Disc_Sect_26 - What single starting material would be...

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Chemistry 104 B/D Discussion Section Worksheet Discussion Section #26 Key Ideas from Lecture #26: General mechanism for the acid catalyzed addition of a nucleophile to a ketone or aldehyde Let’s think about these concepts for a bit. .. What are the differences between the following mechanisms? -acid catalyzed formation of a hemiacetal from an alcohol and aldehyde -acid catalyzed formation of a hemiketal from an alcohol and ketone -acid catalyzed formation of a diol from an aldehyde and water -acid catalyzed formation of a diol from a ketone and water Problems: Spring 2007, Exam #3, Problem 13 13. The following interesting looking product can be synthesized from a single reactant molecule using an acid catalyst (this is a reaction mechanism that you are familiar with).
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Unformatted text preview: What single starting material would be needed to perform the following reaction? HO O starting material acid catalyst (a) 5-hydroxy-2,2,4-trimethylhexanal (b) 6-hydroxy-3,5,5-trimethyl-2-heptanone (c) 5-hydroxy-2,4,4-trimethylhexanal (d) 6-hydroxy-3,3,5-trimethyl-2-heptanone (e) 3,3,5-trimethyl-2,6-hexanediol 1 Chemistry 104 B/D Discussion Section Worksheet Discussion Section #26 2 Spring 2007, Exam #3, Free Response #3 3. (15 points) The following transformation can be performed in two reactions. H 3 CO OH OH Compound A Perform the following: -Fill in the missing reagents for each reaction and the structure of Compound A. -Give the mechanism for the first reaction (make sure to use proper curved arrow notation to get full credit)....
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This note was uploaded on 10/07/2010 for the course CHEM 104 taught by Professor Harwood during the Spring '08 term at University of Illinois, Urbana Champaign.

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Disc_Sect_26 - What single starting material would be...

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