Review - Ch 10
- ID Initiation, Propagation, Termination steps
- Radical stability (allylic > 3° > 2° > 1°)
- Mechanisms and products of radical reactions
- Radical bromination of alkane (Br2, hv)
- Radical bromination of alkene (Br2, ROOR or peroxides)
- Radical bromination of an allylic position (NBS, hv)
Initiation/Propagation/Termination Review - Ch 12
- Alcohol nomenclature (simple)
- Determine oxidation states
- Reductions
- H2, Pt—reduces all below + alkenes and alkyenes
- LiAlH4 (or LAH)—reduces esters, carboxylic acids, ketones, and aldehydes
- NaBH4—reduces ketones and aldehydes
- Oxidations
- Na2Cr2O7—oxidizes all the way (1° OH –CO2H, 2° OH ketone)
- PCC or Swern or DMP—selective oxidation (1° OH aldehyde, 2° OH ketone)
- Grignard reagent
- Alkyl halide + Mg R–MgBr
- Will attack aldehydes/ketones x 1, esters x 2
- Protecting groups
- Protection: TMSCl, pyridine
- Deprotection: TBAF
Determining oxidation states Review - Ch 13
- ID ether functional group
- Synthesis of esters
- Williamson (R–OH + NaH + R–Br R–O–R)
- Alkoxymercuration (Hg(Oac)2 then R–OH)
- Synthesis of epoxides
- MCPBA
- alkene + HBr, H2O halohydrin + NaOH epoxide
- Ring opening of epoxide
Review - Ch 11
- Check “Summary and Strategies” slides from Ch 7 and 8
- To do multi-step sequences, you must know the reactions that have been covered!
- Know regioselectivity and stereospecificity
- ID changes to carbon framework
- ID possible changes to functional groups
- Work forwards and backwards (retrosynthetic analysis)
- Provide the reagents needed to complete the multi-step sequence:
Multi-step syntheses - Provide the reagents needed to complete the multi-step sequence:
Multi-step syntheses - Provide the reagents needed to complete the multi-step sequence:
Multi-step syntheses - Provide the reagents needed to complete the multi-step sequence:
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