21 - 3/9/2012 What is the mechanism of this reaction?...

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Unformatted text preview: 3/9/2012 What is the mechanism of this reaction? Organic Chemistry Review Harriman Hall 137 from 7-9 pm on Tuesday, March 13 + + E R What is the equilibrium constant of the following reaction? Which of the following reactions would be predicted to occur at a faster rate? O O H O CH3 + N CH3 + + C A C N CH3 CH3 CH3 O Cl H + N CH3 B O C N CH3 A. about 1.0 B. much greater than 1.0 C . much less than 1.0 CH3 CH3 What is the mechanism of this reaction? Which of the following carbonyl groups is more stabilized by resonance? O OCH3 Nu O Cl Nu O + + C O CH3 A O O C O CH3 Cl O Cl E B R Cl O OCH3 O Nu O C 1 3/9/2012 Which of the following reactions would be predicted to occur at a faster rate? A Which of the following reactions would you predict to be faster? A B B What is the mechanism of the following reaction? Choose the answer that has the following C=O groups arranged correctly with respect to increasing reactivity towards nucleophiles. O R i N R R R O O ii O R R iii O O R O R N R R R O O O R R O O R A i < ii < iii D ii < iii < i B i < iii < ii E iii < ii < i C ii < i < iii F iii < i < ii What is the mechanism of the following reaction? Order of C=O reactivity. O R Cl R O O O R R O O R R O N R O X R C X Nu R increasing reactivity O R C Nu X R O C Nu energy progress of reaction 2 3/9/2012 Are carboxylic acids and their derivatives found in nature? Aspirin inhibits Cyclooxygenase. How does it do this? prostaglandins Arachidonic acid: Where does it come from and what does it do? Are carboxylic acids and their derivatives found in nature? Arachidonic acid: Where does it come from and what does it do? CRYSTAL STRUCTURE OF ARACHIDONIC ACID BOUND TO THE CYCLOOXYGENASE ACTIVE SITE OF COX2 amino acid serine NH H N chapter 10 prostaglandins cause constriction or dilation in vascular smooth muscle cells cause aggregation or disaggregation of platelets sensitize spinal neurons to pain induce labor decrease intraocular pressure regulate inflammatory mediation regulate calcium movement control hormone regulation control cell growth acts on thermoregulatory center of hypothalamus to produce fever acts on mesangial cells in the glomerulus of the kidney to increase glomerular filtration rate O H O H O amino acid tyrosine Nature, 2000, 405, 97101 3 3/9/2012 How could aspirin inactivate cyclooxygenase (COX)? amino acid serine NH H N NH H N amino acid serine arachidonic acid O H O protein O CH3 O O H O O O H O amino acid tyrosine H O amino acid tyrosine Nature, 2000, 405, 97101 Nature, 2000, 405, 97101 H3C O O H O H3C O O H O H3C O O O amino acid serine NH H N H amino acid serine NH H N prostaglandin O H O O protein O CH3 O O H O O protein O H O amino acid tyrosine O H O amino acid tyrosine Nature, 2000, 405, 97101 Nature, 2000, 405, 97101 CH3 O O O O amino acid serine NH H N O O NH H N amino acid serine aspirin protein H H3C O O H O O O protein O H O amino acid tyrosine H O amino acid tyrosine Nature, 2000, 405, 97101 Nature, 2000, 405, 97101 4 3/9/2012 What is the order of ester reactivity in acylation reactions? amino acid serine NH H N arachidonic acid H3C O O O protein H O amino acid tyrosine Nature, 2000, 405, 97101 How does ibuprofen prevent the COX enzyme from producing prostaglandin? O O amino acid serine NH H N O O ibuprofen protein H H O amino acid tyrosine What is the order of ester reactivity in acylation reactions? 5 ...
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This note was uploaded on 03/27/2012 for the course CHE 322 taught by Professor Staff during the Spring '08 term at SUNY Stony Brook.

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