Nurul Ain Nabilah Binti Mohd Ramzan

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ACTIVITY 2.5

1. Draw molecules:

 Acetic acid.

 Ethanol.

 Trifluoro acetic acid.

 Phenol.

 Cyclohexanol.
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2. Arrange by acidity and conjugated base.

 Acidity
Trifluoro acetic acid > Acetic acid > Phenol > Cyclohexanol > Ethanol
 Conjugated base
Ethanol > Cyclohexanol > Phenol > Acetic acid > Trifluoro acetic acid

 The stronger the acid, the weaker will be its conjugate base.

3. Write answer based on the factors that have been introduced earlier:

i. Molecular electrostatic potential:

 Acetic acid.

 Ethanol.

 Trifluoro acetic acid.

 Phenol.
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 Cyclohexanol.

 The acid usually represent by blue region and the base represent by red region. So, from the
molecular electrostatic potential (MEP) we can see that trifluoro acetic acid have larger
region of blue while ethanol have the least region of blue.

ii. Inductive:

 The answer to judge the acidic strength of compounds almost always lies in the stability of
its conjugate base. In this case, acetic acid dissociates to give 𝐻+ and 𝐶𝐻3𝐶𝑂𝑂−.
Trifluoroacetic acid gives 𝐻+ and 𝐶𝐹3𝐶𝑂𝑂−. Now both the conjugate bases are quite stable
entities due to equivalent resonance of the negative charge between the two 𝑂 atoms.
However, in the second conjugate base, the negative charge is further delocalized because
of the strong -I effect of the three 𝐹 atoms. Hence, due to a more stable conjugate base, the
dissociation is further pushed in the forward direction, and more protons are released. The
phenol more acidic than cyclohexanol because its conjugate base is resonance stabilized
comparison to cyclohexanol where no such thing occurs and it have phenyl group which is
an electron withdrawing group and produce (-I effect). On the otherhand in aliphatic
alcohols the same things happen in terms of the OH- cleavage but the conjugate is not
stabilised by resonance hence it is less likely that a proton is donated. Ethanol is an elctron
donating group whice produce (+I effect).

iii. Hybridization:

 Acetic acid: C,4 —> sp3 H,1 —> s O,2 —> sp

 Ethanol: C,4 —> sp3 H,1 —> s O,2 —> sp
 Trifluoro acetic acid: C,4 —> sp3 H,1 —> s O,2 —> sp F,1 —> s
 Phenol: C,4 —> sp3 H,1 —> s O,2 —> sp
 Cyclohexanol: C,4 —> sp3 H,1 —> s O,2 —> sp
 Increased percent s-character of orbital containing lone pair in conjugate base increases
acidity of corresponding acid. So we can see that trifluoro acetic acid contain the highest
percentage of s orbital.

iv. Acidity constant:

 Acetic acid – 1.77 * 10^-5

 Ethanol – 15.9
 Trifluoro acetic acid – 0.52
 Phenol – 9.95
 Cyclohexanol – 16
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 The lower the pKa value, the acid strength increasing. So we can see that trifluoro acetic acid
have the lowest value of pKa followed by others.

v. Solubility:

 Trifluoride acetic acid and acetic acid soluble in water. The compound will be more acidic if
its can soluble in water.

vi. Structure:

 Since trifluoro acetic acid contain fluorine which is the most electronegativity among others.
H-F is yhe most polarized and most positive. So it loses a proton most readily and the most
acidic.
 The weaker the bond strength the higher the acidity.