Chem 124 Exam #2 Reaction Rules (Alcohols)

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Chem 124 Exam #2 Reaction Rules (Alcohols)
2013-04-16 20:25:35

Chem 124 Exam #2 Reaction Rules (Alcohols)
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  1. What does [H- Donor] , H+ , H2O do with:
    Carboxylic Acids?
    [HDonor] here can only be LiAlH4 or NaBH4

    [H- Donor] , H+ , H2O turns Aldehydes into a Primary Alcohol

    [H- Donor] , H+ , H2O turns Ketones into a Secondary Alcohol

    [H- Donor] , H+ , H2O turns Esters into a Primary Alcohol AND the -O of the Ester takes with it whatever it was attached to, becoming another separate Alcohol piece

    • [HDonor] , H+ , H2O turns Carboxylic Acids into a Primary Alcohol
  2. What does PCC do?
    • PCC turns Alcohols into Functional Groups:
    • Primary Alcohols into an Aldehyde

    Secondary Alcohols into a Ketone
  3. What does CrO3 , [Strong Acid] do?
    • CrO3 , [Strong] Acid turns Alcohols into Functional Groups:
    • Primary Alcohols into Carboxylic Acids

    Secondary Alcohols into Ketones
  4. What is a Grignard Reagent?
    • A Grignard Reagent is an MgBr attached to some series of R groups (ex: CH3CH3MgBr)
  5. What does a Grignard Reagent do?
    - Grignard Reagents react with Carbonyls, turning them into an Alcohol AND adding whatever was with the MgBr onto the original carbon that the Carbonyl was attached to
  6. What can Grignard Reagents NOT react with?
    - Grignard reagents can NOT react with Carboxylic Acids (the R group attached to the MgBr just gains a Hydrogen in place of the MgBr when it leaves)
  7. How does Alcohol Protection work?
    - Alcohol Protection temporarily replaces an alcohol group with a protector (either TMS-Cl or BnCl , Et3N)
  8. What order do alcohols get protected in, in Alcohol Protection reactions?
    What are the names of the Alcohol Protectors?
    • - Alcohol Protection protects Primary Alcohols > Secondary > Tertiary
    • - The Alcohol Protectors are TMS-Cl or BnCl , Et3N)
  9. What can NaBH4 react with?
    NaBHcan react with Carbonyl groups EXCEPT for Carboxyl Groups and Esters

    (.. so - in other words - NaBH4 can only react with Aldehydes, Ketones, and Amides then)
  10. What can LiAlH4 react with?
    LiAlH4 will react with ALL Carbonyl groups (including Carboxyls and Esters)
  11. What are the Sn1 reagents?
    The Sn1 reagents are HCl and HBr
  12. What are the Sn2 reagents?
    The Sn2 reagents are PBr3 and SOCl2
  13. What are the E1 reagents?
    The E1 reagents are H2SO4 and H3PO4
  14. What are the E2 reagents?
    The E2 reagents are POCl3 with Pyridine (these two must be together!)