Chem335_summer09_1_answerkey

Chem335_summer09_1_answerkey - 3 f) (show stereochemistry)...

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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 4 3 5 1 2 2. Name the following compound using IUPAC nomenclature: (4 pts) Me Ph 4-phenyl-2-heptyne 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 Cl OMe NO 2 NO 2 Br Cl Me a) b) c) d) e)
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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
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Unformatted text preview: 3 f) (show stereochemistry) H H 3 CH 2 C 1. n-BuLi 2. Br (be careful O H O Br Br Br Br Ph CH 3 H H 3 CH 2 C + (by E2) 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 CH 3 COCl AlCl 3 O SO 3 H 2 SO 4 O SO 3 H b) NO 2 CH 3 COCl AlCl 3 O H 2 SO 4 HNO 3 O NO 2 Zn(Hg) HCl conc. NO 2 c) NH 2 Br HNO 3 H 2 SO 4 NO 2 Br 2 FeBr 3 NO 2 Br SnCl 2 NH 2 Br d) Me Me Me O Br CH 3 COCl AlCl 3 O Br 2 O Br FeBr 3 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) H H 1. n-BuLi 2. CH 3 CH 2 Br H 1. n-BuLi 2. (CH 3 ) 2 CHCH 2 Br H 2 , Lindlar cat. b) H H Me O H H 1. n-BuLi 2. CH 3 CH 2 CH 2 Br H HgSO 4 H 2 SO 4 , H 2 O O c) H H H O H H 1. n-BuLi 2. CH 3 CH 2 CH 2 Br H 1. BH 3-THF 2. H 2 O 2 /OH-H O...
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This note was uploaded on 09/24/2009 for the course CHEM 333 taught by Professor Baird during the Spring '09 term at UC Davis.

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Chem335_summer09_1_answerkey - 3 f) (show stereochemistry)...

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