Lab # 5

Types of Organic Compounds (Polymers and Esters)

Christina Mollo
Brianne Bohrman
Professor Marino
Chemistry 112

Introduction
 Polymers are
substances whose molecules
have high molar masses and are
composed of a large number of
repeating units. Polymers can be
both naturally occurring or
synthetically made (Shakhashiri). Naturally occurring polymers include proteins, starches,
cellulose, and latex. Synthetic polymers, or plastics, are produced commercially on a large scale
and have a wide range of properties and uses. Polymers are formed by chemical reactions in
which a large number of monomers are joined sequentially, forming a chain. Some polymers use
only one monomer, while others can use two or three (Shakhashiri).

One polymer that only uses a single monomer in a reported chain is polyvinyl alcohol
(PVA), otherwise known as [CH2CH(OH)-]n (Marino). It is a water-soluble synthetic polymer
and is non-hazardous. (Polyvinyl Alcohol (Inactive Ingredient)). PVA is used in many adhesive,
films, and elastomers. It is commonly used to in the preparation of slime in a school setting.
Polyvinyl alcohol is a linear polymer with a repeating vinyl alcohol as its repeating monomer. It
has a molecular weight anywhere from 25,000 to
300,000 (Marino).

Figure 1: The molecular structure of PVA. Note the brackets with the n subscript, indicating that
this vinyl alcohol unit is in a chain, which makes it PVA.

Sodium borate decahydrate (Na2B4O710H2O), otherwise known as borax, is another

common ingredient used to make slime. It contains boron atoms with both tetrahedral and
trigonal planar stereochemistry. (Baker) When it dissolves in water, it hydrolyzes to form a
borate ion-boric acid buffer, which has a pH of around 9 (Marino).
 Figure 2: Equation 1 showing the hydrolysis of sodium borate dechydrate (Baker).

The equilibrium reaction between boric acid and the borate ion is depicted in Figure 3

(Marino):

Esters are derived from carboxylic acids. A carboxylic acid contains the -COOH group,
and the ester replaced the H with a hydrocarbon. This could be an alkyl group like methyl or
ethyl, or one containing a benzene ring such as a phenyl or benzyl group. Many compounds that
contribute to nice aromas and pleasant flavors are esters (An Introduction to Esters). Esters can
be produced by reacting a carboxylic acid with an alcohol in an acidic medium. Although the
reaction is reversible, a greater production of ester can be forced by using an excess of alcohol. A
combination of different carboxylic acids and alcohols produce different esters, producing their
own unique smell (Marino).

Figure 4: The functional group of an ester.

Methyl salicylate, or wintergreen oil, is an organic ester that is naturally produced by

many species of plants, but it can also be synthetically produced. It is used to flavor chewing
gums, mints, and candies. It is used as an antiseptic in Listerine. It can also become a source of
triboluminescence when mixed and dried with sugar, which can gain the tendency build up
electrical charge when crushed or rubbed. Methyl salicylate can be produced by esterifying
salicylic acid with methanol. ( Sigma-Aldrich Co.)
 Figure 5 (Marino): The
esterification of methyl salicylate
(end product). Note that
salicylic acidic (on the far left) is combined with methanol (second reactant) to form the
wintergreen oil.

Ethyl acetate (C4H8O2) is an ether with a sweet, fruity odor. It is found in alcoholic
beverages, cereals crops, radishes, fruit and juice. It can be used as a solvent in the manufacture
of modified hop extract (found in beer) and in decaffeinated tea or coffee. It can also be found in
nail polish removers and glues. Ethyl acetate is the ester of ethanol and acetic acid. It is
manufactured on a large scale and used as a solvent.

Figure 6: (Marino) Esterification of ethyl acetate.

Note the first product, acetic acid is combined with ethanol, a strong alcohol.
Conclusion

Borate polymer I was made in the following procedure. 50mL of 4% polyvinyl alcohol
solution was measured and poured into a small beaker. A few drops of red food coloring was
added and stirred with a stick, solely for aesthetic purposes. 5 ml of 4% sodium borate solution
was added to the beaker with the polyvinyl alcohol solution. This was done by slowly pouring
the sodium borate solution into the solution and constantly stirring with a wooden stick. The
mixture immediately turned into gel, but was continually mixed until the mixture had a smooth
consistency.

Borate polymer II was made in the following procedure. 30 mL of Elmers Glue was
poured into a 150 mL beaker. Glue was used for this polymer, as well as polymer III because it
contains polyvinyl-acetate, which is similar to polyvinyl alcohol. The 4% sodium borate solution
was slowly added while constantly stirring. Instead of having an exact amount of the solution,
the sodium borate was added until no more borate was absorbed. The polymer was then rolled
into a firm ball and rinsed under the water to get rid of any residual glue.

Borate Polymer III was made in the following procedure. 30 mL of Elmers glue was
placed into a small beaker. Similarly to the Borate polymer II, sodium borate was added slowly
until no more was absorbed. However, for the third polymer, 8% sodium borate was used. This
solution is much thicker than the 4% sodium borate solution. This sodium borate was added
while being stirred constantly. This polymer was also rolled into a firm ball and rinsed under
running water, to rid the slime of any residual glue.

Borate polymer I resulted in a slime that was like jello. This slime was not very sticky, it
was more slimy and slippery. This was so because polyvinyl alcohol was used instead of Elmers
glue, and only 4% sodium borate was used instead of 8% sodium borate. Borate polymer II was
thicker than the first, and also very sticky. This stickiness was attributed to the Elmers glue that
was used. The thickness was also attributed to the mixture of sodium borate and Elmers glue.
The borate polymer II could have been thicker than the borate polymer I due to the fact that
polymer II did not require a specific amount of sodium borate, while polymer I required
specifically 5mL. Borate polymer III was the thickest and the stickiest out of the three slimes.
This was due to the fact that 8% sodium borate solution was used. This type of sodium borate
was much thicker than the sodium borate solution used in the prior slimes. Since this was the
case, the slime itself was much thicker. With these results, it was conclusive that 8% sodium
borate and Elmers glue, when combined, made the thickest and stickiest mixture.

The formation of esters was done in the following way. A 150 mL hot water bath was
prepared in a 250 mL beaker over a hotplate. Two esters were made: methyl salicylate and ethyl
acetate.

Methyl salicylate was made by placing 0.1g of salicylic acid in a test tube. It was noted
that the salicylic acid had a strong, vinegar-like smell. 15 drops of methyl alcohol were added,
followed by 3 drops of 6M sulfuric acid. After all was added to the test tube, the tube was shaken
cautiously. The test tube was placed in the hot water bath. After one minute, the aroma was
wafted. It was clear that the vinegar smell had disappeared, and the new smell was a minty,
wintergreen smell. Referring to the introduction, wintergreen oil is produced by esterification of
salicylic acid and methanol, which was the process that was done in the laboratory.

Ethyl acetate was made by combining 20 drops of ethyl alcohol, 2 drops of acetic acid,
and 3 drops of 6M sulfuric acid into a small test tube. The liquids were carefully mixed by
shaking the tube. The tube was placed into the heated water bath. After a minute, the aroma was
wafted. The smell was a sweet smell, much like nail polish remover. The new product, ethyl
acetate, was noted on the data sheet. Referring to the introduction, ethyl acetate is made from the
esterification of acetic acid and ethyl alcohol. The result is ethyl acetate and water.
 Works Cited

"An Introduction to Esters." Chem Guide. N.p., n.d. Web. 20 June 2017.

Baker, Colin. "A crossed-link polymer." Education in Chemistry. N.p., 31 Dec. 2004. Web. 21

June 2017.

Marino, Michae. "Lab #5 Prelab: Types of Organic Compounds (Polymers and Esters)." 20 June

2017. Lecture.

"Polyvinyl Alcohol (Inactive Ingredient)." Drugs.com. Drugs.com, n.d. Web. 21 June 2017.

Shakhashiri, Bassam Z. "Chemical of the Week -- Polymers." Science is Fun. University of

Wisconsin-Madison, n.d. Web. 20 June 2017.

Sigma-Aldrich Co., Methyl salicylate. Retrieved on 2013-05-23.