CHEM1102 Organic Chemistry Reactions

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CHEM1102 Organic Chemistry Reactions
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2013-11-24 23:33:58
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chemistry 1b organic reactions
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CHEM1102 Organic Chemistry Reactions
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  1. Reactions of Alkanes
    1. Combustion
    alkane + O2 --> CO2 + H2O
  2. Alkanes
    2. Halogenation
    R-H + X2 --heat/light--> R-X + H-X
  3. Haloalkanes
    1. Conversion to Alcohols
    R-X + -OH ---> R-OH + X-Can also form alkenes -higher o is more alkene
  4. Haloalkanes
    2. Conversion to Alkenes
    Use large base (physically wide) to avoid creation of alcohol
  5. Haloalkanes
    3. Formation of Amines
    R-X + NH3 --> R-N+H4 + X- --> R-NH2 + H2O
  6. Haloalkanes
    4. Formation of Grignard Reagents
    • RX + Mg --ether--> R-MgX
    • R-MgX <---> R- + +MgX
    • R-MgX + H2O --> R-H + MgX(OH)
  7. Alkenes
    1. Reaction with Hydrogen Halides
    Alkene + H-X --> Haloalkane
  8. Alkenes
    2. Addition of S Acid
    Alkene + H2SO4 --> RCH2-OSO2OH
  9. Alkenes
    3. Addition of water
    Alkene + H2O --acid-cat--> Alcohol (non-terminal generally)
  10. Alkenes
    4. Add H2 (reduc-hydrogenation)
    Alkene + H2 --Pd--> Alkane
  11. Alkenes
    5. Add KMnO4
    Alkene + 2MnO4- + 4H2O --> diol + 2MnO2 + 2OH-
  12. Alkenes
    6. Add Halogens (halogenation)
    Alkene+ X2 --> 1,2-trans haloalkane
  13. Alkenes
    7.Ozonolysis
    Alkene --O3/Zn/H2O--> ketone + aldehydes
  14. Alkynes
    1a. Add Hydrogen Halides
    Alkyne + HX --> Halo-Alkene --HX--> 1,1 Haloalkane
  15. Alkynes
    1b. Add Halogens
    Alkyne + X2 --> 1,2 Haloalkene --X2--> 1,1,2,2 Haloalkane
  16. Alkynes
    1c. Add H2
    • Alkyne + H2 --PtorPd--> Alkene --H2&cat--> Alkane
    • Use LINDLAR Cat to get Alkene
  17. Alkynes
    2. Add H2O
    • Alkyne + H2O --acid cat--> RC(OH)=CHR (enol) <---> RCOCH2R (ketone)
    • called Tautomerism/Enolisation
    • to terminal H requires Hg2+ cat as well
  18. Alkynes
    3. Oxidation (O3 or hot KMnO4)
    • Internal Alkyne ---> 2 Carboxylic acids
    • Terminal Alkyne --> Carbox acid + CO2
  19. Benzene
    1. Nitration
    Benz + HONO3 --acidcat--> QNO2 + H2O
  20. Benzene
    2. Sulfonation
    Benz + SO3 --acidcat--> QSO3H + H2O
  21. Benzene
    3. Halogenation
    Benz + X2 --FeX3--> QX + H2O
  22. Benzene
    4. Friedel-Crafts Acylation
    Benz + RC(=O)Cl --AlCl3--> QC(=O)R + HCl
  23. Alcohol
    1. Salt formation
    • Meth/eth with Na (redox)
    • R-OH + Na --> R-O-+Na + (0.5)H2
    • less acidic (more C's) alcohols with more reactive K
  24. Alcohols
    2. Oxidation
    • Primary RCH2-OH --KMnO4(or)Na2Cr2O7--> C. Acid
    • Secondary R2CH-OH ----> Ketone
    • Tertiary ---> no reaction
  25. Alcohols
    3. Oxidation of 1o alcohols
    Cr2O72- + 14H+ + 6e- ----> 2Cr3+ + 14H2O
  26. Alcohols
    4. Formation of alkenes (Dehydration)
    CH3CH2OH + H+ <----> CH2CH2 + H3O+
  27. Alcohols
    5. Ester Formation
    R-OH + RCOOH <--H+--> RCOOR + H2O
  28. Alcohols
    6. Hydrogen Halide Conversion
    • 10 RCH2OH --HX--> RCH2X   SN2  need acidcat
    • 20 R2CHOH --HX--> R2CHX   SN1
    • 30 R3COH --HX--> R3CX   SN1 faster easier to form stable intermediate
  29. Alcohols
    7. Thionyl Chloride Conversion
    • 1o or 2o
    • ROH ---SOCl2---> R-Cl + SO2 + HCl
    • Sn2
  30. Alcohols
    8. Phosphorus Halide conversion
    • 1o or 2o 
    • ROH ---PCl3---> R-Cl + HOPCl2
    • Sn2
  31. Carbonyls
    1. Reaction with Water
    • RCOR + H2O <--H+--> RC(OH)2R
    • aldehyde more reactive
  32. Carbonyls
    2. Reaction with Alcohol
    Carbonyl + Alcohol <--H+--> R-C(OH)(OCH3)-R <---H+&alcohol---> R-C(OCH3)2-R
  33. Carbonyls
    3. Reaction with Grignard
    R-CO-R + R-MgBr ----> R-CRO--R + Mg+Br --H+--> R-CROH-R
  34. Carbonyls
    4. Reaction with Amine
    R-NH2 + R-CO-R <--H+--> R2C=N-R + H2O
  35. Carbonyl
    5. Reaction with Hydrazine
    R-CO-R + H2NNH2 <--H+--> R2C=NNH2 + H2O
  36. Carbonyls
    6. Reaction with Hydroxylamine
    R-CO-R + H2NOH <--H+--> R2C=NOH + H2O
  37. Carbonyls
    7. Oxidation of Aldehydes
    R-COH ---Oagent--> RCOOH
  38. Carbonyls
    8. Reduction
    • Ketone --H2/Ni--> R-CHOH-R
    • Aldehyde ---1.NaBH4/2.H3O+---> 1o Alcohol
    • Ketone  ---   ^^^ ---> 2o Alcohol
  39. Carboxylic Acids
    1. Acid Chloride Synthesis
    RCOOH + SOCl2(orPCl5) ---> RCO-Cl + HCl + SO2
  40. Carboxylic Acids
    2. Fischer Esterification
    • RCOOH + ROH <--H+--> RCOR + H2O
    • Can be reversed as hydrolysis, depending on pH
    • Reaction reaches Equil
  41. Carboxylic Acids
    3. Esterification From Acyl Chlorides
    RCO-Cl + ROH ----> RCOR + HCl
  42. Carboxylic Acids
    4. Amides from Acid Chlorides
    RCO-Cl + 2R-NH2 ---> RCO-NR + RN+H3Cl-
  43. Carboxylic Acids
    5. Hydrolysis of Amides
    RCO-NH2 + NaOH ---> ROO- + HOH
  44. Amines
    Alkylation of Amines
    R-NH2 + R-CH2-Br ---> R-N+H2-CH2-R  -Br

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