N Heptyl bromide

Prepare a Grignard reagent from 24 -5 g. of magnesium turnings, 179 g. (157 ml.) of n-heptyl bromide (Section 111,37), and 300 ml. of di-n-butyl ether (1). Cool the solution to 0° and, with vigorous stirring, add an excess of ethylene oxide. Maintain the temperature at 0° for 1 hour after the ethylene oxide has been introduced, then allow the temperature to rise to 40° and maintain the mixture at this temperature for 1 hour. Finally heat the mixture on a water bath for 2 hours. Decompose the addition product and isolate the alcohol according to the procedure for n-hexyl alcohol (Section 111,18) the addition of benzene is unnecessary. Collect the n-nonyl alcohol at 95-100°/12 mm. The yield is 95 g. 

Pelargonic acid (n-Nonoic acid), CH3(CH2),COOH. Equip a 1-litre, three-necked flask with a reflux condenser, a mercury-sealed stirrer, a dropping funnel and a thermometer. Place 23 g. of sodium, cut in small pieces, in the flask, and add 500 ml. of anhydrous n-butyl alcohol (1) in two or three portions follow the experimental details given in Section 111,152 for the preparation of a solution of sodium ethoxide. When the sodium has reacted completely, allow the solution to cool to 70-80° and add 160 g. (152 ml.) of redistilled ethyl malonate rapidly and with stirring. Heat the solution to 80-90°, and place 182 5 g. (160 ml.) of n-heptyl bromide (compare experimental details in Section 111,37) in the dropping funnel. Add the bromide slowly at first until precipitation of sodium bromide commences, and subsequently at such a rate that the n-butyl alcohol refluxes gently. Reflux the mixture until it is neutral to moist litmus (about 1 hour). 

Gowenlock and co-workers have shown that the n-heptyl bromide/ sodium reaction leads to cyclohexane [115] whereas the perfluoroheptyl iodide/sodium system does not lead to perfluorocyclohexane [116]. 

The first step would be to perform a sodium fusion which would break the alkyl halides into their components which include halide anions. After acidification and addition of CCI14, we shake with CI2/H2O and observe the results. If the unknown is n-heptyl bromide, the bromide anions will be oxidized to Br2, which will be soluble in cell layer giving it a distinctive red-brown color. If no color is observed, 1,3 dichloro-2-propanol could still be present, as Cl is not converted to CI2 under the previous conditions. To test for the dichloro compound, we simply add AgNOa with a white precipitate, AgCl indicating the presence of chlorine. 

Caspary (1968a) indicated the usefulness of low temperature for the identification of materials having room-temperature spectra which are similar to each other (e.g., -hexyl bromide and n-heptyl bromide -butylamine and n-hexylamine and sebacic acid di-n-butyl ester and azelaic acid di- -butyl ester [Fig. 3.16]). He compared other compounds at room temperature and low temperature, such as various ketones (19686) and aldehydes (1965). These substances, all of which are liquids at room temperature, show many differences at the low temperature. 

Bromoheptane aets.-n-Heptyl bromide] CHg-tCHaL-CHBi-CHs... 

Methyl-2-butenylmagnesium chloride allowed to react 2 hrs. at 0° with 0.5 equivalent n-heptyl bromide in tetrahydrofuran in the presence of Cul 2-... 

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