Hexanols—

Fig. III-9. Representative plots of surface tension versus composition, (a) Isooctane-n-dodecane at 30°C 1 linear, 2 ideal, with a = 48.6. Isooctane-benzene at 30°C 3 ideal, with a = 35.4, 4 ideal-like with empirical a of 112, 5 unsymmetrical, with ai = 136 and U2 = 45. Isooctane-

Use the apparatus detailed in Section 111,20. Dissolve 100 g. (123 ml.) of methyl n-butyl ketone (2-hexanone) (Section 111,152) in 750 ml. of ether and add 150 ml. of water. Introduce 69 g. of clean sodium in the form of wire (or small pieces) as rapidly as possible the reaction must be kept under control and, if necessary, the flask must be cooled in ice or in running water. When all the sodium has reacted, separate the ethereal layer, wash it with 25 ml. of dilute hydrochloric acid (1 1), then with water, dry with anhydrous potassium carbonate or with anhydrous calcium sulphate, and distil through a fractionating column. Collect the fraction of b.p. 136-138°. The yield of methyl n-butyl carbinol (2-hexanol) is 97 g. 

The reaction was very vigorous and external heating was not necessary. A mixture of hexatriene and hexanol condensed in the receiver (note 1). The conversion was terminated by external heating, so that 5-10 ml of hexanol distilled at 55-50 C/ /15 mmHg. The contents of the receiver were "redistilled", using the apparatus... 

Assuming that the rate determining step in the reaction of 1 hexanol with hydrogen bro mide to give 1 bromohexane is an attack by a nucleophile on an alkyloxonium ion write an equa tion for this step Use curved arrows to show the flow of electrons... 

As a second example consider the regioselective dehydration of 2 methylcyclo hexanol to yield a mixture of 1 methylcyclohexene (major) and 3 methylcyclohexene (minor)... 

Acid catalyzed dehydration of 2 2 dimethyl 1 hexanol gave a number of isomeric alkenes including 2 methyl 2 heptene as shown in the following formula... 

In Problem 4 25 you were asked to draw the preferred conformation of menthol on the basis of the information that menthol is the most stable stereoisomer of 2 isopropyl 5 methylcyclo hexanol We can now completely descnbe (—) menthol structurally by noting that it has the R con figuration at the hydroxyl substituted carbon... 

In addition to sp C—H stretching modes there are other stretching vibrations that appear at frequencies above 3000 cm The most important of these is the O—H stretch of alcohols Figure 13 34 shows the IR spectrum of 2 hexanol It contains a broad peak at 3300 cm ascribable to O—H stretching of hydrogen bonded alcohol groups In... 

Outline a synthesis of 2 ethyl 1 hexanol from butanal... 

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