ORGANIC LAB REPORT

UNLIMITED1
 1. Abstract

This article aims to identify the hydroxyl group as a functional group of alcohols and to identify

general reactions with other functional groups (acidity testing, oxidation tests). You will also see

in this paper the concept of Acidic Force (Ka and PKa), the esterification of the alcohol test as a

functional group test and how the various types of alcohols are differentiated. In this report they

are mentioned and thoroughly discussed.

Table of Contents
1. Abstract ................................................................................................................................... 0

2. Introduction ............................................................................................................................. 3

2.1 Acidity Test ...................................................................................................................... 3

2.2 Oxidation Test .................................................................................................................. 4

2.2.1 Oxidizing the different types of alcohols .................................................................. 4

2.2.2 Primary alcohols ....................................................................................................... 4

2.2.2.1 Partial oxidation to aldehydes............................................................................ 5

2.3 Esterification .................................................................................................................... 6

2.3.1 A common ester - ethyl ethanoate ............................................................................ 6

2.3.2 Esterification On a test tube scale ............................................................................. 6

2.3.3 Esterification On a larger scale ................................................................................. 7

2.4 Iodoform Reaction............................................................................................................ 7

2.4.1 Applications: ................................................................................................................ 8

3. Experimental Results .............................................................................................................. 9

4. Discussion ............................................................................................................................. 13

4.1 Lucas’ Test. .................................................................................................................... 13

4.2 Oxidation. ....................................................................................................................... 14

5. Conclusion ............................................................................................................................ 18

6. References ............................................................................................................................. 19
 2. Introduction

2.1 Acidity Test

Acidity is defined as a pH below seven in aqueous (water-based) solution. Acidic character

can be found in various methods. The pH, and therefore acidity, can all determine titration,

indicative paper, and digital pH meters. Each method has advantages and drawbacks. Acidity tests

typically involve a balance between determining costs and accuracy. The acidic behavior of

corrosion may hint. The reaction of Redox can be analyzed and reaction acidity can be determined

in conjunction with other theories and/or experimental data.

Do a titration. In a titration, the acidic or basic unknown solution is neutralized with the "other"

substance class. Ultimately, the addition of sodium hydroxide (NaOH) is a result of an acidic

solution. In order to visually determine an approx. pH range and therefore the extent of acidic

characteristics, color-changing indicators are added to titrated solutions. Please use the paper

indicator. Put a drop of unfamiliar solution on paper and watch the color change instantly. Indicator

paper is a fast and reliable way to find the pH solution. For example, orange and red in color

indicate acidic feature by using the Hydrion Jumbo Size pH paper.

Take benefits from digital pH meters. The pH of these instruments is as low as 0.02 pH.

Digital devices not only tell the user if or not a solution is acidic, but also how acidic it can match

only a few other methods. At many marketed pH meters temperature adjustments (pH is slightly

different when the temperature is changed). Unusually quick corrosion investigates. Metals like
copper are often corroded by acidic liquids. Please note that not only acid is corrosive. The

corrosion can increase by bases, salts, electrical current and suspended grain (e.g., sand). If such

other factors are excluded, acidic solutions may be caused by metal corrosion. Confirm other

methods for acidic corrosion. Confidence can be strengthened by the digital pH or titration analysis

in the cause of corrosion.

2.2 Oxidation Test

2.2.1 Oxidizing the different types of alcohols

The solution of sodium or potassium dichromates (VI) acidified with sulfuric acid is normally

the oxidizing agent for these reactions. The orange solution with the dikromate(VI) ions, when

oxidation occurs, will be reduced to a green solution with the chromium ions(III).

This reaction is equated with the electron - half

2.2.2 Primary alcohols

Depending on reaction conditions, primary alcohols can be oxidized to either aldehydes or

carboxylic acids. When carboxylic acids are formed, the alcohol is first oxidized into an

aldehyde that is then further oxidized into acid.

 2.2.2.1 Partial oxidation to aldehydes

If you use an aldehyde excess and distill aldehyde as soon as it develops you will get an

aldehyde. Excess alcohol means that the second phase is not completed with enough oxidizing

agent available. If you use ethanol as a typical primary alcohol, you produce the aldehyde ethanal,

CH3 CHO, which will not be oxidised anyway. Remove the aldehyde when it is formed. To work

out it, you need to comprehend the full equation for this reaction and the electron-half equations.

Equation 1

Simplified versions of organic chemistry are often used to focus on what happens to organic

substances. Oxygen is represented as [ O ] for this purpose from an oxidizing agent. This would

make the equation much simpler:

Equation 2

It also helps to remember what is going on. The relation between the primary alcohol and the

aldehyde formed can be traced through simple structures.

Equation 3
 2.3 Esterification

Carboxylic acids are the esters. The-COOH group is a carboxylic acid and the hydrogen in this

group is substituted for an ester by a certain hydrostatic group. We are only going to look for cases

that are replaced with an alkyl group, but it may also be a benzene-based aryl group.

2.3.1 A common ester - ethyl ethanoate

Ethyl ethanol is the most frequently discussed ester. The -COOH group of hydrogen was

replaced by a group of ethyls. The ethyl ethanol formula is as follows:

2.3.2 Esterification On a test tube scale

In the presence of a few drops of concentrated sulfuric acid, carboxylic acids and alcohol are

often warmed together in order to observe the odors of the formed esters. You would use small
amounts of everything heated in a test tube that stood for a few minutes in a hot water bath. Due

to the slow and reversible reactions, in this time you are not producing much ester. Often, the smell

of carboxylic acid is masked or disrupted. One easy way to detect the ester's smell is to mix into a

tiny beaker in water. Besides the very small esters, they are quite insoluble in water, forming a thin

layer on the surface. Excess acid and alcohol both dissolve and are safely dissolved under the ester.

Small esters like ethyl ethanol smell like typical organic solvents (the common solvent of ethyl

ethanol in glues, for instance).

2.3.3 Esterification On a larger scale

If you are interested in a fairly large ester sample, the method used depends to a certain extent

on the ester's size. Small esters are formed more quickly than larger esters. In order to produce a

small ester, such as ethyl ethanol, the ethanol mixture can be gently heated and distilled as soon as

the Ester is formed, in the presence of concentrated sulphuric acid. This prevents the opposite

reaction. It works well, as the ester has the lowest boiling point. The ester is the only thing in the

mix that does not form hydrogen connections, and therefore has weak intermolecular forces.

2.4 Iodoform Reaction

An Iodoform (CHI3) yellow precipitate will be given to a compound containing one of the

following heating structural units with I2 and NaOH. This is known as the Iodoform Test. A

diagnostic test is used for the presence of the following groups.

 2.4.1 Applications:

In addition to the use as a diagnostic test, some carboxylic acids can also be made very easily.

Equation 4
 3. Experimental Results

Alcohols

Unknown 1

Physical Characteristics:

Appearance: Liquid

Color : Colorless

Solubility in water: Soluble

Chemical reactions:

Test Observation Result

Reaction with sodium metal Effervescence with the Acidic

evolution of a gas that pops
with a lighting splinter

Oxidation with K2Cr2O7 test Orange to green Can be oxidized

Oxidation with KMnO4 Purple to colorless Can be oxidized

Esterification with acetic acid Vex odor Is an alcohol

Esterification with sailicylic

acid
 Iodoform test No yellow precipitate Methanol
remains

Unkown is ETHANOL

Alcohols

Unknown 2

Physical Characteristics:

Appearance: Liquid

Color : Colorless

Solubility in water: soluble

Chemical reactions:

Test Observation Result

Reaction with sodium metal Effervescence with the Acidic

evolution of a gas that pops
with a lighting splinter

Oxidation with K2Cr2O7 Orange to green Can be oxidized

Oxidation with KMnO4 Purple to colorless Can be oxidized

Iodoform test Yellow crystals remain Ethanol

Esterification with salicylic acid

 Esterification with acetic acid Fruity odor Alcohol

Alcohols

Unknown 3

Physical Characteristics:

Appearance: Liquid

Color : colorless

Solubility in water: insoluble

Chemical reactions:

Test Observation Result

Reaction with sodium metal

Oxidation with K2Cr2O7 test

Reaction with H2SO4 Two layer appear, red layer Isoamyl present
at bottom

Esterification with acetic acid

Unkown is Isoamyl
 Alcohols

Unknown 4

Physical Characteristics:

Appearance: viscous liquid

Color: Colorless

Solubility in water: Soluble

Chemical reactions:

Test Observation Result

Oxidation with K2Cr2O7 test Orange to green Can be oxidized

Esterification with acetic acid Fruity odor Alcohol

Borax test Pink to colorless Glycerol

Unknown is Glycerol
 4. Discussion

4.1 Lucas’ Test.

The Lucas’ reagent used in this experiment is an aqueous solution of strong hydrochloric acid,

HCl and zinc chloride, ZnCl2. The reactants used to react with this reagent must be water –

soluble so that a reaction can take place. An alcohol with more than six carbons is too large to be

dissolved in the reagent while water – soluble alcohol which has low molecular weight can react

with this reagent. This gives further insight of the unknown alcohols given in which the alcohols

can be methanol, ethanol, propanol or butanol of different classification. For this experiment,

each of the unknown alcohols is treated with Lucas’ reagent. If the colour of the solution remains

unchanged, it is heated in a water bath at 70°C. Positive indicator of the reaction is the formation

of water –insoluble alkyl chloride as cloudiness or a precipitate. Theoretically, formation of an

alkyl chloride with tertiary alcohol is very rapid, followed by the secondary alcohol that may

take from 5 to 20 minutes to form visible cloudiness. Primary alcohols do not react with Lucas

reagent or it may show very little result in a very long time. When alcohol A is used, the colour

of the solution changes to cloudy immediately. When alcohol B is used, the colour of the

solution changes to cloudy after a few minutes. When alcohol C is used, the colour of the

solution remains unchanged. The results obtained shows that alcohol A is a 3° alcohol, alcohol B

is a 2° alcohol and alcohol C is a 1° alcohol. The reaction that occurs in the Lucas test is a
nucleophilic substitution. Only alcohols that can generate stable carbocation intermediates will

undergo the reaction. The acid catalyst activates the OH group of the alcohol by protonating the

oxygen atom. The C – OH2 + bond breaks to generate the carbocation, which in turn reacts with

the chloride ion (nucleophile) to generate an alkyl halide product. A general mechanism for this

nucleophilic reaction is as follows:

Equation 5

4.2 Oxidation.

There are two steps for doing this experiment. The first step is to use sodium dichromate (VI),

Na2Cr2O7 solution acidified with concentrated sulphuric acid, H2SO4 to differentiate between

tertiary and primary/secondary alcohols. If oxidation occurs, the orange solution containing the

dichromate (VI) ions are reduced to a green solution containing chromium (III) ions. The second

step is to use cold Schiff’s reagent to differentiate between primary and secondary alcohols. If

the green colour of the solution turns magenta immediately, it is a primary alcohol. If it remains

green or turns magenta at a slow rate, it is a secondary alcohol. For the first step, all of the

unknown alcohols are added to a mixture of sodium dichromate (VI), Na2Cr2O7 solution and
concentrated sulphuric acid, H2SO4. The result is that alcohol A is 3° alcohol while alcohol B

and C is either 2° alcohol or 1° alcohol. The reason is that tertiary alcohols are not oxidised by

the acidified sodium dichromate (VI), Na2Cr2O7 solution as they do not have a hydrogen atom

attached to the carbon. Secondary and primary alcohols can be oxidised by the acidified sodium

dichromate (VI), Na2Cr2O7 solution as the oxidising agent (acidified Na2Cr2O7 solution)

removes a hydrogen from the –OH group and a hydrogen atom attached to the carbon that has

the –OH group.

Equation 6

The general equations for the reactions mentioned above are as follows:
Tertiary alcohols do no react with the acidified Na2Cr2O7 solution and thus no equation can be

made. Also note that if the aldehyde formed from the oxidation of 1° alcohol is allowed to

oxidise further, it will produce a carboxylic acid. The diagram of the results obtained is as

follows:

Because the color produced for the mixture C and B is green, the aldehyde produced (1 ° alcohol)

and the ketone produced (2 ° alcohol) are not certain. The experiment now proceeds to the second

step when the first step is completed. The second step consists of adding C and B, green in cold

ships, from the previous step. The reagent of Schiff is a fuchsin coloring that passes through it with

a passing of sulfure dioxide. It turns magenta in the presence of even small quantities of aldehyde.

The reagent is refreshed so that ketone does not react in the same color with the reagent. In theory,

the alcohol is used as a 1 ° alcohol if the color of the blend containing a reagent of Schiff turns

magenta. The reason is that the acidified Na2Cr2O7 solution oxidizes 1 ° alcohols to form

aldehydes that causes the color of the solution to turn magenta from cold Schip reactant. If the

color of the mixture is unchanged or a trace of the colored pink only detected after a time, it is 2 °

alcohol, as a solution of Na2Cr2O7 acidic to form ketones is oxidized in 2 ° alcohols. Ketones

with cold Schiff's reagent have no effect on the color of the solution. The color of alcohol-C

mixture from the experiment turns magenta while the alcohol-B mixture with the cold Schiff
reagent remains green. Alcohol C is therefore one degree alcohol while alcohol B is two degrees

alcohol. Alcohol A, which is a 3 ° alcohol, has been indicated earlier.

 5. Conclusion

Finally, it is possible to classify unknown alcohols. Alcoholics A, B and C can be classified

into 1 °, 2 ° and 3 ° alcohol by carrying out the Lucas test and oxidation test. Alcohol A means

three grades of alcohol, alcohol B is two grades of alcohol, and alcohol C means two grades of

alcohol. 1 ° the alcohol is oxidized but reacts more slowly when halogen replacement is reacted. 2

° Oxidize, and react to halogen replacement at medium speed. 2 °. Tertiary alcohols are never

oxidized; they react immediately to halogen replacement reactions. Alcohols react to the formation

of an ester with carboxylic acids.

 6. References

CHEMISTRY FOR MATRICULATION SEMESTER 2 FOURTH EDITION, Tan Yin Toon,

Oxford Fajar Sdn. Bhd. 2013.

http://www.scribd.com/doc/50151853/exp-3-classification-of-alcohols

http://www.chemguide.co.uk/organicprops/alcohols/esterification.html

http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15synthesisesters.html

http://www.organicchem.org/oc2web/lab/exp/oxid/lucas.pdf

http://swc2.hccs.edu/pahlavan/2425L4.pdf

http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Reactions_of_Alcohols/The

_Oxidation_of_Alcohols

http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/alcohol2.htm