Scc-Butyl bromide

In this experiment, you will compare the relative nucleophilidties of chloride ions and bromide ions toward each of the following alcohols 1-butanol (n-butyl alcohol), 2-butanol (scc-butyl alcohol), and 2-methyl-2-propanol (f-butyl alcohol). The two nucleophiles will be present at the same time in each reaction, in equimolar concentrations, and they will be competing for substrate. A protic solvent is used in these reactions. 

The yields of 1,4-addition products from sec-butyl crotonate and Grignard reagents are improved by CuCl-catalysis provided that the catalyst is added to the Grignard reagent in small portions concurrently with the ester soln.— E n-Butylmagnesium bromide from n-butyl bromide and Mg in ether treated at 0 with ethereal scc-butyl crotonate and simultaneously with 1.4 mole-% CuCl in small portions over a period of 3 hrs. scc-butyl 3-methylheptanoate. Y 80 to 85%. F. e. s. J. Munch-Petersen and V. K. Andersen, Acta Chem. Scand. 15, 271, 293 (1961) cf. Org. Synth. 41, 60 (1961). 

In the second step of the addition reaction, the scc-butyl carbocation, which has a vacant 2p orbital, acts as a Lewis acid. It accepts an electron pair from the nucleophilic bromide ion. This mechanism accounts for the product predicted by Markovnikov s rule. 

Methyl K-amyl carbinol, 7, 62 Methyl m-Amyl Ketone, 7, <5o, 62 i3-Methyl Anthroquinone, 4, 43 Methylation, 6, 64, 94, 96 Methylation by means of formaldehyde, 1, 75> 79 2, 17 3, 67 Methyl benzoate, 3, 71, 72 Methyl bromide, 3, 29 Methyl m-Butyl Ketone, 7, 62 Methyl mo-Butyl Ketone, 7, 62 Methyl scc-Butylmethyl Ketone,... 

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