Organic Chem I Exam 3: Naming, Radical Formation, & Reactions, Exams of Organic Chemistry

Download Organic Chem I Exam 3: Naming, Radical Formation, & Reactions and more Exams Organic Chemistry in PDF only on Docsity! Chemistry 331 Organic Chemistry I Exam 3 Butadiene ψ4 ψ3 ψ2 ψ1 Points: Q1:10; Q2:20; Q3:20; Q4:20; Q5:10; Q6: 10; Q7:10; Q8: 10 TOTAL: 110 Name ________________________________________________________________ (please print) CH 331, Exam 3 – Page 1 1. Give the IUPAC name for each of the following compounds (10 points): Hint: DON’T FORGET E/Z , cis-trans NOTATION. a) CH3 CH3 (1R,6S)-1,6-dimethylbicyclo[4.1.0]heptane b) Cl CH 1-chloro-5-ethynylbicyclo[4.2.0]octane c) CH CH3 CH3 CH3 (4E,8E)-5,7-dimethyldeca-4,8-dien-1-yne d) CH2 CH2 7,8-divinylcycloocta-1,3,5-triene e) Br Br 6,7-dibromospiro[4.5]decane CH 331, Exam 3 – Page 4 3. Complete the following transformations. Be sure to consider stereochemistry where appropriate. Indicate the type of reaction. For Questions b,c,d name the compound. (4 points each) a) CH CH3 O H2O, H + b) CH3 CH H CH3 O 1. Hydroboration, B2H6 2. Oxidation, H2O2, OH - c) CH2 CH3 CH3 3 Br2, CH2Cl2, ionic BrBr Br d) CH3 CH3 CH3 NBS, CH2Cl2 CH3CH3 BrBr CH3 CH3 CH3 e) CH3 CH3 CH3 CH3 CH3 H H CH3 CH3 CH3 CH3 CH3 Na/NH3 CH 331, Exam 3 – Page 5 4. Which Diene and which Dieneophile could be used to prepare the following compounds. (20 points) a) CH3 N CH3 + CH2 N b) F F F F F F FF c) O O O O CH3 CH3 O O CH3 O O CH3 H CH3 CH3 OH O CH3 CH3 d) CH 331, Exam 3 – Page 6 5. Which of the following materials are aromatic? Briefly explain why (use Hückel’s rule.). (10 points) CH + CH + O O N N N N H CH + CH + A: Not aromatic : 4 pi-electrons B: Aromatic: 18 Pi electrons C: Not aromatic: not all Pi electrons part of a ring system D: Aromatic: 10 Pi electrons ( two from lone pair at nitrogen E: Aromatic: 2Pi electrons. So B,D,E follow Hueckel-rule: (4n+2), for n=0 (E), n=2(D), n=4(B)