Organic Chemistry Lecture II

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Organic Chemistry Lecture II
2010-05-06 23:49:01
Alkenes Benzene Ethers Alcohols

Continually expanding understanding of ORGO material for MCAT
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  1. What E1 reaction yields synthesis of an alkene?
    • Dehydrohalogenation
    • alkylhalide + strong bulky base
    • - proton ripped and halogen drops off in ONE STEP!!!
  2. What E2 reaction yields an alkene as a product?
    • Dehydration of an Alcohol
    • alcohol + hot strong acid
    • - hydroxyl is protonated leaves as water, carbocation forms, follows Zeitzeff Rule!!!
  3. What is the order of carbocation stability? What confers the stability? What is the name of this rule?
    3terciary -- 2secondary -- 1primary -- methyl

    "Electron donating" methyl groups.

    Zeitzeff Rule
  4. What is the product of a "catalytically hydrogenated" alkene and what type of addition are the hydrogens added?
    • A saturated alkane with syn addition.
  5. What reactant oxidizes an alkene and what 3 possible product(s) are yielded?
    O3 ozone

    • Carboxylic acid, Ketone, Aldehyde
    • Double bond broken to yield carbonyl group at both ends!

  6. What happens to an alkene when in the presence of a hydrogen halide?
    Alkyl halide: electrophilic addition of the least substituted carbon, possible skeletal rearrangement, addition of halide to carbocation.
  7. When does addition of a hydrogen halide proceed anti-Markomnikov?
    Radical Reaction: In the presence of Peroxides and ONLY H-Br will add anti-Markov.
  8. How is an alcohol synthesized from an alkene?
    Hydration of an alkene: Cold dilute acid will protonate the least substituted carbon and the resulting carbocation will bind to the hydroxyl group.