Basa uye Maitiro eSodium Cyanide muOrganic Synthesis

ziviso

Sodium Cyanide (NaCN), chena crystalline yakasimba inonyungudika zvakanyanya mumvura, zvese hwaro hwakasimba uye ine simba nucleophile, zvichiita kuti ive yakakosha reagent mu. Organic synthesis. Pasinei nehuturu hwayo hwakanyanyisa, hunoda kuchengetedzwa kwakasimba panguva yekubata, Sodium cyanide inoita basa rakakosha mukuumbwa kweakasiyana organic komisheni, kusanganisira mishonga, agrochemicals, uye mapolymers.

Basa reSodium Cyanide muOrganic Synthesis

Cyanide Ion seNucleophile

The cyanide ion mukati Sodium Cyanide inyukleophile ine simba guru rekuita basa. Nekuda kwekushaikwa kwesimba pa kabhoni atomu uye ne electronegativity yakakwira yeatomu ye nitrogen, inogona kurwisa nzvimbo dze electrophilic mumamorekuru e organic, akadai se carbonyl groups, alkyl halides, uye epoxides.

Kuumbwa kweC - C Bonds

Rimwe remabasa akakosha e sodium cyanide mune organic synthesis ndiko kusikwa kwekabhoni nyowani - kabhoni mabhondi, anowanikwa kuburikidza neiyo nucleophilic kutsiva uye kuwedzera maitiro. Semuenzaniso, apo alkyl halide inopindirana ne sodium cyanide, iyo cyanide ion inotsiva halide ion, zvichiita kuti pave ne nitrile. Kuita uku kunopa nzira iri nyore yekuunza imwe kabhoni atomu mumorekuru. Zvadaro, boka re nitrile rinogona kushandurwa kuita mamwe mapoka anoshanda se carboxylic acids, amines, kana aldehydes kuburikidza nemhando dzakasiyana dzemakemikari.

Synthesis yeAmino Acids - Iyo Strecker Reaction

Sodium cyanide chinhu chakakosha muStrecker reaction, iyo inoshandiswa kugadzira α - amino acids. Mukuita uku, aldehyde kana ketone inosanganiswa neammonium chloride uye sodium cyanide kuita α - amino nitrile. Iyi α - amino nitrile inogona kubva yaitwa hydrolyzed kuburitsa inoenderana α - amino acid.

Mhedzisiro yacho inoitika mumatanho akati wandei: Chekutanga, boka recarbonyl re aldehyde kana ketone rinoita protonation, richiwedzera electrophilicity yayo. Zvadaro, molecule yeammonia inorwisa boka reprotonated carbonyl, rinoteverwa nedeprotonation kuumba hemiaminal. Zvadaro, boka re hydroxyl rehemiaminal rinoitwa protonated, zvichiita kuti kubviswa kwemvura uye kuumbwa kweAn Hemiaum ion. Iyo cyanide ion inobva yarwisa iyo ininium ion kuburitsa iyo α - amino nitrile. Pakupedzisira, hydrolysis ye α - amino nitrile pamberi peasidhi kana chigadziko chinopa iyo α - amino acid.

Synthesis yeNitriles kubva kuAryl Halides - The Rosenmund - von Braun Reaction

MuRosenmund - von Braun reaction, sodium cyanide inoshandiswa kushandura aryl halides, ari halogen - anotsiviwa neanonhuwirira makomisheni, kuita aryl nitriles. Yakagadzirwa nemhangura (I) cyanide uye kazhinji inoda kupisa kwakanyanya, kuita uku kunosanganisira kuumbwa kwemhangura - aryl yepakati. Iyo cyanide ion kubva ku sodium cyanide inobva yaita nepakati ichi kuumba aryl nitrile. Iyi nzira yakakosha pakuunza boka rinoshanda re nitrile parin'i inonhuhwirira, iyo inogona kugadziridzwa zvakare kuitira kuumbwa kweakasiyana siyana anonhuwirira makomisheni, akadai semishonga nedhayi.

Synthesis yeCarbonyl Compounds

Sodium cyanide inobatanidzwawo mukugadzirwa kwecarbonyl compounds. Semuenzaniso, painopindirana ne epoxide, iyo cyanide ion inorwisa atomu yekabhoni yakatsiviwa yemhete ye epoxide, zvichiita kuti mhete izaruke. Inotevera hydrolysis yezvinoguma cyanohydrin inogona kutungamirira pakuumbwa kwekabhonil compound.

Nzira dzeMaitiro Anosanganisira Sodium Cyanide

Nucleophilic Substitution Reactions

SN2 Mechanism: Kana sodium cyanide ikasangana nealkyl halides yekutanga, maitiro acho anowanzo kutevedzera SN2 (bimolecular nucleophilic substitution) maitiro. Iyo cyanide ion inorwisa carbon atomu yakanamatira kune halogen kubva kumashure, yakatarisana nenzvimbo yekusiya halide ion. Uku kuita kwakabatana uko kutyora kabhoni - halogen bond uye kuumbwa kwekabhoni - cyanide bond kunoitika panguva imwe chete. Chiyero chekuita chinoenderana nekudzika kweiyo alkyl halide uye cyanide ion, uye stereochemistry yechigadzirwa inopindurwa kana ichienzaniswa neyekutanga zvinhu.

SN1 Mechanism: Neyepamusoro alkyl halides, maitiro anogona kuenderera kuburikidza neSN1 (unimolecular nucleophilic substitution) maitiro. Chekutanga, iyo alkyl halide inopatsanura kuti iite carbocation yepakati. Zvadaro, iyo cyanide ion inorwisa iyi carbocation kuti igadzire chigadzirwa. Iyo SN1 michina inoratidzwa nekuumbwa kweiyo planar carbocation yepakati, uye chigadzirwa chinogona kuratidza musanganiswa we stereochemistries, chiitiko chinozivikanwa se racemization, nekuda kweiyo nucleophile inorwisa kubva kumativi ese eiyo planar carbocation.

Nucleophilic Addition Reactions

Kuwedzera kune Carbonyl Mapoka: Kana sodium cyanide ikasangana nealdehydes kana ketoni, iyo cyanide ion inotarisa electrophilic carbonyl carbon atomu. Boka re carbonyl rine polarized carbon - oxygen bond, ne carbon atomu iri iyo electrophilic site. Kurwiswa kweiyo cyanide ion kunogadzira kabhoni nyowani - cyanide bond, uye atomu yeokisijeni yeboka recarbonyl inowana mhosva yakaipa. Mudanho rinotevera, sosi yeproton, senge mvura kana asidhi, inoburitsa atomu yeokisijeni kuumba cyanohydrin. Kuita uku kunodzokororwa, uye kuenzana kunogona kugadziridzwa kune chigadzirwa nekudzora maitiro ekuita.

Kuwedzera kune Imines: MuStrecker reaction, kuwedzera kweiyo cyanide ion kune iyo ininium ion, iyo inoumbwa kubva pakuita kwe aldehyde kana ketone neammonia, inotevera imwe yakafanana nucleophilic kuwedzera michina. Iyo itanium ion ine chaji yakanaka paatomu yenitrogen, ichiita iri padyo nekabhoni atomu electrophilic. Iyo cyanide ion inorwisa kabhoni atomu iyi, ichigadzira kabhoni nyowani - cyanide bond uye zvichikonzera kuumbwa kwe α - amino nitrile.

Kufunga Zvekuchengetedza

Izvo zvakakosha kusimbisa kuti sodium cyanide ine chepfu zvakanyanya. Kufemba, kupinza, kana kubata ganda nayo kunogona kuuraya. Paunenge uchishanda nesodium cyanide, mitemo yakasimba yekuchengetedza inofanira kutevedzerwa. Izvi zvinosanganisira kuitisa zviedzo mufume hood inofefeterwa zvakanaka, kupfeka midziyo yekudzivirira yakakodzera senge magirovhosi, magirovhosi, uye jasi rerabhoritari, uye kuve nehurongwa hwekupindura kwechimbichimbi panzvimbo pakaitika njodzi.

mhedziso

Sodium cyanide ine simba uye inoshanda zvakasiyana-siyana reagent mune organic synthesis. Kugona kwayo kuita senucleophile uye kugadzira kabhoni nyowani - kabhoni mabhondi inoita kuti ive chishandiso chakakosha kune vemakemikari mukugadzira huwandu hwakawanda hwezvakagadzirwa organic. Kunzwisisa maitiro ekuita anosanganisira sodium cyanide kwakakosha pakugadzira nzira dzakasimba dzekugadzira uye kufanotaura zvinozoitika. Nekudaro, nekuda kwehupfu hwayo hwakanyanya, kushandiswa kwayo kunofanirwa kudzorwa nekuchenjerera uye kuitwa nehunyanzvi hwekuchengetedza kuchengetedza hutano hwemakemikari uye nharaunda.