Organic Synthesis | Lecture Note - Edubirdie

University:
California State University, Northridge
Course:
CHEM 334/L | Organic Chemistry II and Lab
Academic year:

2020
Views:

330

Pages:

9
Author:

nerdzrkoolh2o

Chemistry 334 Organic Synthesis 1. retrosynthetic analysis A B C D E F G H I retrosynthetic direction: A B synthetic direction: A B an example: O Ph H Ph DMP PhMgBr OH O a.) b.) aq. HCl 2. efficiency avoid product mixtures obtain highest yields use fewest number of steps use convergent syntheses linear: A .90 B .90 C .90 D overall yield: (.90)(.90)(.90) = .73 convergent: E .90 F .90 G .90 D H overall yield: (.90)(.90) = .81 3. carbon framework Construction of the C - C framework often is one of the most difficult tasks. 4. nearby functional groups O CH3 Ph a O Ph CH3 + I CH3 O CH3 Ph b O CH2 Ph + (nBu)2CuLi O CH3 Ph c O Ph ? + ICH3 5. oxidation levels 6. stereochemistry 7. regiochemistry 8. functional group compatibility C C H HO HO C R3SiO C C H C R3SiO C CH3 C CH3

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