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Alcohols (Synthesis (Halohydrin Reaction (Anti, Markovnikov, H-X + H2O,…

- - - - Grignard Reagents
        
        Alcohol Synthesis
        
        Secondary Alcohols
        
        add to ketones
        
        Tertiary Alcohols
        
        (2 eq) add to acid chlorides or esters and protonate
        
        Primary Alcohols
        
        Add to epoxides
        
        add to formaldehyde
        
        Ether solvent
        
        can be formed from alkyl or alkenyl halides, aryl and vinyl
      - Organolithium Reagents
        
        Ether not needed as solvent
        
        R-X + 2Li ----> LiX + RLi
        
        carboxylic acid ----> ketone
        
        may be used as strong bases
        
        R-X to R-H
      - Organocuprates
        
        2RLi + CuX ----> R2CuX
        
        used to couple groups together
        
        Not as reactive towards carbonyls
        
        react with epoxides
        
        attack less substituted carbon
      - Electrophiles that React with Organometallic Reagents
        
        (1) Anhydrides and acid chloride
        
        tertiary alcohols
        
        (2) Formaldehyde
        
        primary alcohols
        
        (3) Aldehydes
        
        secondary alcohols
        
        (4) Ketones
        
        tertiary alcohols
        
        (5) Esters
        
        tertiary alcohols
        
        (6) Cyclic Compounds
        
        tertiary alcohols
        
        (7) amide
        
        (2) tertiary
        
        (8) Weinreb Amide
        
        forms ketone
    - - LAH, H2O
        
        can't be used in alcoholic solvents; use THF
        
        reduces ketones to secondary alcohols
        
        reduces aldehydes, acids, and esters to primary alcohols
      - reduce aldehydes and ketones to alcohols
      - NaBH4, ROH
        
        only reacts with aldehydes and ketones
- - - - Ketones
  - - - Aldehyde
    - - carboxylic acid
  - - - oxidant - (CH3)2SCl+
- - - - LAH, NaBH4, NaH
- - - - form alkoxide
        
        form ether by displacing halogen with alkoxide
- - - - add 2 lithium to R-Br
        
        organolithium reagent
      - add Mg and Et2O to R-Br
        
        grignard
    - - metal replaces halogen
      - typically only used for lithium
    - - metal replaces hydrogen
      - only for alkynes
    - - -OH, -CN, NH2, ketones
    - - alkynes
      - alkenes
      - OR
    - - only with primary halides and lithium reagents