7 points we have now run into cases in which bonds

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(7 points) We have now run into cases in which bonds that look like normal sigma single bonds in a Lewis structure, actually have partial double bond character in the molecule. In the following set of molecules, circle the single bonds that have double bond character (i.e. hindered bond rotation at room tempterature). NOTE: You DO NOT have to circle any bonds WITHIN an aromatic ring. C H H H C O N H C H H H C C C C C C H C H H H H H H H H H H C C C C C C O H H H H H H H C C C C C C C N O H H H H H H H
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Pg 3 _____________(24) Signature_________________________ 5. (12 points) Draw a circle around all of the molecules below that can be considered aromatic. N H N N N 6. (12 points) For each pair of molecules, circle the one that is more acidic. A. or B. OH OH or C. or D. or N N H H H O O O E. or F. or O O O O OH H N
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Pg 4 _____________(19) Signature_________________________ 7. (9 points) On the lines provided, state the hybridization state of the atom indicated by the arrow. H 3 C C H N CH 3 O C C C C C H H H H H N N H H H H C C C C C C Br H H H H H H 8. (10 points) On the lines provided, state the atomic orbital that contains the lone pair of electrons indicated by the arrow. H 3 C C H N CH 3 O C C C C C H H H H H N N H H H H N H H H H H
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Pg 5 _____________(31) Signature_________________________ 9. (20 points) In the spaces provided, draw all the important resonance contributing structures of the indicated species. We have provided template molecules to help you do this more quickly. You must draw all pi bonds, lone pairs of electrons and all formal charges on each of your structures. You DO NOT need to draw arrows to show electron movement. Cl H HO Cl H HO O O H H H H H H H H H H 10. (11 points) Complete the mechanism below that shows how the wicked strong electrophilic species is produced that goes on to react with an aromatic ring. Use arrows to show the movement of all electrons, and be sure to draw all lone pairs of electrons and all formal charges. Your answer should end with formation of the wicked strong electrophilic species, you do not need to show reaction with an aromatic ring. Make sure to show all new species produced in each step. S O O O O H H O N O O H N i t r a t i o n H 2 SO 4 /HNO 3 Wicked Strong Electrophilic Species Cl H HO Cl H HO O O H H H H H H H H H H H H H H H
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C O H O O CH 3 O O CH 3 mild H 3 O + mild H 3 O + HO - Na + LDA CH 3 O - Na + Br mild H 3 O + (no heat) CH O OH O O OCH 3 O O OCH 3 Signature_________________________ A) Pg 6 _____________(18) 11. (2 pts each) In each of the boxes over an arrow, write the minimum number of equivalents of the specified reagent required to carry out the reaction shown t o c o m p l e t i o n . If only a catalytic amount is needed, write "CAT" . Note: You must assume the carbonyl compound starting material is initially present in an amount of 1.0 equivalent.
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  • Spring '08
  • BLOCKNACK
  • Chemistry, Trigraph, H H H C H C N H O H C H H H C C H H C C H H C C H H C C H H C C H O C C H H H H H C H H H C C H C C C O C N H H, Signatur e_________________________, starti ng mat, start ing ma, mol ecul

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