Chapter 8: Alcohols

1. You recognize (based on structure) the alcohol functional group, and whether any particular alcohol is primary, secondary, tertiary or is a phenol.
2. You know how to name an alcohol or a phenol using the IUPAC system.
3. You know where to look in the IR spectrum for the characteristic alcohol band.
4. You know where to look in the ¹H and ¹³C NMR spectrum for characteristic signals for an alcohol, and how to distinguish H-C-(OH) protons from HC-O-H protons.
   
5. You know that alcohols are weak acids, and you understand what the pK_a of an alcohol signifies about the proton transfer reaction between water and an alkoxide.
6. You understand how hydrogen bonding networks are formed in liquid alcohols, and the impact those networks have on physical properties like boiling point and water solubility.
7. You recall how hydroxide converts primary alkyl halides to alcohols via S_N2 substitution, how water converts tertiary alkyl halides to alcohols via S_N1 substitution, and how secondary alkyl halides can be converted to alcohols under either mechanism. (Chapter 7)
8. You recall how alcohols can be created from alkenes in either a Markownikov sense (oxymercuration/demercuration) or anti-Markiwnikov sense (hydroboration/oxidation) (Chapter 12)
9. You understand how nucleophilic organometallic reagents (RLi, RMgX) are made
10. You know how nucleophilic organometallic reagents add to a C=O bond to form first an alkoxide, then (upon protonation) an alcohol.
11. You know several nucleophilic sources of hydride, and how they will add to the C=O group.
12. You know that nucleophilic reagents will open epoxide to form first an alkoxide, then (upon protonation) an alcohol.
13. By looking at the structure of an alcohol, you can perform a simple retrosynthesis and suggest at least two different reactions to make it.
14. You recognize the redox relationship between the alcohol group and the carbonyl group.
15. You understand why primary and secondary (but NOT tertiary) alcohols can be oxidized to aldehydes or ketones.
16. You understand the mechanism by which high-valent chromium (Jones' reagent and PCC) oxidizes primary and secondary alcohols.
17. You recognize the advantages of the Swern Oxidation (DMSO/oxalyl chloride/NEt₃) in oxidizing alcohols without use of chromium reagents.