A compound A derived from isobutanol, soluble in NaOH and with the formula molecular C4H8O2 is capable of reacting with PCl5 and also with NH3, obtaining in each of them a single compound (B or C) of the same number of carbons than A, with very different melting points (pt. f. of B &lt;&lt; melting point of C). Compound B reacts with a compound D, in the presence of AlCl3, providing a product E with molecular formula C10H12O. On the other hand, C is reduced to a compound F with molecular formula C4H11N which, once purified, is reacted with E in the presence of catalytic amounts of acid, obtaining an aromatic compound G with molecular formula C14H21N. What structures do compounds A, B, C, D, E, F, and G have? what kind of reaction happens in each case? (note: reduction of amides produces amines (reduction of Hoftman)).

Question

A compound A derived from isobutanol, soluble in NaOH and with the formula molecular C4H8O2 is capable of reacting with PCl5 and also with NH3, obtaining in each of them a single compound (B or C) of the same number of carbons than A, with very different melting points (pt. f. of B &amp;lt;&amp;lt; melting point of C). Compound B reacts with a compound D, in the presence of AlCl3, providing a product E with molecular formula C10H12O. On the other hand, C is reduced to a compound F with molecular formula C4H11N which, once purified, is reacted with E in the presence of catalytic amounts of acid, obtaining an aromatic compound G with molecular formula C14H21N. What structures do compounds A, B, C, D, E, F, and G have? what kind of reaction happens in each case? (note: reduction of amides produces amines (reduction of Hoftman)).