Ọrụ na usoro nke Sodium Cyanide na Organic Synthesis

Okwu Mmalite

Sodium Cyanide (NaCN), ihe siri ike ọcha nke na-agbaze nke ukwuu na mmiri, bụ ntọala siri ike ma bụrụkwa ihe dị ike na nucleophile, na-eme ka ọ bụrụ ihe bara uru na mmepụta Organic . N'agbanyeghị oke nsí ya, nke chọrọ nlezianya nchekwa siri ike mgbe a na-eji ya, Sodium cyanide na-arụ ọrụ dị mkpa na mmepụta nke ọtụtụ ihe ndị dị ndụ, gụnyere ọgwụ, ihe ọkụkụ, na polymers.

Ọrụ nke Sodium Cyanide na Organic Synthesis

Cyanide ion dị ka Nucleophile

Iọn cyanide dị n'ime Sodium Cyanide bụ nucleophile na-arụ ọrụ nke ọma. N'ihi ebubo na-adịghị mma na atọm Carbon na nnukwu electronegativity nke atọm nitrogen, ọ nwere ike ịwakpo ebe electrophilic dị na molekul organic, dị ka otu carbonyl, alkyl halides, na epoxides.

Nhazi nke C-C Bonds

Otu n'ime ọrụ kachasị mkpa nke sodium cyanide na njikọ organic bụ imepụta njikọ carbon ọhụrụ - carbon, nke a na-enweta site na nnọchi nucleophilic na mmeghachi omume mgbakwunye. Dịka ọmụmaatụ, mgbe alkyl halide meghachiri omume na sodium cyanide, cyanide ion na-anọchi ion halide, na-eduga n'ịmepụta nitrile. Mmeghachi omume a na-enye ụzọ dị mfe isi tinye atọm carbon ọzọ n'ime molekul ahụ. Mgbe nke ahụ gasịrị, otu nitrile nwere ike ịgbanwe ka ọ bụrụ otu ọrụ ndị ọzọ dị ka carboxylic acid, amines, ma ọ bụ aldehydes site na usoro kemịkal 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

Usoro SN2 : Mgbe sodium cyanide meghachiri omume na primary alkyl halides, mmeghachi omume ahụ na-esokarị usoro SN2 (bimolecular nucleophilic substitution). Cyanide ion na-awakpo atọm carbon nke ejikọtara na halogen site n'azụ, n'akụkụ nke ọzọ nke ion halide na-apụ apụ. Nke a bụ mmeghachi omume jikọtara ọnụ ebe mgbawa nke njikọ carbon - halogen na nhazi nke njikọ carbon - cyanide na-eme n'otu oge. Ọnụego mmeghachi omume dabere na njupụta nke alkyl halide na ion cyanide, a na-agbanwekwa stereochemistry nke ngwaahịa ahụ ma e jiri ya tụnyere nke ihe mmalite.

Usoro SN1 : Site na tertiary alkyl halides, mmeghachi omume ahụ nwere ike ịga n'ihu site na usoro SN1 (unimolecular nucleophilic substitution). Nke mbụ, alkyl halide na-ekewapụ iji mepụta etiti carbocation. Mgbe ahụ, cyanide ion na-awakpo carbocation a iji mepụta ngwaahịa ahụ. A na-amata usoro SN1 site na ịmepụta etiti carbocation planar, ngwaahịa ahụ nwekwara ike igosipụta ngwakọta nke stereochemistries, ihe a maara dị ka racemization, n'ihi mwakpo nucleophile site n'akụkụ abụọ nke planar carbocation.

Mmeghachi omume Nucleophilic

Mgbakwunye na Carbonyl Groups : Mgbe sodium cyanide meghachiri omume na aldehydes ma ọ bụ ketone, ion cyanide na-elekwasị anya na atọm carbonyl carbon electrophilic. Otu carbonyl nwere njikọ carbon - oxygen polarized, ebe atọm carbon bụ ebe electrophilic. Mwakpo nke ion cyanide na-emepụta njikọ carbon - cyanide ọhụrụ, atọm oxygen nke otu carbonyl na-enweta chajị na-adịghị mma. Na nzọụkwụ na-esote, isi iyi proton, dị ka mmiri ma ọ bụ acid, na-eme ka atọm oxygen ahụ dị ka cyanohydrin. Mmeghachi omume a nwere ike ịgbanwe, enwere ike ịgbanwe nha nha ahụ na ngwaahịa ahụ site na ijikwa 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 ammonia, na-eso usoro mgbakwunye nucleophilic yiri ya. Ion iminium nwere chajị dị mma na atọm nitrogen, na-eme ka carbon atom dị n'akụkụ electrophilic. Ion cyanide na-awakpo atọm carbon a, na-emepụta njikọ carbon - cyanide ọhụrụ ma na-ebute mmepụta 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.