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Title

Investigation into the Reaction


Mechanisms of Alcohols, Phenols, and
Ethers

 Objective:
To study and compare the reaction mechanisms of alcohols, phenols, and ethers,
highlighting their reactivity in different types of chemical reactions such as
nucleophilic substitution, elimination, and electrophilic substitution.

 Materials and Apparatus:

1. Chemicals:
o Alcohols: Methanol (CH₃OH), Ethanol (C₂H₅OH), Isopropanol
(C₃H₇OH)
o Phenol (C₆H₅OH)

o Ethers: Diethyl Ether (C₂H₅OC₂H₅), Dimethyl Ether (CH₃OCH₃)

o Reagents for reactions (e.g., HCl, NaOH, Br₂, HNO₃, Na metal, etc.)

2. Apparatus:
o Beakers, test tubes, glass rods, Bunsen burner, thermometer, pH
meter, etc.
3. Safety Equipment:
o Gloves, goggles, lab coat.
 Background Theory:

 Alcohols are organic compounds containing one or more hydroxyl (-OH)


groups attached to a saturated carbon atom. They can undergo reactions
like oxidation, dehydration, substitution, and esterification.
 Phenols are similar to alcohols but have the -OH group attached to an
aromatic ring. They are more acidic than alcohols and undergo reactions
such as electrophilic substitution and nucleophilic attack by strong bases.
 Ethers consist of an oxygen atom connected to two alkyl or aryl groups
(R-O-R'). They are relatively inert but can undergo cleavage under acidic
conditions or through nucleophilic substitution.

 Key Reaction Mechanisms:

1. Alcohols:
o Nucleophilic Substitution (SN1 and SN2): Alcohols can undergo
substitution reactions under acidic conditions. For example, in the
reaction with HCl, an alcohol can lose a water molecule (via
protonation) and undergo a nucleophilic attack by chloride ion (Cl⁻).
 Primary alcohol (SN2): CH₃CH₂OH + HCl → CH₃CH₂Cl + H₂O
 Tertiary alcohol (SN1): (CH₃)₃COH + HCl → (CH₃)₃CCl + H₂O
o Dehydration: Alcohols can be dehydrated to alkenes under acidic
conditions. This follows an E1 mechanism where the hydroxyl group
leaves, and a double bond forms.
 C₂H₅OH → C₂H₄ + H₂O (in the presence of acid)
2. Phenols:
o Electrophilic Substitution: The hydroxyl group of phenol is
electron-donating, making the aromatic ring more reactive toward
electrophiles. Reactions like bromination and nitration are common.
 C₆H₅OH + Br₂ → C₆H₄(Br)OH + HBr
 C₆H₅OH + HNO₃ → C₆H₄(NO₂)OH + H₂O
o Reaction with Bases: Phenols are more acidic than alcohols due
to resonance stabilization of the phenoxide ion (C₆H₅O⁻).

 C₆H₅OH + NaOH → C₆H₅O⁻ + Na⁺ + H₂O


3. Ethers:
o Cleavage in Acidic Medium: Ethers can undergo nucleophilic
substitution reactions when exposed to strong acids, breaking the
C-O bond.
 R-O-R' + HCl → R-Cl + R'-OH
 Example: CH₃OCH₃ + HCl → CH₃Cl + CH₃OH (Methoxy group
reacts with Cl⁻)
o Reaction with Alcohols: Ethers can also react with alcohols in the
presence of acids to form alkoxides and alkyl ethers.
 C₂H₅OH + CH₃OCH₃ → C₂H₅OCH₃ + CH₃OH (Ether exchange
reaction)

 REACTION OF ALCOHOLS

1. Reaction with Metal


 When ethanol reacts with sodium metal (a base) sodium ethoxide and
hydrogen gas is
produced.
 2ROH + Na→2RO+Na– + H2

2. Formation of Halides
 Halogens such as chlorine or bromine replace the -OH group in an alcohol.
 ROH+ Zn+HCl → R-Cl
 R2C-OH alcohol + HCl→ R2CCl

3. Reaction with HNO3


 There is oxidation, accompanied by gas evolution (slow but progressive) in
this reaction.
 R-OH + HO-NO2→ R-O-NO2

4. Reaction with Carboxylic Acid (Esterification)

 The reaction of the carboxylic acid with an alcohol and an acid catalyst
leads to the formation of ester (along with water). This is Fischer
esterification.
 R-OH +R’-COOH +H+↔ R’-COOR
Dehydration of Alcohol

 Alcohols dehydrate in an acidic medium. As per the Satyzeff’s Rule, intra-


molecular dehydration leads to the formation of alkene while
intermolecular dehydration forms ether.

Haloform Reaction

 Compound that has the CH3CO- group (or compound on oxidation gives
CH3CO – group) which is bonded with a C or H, in the presence of halogen
and mild alkali gives haloform. CH3-CH2-COCH2-CH3, CH3-CO-Cl, CH3COOH
will not respond to haloform reaction while CH 3CH2OH will respond to the
haloform reaction.
 Reactions of Phenol

1. Formation of Ester

 Phenyl esters (RCOOAr) do not form directly from RCOOH, but for this acid
chlorides or anhydrides react with ArOH in the presence of a strong base.
 (CH3CO)2O + C6H5OH + NaOH → CH3COOC6H5 + CH3COONa + H2O
Phenylacetate
 C6H5COCl + C6H5OH + NaOH → C6H5COOC6H5 + Na+Cl– + H2O
Phenyl benzoate

2. Hydrogenation

 Hydrogenation of phenol forms cyclohexanone.

3. Oxidation of Quinones
 Phenols get easily oxidized to para-benzoquinone. This when reduced
forms quinones.
n

4. ELECTROPHELIC SUBSTITUTION
 The —OH and even the —O(phenoxide) are strongly activating ortho, para
– directing. Electrophilic monosubstitution in phenols happens in special
mild conditions because they are highly reactive and favors both
polysubstitution and oxidation.

5. Halogenation
 There is a formation of monobromophenol, on treating phenols with
bromine in the presence of a solvent of low polarity like CHCl 3 at low
temperature.
 Procedure:

1. Preparation of Alcohols, Phenol, and Ethers:


 Obtain commercial samples of alcohols, phenol, and ethers.
2. Reaction with Acid:
 Perform a nucleophilic substitution reaction by mixing the alcohols
and phenols with HCl and observing the reaction products.
3. Electrophilic Substitution in Phenol:
 Brominate phenol using Br₂ in aqueous solution and observe the
color change or formation of the product.
4. Dehydration of Alcohol:
 Heat ethanol in the presence of concentrated sulfuric acid and
observe the formation of ethene (gas).
5. Ether Cleavage:
 Mix diethyl ether with HCl in a test tube and observe any changes
or reaction products.
6. Testing the Basicity of Phenols:
 Dissolve phenol in water and add NaOH. Observe the formation of
phenoxide ions (pH change).

 Observations:

 Record the changes in the appearance of the solutions (color, formation of


precipitates, gas evolution).
 Note the temperature changes during reactions (exothermic or
endothermic reactions).
 If necessary, use thin layer chromatography (TLC) to identify the products
of some reactions.

 Results and Discussions:


 Compare the reactivity of alcohols, phenols, and ethers in nucleophilic
substitution, dehydration, and electrophilic substitution reactions.
 Explain the mechanisms involved (SN1, SN2, E1, E2, electrophilic
substitution) and the factors that influence the reactivity of each
compound (such as steric hindrance, resonance effects, and stability of
carbocations or transition states).

 Conclusion:

 Summarize the findings from the reactions of alcohols, phenols, and


ethers.
 Discuss the differences in their chemical behavior due to the structural
variations (e.g., alcohol vs. phenol, or alcohol vs. ether).
 Highlight the importance of these reactions in organic synthesis and
industrial applications.

 References:

1. Organic Chemistry by J. Clayden, N. Greeves, S. Warren, and P. Wothers.


2. Advanced Organic Chemistry by Francis A. Carey.
This structure provides a comprehensive approach to understanding the
reactivity of alcohols, phenols, and ethers through various reaction mechanisms.

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