STUFF TO KNOW FOR EXAM 3  

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.

Chapter 19
1.  know how to name aldehydes and ketones (including common trivial names).
2.  know how/why conjugation affects carbonyl stretching frequencies.
3.  know the relative magnitudes for london, dipole-dipole, and H-bonding interactions.  Be able to use these to arrange BP's.
4.  know how carbonyls can H-bond to water.
5.  know the preps for aldehydes/ketones (oxidation, hydroboration, oxymercuration, Freidel Crafts acylation).
6.  know the methods for oxidizing aldehydes (Cr+6 and Tollens)
7.  know the general mechanisms for nucleophilic addition to A/K(both anionic/basic and neutral/acidic versions), be able to apply them in specific    cases.
8.know mechanisms/particulars (equilibrium issues, compatibility with water, specific reagents, necessity for acid catalysis...) for adding the following:  addition of cyanide, hydride, R:-, ROH, HOH, RNH2 (including derivitization variants), R2NH.
9.  Be able to recognize the new functional groups hemiacetal and acetal, hemiketal, ketal,  imine, enamine).
10.  know Le Chatelier's principle and how it applies to A/K additions.
11.  Recognize that acetal/ketal formation can be run in the reverse direction as well.
12.  know how to make Wittig reagents and how to use them,  the mechanism is wierd but know that too.

Chapter 20
1.  Be able to name carboxylic acids (including common trivial names).
2.  See item #2 in Chp 19.
3.  Be able to name carboxylates.
4.  Be able to do simple HNMR analyses for carboxylic acids.
5.  know why carboxylic acids boil higher than esters.
6.  know how to make carboxylic acids (Cr+6, KMnO4 ox, CO2 add'n to Grignard reagents, nitrile synthesis/hydrolysis).
7.  know how to interconvert carboxylic acids and carboxylates and how to exploit this chemistry for mixture separation.

Chapter 21
1.  Be able to identify and name molecules with carboxylic acid derivative functional groups.
2.    Know how to discern various types of carbonyls (aldehydes, ketones, esters, carboxylic acids, acid chlorides, acid anhydrides, amides) spectroscopically (IR, 1H, 13C).
3.  Know the relative energies/reactivities of various carboxylic acid derivatives.
4.  Know how to interconvert carboxylic derivatives and draw mechanisms (NAS, both acidic and basic)
5.  Understand the catalytic roles in NAS rxns played by acids and bases.
6.  Know what thionyl chloride is good for.
7.  Know how nylon 66 is made.

8.  Understand what is necessary to get good yields for carboxylic acid derivatives especially when trying to work up the energy chart (ways to force the equilibrium)

9.  know what a soap and a micelle is.
10.  know the general/old timey definition for an ester.
11.  be fluent in flarp, silly putty, and slime (just kidding).
12.  know the SN2 way to make esters from carboxylic acids.

13.  Understand how penicillin antibiotics work.

14.  Know how amides are hydrolyzed to carboxylic acids/carboxylates and why good yields are possible


There  is a lotta stuff here.  Study hard over multiple days for best results.  Help session Monday nite at 8:00.   If you have any questions call me (321-4186(W)/433-4493(H), see me, or email me.  I'm more than happy to help you.  Types of problems potentially on exam 3:  definitions, multiple choice , nomenclature,  short answer (mostly based on mechanistic considerations),  predict the product, provide reagents, show the mechanism,  and structure/spectroscopic correlations (not much of this). This exam will be focused much more on reactions and mechanism.  Recognize mechanistic patterns to organize the material in your head.  Also, the big scary mechanisms are made up of smaller more comfy parts (acid-base, Nu:-H attack on carbonyl, SN1 for acetal formation for example).  As always,  I'll be shooting for medium tough but fair.  Hard work at studying typically pays off in higher grades!!!!!!! It should be fun/challenging.  Think you'll like the bonus question.