Lecture 39 - In the imine is stable, the two stages can be...

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Reading for Wednesday Chapter 25: 25.9-25.12
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4 th Exam This Thursday! May 5 th 6-7:30 PM 120 Budig Chapters 23 Chapter 24 Chapter 25 (1-3,7)
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Exam 4 Review Session Tuesday May 3 rd 6:00 PM 1001 Malott
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Mon. 6:00-7:30 pm MAL 3092 Tues. 2:30-4:00 PM MAL 2007 PLUS Sessions THIS WEEK
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Preparation of amines (25.7A) Direct nucleophilic substitution (S N 2) Useful for making: 1º amines from NH 3 , used in large excess. Quaternary ammonium salts (use alkyl halide in excess)
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Gabriel Synthesis of 1º amines (25.7A) Phthalimide used as N source Phthalimide is deprotonated and alkylated Hydrolysis of the alkylated phthalimide gives a 1º amine
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Prep. of amines by reduction of other functional groups (25.7B) Nitro compounds 18.14C Nitriles 22.18B Amides 20.7B
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Reductive Amination of Ketones and Aldehydes (25.7C) Two stages to this process: Formation of an imine (or iminium ion) Reduction of the imine (or iminium ion) to an amine
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Reductive Amination of Aldehydes and Ketones (25.7C)
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Unformatted text preview: In the imine is stable, the two stages can be performed in sequence The imine is isolated, and then can be reduced using NaBH 4 This kind of reductive amination was performed in Chem 627 this semester Most imines are not stable. In such cases, they are reduced in situ (i.e. in the same pot in which they are formed) NaBH 3 CN is needed in these cases (weaker reducing agent than NaBH 4 ) Reductive Amination of Aldehydes and Ketones (25.7C) Why NaBH 3 CN and not NaBH 4 ? Imine formation is an equilibrium process; almost always some ketone or aldehyde present at equilibrium NaBH 4 reduces ketones and aldehydes; NaBH 3 CN does not Why NaBH 3 CN and not NaBH 4 ? Reaction typically performed in CH 3 OH at pH ~ 5 This is acidic enough to protonate imines, but not aldehydes/ketones Protonated imines are reactive enough to be reduced by NaBH 3 CN...
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Lecture 39 - In the imine is stable, the two stages can be...

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