chapter 13 16 alcohols ethers and amines n.
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Chapter 13/16: Alcohols, Ethers and Amines. Suggested Problems: Chapter 13:3-12,14,25,26,39,40, 43(a-c), 44( a,b ) Chapter 16 : 3,4,6,7-15. Functional Groups Based on Water. Replacing one hydrogen on water by an organic group affords an alcohol R-O-H

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chapter 13 16 alcohols ethers and amines

Chapter 13/16: Alcohols, Ethers and Amines

Suggested Problems:

Chapter 13:3-12,14,25,26,39,40, 43(a-c), 44(a,b)

Chapter 16: 3,4,6,7-15

functional groups based on water
Functional Groups Based on Water
  • Replacing one hydrogen on water by an organic group affords an alcohol

R-O-H

  • Replacing the second hydrogen on water by an organic groups yields an ether

R-O-R’

functional groups based on ammonia

N

N

N

H

H

R

R

R

R

H

R

R

Functional Groups Based on Ammonia
  • Replacing one or more hydrogens on ammonia (NH3) gives an organic amine
alcohols
Alcohols
  • The functional group of an alcohol is the hydroxyl group
  • The generic formula of an alcohol is

R-OH

CH3-CH2-OH

ethanol

ethyl alcohol

naming alcohols
Naming Alcohols
  • IUPAC:
    • Follow the normal rules
    • Add the suffix ‘-ol’ to the parent chain
    • Give the OH group the lowest number
  • Or, for very simple alcohols
    • Name the alkyl group and call it an alcohol
    • This is a common name
examples2
Examples
  • 4-methyl-2-hexanol

1,2-dibromo-2-butanol

example
Example
  • Aromatic alcohols are called phenols (from phenyl alcohol)
primary alcohols
Primary Alcohols
  • Primary alcohols have one carbon group bonded to the C with the OH
  • Name:
secondary alcohols
Secondary Alcohols
  • Secondary alcohols have two carbon groups bonded to the C with the OH
  • Name:
tertiary alcohols
Tertiary Alcohols
  • Tertiary alcohols have three carbon groups bonded to the C with the OH
  • Name:
ethers
Ethers
  • The functional group of an ether is an oxygen bridging two alkyl groups
  • The generic formula of an ether is R-O-R’

CH3-CH2-O-CH2-CH3

diethyl ether

naming ethers
Naming Ethers
  • Name each alkyl group and call it an ether
  • Give names in alphabetical order if needed
  • Each alkyl group is treated as a separate word
  • This is a common name
examples3
Examples

ethyl methyl ether methyl phenyl ether

amines
Amines
  • The functional group of an amine is a nitrogen bonded to 1, 2 or 3 alkyl groups
  • The generic formula of an amine is

R-NH2or R2NH, or R3N

CH3-NH2

methylamine

naming amines
Naming Amines
  • Name the alkyl groups and call it an amine by tacking amine to the end of the name

Isopropylamine trimethylamine

reactions of alcohols
Reactions of Alcohols
  • One characteristic reaction of alcohols is oxidation
  • In organic chemistry, ‘oxidation’ means
    • adding bonds between C and O or
    • removing bonds between C and H
oxidation of primary alcohols
Oxidation of Primary Alcohols
  • Primary alcohols are oxidized to aldehydes
oxidation of secondary alcohols
Oxidation of Secondary Alcohols
  • Secondary alcohols are oxidized to ketones
  • Tertiary alcohols are not oxidized
    • Carbon can not have five bonds