Experiment # 7 Organic Derivatives of Water
In Partial Fulfillment for the Requirements in Chem 31.1
Submitted by: Niña Krisanta Albelar Nelson Catipay III Jaesen Peter Ismael
Submitted to: Mark Lester G. Viendo April 20, 2017
I.
Introduction
Oxygen can be found in many important organic compounds, but there are some oxygen containing compounds that are known to be as the organic derivatives of water which are known as alcohols, phenols and ethers. These organic compounds replace one or both of the hydrogen atoms present in the water molecule with an organic group. Alcohols replace one of the hydrogen atoms with an aliphatic group, it is replaced by an aromatic group for phenols and for ethers; both hydrogen atoms are replaced (“Organic Derivatives of Water”,2015). Each organic derivative of water mentioned above will be discussed d iscussed and was used in the experiment. ex periment. Alcohols are defined as any class of organic compounds that contains one or more hydroxyl (-OH) groups that is attached to a carbon atom of an alkyl group. Alcohols are known to be one of the most common organic compounds which have a variety of uses (Wade,2011). Alcohols are classified into 3 types which are primary, secondary and tertiary. Primar y alcohols (1°) are alcohols with hydroxyl radical attached to a primary carbon, which have a general formula of RCH2OH (Ramos, 2014). A secondary alcohol (2°) has the hydroxyl group on a secondary carbon atom, which is also bonded to two other carbon atoms, it has a general gen eral formula of RRCHOH. Similarly, a tertiary alcohol has the hydroxyl group on a tertiary (3°) carbon atom, which is bonded to three other carbons and has a general formula of RR’R’’COH where R, R’ and R’’ are for alkyl groups (Wade,2011). Phenols are compounds which contains an aromatic ring that is bonded directly to a hydroxyl group. Its structure is that of an hydroxyl group bonded to a phenyl ring, which is considered to be an aromatic compound. It is much more acidic than alcohol and has its limits when it comes to solubility in water (Frias & Roque; 2011). Phenols have a general formula of C6H5OH and is composed of a benzene ring and hydroxyl(Ramos,2014).
Although phenols also somehow belong to the alcohol family, there are differences between them. One major difference is that the OH present in alcohols are attached to a sp3 hybridized carbon, which can’t have multiple bonds. While phenols are attached to an sp2 hybridized carbon, which means that phenols can have two or more bonds attached to it (“Differences between phenols and alcohols”,2015). Some other differences between the two is that phenols are stronger acids than alcohols and that phenols can be distinguished from alcohols when both are dissolved in an aqueous NaOH solution (Difference Between Alcohols and Phenols, 2011). Ether is another type of alcohol with an oxygen atom connected to two alkyl groups. It is the most unreactive among the three due to its very stable bond. It has an oxygen atom directly bound to either the alkyl or aryl groups (Frias & Roque;2011). Ether has a general formula of ROR where one common example is diethyl ether, which was used as a sample in the experiment. Ether is divided into two types, which is the symmetrical and unsymmetrical ether. If the substituents have the same IUPAC name, the ether is known to be symmetrical but if the substituents have different IUPAC names, it is known to be unsymmetrical (Pagaduan & Peji; 2014). The objectives of the experiment are as follows: to use all the different organic derivatives of water in various experiments as samples in order to be familiarized of their varying chemical properties and to examine then record the different ways of reactivity of alcohols (which is subdivided into primary, secondary and tertiary alcohols), phenols and ethers as they are made to react with some chosen chemical reagents.
II.
Methodology
A. Solubility Behavior
A set of clean, dry test tubes were labelled with the corresponding sample that was to be tested for its solubility behavior, wherein 5 different samples were used, namely; n-butanol, 2 butanol, t-butanol, diethyl ether and phenol. First, about two milliliters of water was poured into a test tube, then 10 drops of a certain sample followed. The mixture was covered with a cork and was shook for a bit. The same procedure was repeated but instead of water, one mL ten percent NaoH was used as the solvent. The test tubes were then examined/observed for any changes and the data was recorded. For the compounds that had insoluble layers, the samples underwent the same procedure but this time concentrated H2SO4 was used as the solvent. All observations made were recorded. B. Chemical Reactivity 1. Reaction with potassium permanganate
The test tubes were labelled with the corresponding sample that was to be poured in it, then about three milliliters of slightly acidic potassium permanganate was placed in a dry test tube, five drops of a certain sample followed. The procedure was repeated until all five samples were used, observations were made with each mixture. The mixture was then covered with a cork and was placed in a water bath wherein the temperature of the hot plate was set to low. After five minutes, the mixture was removed from the water bath and all observation made were recorded. 2. Reaction with Tollen’s reagent
The test tubes that were used in this part of the experiment were washed and dried to ensure that the walls and the test tubes were clean before the experiment was conducted, in order to avoid
error. Three milliliters of Tollen’s reagent was placed in a test tube which was then added with 5 drops of a certain sample, observations were made as the two liquids were mixed. The procedure was repeated until all samples were used. The mixture was then covered with a cork, shook and was heated gently in a water bath. After some time, the mixture was removed from the water bath and observations were made and recorded. 3. Lucas Test: Reaction with HCl- ZnCl 2 mixture
Two milliliters of Lucas’ reagent was placed in a test tube, then five drops of sample was added right after. Right after the drops of sample was added, a timer was started in order to note the time of the appearance of an insoluble layer or if when emulsions formed. The procedure was repeated until all samples were used. A cork was covered to the test tube where the test tube was then allowed to stand until an insoluble layer or emulsions occurred. The time was noted and then observations were made as the insoluble layer or emulsions took place. 4. Reaction with Ferric Chloride (FeCl 3)
First, two drops of a certain sample and 2 milliliters of water was mixed in a test tube. The procedure was repeated until all samples were used. The mixture was then added with several drops of two and a half percent aqueous FeCl3.The mixture was then examined if any changes occurred and the observations made were recorded. 5. Iodoform test: Reaction with I 2, NaOH
One milliliter of a certain sample was placed in a test tube, where 2 milliliters of water was then added. About one milliliter of I2 solution was added, where the solution turned yellow. In order for the color to disappear/become faint, some drops of ten percent NaOH was added into the mixture and the test tube was covered with a cork. The procedure was repeated until all samples
were used. The test tube was then examined and observations were made. If the mixture seemed to have a negative result, the test tube was shook for a bit. The mixture then underwent a water bath where it was heated at a relatively low temperature. The mixture was then re -examined and the observations made were recorded.
III.
Results and Discussion
The organic derivatives of water that were used as samples in the experiment were t-butyl alcohol, phenol, di-isopropyl ether, 1-butanol and 2-butanol. The samples used appeared to be in liquid state except for phenol that appeared to be in solid form. Alcohols fall into different classes depending on how the -OH group is positioned on the chain of carbon atoms. In the experiment, the primary alcohol was the 1-butanol, the secondary alcohol was the 2-butanol and the tertiary alcohol was the t-butyl. The samples undergone several chemical tests to determine the differences in chemical reactivity of primary, secondary and tertiary alcohols, phenols and ether towards selected chemical reagents. The solubility behaviour of each of the samples in different solvents which were water, NaOH and H2SO4, were first tested in the experiment. Basically, the solubility of the samples also follows a simple rule, “like dissolves like”, where it is based on the polarity of the systems such that polar molecules dissolve in polar solvents and non-polar molecules in non-polar solvents (Clackamas Community College, 1998). Table 1.0. Solubility test results Solubility test Samples H2O
10% NaOH
Conc. H2SO4
1-butanol
+
-
+
2-butanol
+
-
+
t-butyl
+
-
+
di-isopropyl ether
+
-
+
phenol
o
+
-
Legend: (+) – Soluble
(o) – Partially insoluble
(-) – Insoluble Water is polar in nature and all the samples used were also polar, so it was expected that they will be miscible with water. Also, they were soluble in water due to their ability to form hydrogen bonds with it (Clark, 2003). But based on the results, only t-butyl alcohol, di-isopropyl ether and 2-butanol were miscible while phenol and 1-butanol were immiscible. For phenol, it was observed to be partially immiscible due to the amount of sample used since it was prepared through estimation because it was in solid form. For ethers, although it was polar, were sparingly soluble in water because of the presence of 2 alkyl groups that makes it impossible to form hydrogen bonds. For alcohols, the solubility decreases as the length of carbon chain increases because as the chain gets longer, more H-bonds in the water must be broken to make room for alcohol thus it cannot compensate since there’s not enough H-bonds in water that can be reformed (Clark, 2003). Since 1-butanol (primary alcohol), had a longer chain compared to 2-butanol (secondary) and t butyl (tertiary), it was expected that the 1-butanol had less solubility in water compared to the two. For 10% NaOH, it was observed that only phenol was miscible in it while the rest were immiscible. For ethers, based on the statement mentioned previously, they will be sparingly soluble in water because they were incapable to form hydrogen bond so they will not react with NaOH solution. Alcohols and phenols are amphoteric (amphiprotic) that they can act as a weak base or as a weak acid. Thus it was expected that alcohols will be less miscible in NaOH (strong base) since in aqueous NaOH, there were mobile Na+ and OH-, so alcohol will not able to react with Na+ to form water and salt , as it can be considered as an acid. ("alcohol," n.d.). Even though phenol is a weak acid, it is more acidic compared to alcohols. Phenol dissolves in NaOH sol’n
because it behaves as an acid that gives up its proton to the hydroxide ion which is a base (Roque, n.d.).
Figure 1. The acidity of Phenol In this reaction, the hydrogen ion has been removed by the strongly basic hydroxide ion in the NaOH sol’n. The samples that were immiscible in NaOH solution, Di-isopropyl ether, 1-butanol, 2 butanol and t-butyl, were then tested to H2SO4 solvent for further experimentation. It was observed that in H2SO4 solvent, all the remaining samples were miscible. It was because the acid protonates the alcohol, making it an ion, more polar than the neutral alcohol, and therefore more soluble in H2SO4 ("SULFURIC ACID," n.d.). For ethers, they act as a weak base in aqueous solutions making them more miscible in acidic solution. Chemical test/reactivity was then conducted in the experiment. Oxidation test was first conducted where KMnO4 was used as a reagent which was also called Baeyer’s reagent.Potassium permanganate (KMnO4) is a very strong oxidant that was used to oxidize unsaturated hydrocarbons leading to the formation alcohols ("organic chemistry," n.d.). Reaction with double or triple bonds in an organic material causes the color to fade from purplish-pink to brown. The disappearance of the purple color and the appearance of brown precipitate concludes that it is a positive test. Often the brown precipitate falls to form and the solution turns reddish brown. Also, easily oxidized gives a positive result.
The chemical reaction may be written as: MnO4- (purple) → HMnO43HMnO4- + H2O → 2MnO2 (brown) + MnO4- + 5HOTable 2.0. Results in Baeyer’s Oxidation test Samples 1-butanol
2-butanol
t-butyl
di-isopropyl ether
phenol
+
+
-
+
-
Baeyer’s Oxidation
Legend: (+) – positive result (-) – negative result Based on the results, out of 3 alcohols used, only t-butyl did not react with KMnO4 and formed 2 distinct layers in the test tube while the other 2 reacted. The outcome of oxidation reactions of alcohols depends on the substituents on the carbinol carbon. In order for each oxidation step to occur, there must be H on the carbinol carbon.
Figure 2. Oxidation mechanism of alcohols The reason behind was the oxidising agent is removing the h ydrogen from the -OH group, and a hydrogen from the carbon atom attached to the – OH (Chem guide, n.d.). Primary alcohols can be oxidised to aldehydes or further to carboxylic acids, secondary alcohols are oxidised to ketones and tertiary alcohols cannot be oxidised. Tertiary alcohols cannot be oxidized because
they don't have a hydrogen atom attached to that carbon thus the reaction cannot take place and it was only applicable for primary and secondary alcohols. Phenol and di-isopropyl ether also reacted with KMnO4 because, same with 1° and 2° alcohols, they also had H on the carbinol carbon which made them capable to be oxidized. Tollen’s oxidation test was then conducted where ammoniacal silver nitrate was used as a reagent. Tollens' reagent is a chemical reagent used to determine the presence of an aldehyde, aromatic aldehyde and alpha-hydroxy ketone functional groups. The reagent con sists of a solution of silver nitrate and ammonia. A positive test with Tollens' reagent is indicated by the precipitation of elemental silver, often producing a characteristic "silver mirror" on the inner surface of the reaction vessel (Pubchem, n.d.). Table 3.0. Results in Tollens’s Oxidation test Samples 1-butanol
2-butanol
t-butyl
di-isopropyl ether
phenol
-
-
-
-
+
Tollen’s Oxidation
Legend: (+) – silver mirror formation (-) – negative silver mirror formation Based on the results, only phenol reacted with tollen’s reagent and the rest of the samples did not. Just like Baeyer’s reagent, tollen’s reagent also serves as a weak oxidizing agent that removes the hydrogen from the -OH group, and a hydrogen from the carbon atom attached to the – OH (Chem guide, n.d.). It indicates that 1° , 2° alcohols, phenols and ethers can be oxidized by Ag+ in tollens’ reagent to form carbonyl compounds for aliphatic alcohols, and a mixture of
compounds for phenols, Ag+ is reduced to Ag(s), and its formation (silver mirror) indicates a positive test. However, in the experiment, only phenol has a positive result thus it indicates that among all the samples, phenols are strongly oxidizable since even if ammoniacal silver nitrate is only a weak oxidizing agent, it’s still oxidized.
Table 4.0. Lucas Test Results Observations Diisopropyl T-butyl Alcohol
Phenol
1-butanol
2-butanol
Ether Reacts with the Form insoluble layer after 1 min
Form cloudy
yellow layer yet
solution after 7
form clear
mins
No changes No reaction
and became
reagent forming
formed
cloudy insoluble layer
In the third test, the five different samples undergo the Lucas test wherein it classifies the alcohols to either primary, secondary or tertiary based on the time it takes to form changes or reactions in the solution. Alcohols with the properties of generating a stable carbocation intermediates will react with ZnCl2 in an acidic solution ("Lucas Reagent", n.d.) where mechanism in this reaction is called the SN1 mechanism, also known as the SN1 nucleophilic substitution which is dependent on the carbocation stability where an – OH ion attracts the H ion to form oxonium ion and leave the group in the form of water while the carbocation intermediate is formed and tend to react with Cl- which is a nucleophile to produce a alkyl halide product ("Chapter 8 : Carbocations", n.d.). The more stable the carbocation, the faster is the SN1 reaction since SN1
nucleophile attacks the planar carbonation that will result to the loss of stereochemistry at the reactive center ("Factors That Stabilize Carbocations", n.d.). In tert-butyl alcohol, the sample and the reagent formed a cloudy solution at room temperature within a minute which classifies ter butyl alcohol to be a tertiary alcohol where in 3 carbon atoms are directly attached to the – OH group. Tertiary alcohols are more stable compared to primary and secondary alcohols which is why it reacts faster to the Lucas reagent ("Primary,Secondary & Tertiary Alcohol", n.d.) . In phenol, no reaction is formed due to the bond of the – OH group in the aromatic compound is quite strong due to resonance and the carbocation of such compound is very unstable ("Alcohols and Phenols: Nomenclature and Classification", n.d.). In diisopropyl ether, there no reaction formed since there is no presence of -OH group in the structure ("Classification of Alcohol- Phenol, Ether", n.d.). Even though oxygen is present in the compound, it is located between two carbon atoms which is uneasily breakable and be replaced with Cl. In 1-butanol, it takes seven minutes for the insoluble layer to appear thus classifies the alcohol as a primary alcohol("Classification of Alcohol- Phenol, Ether", n.d.). Primary alcohols have the OH group attached to a carbon atom which is attached to only one carbon atom only, the reason why it does not react with the Lucas reagent in room temperature, forming the yellowish layer in the solution ("Primary,Secondary & Tertiary Alcohol", n.d.). Since the SN1 reaction is dependent on the stability of carbocation where inductive effect and resonance affects the stability. The R group in the hydrocarbon group is known to be the “electron-releasing” group since it is slightly negative where it can share some of the electron density to the neighboring carbocation that will result to a more distributed charge and more stable but in the case of the primary alcohol, its less stability is due to the presence of only one R group ("Chapter 8 : Carbocations", n.d. and "Factors That Stabilize Carbocations", n.d.).
In 2-butanol, the solution turns cloudy after 7 minutes which classifies the sample to be a secondary alcohol. Secondary alcohols reacts slowly with the Lucas reagent which ran ges from 510 minutes until changes show because secondary carbocation is comparatively less stable than the tertiary also due to the presence of two R group ("Factors That Stabilize Carbocations", n.d.). Table 5.0 Reaction with Ferric Chloride (FeCl3) Observations Diisopropyl T-butyl Alcohol
Phenol
1-butanol
2-butanol
Ether No visible
No visible Formed a dark
difference with
Lighter than the difference with
violet solution the blank
No visible difference with blank solution
the blank
the blank
In the fourth test, samples where tested with ferric chloride solution where in it is a test to determine if there is a presence of phenol group in a compound. Aqueous ferric chloride solution is a clear yellow solution and since the samples are clear transparent solutions, negative result will give a clear yellow solution. Ferric chloride is used to dete rmine the presence of phenols since iron (III) ions form complexes with strong colors to some organic compound including the phenols. The chemical reaction 3ArOH + FeCl3 → Fe(OAr)3 + 3HCl is observed if there is a presence of phenol group ("The FeCl3 Test", n.d.). In the experiment only phenol did react with ferric chloride while the rest show the negative result since all four does not contain a phenolic group in their structure.. Among the five samples, there is only one sample that contains a phenolic group and that is phenol. Alcohols are known to be the hydroxyl derivatives of aliphatic hydrocarbons while phenols are the hydroxyl derivatives of aromatic hydrocarbon (Soloway, & Wilen, 1952). Phenols is chemically structured to have one OH group attached to an aromatic compound. In the reaction,
H ion is being removed from the phenolic group and being replaced by iron(III) ion, that produce strong complexes (Revolvy, n.d. and "Some Reactions of Phenol", n.d.). Table 6.0 Iodoform Test Observations Diisopropyl T-butyl Alcohol
Phenol
1-butanol
2-butanol
Ether Yellow No precipitate
No precipitate
No precipitate
No precipitate precipitate
form
form
form
form formed
In the last test conducted, samples were subjected to iodoform test. Iodoform test is used to determine the presence of methyl group attached to the carbon containing the OH group which is only applicable for secondary alcohols (Ernest, n.d. and Mohamed, n.d.). In the experiment, only 2-butanol reacted and formed the yellow precipitate while the other samples show negative results. 2-butanol is a secondary alcohol determined through the Lucas test in the previous test conducted on the samples. The mechanism in the reaction of iodoform test is first the formation of the oxidizing agent sodium hypoiodate by the chemical reaction I2 + 2NaOH -> NaOI + NaI + H2O then the oxidation of alcohol takes place forming an aldehyde or ketone by sodium hypoiodate Halogenation of the produced aldehyde or keytone with three moles of sodium hypoiodate takes place to form the triiodo derivative where there is a cleavage of the triiodo derivative by NaOH to an acid containing one less carbon atom that results to the formation of CHI3 iodoform as the yellow precipitate with antiseptic odor ("Tests for Aldehydes and Ketones", n.d. and "Triiodomethane (Iodoform) Reaction with Alcohols", n.d.).
IV.
Conclusion and Recommendation
Conclusion
The organic derivatives of water have different properties noatter their similarity in structure. This is either a difference in solubility or chemical property. Alcohols are soluble with water since they are both polar in nature. Alcohols with large number of carbon atoms are largely insoluble in water need either a basic or acidic solution as the solvent. Phenols are only soluble in basic solution while the rest of the samples are soluble in acidic solution. Alcohols of first and secondary degree are oxidizable since the y contain H on the carbinol carbon but both are less oxidizable compared to Phenol since it phenol was oxidized with Ammoniacal silver nitrate, which is a weak oxidizing agent . Third degree alcohols are effectively resistant to oxidation due to the lack of C-H bonds to the C attached to OH group. In the third test where in samples were subjected to Lucas test, the classification of alcohols were determined based on the number of R group attached to carbon containing the OH group ("Classification of Alcohol- Phenol, Ether", n.d.). The 1-butanol is classified under primary with one carbon attached to C-OH group, 2-butanol under secondar y where two carbon atoms attached to C-OH group and ter-butyl under tertiary where three carbon atoms attached to the C-OH group. Phenol is a special type of alcohol where in its OH group is attached to the aromatic compound while diisopropyl ether does not contain an OH group ("Classification of Alcohol- Phenol, Ether", n.d.). In the fourth test wherein samples were subjected to test with the ferric chloride solution, only phenol reacted since the test is used to determine the presence of phenolic group on a compound and only phenol contains the phenolic group ("The FeCl3 Test", n.d.).
In the last test where in samples were subjected to iodoform test, only 2-butanol exhibit the positive result by forming the yellow precipitate iodoform since the test is used to determine the presence of methyl group attached to C-OH group where it most likely to react on secondary alcohols ("Triiodomethane (Iodoform) Reaction with Alcohols", n.d.). Recommendation
In conducting the experiment, the set of experimenters should test the solubility samples on other solvents and varying pH level and temperature to determine the effect on the solubility of samples. The experiment must be conducted in a wider time frame for testing. And also, more test must be conducted or by doing duplicates of test for greater accuracy in order to determine more properties and more details about the organic derivatives of water For the Lucas test, the samples should be subjected to heated solvent and unheated solvent where in the comparison of the results should be exhibit. Samples should also be subjected to other different test wherein it will determine the presence of other function groups present on their structure. The percent purity of each sample and solvent should be known to determine the effect of impurities to the reaction.
V.
References
(2017) (1st ed., pp. 1-3). Leroy G.Wade. Retrieved from https://www.britannica.com/science/alcohol alcohol. (n.d.). Retrieved from www.chem.latech.edu/~deddy/chem252/AlcoholEther.htm Alcohols and Ethers. (2017). Chemed.chem.purdue.edu. Retrieved 20 April 2017, from http://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/alcohols.html Alcohols and Phenols. Retrieved 20 April 2017, from http://www.laney.edu/wp/chelifossum/files/2012/01/6-Alcohols-and-Phenols.pdf ALCOHOLS, PHENOLS, ETHERS, THIOLS, …. (2017). Mpcf aculty.net. Retrieved 20 April 2017, from http://www.mpcfaculty.net/ron_rinehart/30B/alcoholl.htm Chem guide. (n.d.). oxidation of alcohols. Retrieved from http://www.chemguide.co.uk/organicprops/alcohols/oxidation.html Clackamas Community College. (1998). Solubility Rules. Retrieved from http://dl.clackamas.edu/ch105-03/solubili.htm Clark, J. (2003). an introduction to alcohols. Retrieved from http://www.chemguide.co.uk/organicprops/alcohols/background.html Difference Between Alcohols and Phenols. (2017). Differencebetween.com. Retrieved 20 April 2017, from http://www.differencebetween.com/difference-between-alcohols-and-vs-phenols/ Ernest, Z. What is Iodoform test?. Socratic.org. Retrieved 20 April 2017, from https://socratic.org/questions/what-is-iodoform-test Identification of Alcohols. Retrieved 20 April 2017, from http://www.copharm.uobaghdad.edu.iq/uploads/activities%202014/lect.2year%20tagree d/Identification%20of%20Alcohols%20.pdf
Mohamed, R. Iodoform Test. Qoura. Retrieved 20 April 2017, from https://www.quora.com/Describe-iodoform-test-What-type-of-compounds-will-give-a positive-iodoform-test organic chemistry. (n.d.). Retrieved from https://chemistry.stackexchange.com/questions/49542/mechanism-of-the-oxidation-ofalcohols-with-kmno4 Organic Derivatives of Water. (2017) (1st ed., pp. 1 -2). Dasmariñas, Cavite. Retrieved from https://www.scribd.com/doc/48026330/Organic-Derivatives-of-Water Organic Derivatives of water. (2017) (1st ed., pp. 1-2). Dasmariñas, Cavite. Retrieved from https://www.scribd.com/document/232719049/Organic-Derivatives-of-Water Organic derivatives of water. (2017) (1st ed., pp. 1-3). Dasmariñas City, Cavite. Retrieved from https://www.scribd.com/document/84066755/Organic-Derivatives-of-Water Phenolic Compounds. Chemistry.tutorvista.com. Retrieved 20 April 2017, from http://chemistry.tutorvista.com/organic-chemistry/phenolic-compounds.html Pubchem. (n.d.). Ammoniacal silver nitrat. Retrieved from https://pubchem.ncbi.nlm.nih.gov/compound/62774#section=2D-Structure Revolvy, L. "Ferric chloride test". Revolvy.com. Retrieved 20 April 2017, from https://www.revolvy.com/topic/Ferric%20chloride%20test&item_type=topic Roque, J. (n.d.). Organic Derivatives of Water. Retrieved from https://www.scribd.com/doc/48026330/Organic-Derivatives-of-Water Soloway, S., & Wilen, S. (1952). Improved Ferric Chloride Test for Phenols. Analytical Chemistry, 24(6), 979-983. http://dx.doi.org/10.1021/ac60066a017
Some Reactions of Phenol. Chemguide.co.uk. Retrieved 20 April 2017, from http://www.chemguide.co.uk/organicprops/phenol/other.html Tests for Aldehydes and Ketones. Academics.wellesley.edu. Retrieved 20 April 2017, from http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/Cl assificationTests/aldehyde_ketone.html The FeCl3 Test. Harpercollege.edu. Retrieved 20 April 2017, from http://www.harpercollege.edu/tm-ps/chm/100/dgodambe/thedisk/qual/fecl3.htm Triiodomethane (Iodoform) Reaction with Alcohols. Chemguide.co.uk. Ret rieved 20 April 2017, from http://www.chemguide.co.uk/organicprops/alcohols/iodoform.html
VI.
Appendices
A.
Solubility Behaviour
B.
Chemical Reactivity 1. Baeyers’s test
2.
Tollens’ test
3.
Lucas’ test
4.
Reaction with Ferric Chloride
5.
Iodoform test
