Notes:  You will be required to do three formal lab reports.  You can select the labs for which you write your formal lab report.  I suggest you pick the three labs that went especially well and that you enjoyed.  In any case you have to pick three.  Please continue to submit the finished carbon copies for every lab and be prepared to submit three formal lab reports.  The formal lab reports will have the same format as the other reports, but it will be "formal", in other words typed.  Think of your formal lab report as a document you may submit to your boss or as a student, add to your portfolio.  Be sure to include all necessary spectra.

Chapter 8 continued.

A.  Radical Stability
    1.  benzyl radical = allyl radical >  tertiary radical > secondary radical > primary radical > vinyl radical
B.  Radical Substitution Reactions
    1.  Use NBS (N-Bromosuccinimide) as a source of Br radical.
    2.  With unsymmetrical resonance structures, two products are formed.
    3.  Stereochemistry of the reaction
        a.  If one stereocenter is formed, a racemic mixture will be produced.
            1.  the radical intermediate is trigonal planar
        b.  If the reaction is started with one enantiomer of the chiral compound and a new stereocenter is formed, a pair of diastereomers is formed.
            1.  If the original chiral center is close to the reaction site, it may influence the outcome.
    4.  Radical Substitution reactions with cyclic compounds
        a.  same reactions as noncyclic counter parts.
        b.  exception is cyclopropane, cyclopropane behaves as an alkene and addition reactions occur.

C.  Radical Reactions in Biological Systems
    1.  Radicals generated by the interaction with metal ions.
        a.  FeV=O  abstracts a hydrogen atom from an alkane producing an alkyl radical and FeIV-OH
        b.  FeIV-OH dissociates to FeIII and HO. (radical)
        c.  HO. combines with alkyl radical to form alcohol
    2.  RNA to DNA

D.  Radical Inhibitors - Covert a reactive radical into an unreactive radical.
    1.  Hydroquinone goes to semiquinone goes to quinone
    2.  BHA and BHT are synthetic preservatives.
    3.  Natural inhibitors
        a.  Vitamin C and Vitamin E

E.  Radicals and Stratospheric Ozone
    1.  Freons (chlorofluorocarbons)  cleave homolytically to form Cl radicals
    2.  Cl.(radical) +  O3 goes to ClO.(radical)  +  O2  and ClO.(radical)  +  O3 goes to Cl.(radical)  +  2O2
    3.  One chlorine atom destroys 100,000 ozone molecules
 

I.  Reaction Reviews
    A.  Acid / Base Reaction
        1.  Equilibrium lies toward the weakest acid
        2.  pKa
    B.  Electrophilic Addition Reaction to Alkenes and Alkynes - 1,2
        1.  Addition of Hydrogen Halides
        2.  Addition on Halogens
        3.  Addition of Water
        4.  Addition of H2 (hydrogen gas)
    C.  Electrophilic Addition Reaction 1,4
        1.  Addition of Hydrogen halides
        2.  Addition of Halogens
        3.  Diels-Alder
        4.  Kinetic and Thermodynamic Products
    D.  Radical Reactions
        1.  Alkane substitution with halogens
        2.  Substitution at the allylic position (NBS) and benzylic position
    E.  Substitution (SN1 and SN2)
        1.  Ch. 5 - using Acetylide Ions
        2.  Ch. 9 - using alkyl halides
        3.  Ch. 11 - using compounds other than halides
    F.  Elimination Reactions (E1 and E2)
        1.  Ch. 10 - using alkyl halides
        2.  Ch. 11 - using compounds other than halides