Basa uye Maitiro eSodium Cyanide muOrganic Synthesis

ziviso

Sodium Cyanide (NaCN), chinhu chena chinonyungudika mumvura, ihwaro hwakasimba uye nucleophile ine simba, zvichiita kuti ive chinhu chinokosha mukugadzirwa kweOrganic . Pasinei nekuti ine chepfu yakanyanya, iyo inoda matanho akasimba ekuchengetedza panguva yekubata, Sodium cyanide inoita basa rakakosha mukugadzirwa kwemakemikari akasiyana-siyana eorganic, anosanganisira mishonga, agrochemicals, uye polymers.

Basa reSodium Cyanide muOrganic Synthesis

Cyanide Ion seNucleophile

Iyo cyanide ion iri muSodium Cyanide inyukleophile ine simba guru rekuita basa. Nekuda kwechaji isina kunaka paatomu yeCarbon uye electronegativity yakakwira yeatomu yenitrogen, inogona kurwisa nzvimbo dzeelectrophilic mumamorekuru eorganic, akadai semapoka ecarbonyl, alkyl halides, uye epoxides.

Kuumbwa kweC - C Bonds

Rimwe remabasa akakosha e sodium cyanide mukugadzirwa kwe organic synthesis kugadzirwa kwezvisungo zvitsva zve carbon - carbon, zvinoitwa kuburikidza ne nucleophilic substitution uye addition reactions. Semuenzaniso, kana alkyl halide ikapindirana ne sodium cyanide, cyanide ion inotsiva halide ion, zvichiita kuti pave ne nitrile. Kuita uku kunopa nzira iri nyore yekuunza imwe carbon atomu mumorekuru. Zvadaro, boka re nitrile rinogona kushandurwa kuita mamwe mapoka anoshanda senge carboxylic acids, amines, kana aldehydes kuburikidza nemaitiro akasiyana-siyana emakemikari.

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 ikaita ma "primary alkyl halides", "reaction" iyi inowanzo tevedzera "SN2" (bimolecular nucleophilic substitution). "Cyanide ion" inorwisa "carbon atom" yakabatana ne "halogen" kubva kumashure, yakatarisana nenzvimbo ye "leaving halide ion". Iyi i "coherent reaction" apo "carbon-halogen bond" inotyoka uye "carbon-cyanide bond" inoumbwa panguva imwe chete. "Reaction rate" inoenderana nehuwandu hwe "alkyl halide" ne "cyanide ion", uye stereochemistry yechigadzirwa inopindurwa zvichienzaniswa neye "starting material".

SN1 Mechanism : Ne tertiary alkyl halides, reaction inogona kuenderera mberi kuburikidza ne SN1 (unimolecular nucleophilic substitution). Kutanga, alkyl halide inopatsanuka kuita carbocation intermediate. Zvadaro, cyanide ion inorwisa iyi carbocation kuti igadzire chigadzirwa. SN1 mechanism inoratidzwa nekuumbwa kwe planar carbocation intermediate, uye chigadzirwa chinogona kuratidza musanganiswa we stereochemistries, chiitiko chinozivikanwa se racemization, nekuda kwe nucleophile inorwisa kubva kumativi ese e planar carbocation.

Nucleophilic Addition Reactions

Kuwedzera kuCarbonyl Groups : Kana sodium cyanide ikapindirana nealdehydes kana ketones, cyanide ion inonanga paatomu yecarbonyl carbonyl carbon electriphic. Boka recarbonyl rine polarized carbon-oxygen bond, apo carbon atom iri nzvimbo yeelectrophilic. Kurwiswa kwecyanide ion kunogadzira carbon-cyanide bond itsva, uye atomu yeoxygen yeboka recarbonyl inowana negative charge. Padanho rinotevera, proton source, yakaita semvura kana acid, inoburitsa oxygen atomu kuti igadzire cyanohydrin. Kuita uku kunodzoserwa, uye equilibrium inogona kugadziriswa kune chigadzirwa nekudzora mamiriro ekuita.

Kuwedzera kuImines : MuStrecker reaction, kuwedzerwa kweiyoni yecyanide kune iyoni yeiminium, iyo inoumbwa kubva mukupindura kwealdehyde kana ketone ine ammonia, kunotevera nzira yakafanana yekuwedzera nucleophilic. Iyoni yeiminium ine positive charge paatomu yenitrogen, zvichiita kuti atomu yekabhoni iri pedyo ive electrophilic. Iyoni yecyanide inorwisa atomu iyi yekabhoni, ichigadzira chisungo chitsva chekabhoni-cyanide uye zvichikonzera kuumbwa kweα-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.