Problem Set 2: Organic Chemistry, Assignments of Organic Chemistry

Download Problem Set 2: Organic Chemistry and more Assignments Organic Chemistry in PDF only on Docsity! Problem Set #2 1. Draw 2 resonance structures for each of the following molecules (show arrows). 2. Which proton, Ha or Hb is more acidic? Explain using resonance structures. O O Cl O Cl O O O Hb Ha Base Base O O O O O O O opposing res. structures destabilized negative charge O stabilized negative charge stabilized negative charge Hb is more acidic than Ha 3. Encircle the side of the equation that would be favored at the equilibrium. 4. Provide systemiatic (IUPAC) names for each of the following structures: O O H + H2O H3O + O O O F F H + H2OH3O + O F F O H + NH3 NH4 + O Br ClCl Br NH2 I O N HN CH3 CH3 Cl OH 2-bromo-5-ethyl-4-methylheptane 3,3-dichlorohexane N-propyl-1-methylcyclohexanamine 1-bromo-3-methyl-5-propylcyclohexane 3-methoxy-4-methylheptane 3-iodo-2-methylcyclopentanamine N-methyl-N-propyl-3-ethyl-3-methylhexanamine cis-1,3-dimethylcyclohexane trans-4-chlorocyclohexanol 8. Draw the two chair conformers of 1-bromocyclohexane and indicate which one is more stable: 9. Convert the following stick structure to the appropriate chair conformer(s). Br Br H Br H More stable; substituent is equatorial CH3 CH3 CH3 H CH3 H H H3C H CH3 OR Methyls are trans! 10. Draw the bond rotation energy diagram for 2-methylbutane (looking down the C2-C3 bond) with the Newman projections for each point CH3 H H CH3 CH3H H3C H H CH3 CH3H H H3C H CH3 CH3H H H3C H CH3 CH3H E N R G Y (ΔE) Dihedral Angle H H CH3 CH3 CH3H H H CH3 CH3 CH3H CH3 H H CH3 CH3H