NAME________________________________________Organic Chemistry II, CHEM 332Sections 003, Dr. SweetingExam 1, March 1, 2002Full credit: 100 points, maximum with bonuses: 1141. Please complete the following reactions by inserting a sketch of the missing reactantor product as indicated by the question mark. (4 points each, 24 total)+O?BrBr???H2SO4SO3??O2. Please identify (for 14 points) a) whether the following compounds are terpenes (YES / NO)b) any isoprene units in the molecule by circling or otherwise marking themflavor components in beer from hops flavor in spearminthumulene isocohumulone carvoneOOOHOHO3. Please make a sketch which shows the shapes and relativeenergies of the molecular orbitals of benzene. To get full creditfor this question, I suggest you plan the layout of your answerbefore you start – you will not need the whole page. (18 points)4. This question explores your knowledge of the electrophilicnitration of benzene:a) Please outline the mechanism of the reaction of nitric acidwith sulfuric acid to create the nitronium ion. (8 points) b) Please outline the mechanism of the reaction of theelectrophilic nitronium ion with benzene. (8 points)c) By reference to the mechanism above, explain why thenitration of chlorobenzene occurs almost exclusively in thepositions ortho and para to the chlorine. You will probably needto draw some structures to answer this question. (8 points)5. Outline a practical laboratory synthesis of TWO of the followingfrom the reagent indicated. Extra credit for additional synthesessolved. (10 points each) from benzeneCl from benzeneN+OO from anilineNH2N+OOfrom