Organic Derivatives of Water

Roque, Jason R. Frias, Abigail Pauline F. Bachelor of Science in Biology – Major in Human Biology College of Science De La Salle University – Dasmariñas Dasmariñas, Cavite, Philippines ABSTRACT

In this experiment the organic derivatives of water were tested. Based on the characteristic solubility behavior and reactions we were able to distinguish the difference among various organic derivatives of water. 95% ethanol, 2-butanol, tert-butanol, phenol, diethyl ether, and three different unknown samples were placed on different test tubes and were tested through solubility test in water, solubility test in NaOH, Bayer’s oxidation, Chromic acid oxidation, Lucas test and Ferric chloride test. 1-Butanol was found to be positive in all tests except with Lucas and Ferric chloride test. 2-Butanol was found to be reactive except in solubility test in NaOH and Ferric chloride test while tert-butanol was negative in all tests except with solubility test in water and Lucas test. On the other hand all reactive except for solubility in water was the result of phenol. Diethyl ether was found non-reactive in all the tests. At the end of the experiment the unknown samples were identified as sample 1-alcohol, sample 2-ether and sample 3-aromatic alcohol/phenol based on their solubility and reaction profile.

INTRODUCTION Alcohols, Ethers, and Phenols are three different functional groups whose common denominator is the presence of a singly bonded Oxygen atom in their chains. Alcohol is an organic compound in which hydroxyl functional group (-OH). It is bound and connected to a carbon atom or hydrogen atom. The most commonly used alcohol is ethanol, C2H5OH, with the ethane backbone. Alcohols are classified into primary, secondary and tertiary, based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. Namely, the primary alcohols have general formulas RCH2OH,secondary ones are RR'CHOH they are both known to be reactive in various oxidizing agents while tertiary alcohols are RR'R"COH, where R, R' and R" stand for alkyl groups. They are unreactive in oxidizing agents but most reactive to nucleophilic substitution in Lucas reagent. Primary alcohols are found to be unreactive in Lucas reagent while secondary alcohols are quite reactive. (2) A compound which contains a six-membered aromatic ring, bonded directly to a hydroxyl group (OH) is called phenol. (4) Its structure is that of a hydroxyl group (-OH) bonded to a phenyl ring and it is an aromatic compound. It is much acidic compared to alcohol and has limits in solubility in water. On the other hand ethers are stable in bond that results to being generally unreactive. (1)(4) It has an oxygen atom directly bound to two hydrocarbon (alkyl or aryl) groups and its common example is diethyl ether.

In this experiment we assume that those characteristics of alcohol, ether and phenol are to be seen. The unknown samples will react to different tests for them to be classified and by then end of the experiment correct identification will be achieved. MATERIALS / REAGENTS & EXPERIMENTAL PROCEDURE In performing the experiment, there are certain procedures in order to attain the right result. Place 5 drops/1mL of the different samples (1-butanol, 2-butanol, tert-butanol, phenol, diethyl ether, and the other unknown samples) on different dry test tubes. Test the different samples into two kinds of test, the solubility test, which is comprises of solubility in NaOH & water, and the other is chemical test, which is comprises of Bayer’s oxidation test, chromic acid oxidation test, Lucas test, and Ferric chloride test. To make it more detailed, for the solubility of water, add 5 drops/1mL of distilled water to each different sample. Shake, and then observe the solubility. For solubility of NaOH, add 5 drops/1mL also to each kind of sample. Shake also and observes it solubility. In order to determine the solubility of the mixture, for fast reaction, there must be only single layer only, for slow, there will be a cloudy layer and for no reaction, there is a presence of two layers. In the chemical test, for Bayer’s oxidation test, add 5 drops/1mL of the Bayer’s reagent to the samples. For the Chromic acid oxidation test, add 5 drops/1mL of Na2Cr2O7 and 3 drops of concentrated H2SO4. For the Lucas test, add 10 drops of Lucas reagent and observe it for a minimum of 5 minutes and maximum of 10 minutes. For the Ferric Chloride test, add ferric chloride to the sample. Observe every reaction of the different samples. Note: Phenol, concentrated sulfuric acid, sodium dichromate, and NaOH are corrosive substances. Avoid direct skin contact. Di-ethyl ether vapor is toxic, avoid inhalation. (1) DATA & RESULTS In order to determine if the reaction of a compound is fast, slow or no change at all, there must be a basis for every reaction. The table below shows the differentiation of solubility test, by having a single layer, presence of emulsion or formation of two layers. Also, it shows the pertinent reaction of different reagents according to its color or formation of cloudiness. Table 1. Basis for Reaction (1) SOLUBILITY High Soluble / Miscible (++) Slight Soluble / Miscible(+) Insoluble / Immiscible (-) Single Layer Appearance Emulsion Formation of Two Layers

Reagent Bayer’s Reagent Chromic Acid Lucas’ Test Ferric Chloride

Color Dark Violet Yellow Orange Clear with Light Brown Tinge Deep Yellow Orange

CHEMICAL REACTIONS Fast Reaction (//) Slow Reaction (+) Fade & Brown Fade & Brown Precipitate Precipitate Change in Color Change in Color Cloudiness w/o Cloudiness w/o Shaking (Stand in Shaking (Stand in 5 mins.) 10 mins.) Black Violet / Black Violet / Black Greenish Black Greenish

No Reaction (-) No Change No Change No Change No Change

The table below shows the solubility and reactions of different samples that undergone into different test. This table shows the different derivatives of water and their unique characteristics. Certain samples are shown and are the same with the other that shows that they belong to same group. Table 2. Solubility & Reaction Profile (1) Solubility Test Samples H2O NaOH Bayer’s Oxidation ++ ++ + ++ ++ Chemical Test Chromic Acid Lucas Test Oxidation + + + ++ ++ ++ ++ + ++ ++ Ferric Chloride Test ++ ++

Ethanol ++ ++ 2-Butanol + tert-Butanol ++ Phenol Diethyl Ether Unknown 1 + Unknown 2 Unknown 3 ++ Legend: ++ = fast reaction / completely soluble + = slow reaction / slightly soluble - = no reaction / insoluble Identities of Unknown Samples Sample 1: Primary Alcohol Sample 2: Ether Sample 3: Phenolic Compound I. Solubility Test Solubility in Water (H2O): (5)

The different samples that are tested by solubility of water do not contain the same result. It is concluded that there are factors that may occurred or inert to them that may or may not be applicable in soluble in water. - Basically, alcohols are insoluble in water except if they are in Carbon-6. - Compound that is in a polar function group is more soluble. e.g. butanol > butane - The presence of polar functional group (-OH, -NH2, -CO2H) - Like dissolve like. - The more branching is present in a compound, the more it will be soluble. e.g. tert-butanol > sec-butanol > n- butanol - The branching or Carbon chain may also affect the solubility of the compound. - The higher the number of Carbon atom, the more it is insoluble or less soluble. Solubility in Sodium Hydroxide (NaOH): (6) The solubility of organic compound in NaOH is quite different in water. There are certain characteristics that make other compounds soluble in it while insoluble in water. (6) - A compound is deemed “soluble” in NaOH if it is significantly soluble in water. - Some sodium salts with highly substituted Phenols are Insoluble in 5% NaOH.

- Phenols react with sodium hydroxide solution to give a colorless solution containing sodium phenoxide.

Figure 1. Reaction of Phenol with Sodium Hydroxide Phenol dissolves in aqueous sodium hydroxide because phenol behaves as an acid and gives up its proton to the hydroxide ion which is a base. A soluble ionic product is formed. In this reaction, the hydrogen ion has been removed by the strongly basic hydroxide ion in the sodium hydroxide solution. II. Chemical Test Bayer’s Oxidation:

Figure 2. Bayer’s Oxidation Reaction in Alkenes and Alkynes Bayer's reagent (KMnO4) is an alkaline solution of potassium permanganate, which is a powerful oxidant. This reagent is used for oxidation (Bayer’s Oxidation). Reaction with double or triple bonds (C=C- or -C≡C-) in an organic material causes the color to fade from purplish-pink to brown. The disappearance of the purple color and the appearance of a brown precipitates concludes that it is a positive test. Often, the brown precipitate fails to form and the solution turns reddish-brown. Also, easily oxidized gives a positive test. - Positive test is done by most of aldehydes. - Formic acid and its esters give also a positive test. - Traced impurities that are present alcohol will then give a positive test. - Carbonyl compound which decolorizes bromine / carbon tetrachloride will give a negative test. Chromic Acid Oxidation: (7) Chromic acid is capable of many kinds of organic compounds. Chromic acid test, Di-chromate test, and Jones test are the test for oxidizables or any compounds that possess reducing property (has an alpha acidic hydrogen). Chromic acid (acidified dichromate, an oxidizing agent) can also be used to distinguish between types of alcohols by oxidizing the alcohol. Primary alcohols are oxidized to carboxylic acids; secondary alcohols are oxidized to ketones; and tertiary alcohols are not oxidized.

Figure 3. Chromic Acid Oxidation Lucas Test: (8) This test in alcohol will differentiate whether if it is primary, secondary, or tertiary alcohols. It is based on the difference in the reactivity of the three classes of alcohols with hydrogen halides. When an alcohol is reacted with Lucas reagent (anhydrous ZnCl2, HCl), the resulting mixture which is alkyl halide will not be soluble in water, thus presence of cloudiness and second layer will form if only the test is positive. With this reagent, time is essential in order to determine if the compound reacts with it. In tertiary alcohol it reacts immediately, for secondary alcohol, 3 – 10 mins. is needed, while in primary alcohol, it may take an hour or longer or may even not react at all.

Figure 4. Lucas’ Test for Primary, Secondary and Tertiary Alcohol Lucas’ test together with the samples will be considered positive reactions if they have these following characteristics: - No visible reaction (primary, such as normal amyl alcohol, 1-Pentanol) - Solution turns cloudy in 3 5 mins (secondary, such as sec-amyl alcohol, 2-Pentanol) - Solution turns cloudy immediately, and/or phase separate (tertiary, such as tert-amyl alcohol, 2Methyl-2-Butanol) Ferric Chloride Test: (9) It is used to determine the presence or absence of phenols in a given sample. This test is traditional calorimetric test for phenols which uses a 1% iron (III) chloride solution that has been neutralized with sodium hydroxide until a slight precipitate of FeO(OH) is formed. A transient or permanent coloration (usually purple, green or blue) indicates the presence of a phenol or enol, which indicates a positive reaction also.

Figure 5. Ferric Chloride Test REFERENCES (1) (2) (3) (4) (5) (6) Legaspi, G.A., Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010 Retrieved on January 30, 2011. http://www.wikipedia.org/wiki/Alcohol Retrieved on January 30, 2011. http://www.newencylopedia/Phenol Retrieved on January 30, 2011. http://www.newencylopedia/Ethers Retrieved on January 27, 2011. http://www.wikipedia.org/wiki/Solubility Retrieved on January 27, 2011, http://www.chemistry.ccsu.edu/glagovich/teaching/316/qualanal/solubility/naohs (7) Retrieved on January 27, 2011, http://en.wikipedia.org/wiki/Chromic_acid (8) Retrieved on January 27, 2011, http://www.enwikipedia.org/wiki/Lucas’_reagent (9) Retrieved on January 27, 2011, http://www.enwikipedia.org/wiki/Ferric_chloride_test/

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