OChem2 Week 2

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chiroclown
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36805
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OChem2 Week 2
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2010-09-25 00:30:56
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OChem2 Week
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OChem2 Week 2
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  1. Aldehydes
    • AL ending
    • Always on the C-1
    • R-CH=O
    • Bond is polar
    • soluble in water
    • BP increases by 20=
  2. Carboynyl Group
    C=O
  3. Synthesis of Aldehydes
    RAMP
    • Reimer-Tieman Synthesis of Phenolic Aldehydes
    • Acid Chloride Reduction
    • Methyl Benzene Oxidation
    • Primary Alcohol Oxidation
  4. Reimer Tieman Synthes of Phenolic Aldehydes
    • A chlorine is going to leave and take electrons with it.
    • Aldahyde on a benzene ring with OH
  5. Enols and Gemdiols are
    unstable
  6. Acid Chloride Reduction
    • RAMP
    • R-C(Cl)=O or benzene- C(Cl)=O in LiAlH4 -------> R-CH=O + ClLi+ AlH3 or Benzene-CH=O + ClLi + AlH3
    • Chlorine Leaves
    • The H- from the LiAlH4 attacks the group and the Cl leaves
  7. LiAlH4
    • Lithium Aluminum Hydride
    • Suplies the H-
  8. Methyl Benzene Oxidation
    • RAMP
    • Creates Major and Minor
    • Involves a Benzene Ring
    • Major---> Cl2 and heat, Minor---> CrO3
    • In Major- Cl jump onto the C then react in water where OH jump on and Cl jump off. The 2 OH react together creating R-CH=O +H2O
    • In Minor- O jump on the C then react in water. creating R-CH=O
  9. Primary Alcohol Oxidation
    • RAMP
    • Is only a synthesis of aldeyhide with CrO3Cl- (Pyridinium Chlorochromate)
    • DOES NOT proceed to Carboxylic Acid
  10. Synthesis of Ketones
    SOFA
    • Secondary Alcohol Oxidation
    • Organo Copper Compound of Acid Chloride (Corey House)
    • Friedel Craft Acylation
    • Aceto Acetic Ester Synthesis
  11. Secondary Alcohol Oxidation
    • SOFA
    • Reacts in CrO3 or K2Cr2O7
    • Hydrogens from OH and CH are removed by reagent
  12. Ketones
    R-C(R)=O
  13. Organo Copper Compound of Acid Chloride
    • SOFA
    • Like a Corey House---> supplies two R-
    • R- is attacking species
    • R-C(Cl)=O --------> R-C(R-)=O
    • Cl leaves and R- jumps on
    • CH3CH2-CuLi + CH3CH2CH2CH2-C(Cl)=O --------> CH3CH2CH2CH2-C=O-CH3CH2 + CuLi
  14. Friedel Craft Acylation
    • SOFA
    • R+ is attacking species
    • R-C(Cl)=O + AlCl3------> R-C(R)=O + Cl-
    • Cl hangs out with AlCl3 for a little bit then jumps off
  15. Aceto Acetic Ester Synthesis
    • SOFA
    • 1) Aceto acetate ester---> 2) Add Haloalkane to Alpha Carbon----> 3) Creates Carbocylic Acid---> 4) Add Acid for carboxylic acid to dissociate----> 5) add heat and creates Ketone
    • Methly group never ever changes
    • To add a second R group- Do it all again! New haloalkane will attach to Alpha Carbon
  16. Widdig the ROACH pushes the SOFA with the OXO up the RAMP
  17. OXO Process
    • Synthesis of Aldehyde
    • -C=C- + C=O + H2 ------> (Cobalt) -----> -C-C-CH=O
    • Creates an OctaCarbonylDiCobalt (2 Cobalts and 8 Carbonyl Carbons)
    • 1) H2 breaks the the Cobalt-Cobalt Bond
    • 2) One C=O leaves and is replaced by an Alkene
    • 3) A C=O is added to the Alkene and double bond flips out to accomodate
    • 4) Add H2 again: H- to C=O and H+ to other end. The Aldehyde seperates from catalyst
  18. ROACH
    • Reactions of Ketones and Aldehydes
    • Reduction of Aldehydes to 1o alcohols, Ketones to 2o alcohols.
    • Reduction of Aldehydes & Keytones to Alkanes- Clemmensen REduction and Wolf Kischner
    • Oxidation of Aldehydes
    • Addtions Reactions- Gringard Reagent, Alcohol-Acetal, Ketal Formation, Derivatives of Ammonia
    • Cannizzaro Reaction
    • Wittig Reaction
    • Halogenation of Ketones
  19. Reduction of Aldehydes to 1o Alcohols/ Ketones to 2o Alcohols
    • ROACH
    • (R)/H-C(R)=O -----> H2, Pt or Pd or Ni -----> R/H-CH(R)(OH)
    • (R)/H-C(R)=O-----> LiAlH4 or NaBH4-----> R/H-CH(R)(OH)
    • The H- and H+ are supplied from the Reagents.
    • H+ attaches to O and H- attaches to the C
  20. Reduction of Aldehydes & Keytones to Alkanes
    Clemmensen Reduction and Wolf-Kishner
    • ROACH
    • Aldehydes are converted to 1o alcohol then to an Alkane
    • Keytones are converted to 2o alcohol then to an Alkane
    • Major: Zn(Hg) concentrate HCl
    • Minor: HN2-HN2
    • Provides 2 H+ and 2 H-
    • (R)/H-C(R)=O-----> Reagent----> (R)/H-CH(R)=OH-----> (R)/H-CH2-R + H2O
  21. Oxidation of Aldehydes
    • ROACH
    • ONLY Aldehydes- 1o Alcohol
    • Reagent: KMnO4 or K2Cr2O7
    • R-CH2-OH----> Reagent-----> R-CH=O---> Reagent----> R-C(OH)=O
  22. Addition Reactions
    Grignard Reagent
    • ROACH
    • (R)/H-C(R)=O + R-MgX----> (R)/H-C(R)(R)-O-MgX+----> H2O-----> (R)/H-C(R)(R)-OH + MGX+OH-
  23. Addition Reactions
    Alcohol-Acetal, Ketal Formation
    • ROACH
    • (R)/H-C(R)=O + CH3OH---> CH3O-C(R/H)(R)-OH----> CH3-O-C(R/H)(R)+ CH3O---->CH3-O-C(R/H)-CH3O + H2O

  24. Hemi-Acetal
    • Begins as Aldehyde becomes an Acetal (diether)
    • H-C(RO)(R)-OH
    • Must particiate in an ETHER linkage
    • Must have an ALCOHOL group attached to it
    • Formed by addtion to the double bond
    • CH3O-CH(R)-OCH3
  25. Hemi-Ketal
    • Begins as a Ketone becomes a Ketal (diether)
    • R-C(RO)(R)-OH
    • Synthesis then Nucleophilic substitution
    • CH3O-C(R)(R)-OCH3
  26. Cannizzaro Reaction
    • ROACH
    • ALDEHYDE only
    • MUST NOT HAVE ALLYLIC HYDROGENS
    • Products are: The salt of a Carboxylic Acid and an Alcohol
  27. Halogenation of Ketones
    • ROACH
    • Similar to Halogenation of Alkenes
    • CH3-C(=O)-CH3 + Cl2 ------> CH2(Cl)-C(=O)-CH3 + HCl
  28. Wittig Reaction
    • ROACH
    • Converts or Incorporates Ketones or Aldehydes into ALKENES
    • CH3-C(CH3)=O + CH3-C(CH3)=Ylide----> CH3(C)(CH3)=O-Ylide----> CH3-C(CH3)=C(CH3)-CH3 + O=Ylide
  29. ID Tests for Aldehydes
    • Tollen's Test
    • Benedicts and Fehlig's Test
  30. Tollen's Reagent
    • Can be aromatic
    • R-C(=O)-H + Tollen's Reagent----> Heat----> R-C(=O)-O- + Ag(solid)
    • 2Ag+(NH3)2
    • 2NO3-
    • 3Na+
    • 3OH-
  31. Benedicts and Fehling's Test
    • NOT aromatic
    • Gives Brown to Red percipitate of Cu2O
    • R-CH=O + Benedict's/ Fehling's Reagent---> Heat---> R-C(=O)-O- + Cu2O(solid)
  32. ID Test for Allylic-Hydroxy Ketones
    • Will give the Silver Mirror when reacted with Tollen's Reagent
    • -C(=O)-CH(OH)- + Tollen's Reagent ----> Heat----> -C(=O)-C(=O)- + Ag(solid)

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