Chapter 12 (Chapters 10 and 11 appear after chapter 13)
For MS (12.1-12.5), you must be able to interpret a mass spectrum as follows:  1. identify the peak that corresponds to the molecular ion  (M+), assuming that it has been detected; 2.  understand the origin and significance of the M+1 and M+2 isotope peaks; 3.  know how to recognize the presence of chlorine or bromine; 4.  determine one or more of the most probable molecular formulas (best done after determining if oxygen shows up in the IR spectrum);  and 5.  know what causes fragment ions, why different compounds always have different fragmentation patterns, and be able to identify one or two of the most obvious fragmentation products closest in mass to the molecular ion.  Succeeding with all this will require reading the entire chapter and working as many MS spectral problems as possible.  Additional MS problems are available in various chemistry texts in the library, and at numerous sites on the web devoted to spectroscopy..

For IR (12.6-12.9), you must be able to interpret an IR spectrum as follows, from left to right from 4000 cm-1 to 1600 cm-1:  1.  Know how to recognize the presence of NH or OH at 3500(and how to tell one from the other);
2. unsaturated and saturated CH just to the left and right of 3000; 3.  triple bond (nitrile or alkyne) between 2500 and 2200; and 4. carbonyls 1800-1600 cm-1.  In the fingerprint region, the only assignment needed is the C-O-C ether stretch at 1200-1100 cm-1 (strong).  It is particularly important to be able to determine, from IR, whether or not your compound contains oxygen. In addition, you should understand how IR, like MS, can used to "fingerprint" molecules.  As with MS, the material on IR should be read for general understanding, but the "bottom line" here is being able to interpret IR spectra.  Work as many IR problems as you can, including at the end, problems that combine both IR and MS data on a single compound. Utilize the many websites devoted to learning spectroscopy.

Chapter 13
NMR is the single most powerful tool that chemists and biochemists routinely use for the determination of the structures of organic and bio-organic compounds (actually X-ray crystallography is more powerful, but cannot be routinely applied).  The technique is applicable to both large and small molecules, and is, in fact, a major tool for protein structure determination.  The theory of NMR is very complex, and many different NMR experiments can be run.  Your text contains the minimum amount of descriptive background needed to interpret the simplest, but most common NMR experiments involving proton and C-13 NMR.  Interpretation of HNMR involves extracting information from the spectrum as follows:  1.  The number of discrete resonances (a multiplet is one resonance) equals the number of chemically different hydrogens (assuming no resonances overlap); 1.  the relative areas for each resonance are proportional to the relative number of hydrogens producing each resonance; 3.  multiplets give spin-spin splitting information about chemically different neighboring hydrogens; and 4.  the chemical shift of each resonance is related to the chemical nature of the hydrogen(s). The most obvious chemical shift data is to be memorized as follows:  aldehyde H at 9-10ppm, aromatic H at 8-6.5ppm, alkene H at 6.5-5.5ppm, hydrogens on a C alpha to a C=O at 2.0-2.2ppm, and saturated H surrounded by no functional groups is around 1ppm.  The region between 4 and 2ppm contains too many different kinds of hydrogens to memorize easily, but O-CH is most common.  Chemical shift correlation tables are readily available in texts and on the web.  For C-13 NMR, run as fully-decoupled from all protons, the spectra span from 0 to 200ppm, and show all sharp singlets for each chemically different kind of carbon.  No spin-spin splitting is observed, and peak areas are not simply related to the relative numbers of hydrogens.  Carbon chemical shifts to memorize are:  C=O carbon between 180 and 220ppm, aromatic carbon around 150-120ppm, alkene carbons around 100ppm, and saturated carbons between 50 and 10 ppm.  Extensive chemical shift tables are available.  As with MS and IR, the key is to work as many problems as possible, with eventual emphasis upon combination problems utilizing IR, NMR, and MS.

Chapter 10
10.1  Name simple alkyl halides using halogens as substituents (fluoro, chloro, bromo, and iodo)
10.2  Notice dipole moments.  Why is the C-F dipole moment less than that of the C-Cl in table 10.1?
10.3  Review addition of HX to alkenes
10.4-10.6 just read it, but know reaction of allyl H with NBS, and why the allyl radical is resonance stabilized.
10.7  Know reaction of HX with tertiary alcohols, and the reactions of thionyl bromide and thionyl chloride with primary and secondary alcohols.  The mechanisms will be discussed later, in the chapter on alcohols.
10.8  Know how to prepare a Grignard reagent, and how a Grignard is an example of an "organometallic" compound.
10.9  Know how to make a Gilman reagent, and how to react it with an alkyl or aryl halide.
10.10 skip
Summary of reactions (pgs 378 and 379) know how to use all of them.
Suggested problems: 10.18 a,d; 10.19b; 10.21; 10.23 a,d; 10.24 all; 10.30; and 10.38.

Chapter 11
11.1-11.3 just read.
11.4  study this carefully, and utilize the online animation to visualize the reaction.  If you understand, you should be able to do problems 11.2-11.4 on pages 392 and 393.
11.5  Substrate, leaving group, nucleophile, and solvent all affect the Sn2 reaction.  Try to get a general sense of how and why each of these four aspects is involved.  The key ideas on pages 400 and 401 need to be memorized and understood.
11.6 read
11.7 and 11.8 read and utilize the online animation to visualize this mechanism, and to understand how it differs from the Sn2 mechanism in terms of the stereochemical aspects.
11.9  same discussion as 11.5, but here referring to the Sn1 mechanism.  Read, then memorize and understand the key ideas on pages 412 and 413. The practice problem 11.2 on pages 412 and 413 is worth doing.
11.10  memorize Zaitsev's rule
11.11 read and use animation to visualize the one-step E2 mechanism.
11.12 skip
11.13 read to understand what a kinetic isotope effect is, and how it applies to the E2 mechanism with elimination from alkyl halides.
11.14 read and visualize to distinguish from E2 picture.
11.15 contains a good summary in Table 11.4.  Practice problem 11.4 should be done.
11.16  recaps substitution reactions seen so far
Summary of reactions: For substitution, know it all with entire list of nucleophiles from page 396.  For elimination, only KOH/ethanol is to be used.
Suggested problems:  11.25 a-d; 11.29; 11.31 all; 11.39; 11.40; 11.54; and 11.63.  Also try the molecular modeling exercises on page 439.

Chapter 14
14.1-14.2  Know what a conjugated diene is.  Don't be concerned with how they are prepared.  Look carefully at the data in Table 14.1 relating to the extra stability of conjugated dienes.
14.3  Your first introduction to MO theory of carbon pi systems.  Read to know the MO description for the pi system in 1,3-butadiene (table 14.2).  Know what is meant by the LUMO and the HOMO, and the antibonding vs bonding characteristics of the MO's.
14.4 read
14.5 know 1,2 and 1,4 addition reaction, and nature of resonance delocalized allyl cation intermediate.  Do practice problem 14.1.
14.6 skip
14.7 read
14.9 and 14.9  The Diels-Alder reaction is the first example given of a "pericylic" reaction, as opposed to a free-radical or ionic reaction.  Learn the reaction in terms of the general nature of the diene and dienophile and the cyclohexene product produced, and also the strong stereochemical features of the reaction.  Work practice problem 14.2 on page 540, and problem 14.12 on page 542.
14.11-14.13.  You need to understand UV/VIS spectroscopy in terms of the nature of the electronic transitions involved, what molar adsorptivity refers to, and how absorption of light in the visible region leads to colored organic compounds.  Just read section 14.12.  You will not be asked to interpret UV spectra.  In view of the importance of integrated circuits, you should read the article on "resists" starting on page 548.
Know all keywords on page 550.
Suggested problems:  14.20a; 14.21a; 14.26; 14.31 a,b; 14.32; 14.37b.  Also try the Spartan-view exercise 14.61 on page 558.