exam 3 key

exam 3 key - Chem 2210 Organic I Exam III — 03/21/08 —...

Info iconThis preview shows pages 1–9. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
Background image of page 9
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chem 2210 Organic I Exam III — 03/21/08 — 9:05-9:55 a.m. Name: KAE‘; Section: Page #5 16 PI Page #6 _ 10 Page #7 14 . m]— Page #8 10 Page #9 10 . Total 100 This exam has 14 pages total. Pages 13-14 are scratch paper. 1. Draw the most stable isomers of the following compounds. (2 pts) hexene methylcyclohexane M»/ H {A He. { or Mama/M} Ar \ " “a N x h i ’f 2. Name the following compound. (3 pts) (3 CD Br CN Q) Ca) Me -\ Qat- town-org nombaflnca -—\ 12o? hoe-org moon numme 3. The following compound has a large dipole moment. Please Show the direction of the dipole (using a dipole arrow) and a resonance structure that justifies the dipole moment. (Note: lone pairs are implied.2pts) 4. Predict the major product(s) of each reaction (15 pts). 3) ,b) d) Me Me Br Me / 750°C H2804, 100°C M NaOEt, 25°C Mum—)— 1) BZI—Ifi, diglyme 2) H202, NaOH catalytic HBr (0.01 eq) or 5) Predict the product(s) of each reaction (18 pts) a) b) d) Me Me Me Me Me Me Me Me Me Me Me Me / CI’QWO‘OH 0 1 equivalent HBr ——-———->— acetic acid Br}, 1-120 Br2 CHCJ3 1) Ozone, MeOI—I ——-—-——’- 2) H20, Zn Show Stereochemistry 6. For the following reaction provide product arising from a 8N1, 8N2, E1 or E2 mechanism. Draw the rate—determining transition states leading to each product (16pts). Me Br Nuc 5N2 53oz: 7. Provide an arrow pushing mechanism for the following reaction ( 10pts) BF Br2,CHC13 r N —* BN3 + B’VK/ ~99qu +4 Q11" 5: x?— Q0 a 5;“; m \ wp- xi) V V“ 3‘ air a. max M; iii, Kw » ’» “MM 5 3‘5 f- "mm-5% ‘“ -- kw“, (L 5 ,5;de ;_ ¢ » 5%; ‘3‘ firm if; F g V@/ WWWSW <33“: ‘__,.\ H“ gr ,2. m5} 6 8. Provide an arrow pushing mechanism for the following reaction (14pts) 0 Me Me ' A o H H OH T / O HO 110°C Me Me Me Me M a ' “I f w; A M .M‘ 4» Q l f/MHH ‘A h,“ 0 fix”? mi, E‘ [33} a; x ._.__.s \ fl» “a m \%.:R‘MIHW,‘«WM,4 ; @umh flqfi “a I If Ha Me a.” v * ‘ M hwy? a Mt; ,J 3 gr E fiat *1 M W A- H 9°" C3 .1 1-. ‘r W O ? NM 1 _) as; w} " “ ~21; Q“ t C V! {- L's" ‘L' I 11"!” T“ F a . HQ v Hg“ 9. Explain the following observation by using pKa data, showing the intermediates (IOpts). [elative ;a_te OH 100°C ——"'"""“""' 1 OH 100°C —l- catalytic _ 1,000,000,000 H2304 “A W "“ gait-ix {Pg-m3)? fi_ a“ f f Luca, - w‘ mm a \fi '+ +1.. P: g i A s t z 0+ a 01» (3 a M* W my Ema Wm )& A, if, 9/ Exam Qmér " L Q: \¥ 0; ~ 0: " H 9mm 5"" "K 7’? if ’L. \Dfifaei. G‘Q V’VT (“ngggjffigggfi “0; ML \“E «mm» a? mwfiwmuc‘w crime fieggfiggg: tam-mg“ ummmrra‘xwmé {teaacw‘mmm {iqtavfiamgam '1 amaze, :‘w in» azaxswgzi! 10. Synthesize the following from the provided starting material ( 10pts). @éi? Starting Material Product \‘i *1 \i {5c +7— ! f 1* IL .__..—~—‘—-m§ ‘- ' "'w—b dam. 4., MM“... 6 ' ‘ 433‘»- %< b¢$ 4:1. ‘42- ' 5:29 a? . ' Haggai?” a a ‘31:: iv n x f m '- "i f a a ...
View Full Document

Page1 / 9

exam 3 key - Chem 2210 Organic I Exam III — 03/21/08 —...

This preview shows document pages 1 - 9. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online