Hydrogen bromid

Hydrogen Bromid—Hydrobromic acid— Acidum hydrobromi- 

Preparation.—This substance cannot be obtained fromabromid as HCl is obtained from a chlorid. It is produced, along with phosphorous acid, by the action of HjO upon phosphorus tri-bromid PBr,-j-3HjO = HsPOa-1-3HBr or by the action of Br upon paraffin. 

Properties.—A colorless gas produces white fumes with moist air acid in taste and reaction, and readily soluble in HaO, with which it forms a hydrate, HBr 2HjO. Its chemical properties are similar to those of HCl. 

Analytical Characters.—(1.) With AgNOj, a yellowish-white ppt., insoluble in HNOs, sparingly soluble inNHjHO. (2.) With chlorin water a yellow solution which communicates the same color to chloroform and to starch-paste. (3.) With palladio nitrate a black ppt. in the absence of chlorids. 

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MarkownikofT s rule The rule states that in the addition of hydrogen halides to an ethyl-enic double bond, the halogen attaches itself to the carbon atom united to the smaller number of hydrogen atoms. The rule may generally be relied on to predict the major product of such an addition and may be easily understood by considering the relative stabilities of the alternative carbenium ions produced by protonation of the alkene in some cases some of the alternative compound is formed. The rule usually breaks down for hydrogen bromide addition reactions if traces of peroxides are present (anti-MarkownikofT addition). 

Hydrogen bromide cannot be prepared readily by the action of sulphuric acid on a bromide, because the latter is too easily oxidised by the sulphuric acid to form bromine. It is therefore obtained by... 

Hydrogen bromide may also be prepared by dropping bromine into benzene containing aluminium powder, which acts as a catalyst to the reaction ... 

Hydrogen bromide is a colourless gas similar in properties to hydrogen chloride. It is very soluble in water, giving hydrobromic... 

The acid which comes over is a constant boiling mixture containing about 47 hydrogen bromide (density = 1.46 g cm... 

Hydrogen iodide is prepared in a similar way to hydrogen bromide, by the action of water on a mixture of iodine and violet phosphorus. TTie hydrogen iodide evolved may be collected by downward delivery or may be condensed (b.p. 238 K) it reacts with mercury and so cannot be collected over the latter. 

The hydrolysis of phosphorus tribromide or triiodide is used in the preparation of hydrogen bromide and hydrogen iodide respectively ... 

Place 0 5 ml. of the pyridine in a 200 ml. round- or flat-bottomed flask and add 34 ml. (30 g.) of benzene. Fit the flask with a reflux water-condenser, and then place it in a cold water-bath. If the experiment is conducted in a fume-cupboard, the top of the condenser can be closed with a calcium chloride tube bent downwards (as in Fig. 61, p. 105 or in Fig. 23(A), p. 45, where the outlet-tube A will carry the calcium chloride tube) and the hydrogen bromide subsequently allowed to escape if, however, the experiment is performed in the open laboratory, fit to the top of the condenser (or to the outlet-tube A) a glass delivery-tube which leads through a piece of rubber tubing to an inverted glass funnel, the rim of which dips just below the surface of some water... 

A solution prepared by dissolving 2 g. of biomine in 100 g. of carbon tetra. chloride is satisfactory. Carbon tetrachloride is employed because it is an excellent solvent for bromine as well as for hydrocarbons it possesses the additional advan. tage of low solubility for hydrogen bromide, the evolution of which renders possible the distinction between decolourisation of bromine due to substitution or due to addition. 

The bromine adds on at the ethylenic linkage to form thedibromo compound (I), which easily loses hydrogen bromide to give the mono-bromo keto ester (II) ... 

Place 50 g. (57 ml.) of dry A.R. benzene and 0 5 ml. of dry p rridine (1) (dried over potassium hydroxide pellets) in a 500 ml. round-bottomed flask. Attach a reflux condenser to the flask and an inverted funnel (just dipping into some water in a beaker) to the top of the condenser (Fig. II, 13, 8, b). Partially immerse the flask in a bath of cold water, supported upon a tripod and gauze. Carefully pour 125 g, (40 ml.) of bromine (for precautions to be taken with bromine, see Section 111,35, Note 1) through a condenser and immediately insert the absorption device into the upper end of the condenser. A vigorous reaction soon occurs and hydrogen bromide is evolved which is absorbed by the water in the beaker when the reaction slackens, warm the bath to 25-30° for... 

I hour. Finally raise the temperature of the bath to 65-70° for a further 45 minutes or until all the bromine has disappeared (no red vapours visible) and the evolution of hydrogen bromide has almost ceased. Keep the solution of hydrogen bromide in the beaker (2). 

Other halogen carriers may be used, e.g., 1-2 g. of iron filings, or 1 g. of aluminium amalgam. The bromine must then be added slowly from a dropping funnel to the benzene warmed on a water bath the apparatu.s shown in Fig. II, 13, 9 is suitable and a trap for the hydrogen bromide must, however, be inserted into the top of the condenser. After all the bromine has been introduced, the mixture is heated on a water bath until no red vapours are visible above the liquid. The Subsequent procedure is as above. 

Use a 500 ml. three-necked flask equipped as in Section IV,19, but mounted on a water bath. Place 128 g. of naphthalene and 45 ml. of dry carbon tetrachloride in the flask, and 177 g. (55 ml.) of bromine in the separatory funnel. Heat the mixture to gentle boiling and run in the bromine at such a rate that little, if any, of it is carried over with the hydrogen bromide into the trap this requires about 3 hours. Warm gently, with stirring, for a further 2 hours or until the evolution of hydrogen bromide ceases. Replace the reflux condenser by a condenser set for downward distillation, stir, and distil off the carbon tetrachloride as completely as possible. Mix the residue with 8 g. of sodium... 

Phenylpropiolic acid. This is an example of an aromatic acetylenic acid, and is made by adding bromine to the ethylenio linkage in ethyl cinnamate, and treating the resulting dibromide with alcohobc potassium hydroxide which eliminates two molecules of hydrogen bromide ... 

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