10 Solved Questions on Resonance Compounds - Exam 1 | CHEM 109B, Exams of Organic Chemistry

Download 10 Solved Questions on Resonance Compounds - Exam 1 | CHEM 109B and more Exams Organic Chemistry in PDF only on Docsity! Chem 109B Name_________________________ Prof. Bode Winter 2006, MWF 13-14 Perm No.______________________ Exam I (111 points) 1. Draw five non-equivalent resonance structures for the following compounds. Be sure to clearly indicate electron pairs, formal charges, and arrows. (7.5 points) O– N OO CH3 O 2. Rank the following compounds: (9 points) (a) In order of acidity: H3C OH H3C OH H3C OH O < < A B C least most (b) In order of acidity: CH3CH2 H CH3CH2O H HH3C < < A B C least most (c) In order of acidity: NC OH CN H3C OH NC OH < < A B C least most Page 2 of 7 Name_________________________ 3. Circle the compounds that are aromatic. (9 points) N H H N CH3 N O N N 4. Draw structures for the following compounds, showing the proper stereochemistry: (6 points) (a) (S)-3-propyl-2-hexanol (b) tert-butylmagnesium bromide 5. Draw a mechanism for the following reaction: (6 points) CH3 CH3 CH3HO heat H2SO4 CH3 CH3 Page 5 of 7 Name_________________________ 9. Fill in the missing reagent or reactant. (18 points) (a) + MgBr (b) + Cl O O O H H3C O H3C (c) H3C CH3 + + H3C CH3 (d) + CH3 Cl Cl H3C (e) O Br + + CH3 HO Br + Workspace: Page 6 of 7 Name_________________________ 10. Propose multi-step synthesis of the following compounds from the given starting materials. You may use any reagents or reactions covered in this class. Each one can be prepared in four steps or less, however any chemically logical sequence is acceptable. (16 points) (a) OH H3C from H CH3 and (b) CH3 OH HO from HO Br O CH3 and Hint: see 9(e)! Page 7 of 7 Name_________________________ Points Possible Points Page 1 / 16.5 Page 2 / 21 Page 3 / 22 Page 4 / 17.5 Page 5 / 18 Page 6 / 16 Total / 111 (total includes 11 points of “extra credit”)