Chemistry Exam for Course 3331: Solutions for First Exam - Prof. Randolph Thummel, Exams of Organic Chemistry

Download Chemistry Exam for Course 3331: Solutions for First Exam - Prof. Randolph Thummel and more Exams Organic Chemistry in PDF only on Docsity! CHEMISTRY 3331 Name______________________________________ FIRST EXAM (print, legibly) Last First Dr. R. Thummel 15 February, 2008 Last 4 digits of student number ___________________ Please read all directions carefully. Write all answers legibly in the appropriate spaces and THINK about what you are doing. Give only ONE answer for each question (100 pts total). 1. (16 pts) Give a complete and acceptable name for each of the molecules shown below. Be sure to indicate stereochemistry where this is peetinent. (a) BrBr Br H (b) (c) (d) CH3 2. (12 pts) Carefully draw both chair conformations of all cis -1,3-dibromo-2-chlorocyclohexane and put a star under the most stable conformation. 5. (16 pts) In addition to the structure shown below, there are FOUR OTHER resonance forms. Draw these four other resonance forms in the boxes below:. NH 6. (17 pts) (a) Calculate the overall heat (ΔH0) of the following reaction using the Table of Bond-Dissociation Energies attached to this exam. Show all work. CH3CH2CH3 + HO–OH CH3CHCH3 + H2O OH hv (b) On the reaction coordinate below, diagram the first propagation step (shown) of this reaction. Indicate the positions of starting materials, products and transition state. CH3CH2CH3 + HO CH3CHCH3 + H2O Is this step exothermic or endothermic (circle one)? Reaction coordinate Energy (c) Draw the structure of a possible termination product for this reaction. 7. (12 pts) Various stuff: In the box, draw the structure of: (a) The conjugate base of ethane: (b) A non-polar molecule with the formula C2Cl4 (c) A compound with the formula C2H3N which contains one sp and one sp3 hybridized carbon.