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Experiment 12

1) The objective of this experiment is to distinguish between primary, secondary, and tertiary alcohols using qualitative chemical tests. 2) Three tests are used: the Ritter test identifies tertiary alcohols, the Lucas test separates alcohols by reaction rate, and the iodoform test indicates secondary alcohols. 3) The combination of these three tests is sufficient to distinguish between primary, secondary, and tertiary alcohols based on their observed reactions.

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Rohit Biswas
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59 views

Experiment 12

1) The objective of this experiment is to distinguish between primary, secondary, and tertiary alcohols using qualitative chemical tests. 2) Three tests are used: the Ritter test identifies tertiary alcohols, the Lucas test separates alcohols by reaction rate, and the iodoform test indicates secondary alcohols. 3) The combination of these three tests is sufficient to distinguish between primary, secondary, and tertiary alcohols based on their observed reactions.

Uploaded by

Rohit Biswas
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Experiment 12

Title: Qualitative Tests to Identify Primary, Secondary, and Tertiary Alcohols

Objective:

The main objective of this experiment is to perform multiple tests in order to


distinguish primary, secondary and tertiary alcohols.

Introduction:

In this experiment, we will perform classification tests to distinguish primary,


secondary, and tertiary alcohols. Alcohols are derived from water by replacing
one of the hydrogen atoms with an alkyl group. Hydroxyl (OH) groups in alcohols
are bonded to aliphatic hydrocarbons (straight-chain and cyclical alkanes,
alkenes, and alkynes). On the other hand, phenols are aromatic compounds in
which hydroxyl groups bonded to aromatic rings (cyclical rings with alternate
single and double bonds, for example, benzene rings). Alcohols are neutral (pKa
= ~16) whereas phenols are acidic (pKa = 8-11). Phenols from resonance-
stabilized phenoxide whereas alkoxides from alcohols are not resonance
stabilized.

Alcohols are versatile synthetic intermediates because the alcohol function group
(OH) will be converted into most other functional groups. For example, oxidation
of primary alcohols gives aldehydes and carboxylic acids, secondary alcohols
give ketones. Oxidation is loss of H₂. The requirement for oxidation of alcohols is
the presence of a hydrogen atom bonded to oxygen and at least a hydrogen
atom bonded to the carbonyl carbon (OH group bonded carbon, C-O-H). In
primary and secondary alcohols these two hydrogen atoms are present whereas
in tertiary alcohol only one hydrogen atom is present.
Procedure:

In order to distinguish between these types of alcohol, we will perform multiple


tests.

1. Ritter Test: This test distinguishes primary and secondary alcohols from
tertiary alcohols.

In a large test tube, we add ~ 2.0 mL of glacial acetic acid followed by 3 drops of
an unknown alcohol. To the test tube, add dropwise, with swirling to mix the
contents for each addition, a saturated aqueous solution of potassium
permanganate.
We must note any change in the color of the solution. If the alcohol is tertiary, the
purple permanganate color persists after adding 1 or 2 drops of KMnO4. Primary
and secondary alcohols decolorize purple permanganate color and remain
colorless or clear until sufficient permanganate has been added.

Sl. No. Alcohol Observation

1 Primary Alcohol Decolorize purple permanganate color and


remain colorless

2 Secondary Alcohol Decolorize purple permanganate color and


remain colorless

3 Tertiary Alcohol No reaction took place thus the color remained


purple

2. Lucas Test: To a 0.5 mL (10 drops) of the alcohol in a test tube add quickly
about 3.0 mL of the Lucas reagent (concentrated hydrochloric acid zinc chloride
combination). Close the test tube with a cork, shake and then allow the mixture to
stand. Immediate separation of two layers (aqueous solution bottom and alkyl
chloride at the top) indicates the presence of tertiary alcohol. Secondary alcohols
require about 5 min for the separation of layers. Most primary alcohols do not
react in less than an hour.
Sl. No. Alcohol Observation

1 Primary Alcohol No separation at all or takes at least 1 hour

2 Secondary Alcohol Separation of two layers after 5-7 mins

3 Tertiary Alcohol Immediate separation of two layers

3. Iodoform Test.

This test is positive for secondary alcohols.

To a clean test tube, we add 5 drops of liquid (If solid add about 100 mg of solid
to a test tube and 2 mL of methanol). To this, add 2 mL of 10% aqueous sodium
hydroxide solution then add dropwise, with shaking, a 10% solution of iodine in
potassium iodide (1₂/KI) until a definite brown color indicating an excess of
iodine. For some compounds, immediate formation of yellow iodoform precipitate
can be observed, indicating a positive test. If the yellow precipitate does not
appear within 5 minutes, warm the solution in a beaker containing about 60° C
water. The formation of a yellow precipitate indicates secondary alcohol.

Sl. No. Alcohol Observation

1 Primary Alcohol No immediate change

2 Secondary Alcohol The formation of a yellow precipitate

3 Tertiary Alcohol No immediate change

Conclusion:

The combination of these three tests is sufficient to distinguish between primary,


secondary, and tertiary alcohol.
Post laboratory Questions:
1) Why do tertiary alcohols react faster with Lucas Reagent than secondary and
primary alcohols? Explain.

Tertiary alcohols react immediately with Lucas reagent because of the low solubility of
the organic chloride in the aqueous mixture as well as due to the higher stability of the
intermediate tertiary carbocation.

2) Why phenols are more acidic than alcohols? Explain.

Phenols are aromatic alcohols, the OH group is attached to the aromatic ring. After the
loss of a proton, the conjugate base is stabilized by the resonance of the aromatic ring.
For alcohols, there is no such stabilization by resonance to conjugate base. Thus
phenols are more acidic than alcohols because of resonance.

3) Why do primary and secondary alcohols undergo oxidation whereas tertiary alcohols
do not? Explain.

To undergo oxidation alpha hydrogens are necessary. tertiary alcohols don’t have alpha
hydrogen hence they cannot be oxidized whereas primary and secondary alcohols have
alpha hydrogen hence undergo oxidation.

4) What test could be used to distinguish between 2-methyl-2-propanol and 1-butanol?

Lucas test can be used to distinguish between 1-butanol from 2-methyl-2 propanol. 1-
butanol is primary alcohol so it will form turbidity.

5) Comment on the green chemistry of this experiment. That is, the nature and amount
of solvent (for example water, etc.), and atom economy (number of atoms in the
reactants versus products) in this experiment.

In this entire experiment, we use multiple batches of the three unknown alcohol is
provided with each being 2_3 ml, and other agents like potassium permanganate and a
combination of hydrochloric acid and zinc chloride. There are no adverse effects of this
experiment in any form does it can be totally termed as green accept the fact that the
alcohols other reagents used cannot be recovered for reuse in any form.

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