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Lecture

07-31 - Retrosynthetic Analysis, Deprotonation of Alcohols, PBr3 Chemistry, Dehydration of Alcohols.docx

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Department
Chemistry
Course
CHEM 2OA3
Professor
Jeff Landry
Semester
Winter

Description
Retrosynthetic Analysis  Cyclohexane with an MgX connected to one carbon + (H)(CH )>C=O ---a→ 3  CH C3--C(2H)(CH -CH -CH2-CH 2-CH -2H -C3 2 2 3 o Break bond A: previous step would be CH CH MgX + 3eep 2he other the same, just cleave off the hydrogen and carbon chain we used and double bond to oxygen o Break bond B: previous step would be CH CH CH MgX 3 kee2 th2 other the same, just cleave off the hydrogen carbon chain we used and double bond to oxygen o Break bond C: previous step would be CH CH CH CH3MgX2+ ke2p t2e other the same, just cleave off the hydrogen carbon chain we used and double bond to oxygen  CH -3H -C2OH)(H)-CH -CH -CH2-CH 2 2 3  LEARN WHAT AN LDA IS IN AN E REACTION!!!!!!2  Practice a bunch of these Retrosynthetic Analysis problems, and learn all the reaction types!!!!!!  Learn Carbon-Carbon Bond Forming Reactions!!!!! (Grinyard) o PCC? Deprotonation of Alcohols -  R-O-H + Base → RO (Alkoxide) + H:Base o Want to use a REALLY STRONG base to make an alkoxide o CH OH + N (two CH CH-CH branches on it)Li → CH O Li + N(two CH - + 3 3- 3 3 3- CH-CH )H3 - +  CH C3 OH 2 CH CH CH C3 -Li2→ C2 CH 2 Li + CH CH 3H CH2(pKa ~50) 3 2 2 3  CH C3 OH 2 K -H → CH CH O K + H 3pKa 240) + 2  2 H-O-H + 2 Na → 2 Na
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