09-14 - 9/14/2009 Using the reaction library propose a...

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Unformatted text preview: 9/14/2009 Using the reaction library propose a synthesis of compound A. H H OH C C C C H2 Pd/C OH H 1. Li C Li Br 2. 1. C O 3. 2. H2O Li C C OH Br C OH PCC Propose a synthesis of A from compounds containing 4 carbon atoms or less. H H C O Br C C Br C C Br OH C C C C OH H PCC Br C C O Br OH C C C H C H C C H2 Pd/C C H C H C Br 1. Li 2. C O 3. H2O C C OH floral fragrance OH ? C Br C Li ? A OH ? ? A Thyme 1 Propose a synthesis of A from compounds containing 4 carbon atoms or less. H H C C Br OH C C A B C C OH H PCC Br Propose a synthesis of A from compounds containing 4 carbon atoms or less. H H C C O Br C C OH C Br OH C C C C OH H PCC Br C C O Br D H2 Pd/C C H C H OH C C 1. Li E ? C Br 2. C 3. H2O O (?) C C C OH C H2 Pd/C C H C H C Br 1. Li 2. C O 3. H2O C C OH ABC 1. Li OH ? A OH 2. C O (?) 3. H2O ? OH A Which reaction will be involved in the last step? Which bond will be formed in the last step? Choose the reactants of the last step. H H C C Br OH C C C C OH H PCC Br Propose a synthesis of A from compounds containing 4 carbon atoms or less. H C C O Br H C OH C Br OH C C C C OH H PCC Br C C O Br OH C C H2 Pd/C C H C H C Br 1. Li 2. C 3. H2O O (?) C C OH C C H2 Pd/C C H C H C Br 1. Li 2. C 3. H2O O (?) C C OH 1. Li OH 2. C O (?) 3. H2O 1. Li ? Br Br Br OH 2. C O (?) 3. H2O A A + H C H O B + O C + H C H O 1 9/14/2009 Propose a synthesis of A from compounds containing 4 carbon atoms or less. H H C C Br OH C C C C OH H PCC Br Propose a synthesis of A from compounds containing 4 carbon atoms or less. H H C C O Br C OH C Br OH C C C C OH H PCC Br C C O Br OH C C H2 Pd/C C H C H C Br 1. Li 2. C 3. H2O O (?) C C H O (?) Br +H C O OH OH C C H2 Pd/C C H C H C Br 1. Li 2. C O 3. H2O C C H Br H C O OH 1. Li OH 2. C 3. H2O OH 1. Li 2. CH2=O 3. H2O A H2O CH2=O Li Li Propose a synthesis of A from compounds containing 4 carbon atoms or less. H H C C Br OH C C A B 1. Li 2. CH2=O 3. H2O C C OH H PCC Br Propose a synthesis of A from compounds containing 4 carbon atoms or less. H H C C O Br C C OH C Br OH C C C C OH H PCC Br C C O Br D H2 Pd/C C H C H OH C C 1. Li E C Br 2. C O C C C OH C H2 Pd/C C H C H C Br 1. Li 2. C O 3. H2O C C OH 3. H2O OH Br ? ? A OH 1. Li 2. CH2=O 3. H2O Br H Br OH A What is the next reaction in this synthesis? What is(are) the next reactant(s) in this synthesis? 1. Li 2. Br O 3. H2O Propose a synthesis of A from compounds containing 4 carbon atoms or less. H C 1. Li Br 2. CH2O 3. H2O OH PCC C O OH PCC 1. Some synthetic problems: Using the following reactions, propose syntheses for the following compounds from reactants containing four carbon atoms or less. H Li H O C C Br OH C C C OH H PCC Br C C O Br 2. H2O 1. Li 2. CH2=O 3. H2O C C H2 Pd/C C H C H C OH OH Br H Br OH C 1. Li Br 2. C O 3. H2O C C OH A 1. Li O Br O Is there another synthesis of compound A? 2. Br 3. H2O some solutions are at the end of these notes 13 2 9/14/2009 Choose Choose the correct order with respect to increasing boiling increasing boiling points points of the following compounds. H H H O H H N H H C H H Choose the correct order with respect to increasing boiling increasing boiling H points points of the following compounds. H H O H O H H H H H C H H N H H N H H C H H H A. A. D. B. E. C. F. A. A. D. B. E. C. F. Non-covalent Non-covalent forces do not exist between between molecules in the gas. Non-covalent Non-covalent forces are present in the liquid. liquid. electronegativities: electronegativities: H 2.1 C N O 2.5 3.0 3.5 Choose Choose the correct order with respect to increasing boiling increasing boiling H points points of the following compounds. H H O H O H H H H H C H H N H H N H H C H H H Non-covalent interactions. Are they strong? intramolecular intramolecular interactions (covalent (covalent bonds) HO H bp = 100 hydrogen bonding (very strong) bp = -33 hydrogen bonding (weaker) bp = -161 van van der Waals (very weak) 460 kJ/mole 21 kJ/mole intermolecular intermolecular interactions (noncovalent (noncovalent bonds) HO H OH H Non-covalent interactions. Are they Important? molecular chemistry (chemistry (chemistry of the covalent covalent bond) O HO H light Non-covalent Non-covalent interactions in biology. CH2OH CHOH CHOH CHOH CHOH CHO CH2OH O HO H light + C O + O2 molecular chemistry CHOH CHOH CHOH CHOH CHO + C O + O2 glucose supramolecular chemistry (chemistry (chemistry of the noncovalent noncovalent bond) HO H glucose supramolecular supramolecular chemistry chemistry snow flake 3 9/14/2009 What are these non-covalent interactions? non-covalent ion-ion: ion-ion: Na Cl What What are these non-covalent interactions? non-covalent ion-ion: ion-ion: Na Cl dipole-dipole dipole-dipole C O C H O H O ion-dipole ion-dipole H H O H O H ion-dipole ion-dipole H H O dipole-induced dipole-induced dipole C O Na H O H O H H H O H Na O H H dipole-dipole dipole-dipole H3C O H O H CH3 hydrogen bonding H3C O H O H CH3 van van der Waals H H C HH H C HH H Choose Choose the correct order with respect to increasing boiling increasing boiling points points of the following compounds. CH 3 CH2 CH3 CH3 CH2 OH CH3 O CH 3 Choose the correct order with respect to increasing boiling increasing boiling points points of the following compounds. CH 3 CH2 CH 3 CH3 CH2 CH 3 CH3 CH2 OH CH3 O CH 3 H O CH2 CH3 CH3 O CH 3 A. A. D. B. E. C. F. van der Waals hydrogen hydrogen bonding dipole-dipole dipole-dipole A. A. D. B. E. C. F. increasing boiling Choose the correct order with respect to increasing boiling points points of the following compounds. CH 3 CH2 CH 3 CH3 CH2 CH 3 CH3 O CH 3 CH3 CH2 OH Is there a model for the behavior of molecules in water? CH 3 CH2 CH3 CH3 O CH 3 CH3 CH2 OH H CH3 O CH 3 O CH2 CH3 van der Waals bp = -42 dipole-dipole dipole-dipole bp = -23 hydrogen hydrogen bonding bp = +80 Choose Choose the correct order of increasing solubility in water for the the above compounds. A. A. D. B. E. C. F. A. A. D. B. E. C. F. 4 9/14/2009 Is there a model for the behavior of molecules in water? Why is methanol soluble in water? H O H H O H H H H O H H H O H O H H O H H H H O H H H O H O H H O H H O H H O H H O H H H H O H H H O H O H H O H H H H O O H H O H H O H H O H O H O H H O H H O H H O H O H O H H H H O H O H H O H CH3 H O H O H O H O H H O H H O H H O H O H H O H O H H Why are hydrocarbons insoluble in water? H O H H O H H H H O H H H O H O H H O H H H CH3 O H H O H H O Parts Parts of molecules that can form hydrogen bonds with with water will be soluble (hydrophilic). Parts of (hydrophilic). molecules that cannot form hydrogen bonds to water will will not be soluble (hydrophobic). (hydrophobic). H Which Which of the following compounds will be more soluble soluble in water? H O H O H O H H H H O H O H H O H H3C CH 3 H O O C OH A H O H O H H O H O H CH3 O OH H B Which Which of the following molecules will be more soluble in in water? O C Which Which of the following molecules will be more soluble in in water? O C H O H O O O H H O O H H H O H O H H O O H O H H H H H H H3C H O H H O O H O H H H3C OH O CH3 OH CH3 H H H 5 9/14/2009 Choose Choose the order that has the following compounds arranged correctly correctly with respect to increasing solubility in water? O CH3 O CH3 O CH3 O H O Na O CH3 H O H O O O H H H O H H 1 2 3 231 increasing solubility Na OH O H H O H O O H H H H H O Na O O H H O H H O H H A 123 increasing solubility B 132 increasing solubility C 21 3 increasing solubility D Ibuprofen Ibuprofen (Advil) and aspirin inhibit pain due to inflammation by inhibiting prostaglandin synthetase. Which amino acid residue would be predicted to be most effective at forming a strong intermolecular interaction with ibuprofen? O O ibuprofen H H H NH O O O NH NH O H N O N O H H N H N H A arginine NH B aspartic aspartic acid acid C phenyl phenyl alanine alanine D lysine 6 ...
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