organic chem 1 review fall 10

organic chem 1 review fall 10 - ORGANIC I COMPLETE REACTION...

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ORGANIC I COMPLETE REACTION SUMMARY Below is a list of most of the reactions we covered in organic I. Not specifically listed are S N 1, S N 2, E1 and E2 reactions which are VERY important reactions in organic chemistry. NOTE: R = C,H alkane chain & X = Cl or Br Alkene reaction summary C C X R H H R R NaOC(CH 3 ) 3 C C R H R R An E2 reaction C C R H R R C C R Br Br H R R KI, acetone Goes through an E2-like mechanism and both Br’s leave when they are anti & coplanar to one another C C R H R R C C R H OH H R R H 2 SO 4 , H 2 O This is a highly reversible reaction. C C R H R R C C R H OH H R R POCl 3 , pyridine C C R H R R H 2 / Pd C C H R H H R R C C R H R R HX CCl 4 C C X R H H R R HBr in the presence of peroxides gives anti-Markov product C C R H R R X 2 CCl 4 C C R X X H R R X’s are added trans to one another C C R H R R X 2 H 2 O C C R OH X H R R -OH is added in trans to X and the OH is put on the more substituted C
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C C R H R R 1. Hg(OAc) 2 H 2 O 2. NaBH 4 C C H H OH R R R OR H H 2 O an alcohol in place of water in step 1 will give an ether product. The H and OH will add trans to one another and the OH is on the more substituted C C C R H R R 1. BH 3 , THF 2.H 2 O 2 , OH C C H R OH H R R Anti-Markov product, H & OH add in syn- C C R H R R RCO 3 H CH 2 Cl 2 C C R H R R O C C R OH OH H R R H, H 2 O trans diol C C R H R R KMnO 4 cold, dilute, basic C C OH R OH H R R OR OsO 4 , H 2 O 2 cis 1,2-diol C C R H R R O C R OH C O R R KMnO 4 warm, acidic, concentrated CO 2 is formed on a terminal alkene C C R H R R O C R H C O R R 1. O 3 2. (CH 3 ) 2 S CH 2 O is formed on a terminal alkene Alkyne reaction summary C C X H H X R R C C R R Excess KOH heat R C CH 2 H 2 C R Pt, Pd or Ni CH 3 H H adds H’s in cis- R C CH Na, NH 3 C CH H R H adds H’s in trans-
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R C CH H 2 , Pb/BaSO 4 C CH H R H quinoline this is H 2 over Lindlar’s catalyst, adds H’s in cis-
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This note was uploaded on 02/13/2011 for the course CHEM 2344 taught by Professor Slack,wu during the Spring '11 term at University of Houston.

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organic chem 1 review fall 10 - ORGANIC I COMPLETE REACTION...

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