CHEM1102 Organic Chemistry

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CHEM1102 Organic Chemistry
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2013-11-20 17:39:52
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chemistry 1b organic
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CHEM1102 Organic Chemistry
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  1. Homolysis?
    Heterolysis?
    Radical Reaction?
    Ionic Reaction?
    • A <-> B
    • A <<- B
    • A. + .B
    • A+-B
  2. Nucleophile and Electrophile?
    charge, gives or takes electrons?
    • Nucleophile -ve
    • gives electrons (is evil and attacks others)

    • Electrophile +ve
    • accepts electrons
  3. Reactions of Alkanes?
    Products?
    • 1. Combustion
    • + O2 --> CO2 + H2O

    • 2. Halogenation
    • R-H + X2 --heat/light--> R-X + H-X
  4. Reactions of Haloalkanes?
    Products?
    • 1. Conversion to Alcohols
    • R-X + -OH ---> R-OH + X-
    • Can also form alkenes -higher o is more alkene

    • 2. Conversion to Alkenes
    • Use large base (physically wide) to avoid creation of alcohol

    • 3. Formation of Amines
    • R-X + NH3 --> R-N+H4 + X- --> R-NH2 + H2O

    • 4. Formation of Grignard Reagents
    • RX + Mg --ether--> R-MgX
    • R-MgX <---> R-+MgX
    • R-MgX + H2O --> R-H + MgX(OH)
  5. Tertiary Haloalkane Substitution Reaction
    • Sn1
    • Rate = a[(CH3)3CCl]   (first order)
    • Racemisation of config
    • electronic effects
    • Requires polar solvent
    • proceeds by ionisation
    • 1 intermediate, 2 transition

    (CH3)3CCl + Br- --> (CH3)3C+ + Cl- + Br- --> (CH3)3CBr + Cl-
  6. Primary Haloalkane Substitution Reaction
    • Sn2
    • Rate = a[OH-][CH3Br]   (bimolecular)
    • Inversion of config
    • stereo effects
    • 0 intermediate, 1 transition

    OH- CH3-Br -> [HO-CH3-Br]- -> HO-CH3 +Br-
  7. Why Sn2 with Primary Haloalkane?
    • Have little steric hindrance to attack by a Nu at C
    • Sn2 pathway lowest energy, new bond partially made as old broken
  8. Why Sn1 with Tertiary Haloalkane?
    • Three alkyl prevent direct approach of Nu
    • After ionisation, more room
    • Carbocation has energy lowered by spreading charge
  9. Reactions of Alkenes?
    Products?
    • Electrophillic reactions
    • 1. Hydrogen Halides
    • Alkene + H-X --> Haloalkane

    • 2. Addition of S Acid
    • Alkene + H2SO4 --> RCH2-OSO2OH

    • 3. Addition of water
    • Alkene + H2O --acid-cat--> Alcohol (non-terminal generally)

    • 4. Add H2 (reduc-hydrogenation)
    • Alkene + H2 --Pd--> Alkane

    • 5. Add KMnO4
    • Alkene + 2MnO4- + 4H2O --> diol + 2MnO2 + O2H-

    • 6. Add Halogens (halogenation)
    • Alkene+ X2 --> 1,2-trans haloalkane

    • 7.Ozonolysis
    • Alkene --O3/Zn/H2O--> ketone + aldehydes

    8. Polymerisation
  10. Zaytsev Rule
    When two or more Hs are available on the adjacent Cs, the major product is the most stable product, the most substituted alkene (the alkene with least Hs attached).

    Poor get poorer!
  11. Markovnikov's Rule
    • Alkyl Group donate e- to +ve carbon to increase stability
    • ie: higher order cation (more C's attached) tends to have +ve charge
    • ie: H in HX tends to go to C with lower order, more H's

    Rich get Richer!
  12. Reactions for Alkynes?
    Products?
    • 1a. Add Hydrogen Halides
    • Alkyne + HX --> Halo-Alkene --HX--> 1,1 Haloalkane

    • 1b. Add Halogens
    • Alkyne + X2 --> 1,2 Haloalkene --X2--> 1,1,2,2 Haloalkane

    • 1c. Add H2
    • Alkyne + H2 --PtorPd--> Alkene --H2&cat--> Alkane
    • Use LINDLAR Cat to get Alkene

    • 2. Add H2O
    • Alkyne + H2O --acid cat--> RC(OH)=CHR (enol) <---> RCOCH2R (ketone)
    • called Tautomerism/Enolisation
    • to terminal H requires Hg2+ cat as well

    • 3. Oxidation (O3 or hot KMnO4)
    • Internal Alkyne ---> 2 Carboxylic acids
    • Terminal Alkyne --> Carbox acid + CO2
  13. Benzene Reactions?
    Products?
    • 1. Nitration
    • Benz + HONO--acidcat--> QNO2 + H2O

    • 2. Sulfonation
    • Benz + SO3 --acidcat--> QSO3H + H2O

    • 3. Halogenation
    • Benz + X2 --FeX3--> QX + H2O

    • 4. Friedel-Crafts Acylation
    • Benz + RC(=O)Cl --AlCl3--> QC(=O)R + HCl
  14. Benzene Mechanism
    • 1. Ep Attack
    • electron pair from a double bond goes to Ep and attaches the Ep (endo)

    • 2. loss of proton from carbocat in intermediate
    • electron pair attaching H next to Ep goes back to form double bond again, releasing the H. (exo)

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