Group 1

1. Considering the differences between C=O and C=C thermodynamically, discuss the C=N bond, and rank it thermodynamically in terms of its stability relative to these former two bond types. Explain your reasoning in detail, using a resonance theoretical representation of the C=N. Draw a simple example of a compound containing the C=N bond and point out the hybridization states of C and N. What type of orbital does the N unshared pair occupy?

2. Consider a general reaction between reactants represented as R and products represented as P and draw a one step reaction path diagram for this reaction, showing what quantity controls the position of the equilibrium and what quantity controls the rate of the reaction. Give the equation which relates the one quantity to the equilibrium constant K and another equation which relates the other quantity to the rate constant k. Also, provide the equation which describes the relationship between K and the forward and backward rate constants.

3.Explain in terms of some feature of the structure (e.g. bond strength) or charge characteristic (e.g., anion stability) of the reactants and/or products why the addition of a Grignard reagent to a carbonyl group goes to completion.

4. Sketch a synthesis of the following alcohols, using any organic molecules having four carbons or less and also either bromobenzene or benzyl chloride as a source of aromatic rings.

(a)3-heptanol (b)2-methyl-1-phenyl-1-propanol