Question

The unsaturated hydrocarbons A and A1 react according to the following not balanced equations to form the compounds D, E and F.

Consider the following information:
 C and C1 are heated in the molar ratio of 1 : 1.
 The elementary analysis of D, E and F provides the following data:
D: 55.82 % C, 11.71 % H, 32.47 % N
E: 59.88 % C, 12.01 % H, 28.11 % N
F: 62.98 % C, 12.30 % H, 24.72 % N
 D, E and F are heterocyclic compounds.
 D, E and F are bases.
 D, E and F can be catalytically dehydrated to form aromatic heterocyclic compounds.
 The 1H-NMR spectrum (CDCl3) of compound D shows two singlets in the ratio 1 : 4 (chem. shift: 1.66 ppm, 2.84 ppm).
 If D, E and F react with an N-alkylation agent the compounds D*, E* and F* form. During this reaction D, E and F add 4 methyl groups each.

Answer 1

a) Complete the reaction scheme above with the compounds A to C and A1 to C1.