Sodium acetylide reaction with

MERCURIC BICHLORIDE (7487-94-7) HgClj Contact with acids or acid fumes evolves chloride and mercury vapors. Possible violent reaction with chlorine nitrate, sodium acetylide. Incompatible with albumin, alkalis, alkaloid salts, anhydrous ammonia, antimony, arsenic, borax, bromides, carbonates, chloric acid, copper, formates, gelatin, hydrozoic acid, infusions of cinchona, iron, lead and silver salts, lime water, light metals, methyl isocyanoacetate, oak bark or senna, phosphates, potassium, reduced iron, sodiiun, sodium peroxyborate, sulfides, sulfites, tannic acids, trinitrobenzoic acid, urea nitrate, vegetable astringents. Decomposed by sunlight. On small fires, use water spray, fog, foam, dry chemical powder, or CO2 extinguishers. 

PERCHLORIDE of MERCURY (7487-94-7) HgCl, Contact with acids or acid fumes evolves chloride and mercury vapors. Possible violent reaction with chlorine nitrate, sodium acetylide. Incompatible with albumin, alkalis, alkaloid salts, anhydrous ammonia, antimony, arsenic, borax, bromides, carbonates, chloric acid, copper, formates, gelatin, hydrozoic acid, infusions... 

ARSENATE of LEAD (7784-40-9) Decomposes on contact with acids or acid fumes, emitting arsenic fumes. Contact with strong oxidizers may cause fire and explosions. Violent reaction with sodium acetylide. Incompatible with mercurous chloride. May form impact-sensitive explosive materials with ethanediamine, A.A -dinitro-, pyrogallic acid. Aqueous solutions decompose on contact with active metals, emitting fumes of arsenic. 

NITRATO de ZIRCONIO (Spanish) (13746-89-9) A powerful oxidizer. Violent reaction with reducing agents, combustible materials, powdered metals, organic substances, acetic anhydride, tert-butylhydroperoxide, metal cyanides, thiocyanates, sodium acetylide. Incompatible with amines, ammonium hexacyanoferrate(II), boranes, cyanides, citric acid, esters, hydrazinium perchlorate, isopropyl chlorocarbonate, nitrosyl perchlorate, organic azides, organic bases, sodium thiosulfate, sulfamic acid. Incompatible with esters, many other substances. Attacks metals. 

Sodium acetylides react with primary alkyl halides in a substitution reaction to give alkynes of carbon skeleton greater than two. Hence, if methyl iodide is added to sodium acetylide, propyne results ... 

Alkynyl anions are more stable = 22) than the more saturated alkyl or alkenyl anions (p/Tj = 40-45). They may be obtained directly from terminal acetylenes by treatment with strong base, e.g. sodium amide (pA, of NH 35). Frequently magnesium acetylides are made in proton-metal exchange reactions with more reactive Grignard reagents. Copper and mercury acetylides are formed directly from the corresponding metal acetates and acetylenes under neutral conditions (G.E. Coates, 1977 R.P. Houghton, 1979). 

The terminal diyne 320 is prepared by coupling of the zinc acetylide 318 with /rfln.s-l-iodo-2-chloroethylenc (319), followed by elimination of HCI with sodium amide[231]. Similarly, terminal di- and triynes are prepared by using cw-l,2-dichloroethylene[232]. The 1-alkenyl or l-aryl-2-(perefluoroalkyl) acetylene 321 is prepared by the reaction of a zinc acetylide with halides[233]. 

The properties of organometallic compounds are much different from those of the other classes we have studied to this point Most important many organometallic com pounds are powerful sources of nucleophilic carbon something that makes them espe cially valuable to the synthetic organic chemist For example the preparation of alkynes by the reaction of sodium acetylide with alkyl halides (Section 9 6) depends on the presence of a negatively charged nucleophilic carbon m acetylide ion... 

Reactions in liquid ammonia (cf. Chapter 3, Section III) require a certain amount of care, since the solvent is low boiling (—33 ) and its fumes are noxious. Nevertheless, with reasonable caution, the preparation of an ammonia solution of sodium acetylide can be carried out as described. The reagent so prepared can then be directly used for displacements on alkyl halides or for additions to suitable carbonyl compounds. Examples of both reactions are given. 

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