū maha.

Te Whakakotahitanga o nga Waikawa Amino - Te Tauhohenga Strecker

Ko te konutai cyanide tetahi waahanga matua o te tauhohenga Strecker, e whakamahia ana mo te whakahiato o te α - waikawa amino. I tenei tauhohenga, ka hono tetahi aldehyde, ketone ranei ki te haukinia pūhaumāota me te konutai cyanide ki te hanga i te α - amino nitrile. Ko tenei α - amino nitrile ka taea te hauwai ki te whakaputa i te α - waikawa amino e rite ana.

Ka puta te tauhohenga i roto i nga waahanga maha: Tuatahi, ko te roopu waro o te aldehyde me te ketone ka pa ki te protonation, ka piki ake te hikohiko. Na, ka whakaekea e tetahi ngota ngota haukinia te roopu waro irahiko, ka whai i te whakahekenga hei hanga hemiaminal. I muri mai, ko te roopu hydroxyl o te hemiaminal ka protonated, ka mutu te whakakore i te wai me te hanganga o te katote iminium. Ka whakaekea e te katote cyanide te katote iminium ki te whakaputa i te α - amino nitrile. Ka mutu, ko te hauwai o te α - amino nitrile i te aroaro o te waikawa, te turanga ranei ka homai te α - waikawa amino.

Te whakahiato o Nitriles mai i Aryl Halides - Te Rosenmund - von Braun Reaction

I roto i te tauhohenga Rosenmund - von Braun, ka whakamahia te konutai cyanide ki te huri i nga aril halides, he halogen - kua whakakapia nga puhui kakara, ki nga nitriles aril. I whakakorikorihia e te konukura(I) cyanide me te hiahia kia nui te pāmahana, ka uru ki roto i tenei tauhohenga te hanganga o te konukura - aril takawaenga. Ka tauhohe te katote cyanide mai i te konutai cyanide ki tenei takawaenga ki te hanga i te aryl nitrile. He mea nui tenei tukanga mo te whakauru i tetahi roopu mahi nitrile ki runga i te mowhiti kakara, ka taea te whakarereke mo te whakahiatotanga o nga momo puhui kakara, penei i nga rongoa me nga waikano.

Te Whakakotahitanga o te Waowao Puhui

Ka whai wāhi hoki te konutai cyanide ki te whakahiatotanga o nga pūhui waro. Hei tauira, ka tauhohe ki te epoxide, ka whakaekea e te katote cyanide te ngota waro iti kua whakakapia o te mowhiti epoxide, ka tuwhera te mowhiti. Ko te hauwai o muri mai o te cyanohydrin ka puta ka taea te hanga i tetahi puhui waro.

Nga Hangahanga o nga Tauhohenga e whai ana i te konutai Cyanide

Tauhohenga Whakakapi Nucleophilic

Tikanga SN2 : Ina tauhohe te konutai cyanide ki ngā alkyl halide tuatahi, ko te tauhohenga he tikanga SN2 (bimolecular nucleophilic substitution). Ka whakaekea e te katote cyanide te ngota waro e piri ana ki te halogen mai i te taha whakamuri, i te ritenga kē atu i te tūranga o te katote halide e wehe atu ana. He tauhohenga whakakotahi tēnei e motu ai te here waro-halogen me te hanganga o te here waro-cyanide i te wā kotahi. Ko te tere o te tauhohenga e whakawhirinaki ana ki ngā kukū o te alkyl halide me te katote cyanide, ā, ka hurihia te stereochemistry o te hua ki te whakataurite ki te rauemi tīmatanga.

Tikanga SN1 : Mā ngā alkyl halide tuatoru, ka taea te tauhohenga mā te tikanga SN1 (unimolecular nucleophilic substitution). Tuatahi, ka wehea te alkyl halide hei hanga i tētahi takawaenga carbocation. Kātahi, ka whakaekea e te cyanide ion tēnei carbocation hei hanga i te hua. Ko te āhuatanga o te tikanga SN1 ko te hanganga o tētahi takawaenga carbocation papatahi, ā, ka whakaatuhia pea e te hua he ranunga o ngā stereochemicals, he āhuatanga e mōhiotia ana ko te racemization, nā te whakaekenga a te nucleophile mai i ngā taha e rua o te planar carbocation.

Tauhohenga taapiri Nucleophilic

Tāpiri atu ki ngā Rōpū Kāponiira : Ina tauhohe te konutai cyanide ki ngā aldehyde, ki ngā ketone rānei, ka aro te katote cyanide ki te ngota kāponiira hiko-whakaaro. He here kāponiira-hāora kua whakarōpūtia te rōpū kāponiira, ko te ngota kāponiira te pae hiko-whakaaro. Mā te whakaekenga a te katote cyanide ka hangaia he here kāponiira-hāora hou, ā, ka whiwhi te ngota hāora o te rōpū kāponiira i tētahi utu kino. I te taahiraa e whai ake nei, ka whakaporotinihia te ngota hāora e tētahi pūtake pūtorino, pērā i te wai, i te waikawa rānei, hei hanga i tētahi cyanohydrin. Ka taea te huri i tēnei tauhohenga, ā, ka taea te whakarerekē i te taurite ki te hua mā te whakahaere i ngā āhuatanga tauhohenga.

Tāpiri atu ki ngā Imine : I roto i te tauhohenga Strecker, ko te tāpiritanga o te ion cyanide ki te ion iminium, i hangaia mai i te tauhohenga o te aldehyde, te ketone rānei me te haukini, ka whai i tētahi tikanga tāpiri nucleophilic rite tonu. He utu pai tō te ion iminium i runga i te ngota hauota, ka hanga i te ngota waro e tata ana he electrophilic. Ka whakaekea e te ion cyanide tēnei ngota waro, ka hanga he here waro-cyanide hou, ā, ka hua ake he hanganga o te α-amino nitrile.

Ngā Whakaaturanga Haumaru

He mea nui ki te whakanui he tino paitini te konutai cyanide. Ko te horohanga, te horomia, te pa ki te kiri ka mate pea. I te wa e mahi ana me te konutai cyanide, me u ki nga tikanga haumaru. Kei roto i tenei ko te whakahaere i nga whakamatautau i roto i te puohu kohu hau pai, te mau taputapu whakamarumaru whaiaro e tika ana penei i nga karapu, nga karaehe, me te koti taiwhanga, me te whakarite i nga mahere urupare tika inaa ka puta ohorere.

Opaniraa

Ko te konutai cyanide he tauhohenga kaha me te whai kiko ki te whakahiato waro. Ko tana kaha ki te mahi hei nucleophile me te hanga waro hou - here waro he taputapu tino nui mo nga tohunga kemu ki te whakahiato i te maha o nga puhui waro. He mea nui te mohio ki nga tikanga tauhohenga e pa ana ki te konutai cyanide mo te hanga huarahi waihanga pai me te matapae i nga putanga tauhohenga. Heoi, na te nui o te paitini, me ata whakarite te whakamahinga me te whakahaere i runga i nga tikanga haumaru hei tiaki i te oranga o nga tohunga kemu me te taiao.