Download - Chapter 6
Chapter 6
Nomenclature
C C
C C
C C
C F
C Cl
C Br
C I
O
HO
C OH
C N
C N
C N
C CO
C SH
C CS
H
H
H
Alkane
Alkene
Alkyne
Cycloalkane
Halide
Phenyl
Carboxylic Acid
Alcohol
Ether
Amine
Thioether
Thiol
Alcohol Nomenclature
OH
1) Find the longest carbon chain containing the alcohol
2) Start numbering from the end closest to the alcohol
3) Finish with -ol as the suffix (takes priority over -ene & -yne)
2-pentanolhydroxyl group
HO
Alcohol Nomenclature
1,2-ethanediol
ethylene glycol
OH
OH OHHO OH
1,2,3-propanetriol
glycerine
Amine Nomenclature
1) Name all of the substituents coming off the nitrgoen (ignore hydrogens)
2) Place them in alphabetical order add a space then amine
methylpropyl amine
NH
Best way to name amines until the structures become too complicated
Alternative Amine Nomenclature
1) Find the longest carbon chain containing the amine
2) Start numbering from the end closest to the amine
3) Finish with -amine as the suffix (does NOT take priority over -ol, -ene, or -yne)
2-pentanamineamino group
NH2
N
Amine Nomenclature
NH2
NH
N
N+
primary amine
secondary amine
tertiary amine
ammonium ion
Figure 6.29
NH2R
NHR2
NR3
N+R4
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N
O
OHO
NH
OH OH
F
Lipitor
O
ON
S
Cl
Plavix
OH
NH
O
OH
OH
Advair (Salmeterol)
Ether Nomenclature
1) Name both substituents coming off the oxygen
2) Place them in alphabetical order add a space then ether
methylpropyl ether
O
O CH3 OCH3
OCH3
methoxy group ethoxy group propoxy group
Thiol Nomenclature
1) Find the longest carbon chain containing the thiol
2) Start numbering from the end closest to the thiol
3) Name normally then add thiol to the end
2-pentanethiolmercapto groupSH
HS
SS
disulfide
Thioether Nomenclature
1) Name both substituents coming off the sulfur
2) Place them in alphabetical order add a space then sulfide
methylpropyl sulfide
S
Solvents in Organic Chemistry
Adapted from: Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; New York: Harper & Row, 1987.
Solvation
H
Br
H Br
H
Br
Acid-Base Properties of Alcohols
R O H R OB B
R OH
H
pKa pKa
R = H
R = CH3
R = CH2CH3
R = C(CH3)3
-1.74 15.7
-2.2
-1.9
-2.6
15.5
15.9
17
Acid-Base Properties of Amines
NRR
R
NRR
R
HH
Amine pKa
NH3
CH3NH2
(CH3)2NH
(CH3)3N
9.24
10.63
10.78
9.80
Activation of Alkyl Halides
R X
Mg 2 Li
R Mg X R Li + LiX
Mg Cl + MeOH H + HO Mg X
Li + HH H + LiH
N
R
RR
N
R
RR
N
R
RR
Nitrogen Inversion
NCH2CH2CH3H3C
H3CH2C
Nitrogen Inversion
NCH2CH2CH3H3C
H3CH2C
H
N
R
RR
N
R
RR
H H