19 - Propose a good synthesis of limonene from compounds...

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Unformatted text preview: 3/5/2012 Propose a good synthesis of limonene from compounds containing four carbon atoms or less. Note: Because simple alkenes are unreactive in the DielsAlder reaction the following is not a good synthesis of limonene. How could limonene be prepared from the following ketone? limonene limonene How could limonene be prepared from compounds containing four carbon atoms and any necessary reagents? What is the mechanism of this reaction? limonene limonene What is wrong with this synthesis of limonene? How could the diene be prepared from compounds containing four carbons or less? C B A D limonene limonene 1 3/5/2012 How could the diene be prepared from compounds containing four carbons or less? O H 1. H-Al(i-butyl)2 2. H3O O O CH3 1. LiAlH4 2. H3O OH limonene How can the ester be converted into the aldehyde, alcohol, acid or amide? Which of the following Wittig reagents would you predict to react faster? Ph3P CH2 A O Ph3P O O CH3 Ph3P CH CH C O C O energy Ph3P CH2 O reaction O O H H H C H O H C H O O + H H H O C H C OCH3 Ph3P CH C OCH3 OCH3 O H very, very slow! B Which of the following Wittig reagents would you predict to react faster? Why O Br CH2 C OCH3 (EtO)3P: O P OEt O O O CH3 EtO P OEt CH O EtO CH2 C Na H O C OCH3 H O H C H O C OCH3 [H ][ OAc] [HOAc] = 10-4.76 O O H H H C H O + H A O O CH3 Ph3P CH O C OCH3 O ~1.0 M/L small but H ~ OAc What is the pH of a 1.0 molar solution of acetic acid? B A. 0 B. 1.0 C. 2.38 D. 4.76 E. 9.52 2 3/5/2012 [H ]2 [ 1.0 ] O H H C H C O H H H C H = 10-4.76 [H ][ OAc] [HOAc] O = 10-4.76 O O + H H H C H O O H H H C H O + H C ~1.0 M/L small but H ~ OAc What is predominant species present at pH = 7.0? What is the pH of a 1.0 molar solution of acetic acid? A. 0 B. 1.0 C. 2.38 D. 4.76 E. 9.52 [H ] [H ] O H H C H C O H H H C H = 10-4.76/2 = 10-2.38 O O + H H H C H O C [10-7][ OAc] [HOAc] = 10-4.76 O O H H H C H O + H ~1.0 M/L small but H ~ OAc What is predominant species present at pH = 7.0? What is the pH of a 1.0 molar solution of acetic acid? A. 0 B. 1.0 C. 2.38 D. 4.76 E. 9.52 [H ][ OAc] [HOAc] O H H C H C O H H H C H = 10-4.76 [ OAc] [HOAc] O = 10-4.76 10-7 O O + H H H C H O O H H H C H O + H C What is the pH of a solution of 0.5M sodium acetate and 0.5M acetic acid? A. 0 B. 1.0 C. 2.38 D. 4.76 E. 9.52 What is predominant species present at pH = 7.0? 3 3/5/2012 [ OAc] [HOAc] O H H C H C O H H H C H = 10 2.24 H O H N C H C O H H H H N H C H O C O H O O + H H O H N H C H C O H H O H H C H C O H H H C H O C N H H i ii iii 2.35 What is predominant species present at pH = 7.0? i < ii < iii increasing acidity 4.75 16 i < iii < ii increasing acidity ii < i < iii increasing acidity ii < iii < i increasing acidity iii < i < ii increasing acidity iii < ii < i increasing acidity A B C D E F What is the correct order of the following acids with respect to increasing acidity? Carboxylic acids. How are they prepared? H O H N H C H C O H H O H H C H C O H H H C H O C N H H i ii iii i < ii < iii increasing acidity i < iii < ii increasing acidity ii < i < iii increasing acidity ii < iii < i increasing acidity iii < i < ii increasing acidity iii < ii < i increasing acidity A B C D E F H O H N C H C O H H O H H C H C O H H C H O C N H Which of the following could be used to prepare phenyl acetic acid? H O H N H C H C O H H O H H C H C O H H H C H O C N H H phenyl acetic acid i ii iii 2.35 4.75 16 A. i + ii B. i + iii C. ii + iii D. i E. ii F. iii i < ii < iii increasing acidity i < iii < ii increasing acidity ii < i < iii increasing acidity ii < iii < i increasing acidity iii < i < ii increasing acidity iii < ii < i increasing acidity A B C D E F 4 3/5/2012 Which of the following could be used to prepare phenyl acetic acid? phenyl acetic acid Which of the following could be used to prepare phenyl acetic acid? phenyl acetic acid 5 ...
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