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Chapter 4: Alcohols and Alkyl Halides



Summary | Alcohols | Alky halides | Nucleophilic Substitution Reactions | Radical Substitution Reactions | Preparations of Alkyl Halides | Self Assessment | Quiz |


Alcohols

Chapter 4: Alcohols and Alkyl Halides


In order to view some of the structures for this section, you will need the web "plug-in", "CHIME". If you do not have it already installed, you should be able to download it for free from the linked Website. CHIME is a browser that allows you to visualize and manipulate molecules as 3D structures.  Check here if you don't know how to use Chime.

Nomenclature:
Functional group suffix = -ol (review)
Functional group prefix = hydroxy-
Primary, secondary or tertiary ? Alcohols are described as primary (1o), secondary (2o) or tertiary (3o) depending on how many alkyl substiutents are attached to the C-OH unit.
 

ethanol
2-propanol
t-butanol 
2-methyl-2-propanol
1o
2o
3o
Check the designations of primary, secondary and tertiary by counting the number of C atoms attached to the C with the O attached.

Physical Properties:

Structure: Reactivity:
electrostatic potential of methanol The image shows the electrostatic potential for methanol. 
The more red an area is, the higher the electron density and the more blue an area is, the lower the electron density.
  • The alcohol O atom are a region of high electron density (red) due to the lone pairs.

  • (red)
  • Alcohol oxygen atoms are Lewis bases.
  • So alcohols can react as either bases or nucleophiles at the oxygen.
  • There is low electron density (blue) on H atom of the -OH group alcohol, i.e. H+ character.
  • So alcohols are acidic (pKa ~ 16).
  • Removal of the proton generates the alkoxide.
  • The -OH group is a poor leaving group and needs to be converted to a better leaving group before substitution can occur.

Acidity:

Reaction of Na with ROH or H2O
Help with chime files


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