N-Propyl carbinol

B. 2-Pentene. Proceed as in A, but use the following quantities 50 ml. of water and 50 ml. of concentrated sulphuric acid 40 g. of methyl n-propyl carbinol (4). Collect the distillate passing over below 40°. Pure 2-pentene boils at 36-5°. 

Dimethyl n-propyl carbinol, CH3(CH2)2COH(CH3)2. From n-propyl magnesium bromide and acetone. Collect the tertiary alcohol at 121-124°. 

Ghloropentane. Use the quantities given in the previous preparation, but substitute 22 g. (27 ml.) of methyl n-propyl carbinol (b.p. 118-5°) for iso-amyl alcohol. Collect the 2-chloropentane at 96-98°. 

Bromopentane. Proceed as for n-Amyl Bromide, but use 88 g. (108 ml.) of methyl n-propyl carbinol (2-pentanol), b.p. 118-5°. During the washing with concentrated hydrochloric acid, difficulty may be experienced in separating the acid layer this is overcome by adding a little water to decrease the density of the acid. Distil the purified product through a fractionating colunm some amylene passes over first, followed by the 2-bromopentane at 115-118° (120 g.). 

Dimethyl n-propyl carbinol Reactions and characterisation of aliphatic alcohols... 

Triphenylcarbinol, 811, 813, 814, 816 Triphenylchloromethane, 811, 815, 952 Triphenylguanidine, 643 Triphenylmethane, 509, 515 Triphenylmethyl sodium, 477,479 Triple point, 37, 38 Tri-n-propyl carbinol. 259 Trityl chloride, 815... 

Increase in the chain length, symmetrically, increased the reactivity of the secondary tosyloxy group (p-toluenesulfonic ester of dimethyl carbinol, 7.5 of diethyl carbinol, 23 of di-n-propyl carbinol, 24% of NaOTs, after 2 hours at 25°). 

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