Iyo Yakasiyana-siyana Mashandisirwo eSodium Cyanide mune Organic Synthesis

ziviso

Sodium cyanide (NaCN), ine fomura yemakemikari NaCN, isimbi chena yekristaro kana upfu inonyungudika zvakanyanya mumvura uye ine hwema hushoma, hunovava hwemaarumondi. Nekuda kwekuita kwayo zvakanyanya, yakashandiswa zvakanyanya mumhando dzakasiyana dzekuita kwekugadzirwa kweorganic . Zvisinei, zvakakosha kuziva kuti sodium cyanide ine chepfu zvakanyanya uye inofanira kubatwa nekungwarira kwakanyanya uye zvichienderana nemitemo yekuchengetedza. Chinyorwa chino chinoongorora mashandisirwo akasiyana-siyana eSodium Cyanide mukugadzirwa kweorganic.

Zvishandiso muOrganic Synthesis

Strecker Reaction

Imwe yenzira dzinozivikanwa dzekushandisa Sodium cyanide mukugadzirwa kweorganic ndeyeStrecker reaction. Iyi reaction inzira ine simba yekugadzira α - amino acids. MuStrecker reaction, aldehyde kana ketone inopindirana neammonium chloride (NH₄Cl) uye sodium cyanide. Maitiro ese ekuita reaction ndeaya anotevera:

1. Kutanga, aldehyde kana ketone inopindirana neammonia (inoumbwa mu - situ kubva ku ammonium chloride) kuti igadzire imine. Boka reCarbon yl re aldehyde kana ketone rinogadzirwa ne proton, zvichiita kuti rive electrophilic zvakanyanya. Zvadaro, ammonia inorwisa protonated carbonyl carbon, yozoteverwa ne deprotonation kuti igadzire imine.

2. Zvadaro, iyo cyanide ion (CN⁻) inobva ku sodium cyanide inoshanda se nucleophile uye inorwisa ine kabhoni. Izvi zvinoumba α - amino nitrile yepakati.

3. Chekupedzisira, hydrolysis ye α - amino nitrile pasi pe acidic kana basic mamiriro inoburitsa inoenderana α - amino acid.

Iyo Strecker reaction inopa nzira yakatwasuka yekusuma ese ari maviri amino boka uye carboxyl boka (mushure me hydrolysis ye nitrile) pane imwechete kabhoni atomu, iyo yakakosha pakuumbwa kwemaamino acids, zvivharo zvekuvaka zvemapuroteni. Semuenzaniso, apo formaldehyde (HCHO) inopindirana neammonium chloride uye sodium cyanide, inoteverwa nehydrolysis, glycine (NH₂CH₂COOH), iyo iri nyore amino acid, inogona kuwanikwa.

Kugadzirira kweNitriles

Sodium cyanide inowanzoshandiswa kugadzira nitriles. Mukutsiva maitiro, alkyl halides (yakadai semethyl bromide, CH₃Br) inopindirana nesodium cyanide mune polar aprotic solvent se dimethyl sulfoxide (DMSO) kana acetone. Mhedzisiro yacho inoenderera kuburikidza neSN2 michina, apo iyo cyanide ion inorwisa kabhoni atomu yakasungirirwa kune halogen. Iyo halogen atomu inobviswa, uye alkyl nitrile inoumbwa. Semuyenzaniso:

CH₃Br + NaCN → CH₃CN + NaBr

Aryl nitriles inogonawo kugadzirwa uchishandisa sodium cyanide mune zvimwe zviitiko. Semuenzaniso, mune imwe shanduko - simbi - catalyzed reactions, aryl halides inogona kuita nesodium cyanide pamberi peiyo catalyst semhangura (I) cyanide (CuCN) kana palladium catalysts. Kuita uku kunobvumira kuunzwa kwe - CN inoshanda boka parin'i inonhuhwirira, iyo inobatsira mukugadzirwa kwemishonga yakasiyana siyana, agrochemicals, uye dhayi.

Benzoin Condensation

Iyo benzoin condensation ndiyo imwe nzira yakakosha apo sodium cyanide inoita basa rinokosha. Mukuita uku, aldehydes inonhuhwirira (aldehydes ine mhete inonhuhwirira, yakadai se benzaldehyde, C₆H₅CHO) inobata pamberi pehuwandu hwehuwandu hwe sodium cyanide mumhinduro yedoro. The reaction mechanism inosanganisira matanho anotevera:

1. Iyo cyanide ion inotanga kuwedzera ku carbonyl carbon ye benzaldehyde, ichiita se nucleophile. Ichi chigadzirwa chekuwedzera ndeye cyanohydrin - senge yepakati.

2. Kuchaja kwakashata paatomu reokisijeni yecyanohydrin - seyepakati inogona kurwisa carbonyl kabhoni yeimwe benzaldehyde molecule.

3. Mushure mekutevedzana kwematanho ekutamisa proton uye kubviswa kweiyo cyanide ion, benzoin (α - hydroxy - ketone) inoumbwa.

Iyo benzoin condensation inopa nzira yekugadzira kabhoni nyowani - kabhoni bond pakati pemamorekuru maviri ealdehyde, ayo akakosha mukuumbwa kwemamwe mamorekuru akaomarara. Kunyangwe mumakore achangopfuura, kuedza kwakaitwa kutsiva sodium cyanide nezvimwe zvinokonzeresa zvakatipoteredza senge thiazolium munyu kana vhitamini B₁, nzira yechinyakare kushandisa sodium cyanide ichiri kushanda mune dzimwe nguva.

Kuwedzera Maitiro kune Unsaturated Compounds

Sodium cyanide inogonawo kutora chikamu mukuwedzera maitiro kune unsaturated compounds. Semuenzaniso, muhupo hwekugadzirisa, inogona kuwedzera kune α, β - unsaturated carbonyl compounds (yakadai se acrolein, CH₂=CHCHO). Maitiro acho anotevera Michael - type yekuwedzera michina, apo iyo cyanide ion inorwisa β - kabhoni ye α, β - unsaturated carbonyl compound. Kuita uku kunogona kushandiswa kuunza boka recyanomethyl (-CH₂CN) pane iyo unsaturated system, iyo inogona kushandurwazve kuva mamwe mapoka anoshanda. Semuenzaniso, chigadzirwa chinoguma chinogona kuve ne hydrolyzed kuita carboxylic acid kana kuderedzwa kuita amine.

Kufunga Zvekuchengetedza

Sezvambotaurwa, sodium cyanide ine muchetura zvakanyanya. Kufema, kupinza, kana kubata ganda nesodium cyanide kunogona kuuraya. Inopindirana nemaasidhi kugadzira hydrogen cyanide (HCN), gasi rine muchetura. Paunenge uchibata sodium cyanide, anotevera matanho ekuchengetedza anofanirwa kunyatso kuteedzerwa kune:

1. Shandisa mufume hood inofefeterwa zvakanaka kudzivirira kuvakwa kwegasi rine muchetura.

2. Pfeka midziyo yekudzivirira yakakodzera, kusanganisira magirovhosi, magirazi uye jasi rerabhoritari. Mune zvimwe zviitiko, mushonga wekufema unogona kudiwa.

3. Chengetedza sodium cyanide mumudziyo wakachengeteka, wakanyorwa kure neasidhi uye mamwe makemikari anoshanda.

4. Iva nehurongwa hwakakodzera hwemhinduro yechimbichimbi nemidziyo iripo kana pakaparara kana tsaona.

mhedziso

Sodium cyanide inogoneka uye yakakosha reagent mune organic synthesis. Inogonesa kuumbwa kweakasiyana akakosha anoshanda mapoka akadai seamino acids, nitriles, uye α - hydroxy - ketones, uye anotora chikamu mune yakakosha kabhoni - kabhoni bond - kugadzira maitiro. Pasinei nehuturu hwayo, kana ichibatwa nekuchenjerera kwakanyanya uye mukuteerera mitemo yekuchengetedza, inoramba iine chigadziro chakakosha mukugadzirwa kwechemist's toolkit yekugadzirwa kwemhando dzakasiyana-siyana dzemakemikari, kubva kumishonga kusvika kumakemikari akanaka. Nekudaro, kuedza kuenderera mberi kwekutsvaga kwakanangana nekugadzira dzimwe nzira, dzakachengeteka dzekuzadzisa zvinangwa zvakafanana zvekugadzira.