10 Solved Problems in Exam 1 on Organic Chemistry II | CHEM 3020, Exams of Organic Chemistry

Download 10 Solved Problems in Exam 1 on Organic Chemistry II | CHEM 3020 and more Exams Organic Chemistry in PDF only on Docsity!

108 pts Name. k eV CHEM 3020 Exam 1, Ch. (15-18), February 9, 2012 Show work for partial credit. You may use the periodic table and other information provided. Read the questions carefully, Good Luck! Part I. The Brain Warm-up 1. Provide the following: (7 pts) a. Structure for p-iodoaniline _b. two resonance structures for the benzyl radical wr ete OS CS 9 er. 2. The inverted polygon method can be used to predict molecular orbital energy levels for heterocyclic compounds, such as pyrrole, below. (8 pts) e LUMO Ҥ Oa a. Use the inverted polygon method predict energy levels for pyrrole. b. Fill the pi electrons into the molecular orbitals. c. Label the HOMO and LUMO orbitals. = d. Classify pyrrole ag aromatic, ti-aromatic, or non-aromatic. 6 & 3. A fluorine (F) substituent de-activates a benzene ring toward substitution, yet it is an ortho/para director. Explain in terms of EWG (acceptor) and EDG (donor) ability, using both inductive and resonance arguments. (5 pts) Fuuntar 1S an iaductue EWG (mest eldonegedye erred, ) bus a EDG by resonance (lore pair pusrrs elackons met ) Since pesonance. 15 usoely the domndint act oy stabiliay Be cadin , orths, pave dutcnny. * . By > ae GWG- ' slews dom fe pechm, 20 deachy : 4. One phenyl ring of the molecule below undergoes electrophilic aromatic substitution faster than the other. Predict the major product(s) based on activation and directing ability. (4 pts) 20% Ǣ 10 Q Co = Pr 4 E+ - 4 es a oa ) o's jewels 4 } wer a N- | \