326Exam 3 Review_2009

326Exam 3 Review_2009 - A few words about lipids/fatty...

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A few words about lipids/fatty acids They will be covered by the exam. Thioesters (nature’s acyl chlorides): R O S R 1 R O S R 1 R O R 1 O R O R 1 O Thioester Ester The thioester is more reactive because: - Bad π overlap between S and C (2p with 3p, big difference). - RS - is a better leaving group than RO -
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Chapter 20, Amines Basicity of amines Rank the following amines with respect to basicity. A is the most basic since the lone pair of the N is in an sp 3 orbital and localized. C is the least basic since the lone pair is strongly delocalized into the benzene ring by the nitro group. B is intermediate out of the three. NH 2 NH 2 NH 2 N O O A B C
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Consider the following separation scheme.* H 2 O ether N H NH 2 OH ) 2. add NaOH(aq 1. add ether H 2 O ether 1. acidify with HCl 2. add ether A B H 2 O ether 1. basify with NaOH 2. add ether C D H 2 O ether add HCl(aq) E pKa = 9.5 *The following problem is on-loan from Prof. Lauher Adventures in Separation (or where the hell is my compound?!)
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Where is 2-napthol? H 2 O ether ) N H NH 2 OH 2. add NaOH(aq 1. add ether H 2 O ether 1. acidify with HCl 2. add ether A B H 2 O ether 1. basify with NaOH 2. add ether C D H 2 O ether add HCl(aq) E 2-napthol OH pKa = 9.5
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Where is tryptamine? H 2 O ether ) N H NH 2 OH 2. add NaOH(aq 1. add ether H 2 O ether 1. acidify with HCl 2. add ether A B H 2 O ether 1. basify with NaOH 2. add ether C D H 2 O ether add HCl(aq) E tryptamine OH N H NH 2 pKa of conjugate acid ~ 10 of tryptamine
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Synthesis of Amines Br NH 3 NH 3 + Br NH 3 NH 3 NH 2 NH 4 + And we’re done…right? Unfortunately, multiple alkylations often occur since the product
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326Exam 3 Review_2009 - A few words about lipids/fatty...

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