Orgo Ch 7 Ppt.

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Orgo Ch 7 Ppt.
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  1. one element of unsaturation corresponds to what?

    Formulas of:
    - a saturated hydrocarbon
    -a saturated hydrocarbon with oxygen
    - a saturated hydrocarbon with nitrogen
    either a ring or a double bond, not both

    • - CnH2n+2
    • - CnH2n+2O
    • - CnH2n+3N
  2. Structure of :
    - a methylene alkyl group
    - a vinyl alkyl group (aka: ethenyl)
    - an allyl group (aka: 2-propenyl)
    • -H2C=X
    • -H2C=CH-X
    • -H2C=CH-CH2-
  3. __ groups are double bonds fused to rings

    Explain E and Z prioritizing

    What do you do if you have multiple bonds?
    • alkylidene
    • E double bond (higher priority groups are on opposite sides
    • Z double bond (higher priority groups are n the same side)

    if its a double bond, act like its bonded to the atom twice; if triple, three times
  4. If a double bond is in the ring, it is __.

    Scenario:
    If you have a nine carbon ring with one double bond, but the hydrocarbon has multiple double bonds, what do you do?
    cis

    take the longest chain containing all of the double bonds
  5. __ helps to determine stability. 

    What is hydrogenation of alkenes? What does the energy difference lie in? If the energy difference is lower, what does that mean?
    hydrogenation data

    adding H across the pi bond, saturating it

    • lie in the stability of the product; in the difference of reactants
    • it's lower in energy
  6. __ is more stable than __.

    Explain relative stabilities in terms of substitution?
    • E (trans) 
    • Z (cis)

    tetra > tri > di > mono
  7. What is hyperconjugation?
    pi bond associates with an adjacent C-H signma bond
  8. Explain the Addition Reaction
    • - attack of the pi bond on the electrophile forms a carbocation
    • - attack by a nucleophile gives the product of addition
  9. Explain the HBr addition
    • 1) protonation of the double bond forms a carbocation
    • 2) bromide ion attacks the carbocation
    • -- The electrophile HBr is attacked by the pi bond electrons of the double bond, and a new C-H sigma bond is formed. This leaves the other carbon atom with a + charge and a vacant p orbital
    • --Br- donates an electron pair to the positively charged carbon atom, forming a C-Br sigma bond and yielding a neutral addition product
  10. Mark's rule

    __ is determined by stability of the intermediate.

    Carbocation stability
    the addition of H-X across a pi bond results in the more highly subbed alkyl halide as the major product

    regiochemistry

    tertiary > secondary > primary > methyl
  11. Definitions:
    - regioisomers
    - regiospecific
    - regioselective
    two constitutional isomers that could result from an addition reaction

    only one regioisomer forms at the expense of the other

    both regioisomers are formed, but one is formed in preference
  12. When will rearrangements occur?

    Endo transition state looks like __

    Exo transition state looks like __.
    to stabilize the carbocation

    product

    reactant
  13. What is Hammond's Postulate
    related species that are close in energy are close in structure

    in an endothermic rxn, the TS is similar to the product in structure and stability

    In an exothermic reaction, the transition state is similar to the reactant in structure and stability 

    the structure of the TS resembles the structure of the most stable species
  14. __ rxns allow us to make double bonds 

    Markovnikov rule?

    First step of addition?

    What determines the product?
    elimination

    if you have an asymmetric alkene, the more highly subbed will be formed 

    protonation (the H is taken by the electrons of the double bond)

    the intermediate
  15. What is the rate-determining step in an addition rxn?

    Regiospecific reaction?
    protonation becuase you're going from stable to high energy

    • one product forms; the other doesnt 
    • - the more carbons there are, the more overlap there is
  16. When will E/Z prioritizing not occur?

    When we can form two products, we call it __.

    Regioselective vs. Regiospecific?
    if there are same groups on the same carbon

    regioisomers

    regioselective: one was preferred over another, but still a mix was made; two products form

    regiospecific: one product forms
  17. Rearrangements
    - if the double bond has equal substitutions and you want to find how it happened, what do you do?
    - when will a shift occur?

    For these reactions, you are going straight through __. Why?
    • propose a mechanistic pathway
    • in favor of the more stable carbocation

    • E1
    • becuase product is being removed as it forms; no Sn1 competition

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