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Organic Derivatives of Water

Rocelyn Ann C. Ramos Human Biology 22 De La Salle University-Dasmarias Dasmarias City, Cavite, Philippines

ABSTRACT Alcohols, hydroxyl groups, have different types, namely, primary, secondary, tertiary alcohols, phenols and ethers. The solubility and reactivity of alcohols were tested in the experiment to distinguish the uniqueness of each type. Primary alcohol used in the experiment is ethanol which has positive reaction in Bayers oxidation, originally deep purple in color, producing brown precipitates and in Chromic acid oxidation, originally a yellow orange solution, which turned ethanol into a bluish green solution. In secondary alcohol, 2-butanol in the experiment, only Ferric chloride has the negative reaction. In Bayers and Chromic acid oxidation, same reaction happened in 2-butanol and in ethanol. And in Lucas Test, 2butanol produced a cloudy-like structure in the solution. Tert-butanol is the simplest tertiary alcohol used in the experiment. It reacted only in Lucast test with a fast reaction. It cannot be oxidize because hydrogen bond cannot be removed and oxygen cannot be added without breaking the single bonds of Carbon. Phenol, hydroxyl group attached in benzene ring, reacted slowly in Chromic acid oxidation but reacted fast in Ferric chloride test. Phenol is the only alcohol that reacted positively in Ferric chloride test. Diethyl ether is obviously, ether is the most stable alcohol that results to negative reactions in all reagents.

INTRODUCTION Alcohol is any compound with hydroxyl functional group (OH) attached to hydrocarbons. (1) It can be classified according to the alkyl groups connected on the carbons with hydroxyl group. (2) Primary alcohols are alcohols with hydroxyl radical attached to a primary carbon. It has general formula of RCH2OH while secondary alcohols have RR'CHOH. These alcohols react on many oxidizing agents. Tertiary have RR'R"COH, where R, R', and R" stand for alkyl groups. This type of alcohol is not reactive but in nucleuphilic substitution, it is the most reactive one. Phenols are also known as carbolic acid or phenic acid. Its general formula is C6H5OH and composed of benzene ring and hydroxyl group. It is oxidized via the strongest oxidative agents only. Ether is another type of alcohol with oxygen atom connected to two alkyl groups. It is the most unreactive among the types of alcohol because of its very stable bond. (2)

MATERIALS AND METHODS Five drops of 1-butanol, 2-butanol, tert-butanol, phenol, diethyl ether and each of the unknown samples were placed on separate dry test tubes. The new set of samples was prepared for each of the test below: a.) Solubility in water added five drops of distilled to each sample, then, shaken and observed its solubility. b.) Solubility in NaOH added five drops, then, shaken and observed. c.) Bayers Oxidation added five drops of Bayers reagent, then, shaken and observed. d.) Chromic acid Oxidation added five drops of Na2Cr2O7 and three drops of concentrated H2SO4. Then, reaction was observed. e.) Lucas Test added ten drops of Lucas reagent, then, shaken and observed for about five to ten minutes. f.) Ferric Chloride Test added five drops, then, shaken and observed. The unknown samples were identified using the solubility and reaction profile of the known ones.

RESULTS AND DISCUSSIONS Alcohols have dissimilar reaction towards different reagents. In the experiment, the alcohols used were ethanol, 2-butanol, tert-butanol, phenol and diethyl ether with other three unknown samples to test its reactivity to various reagents. Each structure of samples is shown below.

OH H3C Ethanol OH

H3C H3C

OH CH3

H3C

CH3

2-butanol

Tert-butanol

OH H3C O CH3

Phenol

Diethyl ether
Figure 1. Structures of Alcohols Used

Ethanol is a primary alcohol with molecular formula of CH3CH2OH. It is flammable, volatile, colorless liquid which is often use as major ingredient in alcoholic beverages. The next type of alcohol used in the experiment is 2-butanol which is a secondary alcohol. This alcohol is also called sec-butanol with formula of CH3CH(OH)CH2CH3. It is totally miscible with polar organic solvents. (4) Tert-butanol, a tertiary alcohol, is a lucid fluid with a camphor-like smell. It is completely soluble with water and miscible with diethyl ether and ethanol. (5) Phenol is found in animal wastes and organic materials but mainly a man-made chemical. It evaporates slower than water and fairly soluble in water. (6) Lastly, diethyl ether, an ether class, is a highly volatile, flammable and transparent liquid. It is commonly used as solvent.

The experiment was performed to identify and compare the solubility and reactivity of the different types of alcohol. The table below shows the types of alcohol reacted or dissolved in reagents given.

Table 1. Solubility and Reactivity Profile of Alcohols SAMPLES Ethanol 2 - butanol Tert-butanol Phenol Diethyl ether Unknown 1 Unknown 2 Unknown 3 Chromic Solubility in Solubility in Bayers acid Lucas Test H2O NaOH Oxidation Oxidation ++ ++ + ++ ++ + + ++ ++ ++ + + + + + Legend: (+) slow reaction; (++) fast reaction; ( - ) no reaction Ferric Chloride Test ++ ++

Ethanol reacted only in Bayers reagent and Chromic acid oxidation. In Bayers, ethanol turned into brownish solution with brown precipitate resulting to a positive and fast reaction. In Chromic acid oxidation, it turned bottle green which means, it is a positive reaction. Then, after ethanol, 2-butanol was tested. The table shows that it reacted in Bayers oxidation with dark brown precipitate, Chromic acid oxidation with bluish green solution and Lucas Test with cloudy solution and soluble in water. Tert-butanol is unreactive to all the reagents except in Lucas test, it has a positive reaction with cloudy solution. Tertiary alcohols cannot be oxidized because hydrogen cant be detached or attach oxygen without breaking the single bonds of carbon. Phenol reacts in strong acids, like, Chromic acid and Ferric chloride and soluble in both water and NaOH. In Chromic acid oxidation and Ferric chloride, the solution turned black. Diethyl ether is the most stable alcohol used in the experiment which results to negative reactions to all the reagents given. It is also insoluble with water and NaOH. Unknown 1 reacts with Bayers oxidation and Chromic acid oxidation, which means, it is a primary alcohol like ethanol. Unknown 2 is unreactive like diethyl ether which means, it is ether. Lastly, unknown 3 is a phenol because it is reactive on both Chromic acid oxidation and Ferric chloride test. Bayers reagent is also known as alkaline Potassium Permanganate (KMnO 4). Its original color is a deep purple solution that used in the experiment to oxidize alcohols. The positive reactions in Bayers oxidation are primary and secondary alcohol, wherein, the primary alcohol is the ethanol and secondary alcohol is a 2-butanol. These two alcohols, when added with Bayers reagent, formed a brown precipitate as well as, the solution turned into dark brown. The pertinent general reactions of the two alcohols are shown below.

OH H3C OH KMnO4 H3C OH

MnO2

Figure 2. Pertinent Reaction of Ethanol in Bayers Oxidation

OH KMnO4 H3C CH3 OH H3C

OH

+
CH3

MnO2

Figure 3. Pertinent General Reaction of 2-butanol in Bayers Oxidation Chromic acid oxidation, also known as Jones test, allows a moderately inexpensive alteration of secondary alcohols to ketones and of mainly primary alcohols to carboxylic acids. (3) Its original color is yellow orange but when reacted positively, the solution turns into greenish or bluish solution. Phenols, primary and secondary alcohols have the positive reaction in Chromic acid oxidation. The pertinent general reactions of the three alcohols are illustrated below.

H3C

OH

H3C

Figure 4. General Reaction of Ethanol in Chromic Acid Oxidation

OH Na2Cr2O7 H3C CH3 H2SO4 H3C

CH3

Figure 5. General Reaction of 2-butanol in Chromic Acid Oxidation

OH Na2Cr2O7 H2SO4

Figure 6. General Reaction of Phenol in Chromic Acid Oxidation Lucas Test ( ZnCl2, HCl) is use to identify and differentiate alcohols of low molecular weight. It is a substitution wherein chloride replaces hydroxyl group. Its original color is a clear to pale yellow but when alcohols react, the solution turned into a cloudy mixture. This cloudy mixture is visible to secondary and tertiary alcohols. In tertiary alcohol, which in the experiment is the tert-butanol, the reaction is faster than in secondary alcohol. The figure below shows the general reaction of the two in Lucas test.

OH

Cl

+
H3C CH3

HCl

ZnCl2 H3C

+
CH3

H2O

Figure 7. General Reaction of 2-butanol in Lucas Test

CH3 H3C OH CH3

CH3

HCl

ZnCl2

H3C Cl

CH3

H2O

Figure 8. General Reaction of Tert-butanol in Lucas Test The mechanism below shows the nucleophilic substitution of tertiary alcohols, like tert-butanol, in Lucas test.
CH3 H3C CH3 OH ZnCl2 H3C CH3 ZnCl 2 CH3 H3C CH3 Cl
-

+H
CH3

+
CH3

H3C CH3

Cl

Figure 9. Mechanism of Tertiary Alcohol in Lucas Test Ferric chloride is a yellow orange solution that when reacted into the solution, it became a dark color solution, like dark green, blue, etc. In the experiment, only phenol reacted in Ferric chloride. The reaction is shown below.

OH HO FeCl3 OH OH Fe
2+

Figure 10. General Reaction of Phenol in Ferric Chloride Test Phenols are more acidic than comparable cyclic and acyclic alcohol because it can delocalize its + electrons and remove its H but it is also one of the weakest among other acids. Phenol can be capable of losing a hydrogen ion since the phenoxide ion created is stabilized to some extent. Alcohols are widely used as major ingredients of alcoholic beverages which according to studies have some health benefits in our body. It can also use as alternative for fossil fuels because it only produce carbon dioxide and water. Ethanol is the least lethal of the alcohols it is applied in perfumes to prevent the plant and animal extracts from leaving off. (7) Phenol used before as antiseptic but by the end th of the 19 century, it is widely used in the synthesis of dyes and aspirin. (8) Lastly, ethers are used as a solvent and general anesthetic.

Polyphenols refers to a chemical structure created by adding to an aromatic benzenoid (phenyl) ring, a hydroxyl (-OH) group like to that found in alcohols. It acts as antioxidant that blocks the action of enzymes that many degenerative diseases such as cancer, Alzheimers and cardiovascular diseases need for growth. They guard cells and body chemicals against damage rooted by free radicals, reactive atoms that give tissue damage in the body.

REFERENCES (1) Clark, J. 2003. Oxidation of Alcohols. http://www.chemguide.co.uk/organicprops/alcohols/oxidation.html (2) Legaspi, G. A. and Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010. Philippines. (Evaluation Copy) (3) Organic Chemistry Portal. Jones Oxidation. http://www.organicchemistry.org/namedreactions/jones-oxidation.shtm

(4) Chemicalland21. 2-Butanol.http://www.chemicalland21.com/industrialchem/solalc/2BUTANOL.htm (5) Chemicalland21. Tert-Butanol.http://www.chemicalland21.com/industrialchem/solalc/TERTBUTYL%20ALCOHOL.htm

(6) Haeback, M. Eco-usa.net: Phenol. 1989. Retrieved 2010 from http://www.ecousa.net/toxics/chemicals/phenol.shtml (7) At Bristol. Alcohol Uses. http://www.alcoholandyou.org.uk/facts/uses.html

(8) Greener Industry. Phenol Uses. http://www.greenerindustry.org.uk/pages/phenol/2PhenolUses.htm