STUFF TO KNOW FOR 22105 EXAM 1(updated 1/28/05)

 General (220 stuff):  Lewis structures, formal charges, hybridization rules and corresponding geometries, basic requirements for a H-bond, curved arrow notation for polar rxns, recognition of electrophiles, nucleophiles, and leaving groups, general mechanisms for acid-base, SN2, E2, SN1, E1, addition of HX to alkenes, IR "walkin' around knowledge", noble gas rule

Radicals (Chp 5,7, 10)
1.    definition for radical
2.    curved arrow notation for radical rxns
3.    definition of an initiator
4.    typical structures for initiators (peroxides, AIBN)
5.    definition of bond dissociation energy
6.    use of BDE's to calculate rxn enthalpies
7.    mechanism for halogenation of alkanes
8.    understand the terms initiation, propagation, and termination, and radical chain rxn
9.    know the factor responsible for the  modest regiocontrol in radical halogenation
10.  why is radical halogenation feasible for C12 and Br2 but not F2 and I2?
11.  for the hydrobromination of alkenes, know both mechanisms and how to diagnose which is operative in a given situation
12.  understand the basis for regiocontrol for both HBr addition mechanisms
13.  know the mechanism for polymerization of substituted ethenes via radical addition
14.  know how to draw the resultant polymers
15.  understand the basis for regiocontrol in this rxn

16.    understand the basic idea behind detoxification of radicals in biological systems

Mass Spectroscopy (Chp 12)
1.  definition of spectroscopy

2.  basic workings of an electron impact mass spectrometer
4.  realize that nonbonding electrons get knocked out easier than bonding electrons
5.  know how to pick out the molecular ion, isotope peaks, and base ion
6.  recognize the importance and utility of M+2 peaks for chlorinated and brominated molecules
7.  know the nitrogen rule and how to use it to help determine molecular formula

NMR spectroscopy (Chp 13)
1.    understand that many nuclei behave like teenie weenie magnets
2.    know what happens when magnetically active nuclei are placed in an external magnetic field
3.    understand the parallel, antiparallel energy gap, and how it differs for different nuclei
4.    have a qualitative understanding Beff = Bo-Blocal
5.    understand where shielding comes from
6.    understand how electron density affects chemical shift for 1H and 13C
7.    know how chemical shifts are calculated
8.    know how to recognize chem shift equivalence for 1H and 13C
9.    know the general ranges and trends for 1H and 13C
10.  realize peak area is proportional to #H per signal, and how to use integration to determine relative #H per peak
11.  know how to use coupling patterns to determine the #H on neighboring C's (also be able to go the other way)
12.  understand the whole symmetry thing for # of 13C peaks
13.  recognize that C's without H's give little peaks ( and that integration is not a viable process for 13C peaks)
14.  know why 13C is a less sensitive technique than 1HNMR
15.  The biggie, know how to use your vast knowledge to assemble structures from different types of complimentary spectral
       information (MS, IR, 1H-NMR, 13C-NMR)

Alcohols (Chp 17 and a bit of 18)
1.    know why the C and O of the alcohol func group are sp3 hybridized
2.    know the nomenclature rules for acyclic alcohols
3.    know the rules also for cyclic alcohols
4.    be able to draw alcohol/alcohol and alcohol/water H-bonding interactions
5.    know why alcohols boil so much higher and are so much more water soluble than alkanes
6.    be able to distinguish primary, secondary, and tertiary alcohols
7.    know why there is usually no coupling between the H-C-O-H (exchangeability)
8.    know how extent of H-bonding and chemical shift are related
9.    recognize the use of D2O for removing OH NMR signals
10.  know the methods for converting alcohols to good leaving groups
11.  using the resultant species (in 10) to do substitution rxns (understand what is required for SN2 and SN1)

12.    know the mechanism and characteristics of the E2 rxn, also synthetic necessities for alcohol to alkene
13.    Using alcohols as nucleophiles to make ethers.  Understand strategy for selecting nucleophile and electrophile.

14.    know how to discern whether a transformation is an oxidation, a reduction, or neither
15.    know the structures of the Cr (VI) reagents used for alcohol oxidation
16.    know how alcohol oxidations differ by subclass and reagent
17.    know the mechanism for alcohol oxidation (chromate ester to carbonyl)
18.    understand the use of H2CrO4 as a qualitative test for alcohols, also how H2CrO4 is made.

Study hard over multiple days for best results.  We'll talk about the alcohol homework (or whatever you want) during our help session.    If you have any questions call me 321-4186, see me, or e-mail me.  I'm more than happy to help you.  Types of problems potentially on exam 1:  definitions, multiple choice (probably from old MCAT exams if I can get a hold of them), short answer, predict the product, provide reagents, and assemble structure from spectra.  I'll be shooting for medium tough but fair.  Good luck!