Ọrụ na usoro nke Sodium Cyanide na Organic Synthesis

Okwu Mmalite

sodium Cyanide (NaCN), kristal na-acha ọcha siri ike na-agbaze nke ukwuu na mmiri, bụ ma ntọala siri ike yana nucleophile dị ike, na-eme ka ọ bụrụ reagent bara uru. Ngwakọta organic. N'agbanyeghị oke nsi ya, nke na-achọ nlezianya nchekwa siri ike n'oge njikwa, sodium cyanide na-arụ ọrụ dị oke mkpa na njikọ nke ogige organic dị iche iche, gụnyere ọgwụ, agrochemicals, na polymers.

Ọrụ nke Sodium Cyanide na Organic Synthesis

Cyanide ion dị ka Nucleophile

The cyanide ion n'ime sodium cyanide bụ nucleophile na-emeghachi omume nke ukwuu. N'ihi ebubo na-adịghị mma dị na ya. carbon Atọm na oke elektrọniki nke atọm nitrogen, ọ nwere ike ịwakpo ebe elektrọniki dị na molekul organic, dịka otu carbonyl, alkyl halides, na epoxides.

Nhazi nke C-C Bonds

Otu n'ime ndị kasị ịrịba ọrụ nke sodium cyanide na organic synthesis bụ ihe e kere eke nke ọhụrụ carbon - carbon bond, nwetara site nucleophilic nnọchi na mgbakwunye mmeghachi omume. Dịka ọmụmaatụ, mgbe alkyl halide na-emeghachi omume na sodium cyanide, ion cyanide na-anọchi ion halide, na-eduga n'ịmepụta nitrile. Mmeghachi omume a na-enye ụzọ dị mfe isi webata atom carbon ọzọ n'ime molekul. N'ikpeazụ, otu nitrile nwere ike gbanwee ka ọ bụrụ otu ọrụ ndị ọzọ dị ka carboxylic acid, amines, ma ọ bụ aldehydes site na usoro kemịkalụ dị iche iche.

Synthesis nke Amino Acids - Mmeghachi omume Strecker

Sodium cyanide bụ isi ihe dị na mmeghachi omume Strecker, nke a na-eji maka njikọ nke α-amino acid. Na mmeghachi omume a, aldehyde ma ọ bụ ketone na-ejikọta na ammonium chloride na sodium cyanide iji mepụta α-amino nitrile. Nke a α-amino nitrile nwere ike imezi hydrolyzed iji mepụta α-amino acid kwekọrọ.

Mmeghachi omume na-apụta n'ọtụtụ usoro: Nke mbụ, otu carbonyl nke aldehyde ma ọ bụ ketone na-enweta protonation, na-abawanye electrophilicity ya. Mgbe ahụ, molecule amonia na-awakpo otu carbonyl protonated, na-esote deprotonation iji mepụta hemiaminal. Na-esote, a na-emepụta ìgwè hydroxyl nke hemiaminal, na-eme ka ikpochapụ mmiri na ịmepụta ion iminium. Ion cyanide na-awakpo ion iminium iji nye α-amino nitrile. N'ikpeazụ, hydrolysis nke α-amino nitrile na ọnụnọ nke acid ma ọ bụ isi na-enye α-amino acid.

Synthesis nke Nitriles sitere na Aryl Halides - The Rosenmund - von Braun Reaction

Na mmeghachi omume Rosenmund - von Braun, a na-eji sodium cyanide mee ihe iji gbanwee aryl halides, nke bụ halogen - ogige aromatic dochie anya, n'ime aryl nitriles. Catalyzed site na ọla kọpa (I) cyanide ma na-achọkarị okpomọkụ dị elu, mmeghachi omume a gụnyere nhazi nke ọla kọpa - aryl intermediate. Ion cyanide sitere na sodium cyanide na-emeghachi omume na etiti a ka ọ bụrụ aryl nitrile. Usoro a dị mkpa maka iwebata otu nitrile na-arụ ọrụ na mgbanaka aromatic, nke nwere ike gbanwee maka njikọ nke ogige aromatic dị iche iche, dị ka ọgwụ na ihe eji esiji ákwà.

Njikọ nke Carbonyl Compound

Sodium cyanide na-ekerekwa òkè na njikọ nke ogige carbonyl. Dịka ọmụmaatụ, mgbe ọ na-emeghachi omume na epoxide, ion cyanide na-awakpo obere carbon atom nke mgbanaka epoxide, na-eme ka mgbanaka ahụ mepee. Hydrolysis nke cyanohydrin na-esote nwere ike iduga n'ịmepụta ogige carbonyl.

Usoro mmeghachi omume metụtara sodium Cyanide

Mmeghachi omume nnọchi Nucleophilic

SN2 usoro: Mgbe sodium cyanide na-emeghachi omume na isi alkyl halides, mmeghachi omume na-agbaso usoro SN2 (bimolecular nucleophilic substitution). Igwe cyanide na-awakpo atom carbon nke etinyere na halogen site na azụ azụ, na-emegide ọnọdụ nke ion halide na-ahapụ. Nke a bụ mmeghachi omume jikọrọ ọnụ ebe nbibi nke carbon - halogen bond na nguzobe nke carbon - cyanide bond na-eme n'otu oge. Ọnụ ọgụgụ mmeghachi omume na-adabere na nchịkọta nke ma alkyl halide na cyanide ion, na stereochemistry nke ngwaahịa na-atụgharị ma e jiri ya tụnyere nke mmalite ihe.

SN1 usoro: Site na tertiary alkyl halides, mmeghachi omume nwere ike ịga n'ihu site na usoro SN1 (unimolecular nucleophilic nnọchi). Nke mbụ, alkyl halide na-ekewa ka ọ bụrụ etiti carbocation. Mgbe ahụ, ion cyanide na-awakpo carbocation a iji mepụta ngwaahịa ahụ. A na-eji usoro SN1 eme ihe site na nhazi nke etiti carbocation planar, na ngwaahịa ahụ nwere ike igosi ngwakọta nke stereochemistries, ihe omume a maara dị ka agbụrụ agbụrụ, n'ihi nucleophile na-awakpo n'akụkụ abụọ nke carbocation planar.

Mmeghachi omume Nucleophilic

Mgbakwunye na Otu Carbonyl: Mgbe sodium cyanide na-emeghachi omume na aldehydes ma ọ bụ ketones, ion cyanide na-elekwasị anya na electrophilic carbonyl carbon atom. Otu carbonyl nwere carbon polarized - njikọ oxygen, yana carbon carbon bụ saịtị electrophilic. Mwakpo nke ion cyanide na-emepụta carbon ọhụrụ - cyanide bond, na ikuku oxygen nke otu carbonyl na-enweta ụgwọ na-adịghị mma. Na nzọụkwụ na-esote, isi iyi proton, dị ka mmiri ma ọ bụ acid, na-emepụta ikuku oxygen ka ọ ghọọ cyanohydrin. Mmeghachi omume a na-agbanwe agbanwe, enwere ike ịhazi nha nha na ngwaahịa site na ịchịkwa ọnọdụ mmeghachi omume.

Mgbakwunye na Imines: Na mmeghachi omume Strecker, mgbakwunye nke cyanide ion na iminium ion, nke a na-emepụta site na mmeghachi omume nke aldehyde ma ọ bụ ketone na amonia, na-agbaso usoro mgbakwunye nucleophilic yiri ya. Ion iminium nwere ụgwọ dị mma na atom nitrogen, na-eme ka carbon atom electrophilic dị n'akụkụ. Ion cyanide na-awakpo carbon carbon atom, na-eme ka carbon-cyanide njikọ ọhụrụ wee bute nguzobe nke α-amino nitrile.

Ntụle Nchekwa

Ọ dị mkpa iji mesie ya ike na sodium cyanide dị oke egbu egbu. Ikuku ume, iri nri, ma ọ bụ mmetụ akpụkpọ ahụ na ya nwere ike ịnwụ. Mgbe ị na-arụ ọrụ na sodium cyanide, a ga-agbasorịrị ụkpụrụ nchekwa nchekwa siri ike. Nke a na-agụnye ime nnwale n'ime mkpuchi anwụrụ ọkụ ikuku ventilasị, iyiri akụrụngwa nchedo onwe onye kwesịrị ekwesị dị ka uwe aka, enyo enyo, na uwe ụlọ nyocha, na inwe atụmatụ nzaghachi mberede kwesịrị ekwesị n'ọnọdụ ọ bụrụ na ekpughere ya na mberede.

mmechi

Sodium cyanide bụ ike na vasatail reagent na organic njikọ. Ikike ya ime ihe dị ka nucleophile na imepụta carbon ọhụrụ - carbon bond na-eme ka ọ bụrụ ihe dị mkpa maka ndị na-ahụ maka kemịkalụ n'ịmepụta ọtụtụ ogige organic. Ịghọta usoro mmeghachi omume nke gụnyere sodium cyanide dị mkpa maka ịmepụta ụzọ synthetic nke ọma na ịkọ nsonaazụ mmeghachi omume. Otú ọ dị, n'ihi oke nsi ya, a ghaghị iji nlezianya chịkwaa iji ya mee ihe site na nchekwa nchekwa zuru oke iji chekwaa ọdịmma nke ndị na-ahụ maka ọgwụ na gburugburu ebe obibi.