3. Formamidine is the simplest compound containing the amidine functional group. (16 pts) HN NH2 a) Amidines are substantially more basic than typical nitrogen-containing functional groups such as amines and amides. Draw the structure of the conjugate acid you expect to be Formamidine formed when formamide is protonated at its most basic position and use your structure to explain the unusually strong basicity of formamidine. b) The a molecular orbitals of formamidine can be represented using an orbital energy diagram as shown below. Fill in the appropriate number of electrons on the diagram, and clearly explain how you chose the number of electrons you did. In addition, identify the HOMO and LUMO, and draw a picture of the highest energy te molecular orbital, 1 3, making sure to include shading to indicate phase. 03 42 1 4. Fill in the blanks with the best answer (20 pts): a) The presence of a nearby heteroatom can stabilize a conjugate base either by direct delocalization of formal charge via or by an) effect as a result of its high electronegativity b) We expect the pK, of an alkane hydrogen to be than that of an alkene hydrogen due to the difference in between the two carbon atoms. c) While HI might be expected to have the highest boiling point of the hydrogen halides, since its large size should give it the strongest forces, the highest boiling member of the group is actually HF, due to its ability to form d) A(n) bond is characterized by end-to-end overlap of atomic orbitals, leading to a combined bonding orbital with cylindrical about the bond axis. e) We can reliably increase the forward and reverse rates of a reaction by raising the of the system, since this increases the fraction of reactant molecules that have the necessary to be converted to products, and vice versa