III.

Results and Discussion

A. Solubility and Acidity of Carboxylic Acid

Table A.1 Summary of the reaction of samples to different solvents to test its solubility in
water

Sample Solubility in H20 Blue Litmus Paper test

Acetic acid Soluble turned red
Sodium benzoate Insoluble (white remained blue
precipitate)
Benzoic acid soluble turned red

A.1 Water Solubility test

Acetic acid, benzoic acid, and sodium benzoate are the samples used in the

water solubility test and test for acidity using blue litmus paper. Based on the results, only

benzoic acid was insoluble in water. On the other hand, only sodium benzoate did not change

the color of blue litmus suggesting it is a basic compound.

Acetic acid is an organic compound that has a chemical formula of

CH3COOH. In water solubility test acetic acid is soluble in water. The C=O and OH bonds

are polar. C=O pulls electron density away from OH; thus making H more readily available

and can easily be donated. Acetic acid is polar so it dissolves in polar water. Also, it has a pka

of 4.76 while H2O has a nominal pka of 14 at 25C. Thus, there is a significant fraction of

acetic acid which will deprotonate the acetate ion (CH3COO-) in H2O and the pH decreases

upon addition of acetic acid where the solution would contain acetic acid, water, H + and the

ionized versions of water (OH and H3O +) (Carson, 2016;Giri, 2016; Kessler, 2016). The

reaction would be

CH3COOH + H2O <---> CH3COO- + H3O+

It is an acid because it donates H+ in solution. This was then indicated and supported when

blue litmus paper turned red

Sodium benzoate is a sodium salt of benzoic acid. Ionic and easily dissolves in water .

(Wibbertmann, et al, 2005). The presence of C=O makes the compound polar and H+ in

water molecules are attracted to the O in C=O. Then hydrogen bonds are formed. Na+ is also

attracted to negatively charged OH- in water which makes the solution basic as indicated by

blue litmus paper. The reaction would be

C6H5COO-Na+ + HCl -------> C6H5COOH + NaCl

On the other hand, benzoic acid was found to be insoluble and acidic. In benzoic acid,

the COOH group is attached to the stable benzene ring. It may be insoluble in water because

of its very long carbon chain. (Wibbertmann, et al., 2005). As the length of the chain

increases, the polarity of the x`molecule decreases. However it is slightly soluble in water

because of the strong intermolecular hydrogen bonds due to its C=O and OH. The C=O and

OH make it polar which is soluble in polar water. In solvation, the H+ in water is attracted to

O in C=O and H+ is attracted to O in water. Moreover it is acidic since it can donate its H +

and this is supported by the blue litmus paper turning into red.

A.2 Relative acidities of carboxylic acids and phenols

Table A.2 Summary of the reaction of benzoic acid and phenol to NaoH and NahCO3

Sample 10% NaOH 10%NaHCO3

Benzoic acid clear solution with white
ppt at the bottom
Phenol slightly cloudy solution
with white ppt as the
bottom
clear solution with white
ppt at the surface
clear solution with white
jelly liquid at the bottom

Benzoic acid and phenol are the samples tested for their solubility in

sodium hydroxide and sodium hydrogen carbonate. The results showed that only benzoic acid

is soluble in NaOH while both samples did not dissolve in NaHCO3.

 The benzoic acid has C=O where the carbonyl withdraws electrons from the oxygen

of the OH group. This makes benzoic acid a stronger acid than phenol because the OH bond

becomes easier to break and H+ donation is very easy. Another reason for the increased

acidity of the carboxylic acid such as benzoic acid is the resonance energy of the carboxylate

anion. The carboxylate anion has greater resonance energy than carboxylic acid because the

anion has two stable resonance contributors while the carboxylic acid has only one resonance

contributor. Therefore, loss of a proton from carboxylic acid is accompanied by an increase in

resonance energy. Thus, since phenol is basic compared to benzoic acid and more reactive to

NaHCO3 (Rapoport, 2003).

An aromatic alcohol such as phenol is a strong acid but is weaker than benzoic acid.

Electron withdrawal in phenol is not as great as in benzoic acid. Phenol can lose a hydrogen

ion where the phenoxide ion is stabilized. Thus, there is electron delocalization in phenol

anion but not as great as in a carboxylate anion, where the negative charge equally shared by

two oxygen. As a result, the resonance energy of the phenolate anion is less than that of

carboxylate anion (Clark, 2004). Since benzoic acid is a stronger acid than phenol, its H+ is

readily donated when reacted with NaOH base. Phenol also loses its H+ but not as easy as

benzoic benzoic acid. Both also loses H+ when reacted with NaHCO3.
 Also, benzoic acid is more acidic than phenol because the OH- is attached to a carbon

with another O attached to it, leading to greater stability when H is released

Saponification of Coconut oil.

Formation of soap consists of boiling of oil in aqueous sodium hydroxide and adding sodium

chloride to precipitate the soap (Saponification, nd). An example of soap precipitation is:

Saponification is a primitive organic chemical reaction in preparing soaps. Natural soaps such

as in this experiment, are salts of fatty acids or oils that when hydrolyzed yields glycerol and

crude soap. Sodium hydroxide is heated with oil in order to hydrolyze fats. Lipids containing

fatty acid ester linkages can undergo hydrolysis catalyzed by a stronger base or acid. The

triglyceride in the acid released a single glycerol molecule where the fatty acid reacts with the

OH- in the base to form crude soap. The crude soap obtained from the saponification reaction

contains sodium chloride, sodium hydroxide, and glycerol (Saponification, nd).

D. Comparisons of soaps and detergent

Table 3. Behavior of soap and detergent in four different methods/solvents

Soap Detergent
1. Hydrolysis Slightly bluish solution; Slightly bluish solution;

soluble soluble
2. Reaction with Acid Cloudy solution excessive bubble formation
3. Reaction with soft

and hard water

4. Emulsifying reaction
The polar head of a detergent is negatively charged so it is an anion surfactant.

When detergent is reacted with water, the result is a basic as indicated by blue

litmus paper. In this experiment, it was determined that both mixtures are of a

basic attitude with water. However, when it comes to the reactivity with an acid,

there exists an important difference between the two that is the sensitivity of

soaps to acidic conditions. When putting a soap into an acidic solution having pH

less than 4.5 it protonates the carboxylate group. The protonated soap molecule

does not have a charged head, making it insoluble in water. The soap molecules

precipitate out thereby producing a cloudy mixture that leads to the formation of

a scum. Hence, we can say soaps are not suitable for uses in acidic conditions.

As seen in the observations indeed a foggy texture was experienced compared to

the almost clear detergent solution.

References

Carson, S (2016). Quora. Retrieved November 27, 2016 from https://www.quora.com/What-

is-the-reaction-of-acetic-acid-in-water
Clark, J (2004). The acidity of Phenol. Retrieved November 27, 2016 from

http://chemguide.co.uk/organicprops/phenol/acidity.html

Giri, D. (2016). Quora. Retrieved November 27, 2016 from https://www.quora.com/What-is-

the-reaction-of-acetic-acid-in-water

Kessler, M. (2016). Quora Retrieved November 27, 2016 from https://www.quora.com/What-

is-the-reaction-of-acetic-acid-in-water

Rapoport, Z. 2003. The chemistry of phenols. Retrtieved form:

http://rushim.ru/books/mechanizms/chemistry-of-phenols.pdf

Saponification (nd). Retrieved November 29, 2016 from

http://chemistry.about.com/od/chemistryglossary/ss/Saponification-Definition.htm

Wibbertmann A, J. Kielhorn J, G. Koennecker G, I. Mangelsdorf I, C. Melber C.( 2005).

Benzoic Acid and Sodium Benzoate. Retrieved from:
http://www.who.int/ipcs/publications/cicad/cicad26_rev_1.pdf