04Exam1_q - CHEMISTRY 35 Spring 2004 FIRST EXAM SIS NAME...

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CHEMISTRY 35 – Spring 2004 – FIRST EXAM SIS # ________________ NAME___________________________ 1. (16 points) Draw the important resonance structures that contribute to the resonance hybrids of the following molecules. If there is more than one important resonance structure, indicate which is (are) major and which is (are) minor contributors . PROVIDE the correct formal charge for any charged atom in each resonance structure. A. B. C. D. If the C=O group of the amino ketone in part A is replaced by a CH 2 group, does the C–N bond length decrease, stay the same or increase? Briefly explain your anwer. N O B O N
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CHEMISTRY 35 – Spring 2004 – FIRST EXAM SIS # ________________ NAME___________________________ 2. (17 points) (A) Draw an energy versus dihedral angle diagram for rotation about the C2 – C3 bond of 2-methylbutane. Use C1 and C4 to define the dihedral angle for your plot. (B) For each energy maximum and each energy minimum, sketch the Newman Projection of the conformer and estimate it’s energy relative to the lowest energy conformer (whose energy we will define as 0 kcal/mole).
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