Cyclohexanole

Colourless liquid with a strong peppermintlike odour b.p. 155" C. Manufactured by passing cyclohexanol vapour over a heated copper catalyst. Volatile in steam. Oxidized to adipic acid. Used in the manufacture of caprolactam. Nylon, adipic acid, nitrocellulose lacquers, celluloid, artificial leather and printing inks. 

Figure Bl.16.19. (a) CIDEP spectrum observed in die photolysis of xanthone (1.0 x 10 M) in cyclohexanol at room temperature. The stick spectra of the ketyl and cyclohexanol radicals with RPM polarization are presented, (b) CIDEP spectrum after the addition of hydrochloric acid (4.1 vol% HCl 0.50 M) to the solution above. The stick spectra of the ketyl and cyclohexanol radicals with absorptive TM polarization are presented. The bold lines of the stick spectra of the cyclohexanol radical show the broadened lines due to ring motion of the radical. Reprinted from [62].

Alcohols. Methanol, ethanol, n propanol, propan-i-ol.n-butanol, glycol, glycerol, benzyl alcohol, cyclohexanol. 

Physical Properties. All colourless liquids, completely miscible with water, except benzyl alcohol and cyclohexanol, which are slightly soluble. Pure glycol and glycerol have high viscosity, which falls as the hygroscopic liquids absorb water from the air. 

Cyclohexanol gives thenon-volatile adipicacid,HOOC (CH2)4COOH. After heating the mixture under reflux for 10 minutes, cool e flask. 

Cyclohexanone, This is readily oxidised by a KjCr 07 - HjSO mixture to the crystalline adipic acid, m.p. 152 , precisely as for cyclohexanol (p. 335). 

Note 1. The chlorocyclohexane should be free from cyclohexanol, which may lead to inactivation of the magnesium. 

Alkylation of 2-methylaminothiazole (204) with ROH in 85% sulfuric acid gives 2-methylimino-3-alkyl-4-thiazoIine (54). 2-Amino-4-rnethyl-thiazoie alkylated with an excess of isopropanol, however, gives 95% of 2-isopropylamino-4-methyl-5-isopropylthiazole (56). The same result is obtained with cyclohexanol (242). These results and those reported in Sections III.l.C and IV.l.E offer interesting new synthetic possibilities in thiazole chemistry. The reactive species in these alkylations is the conjugate acid of 2-aminothiazole. and the diversity of the products obtained suggests that three nucleophilic centers may be operative in this species. 

Assuming that the rate determining step in the reaction of cyclohexanol with hydrogen bro mide to give cyclohexyl bromide is unimolecular write an equation for this step Use curved arrows to show the flow of electrons... 

Two stereoisomers of 1 bromo 4 methylcyclohexane are formed when trans 4 methyl cyclohexanol reacts with hydrogen bromide Write structural formulas or make molecular mod els of... 

In Problem 5 17 (Section 5 13) we saw that acid catalyzed dehydration of 2 2 dimethyl cyclohexanol afforded 1 2 dimethylcyclohexene To explain this product we must wnte a mecha nism for the reaction in which a methyl shift transforms a secondary carbocation to a tertiary one Another product of the dehydration of 2 2 dimethylcyclohexanol is isopropyhdenecyclopentane Wnte a mechanism to rationalize its formation... 

Let s begin with a simple example Suppose you wanted to prepare cyclohexane given cyclohexanol as the starting material We haven t encountered any reactions so far that permit us to carry out this conversion m a single step... 

Recognizing that cyclohexene may be prepared by dehydration of cyclohexanol a prac tical synthesis of cyclohexane from cyclohexanol becomes apparent... 

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