Exam4b 2006 - CHEM 2535 Organic Chemistry December 1, 2006...

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CHEM 2535 Organic Chemistry Exam 4b December 1, 2006 Exam4b.doc Name:_________________________________________________ Selected Pauling’s Electronegativity Values IA IIA IIIA IVA VA VIA VIIA Group 1 2 3 4 5 6 7 valence electrons H 2.1 Li 1.0 Be 1.5 B 2.0 C 2.5 N 3.0 O 3.5 F 4.0 Na 0.9 Mg 1.2 Al 1.5 Si 1.8 P 2.1 S 2.5 Cl 3.0 K 0.8 Ca 1.0 Br 2.8 I 2.5 IUPAC name Chemical Abstracts name Abbreviation Condensed Formula Skeletal structure methyl methyl Me CH 3 S N 2 S N 1E 2 1. RX, primary Y N N Y RX, primary allylic Y Y Y N RX, primary benzylic Y Y N N RX, secondary Y Y Y Y RX, tertiary N Y Y Y RX, X-C-C-H Y Y Y Y RX, no X-C-C-H Y Y N N 2. Good Nu, weak base Y Y Y N Good Nu, strong base Y N N Y Great Nu, (RS , CN) Y Y N N Poor Nu, weak base N Y Y N Bulky strong base N N N Y 3. Polar aprotic solvent Y N N Y Polar protic solvent Y Y Y Y 4. High temperature Y Y YY YY ethyl ethyl Et CH 3 CH 2 propyl propyl Pr CH 3 (CH 2 ) 2 isopropyl (1-methylethyl) i -Pr (CH 3 ) 2 CH– butyl butyl Bu CH 3 (CH 2 ) 3 isobutyl (2-methylpropyl) i -Bu (CH 3 ) 2 CHCH 2 sec -butyl (1-methylpropyl) s -Bu (CH 3 CH 2 )(CH 3 )CH– tert -butyl (1,1-dimethylethyl) t- Bu (CH 3 ) 3 C– * * * * * * * * IUPAC name Condensed structure methane CH 4 ethane CH 3 CH 3 propane CH 3 CH 2 CH 3 butane CH 3 (CH 2 ) 2 CH 3 pentane CH 3 (CH 2 ) 3 CH 3 hexane CH 3 (CH 2 ) 4 CH 3 heptane CH 3 (CH 2 ) 5 CH 3 octane CH 3 (CH 2 ) 6 CH 3 nonane CH 3 (CH 2 ) 7 CH 3 decane CH 3 (CH 2 ) 8 CH 3 undecane CH 3 (CH 2 ) 9 CH 3 dodecane CH 3 (CH 2 ) 10 CH 3 cyclohexane, C 6 H 12 cyclopentane, C 5 H 10 cyclopropane, C 3 H 6 cyclobutane, C 4 H 8 Out In In Out In Out In Out In In Out Out Out Out In In In Out In Out Out In In Out In Out In Out Out In In Out Out Out In In In In Out Out Out In In Out In Out In Out Enantiomeric TS structures
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CHEM 2535 Organic Chemistry Exam 4b December 1, 2006 Page 2 of 7 H:\Chem2535\Fall2006\Exams\Exam4b.doc 1(26) 2(14) 3(6) 4(6) 5(12) 6(12) 7(8) 8(16) Bonus(8) Total(100) 1. In the boxes provided, write the MAJOR product(s) of the reactions. Use stereochemical descriptors in the product where appropriate . (26 points) C HC CH CH 3 CH 3 H 2 O, H 2 SO 4 HgSO 4 excess Cl 2 CH 2 Cl 2 C C H C CH 2 CH 2 CH 3 1. disiamylborane
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This note was uploaded on 04/21/2008 for the course CHEM 2535 taught by Professor Mbbump during the Fall '06 term at Virginia Tech.

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Exam4b 2006 - CHEM 2535 Organic Chemistry December 1, 2006...

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