Consider The Following Anion CH CH CHCH
Consider The Following Anion CH CH CHCH
Consider The Following Anion CH CH CHCH
O O
Use the arrow pushing technique to write two other resonance structures.
.
Consider the pentadienyl radical, CH2 = CHCH = CHCH2
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Example: Draw Lewis structures for the three isomers having the molecular
formula C3H8O.
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N.B. The molecules of the branched chain isomer are more spherical in shape than
straight chain molecules so they will not tangle as much with their sister
molecules. As a result, dispersion forces are weaker and a lower boiling point
results.
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C3H6Br2
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2-Bromopropane CH3CH(Br)CH3
Dimethylamine (CH3)2NH
Triethylamine (CH3CH2)3N
Ethanol CH3CH2OH
CH2 CH2
CH3CHCH2CH(OH)CH = C(CH3)2
CH2N(CH3)2
CH(CH 3)2
CH3CH2C CCH2CH2CH 3
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C C H Aldehyde
to at least one H atom
carbonyl group is bonded to at least one hydrogen atom.
O
Ketone
C C C
carbonyl group is bonded to two carbon atoms.
C O C Ether
R C O R' Ester
R C NH2 Amide
ACID STRENGTH
• HCl is a strong acid because it ionizes completely in water.
HCl + H2O H3O+ + Cl-
• The term pKa can also be used to denote the strength of an acid.
pKa = - log Ka
Thus for HCl, pKa = -log (1 X 107) = -7 and HCl is a strong acid.
Acetic acid, CH3CO2H; Ka = 1.8 X 10-5 ; pKa = 4.74. Acetic acid is a weak acid.
Problem: Which is the stronger acid: formic acid, HCO2H (pKa = 3.7) or picric
acid, C6H3N3O7 (pKa = 0.3)? Write equations for their ionization.
Problem: The pKa of water is 15.74 and that of ethanol is 16.00. Which is the
stronger acid? Write a possible reaction that could occur when the two substances
are mixed?
H2O H+ + OH-
The conjugate base F- is more stable than the conjugate base OH- because F is
more electronegative than O and is thus better able to accommodate a negative
charge.
Likewise, since N is more electronegative than C, the conjugate base NH2- is more
stable than the conjugate base CH3-. So NH3 is more acidic than CH4. In fact, CH4
and other alkanes, as well as NH3, are not called acids.
HI H+ + I- vs. HF H+ + F-
Rationale: here the large size of the I- can easily disperse the negative charge over
its large surface. However the small size of the F atom means that the negative
charge on F- is localized or concentrated in a smaller region of space. This makes I-
a weaker base than F-, so HI is a stronger acid than HF.
H C C H 1 x 10-25 25
The above data shows that the three hydrocarbons are essentially non acidic.
However, of the three, acetylene, C2H2, is the strongest acid.
Consider what happens if CH4 acts as an acid and loses a proton. The resulting
methyl anion is a very strong base as the lone pair is in an sp3 orbital that extends
far from the nucleus and thus can easily be donated to a positive species such as
H+. As a result CH4 is not acidic.
Sketch:
Compare with the anion that results when acetylene loses a proton, The resulting
acetylide anion has a lone pair of electrons in a sp hybrid orbital which is relatively
close to the carbon nucleus. So the lone pair is less easily donated, the anion is less
basic and as a result C2H2 is more acidic than CH4.
Sketch:
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2. Sodium amide, NaNH2, where the basic species is the amide ion, NH2-.
NH2- is a stronger base than CH3O-. (N is less electronegative than O).
Example: NaNH2 + HCO2H
b) ethyllithium, CH3CH2Li, where CH3CH2-, the ethyl anion, is a very strong base.
4. Sodium hydride, NaH i.e. Na+H- The hydride ion is a very strong base.
Problems: Write the products expected in each of the following reactions; then
write the net ionic equation using the arrow pushing technique.
NaNH2 + CH3OH
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CH3Na + CH3CO2H
NaH + H2O
Add all missing lone pairs in the following reaction. Identify the Lewis acid and
Lewis base. Write the arrow pushing mechanism.
H F H F
H N B F H N B F
+
H F H F