Chem335_summer09_1

Chem335_summer09_1 - Me Cl OMe NO 2 NO 2 Br Cl Me a b c d e...

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Name : Organic Chemistry II , Chem 335 Student ID#: Exam # 1.0 , July 1, 2009 Read all the questions carefully. Also draw your structures carefully, paying attention to details (e.g., are hydrogens missing, is the stereochemistry correct, is the ring size correct, et.). You can use the reverse side of pages for scratch. No electronic devices (cell phones, laptops, etc) may be used or consulted during the exam . 1. Rank the following substituted benzenes in order of decreasing reactivity toward electrophilic aromatic substitution (most reactive 1, least reactive 5). (4 pts) O Me Cl NO 2 Me 2. Name the following compound using IUPAC nomenclature: (4 pts) Me Ph 3. Indicate, using arrows, the site(s) of attack by an electrophile when the following aromatic compounds are subjected to electrophilic aromatic substitution. (20 pts) O Me
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Unformatted text preview: Me Cl OMe NO 2 NO 2 Br Cl Me a) b) c) d) e) 4. Complete the following equations by providing the structure(s) of the major organic products. (30 pts) a) H HgSO 4 , H 2 O, H 2 SO 4 b) H 1. BH 3-THF 2. H 2 O 2 /OH-c) CH 3 Br 2 (show stereochemistry) d) H 2 HBr e) Ph CH 3 Na, liq. NH 3 f) (show stereochemistry) H H 3 CH 2 C 1. n-BuLi 2. Br (be careful 5. Show how you might accomplish the following transformations in a efficient manner. More than one step will be necessary in each case. You may use any organic or inorganic reagents. (24 pts). a) O Me SO 3 H b) NO 2 c) NH 2 Br d) Me Me Me O Br 6. Show how the following compounds can be prepared starting from acetylene (ethyne). More than one step will be required (18 pts). H H CH 2 CH(CH 3 ) 2 H H 3 CH 2 C H a) b) H H Me O c) H H H O...
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