16 - Muscone is a 15 membered ring ketone used in perfume...

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Unformatted text preview: 2/27/2012 Muscone is a 15 membered ring ketone used in perfume. It was originally isolated from the musk deer but it is now prepared from citronellal. O H What is the structure of the alkene intermediate is a synthesis using citronella? O O H O muscone H CH3 H citronellal CH3 H CH3 H citronellal CH3 How could muscone be prepared from citronellal? ? O O O musk deer lemon grass A H CH3 B H CH3 C H CH3 What carboncarbon bond forming reaction would be best for the synthesis of large rings? O O H What is the next likely reaction in this synthesis? O H O H CH3 H citronellal CH3 H2/Pd-C H O CH3 H citronellal CH3 A Ru H CH3 O B ? ? C A B H CH3 What is a likely last step in the synthesis of muscone from citronellal using olefin metathesis? O O H How could the diene for the olefin metathesis reaction be prepared? O H O H CH3 H citronellal CH3 H2/Pd-C H O CH3 H citronellal CH3 Ru H CH3 O OH H CH3 H CH3 1 2/27/2012 How could citronella be converted into the alcohol? How could the organo lithium reactant be prepared from compounds containing four carbon atoms or less? O O H Bond Energies (kJ/mol) C=C = 590 C=O = 803 C=O = 120 H2/Pd-C H O CH3 H citronellal CH3 C=C = 134 Bond Lengths (pm) four carbon atoms or less Ru H CH3 O OH C-C = 331 C-O = 326 Why do C=C bonds readily add acids but C=O bonds do not? H CH3 H CH3 What is the product when a C=O bond adds water? How can the addition of water do double bonds be catalyzed? O O H H2/Pd-C H O CH3 H citronellal CH3 Ru H CH3 O OH H CH3 H CH3 Do both C=C and C=O readily undergo addition products with acids? A. yes B. no Is the hydration of formaldehyde (A) more or (B) less than acetaldehyde? Why? 103.36 (2290) formaldehyde Keq 100.03 (1.07) formaldehyde acetaldehyde E G = RTlnKeq R 2 2/27/2012 What is an unambiguous name for the following ketone? 10-2.85 (.0014) acetone A. 2isopropyl5methylcyclohexanone B. 5isopropyl2methylcyclohexanone Keq 100.03 (1.07) acetaldehyde O C. 5propyl2methylcyclohexanone D. trans2isopropyl5methylcyclohexanone E. None of these Is the hydration of acetaldehyde (A) more or (B) less than acetone? acetaldehyde O H H O E G = RTlnKeq R H H What is an unambiguous name for the following ketone? What is an unambiguous name for the following ketone? A. 2isopropyl5methylcyclohexanone B. 5isopropyl2methylcyclohexanone O O C. 5propyl2methylcyclohexanone D. trans2isopropyl5methylcyclohexanone E. (2R, 5R)2isopropyl5methylcyclohexanone menthone O H F. None of these H O Pennyroyal (Mentha pulegium) H H What is an unambiguous name for the following ketone? What is an unambiguous name for the following ketone? A. 2isopropyl5methylcyclohexanone B. 5isopropyl2methylcyclohexanone O C. 5propyl2methylcyclohexanone D. None of these O A. 2isopropyl5methylcyclohexanone B. 5isopropyl2methylcyclohexanone C. 5propyl2methylcyclohexanone D. trans2isopropyl5methylcyclohexanone E. (2R, 5R)2isopropyl5methylcyclohexanone F. None of these O H O H (2S, 5R)2isopropyl5methylcyclohexanone H H 3 2/27/2012 How could the following transformation be accomplished? O H The distinctive Frangipani has a warm, melodious scent. It has memories of honeysuckle and jasmine, but is neither. This unique fragrance oil lingers on the skin, reminiscent of a warm summer evening when the heat of the day has warmed the scent of the flowers to a rich cocktail of floral notes with a hint of honey. How can this compound be prepared? What is a good mechanism for the following transformation? What is a good mechanism for the following transformation? What is the structure of the first intermediate? 4 ...
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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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