22005                  STUFF2KNOW                  (EXAM 2)

Old stuff (Success on this test is imposssible without knowing this background material)
functional groups, electronegativity, nucleophile, electrophile, leaving group, formal charge, Lewis structure, curved arrow formalism, hybridization states and resultant bond angles.

New stuff

Chp. 2
1.  Bronsted Acid-Base theory
2.  Curved arrow notation
3.  resonance (drawing, interconversion, evaluation of structures)
 

Chp. 5
1. Free energy, entropy, enthalpy
2. Rxn energy diagrams
3. Free energy of activation, transition states, intermediates
4.  Exothermic, endothermic, exergonic, endergonic, intermediate, transition state, forward/backward rxns
5.  Polar mechanistic categories such as nucleophilic substitution, acid-base, electrophilic addition to pi bonds.....
 (be able to pick out reactive parts, draw curved arrows, determine products - will not be asked to create from scratch - see EP 4)

Chp. 6
1. alkene/cycloakene nomenclature
2. why doesn’t the alkene func. group have free rotation  (cis/trans)?
3. Would cis or trans alkenes be more stable?
4. Addition of HX to alkenes- mechanism, regiochemistry  (Markovnikov), synthetic aspects
5. Carbocations, stability order, and reasons behind it,  and synthetic ramifications (sounds scary but really  just 4 above)
5. Carbocation rearrangements (be able to rationalize and  draw mechanisms after the fact)

Chp. 7
1. Addition of X₂- mechanism, stereochemistry, synthetic  aspects
2. Addition of X₂/H₂O-mechanism, stereochemistry,  regiochemistry, synthetic aspects
3. Addition of Hg(OAc)₂, H₂O then  NaBH₄-mechanism,stereochem of step 1.  Net effect,  regiochemistry of whole process, synthetic aspects.
4. hydroboration with BH₃-mechanism (of hydroboration  itself), regiochemistry, stereochemistry, synthetic  aspects
5.  Hydrogenation of alkenes (catalyst, stoichiometry, direction of addition)
6.  Hydroxylation of alkenes (catalytic reagent, stoichiometric oxidant, direction of addition, intermediate)
7.  Ozonolysis of alkenes (reagents, product(s))

Chp. 8
1.  Nomenclature, band angles, hybridization issues for alkynes
2.  Addition of HX to alkynes (regiochemistry, mechanism, addition of 1 vs. 2 equiv. of HX)
3.  Addition of X₂ to alkynes (stereochemistry, 1 vs. 2 equiv of X₂)
4.  Hydration via Hg²⁺ (regiochem, tautomerization, synthetic aspects)
5.  Hydration via BH₃ (regiochem, tautomerization, synthetic aspects)

Study hard over multiple days for best results on organic exams.  This exam will definitely be more challenging than the last one!  Practice mechanisms.  Make sure you are an expert at Lewis structures, formal charges, recognition of Nu:^-, E⁺, L.G., and curved arrow notation.  Recognize that all of the mechanisms, with the exception of hydroboration, occur by essentially by the same mechanism.  We will have help session Tuesday nite at 8:45 - come with questions.    Look at your old quizzes, hmwks, and extra problem questions. Feel free to come by with questions anytime .  I wish you all godspeed.  Bonus will come from the Greazy Stuff PowerPoint.