Alcohols, Phenols and Ethers
Case Study Based Questions
Case Study 1
A phenol contains-OH group(s) directly attached to carbon atom(s) of an aromatic
system (CH₂OH). In phenols, the OH group is attached to sp²-hybridised carbon of an
aromatic ring. The carbon-oxygen bond length (136 pm) in phenol is slightly less than
that in methanol. This is due to
(i) partial double bond character on account of the conjugation of unshared electron pair
of oxygen with the aromatic ring and (ii) sp³-hybridised state of carbon to which oxygen
is attached. It can be prepared by various means or methods. Some important methods
are alkali fusion of sulphonates, hydrolysis of diazonium salts, decarboxylation of
salicyclic acid and from Grignard reagent. Commercially, it is prepared from Dow's
process and from cumene. In Dow's process, phenol is obtained when chlorobenzene is
heated with 6-8% NaOH at 623 K under 320 atm pressure. Aerial oxidation of cumene
produces cumene hydroperoxide which upon subsequent hydrolysis with an aqueous
acid gives phenol and propanone. Benzene is sulphonated with oleum and benzene
sulphonic acid so formed is converted to sodium
phenoxide on heating with molten sodium hydroxide. Acidification of the sodium salt
gives phenol. Diazonium salts are hydrolysed to phenols by warming with water by
treating with dilute acids.
Read the given passage carefully and give the answer of the following questions:
Q1. The structural formula of cumene is:
Q2. Which of the following hydrocarbon is used for the world wide production of phenol?
a. Iso-butylbenzene
b. Iso-propylbenzene
c. Iso-pentylbenzene
d. None of the above
Q3. The name of product which is obtained by the decarboxylation of sodium salt of
salicylic acid with soda-lime is:
a. phenol
b. toluene
c. benzene
d. benzoic acid
Q4. Which of the following reagents is used for the conversion of benzene sulphonic acid
to phenol?
a. CaCO3
b. NaOH, HCL
c. Ca(OH)2
d. None of these
Answers
1.
2. (b) Iso-propylbenzene
3. (a) Phenol
4. (b) NaOH, HCL
Case Study 2
Alcohols and Phenols are acidic in nature. Electron withdrawing groups in phenol
increase its acidic strength and electron donating groups decrease it. Alcohols undergo
nucleophilic substitution with hydrogen halides to give alkyl halides. On oxidation
primary alcohols yield aldehydes with mild oxidising agents and carboxylic acids with
strong oxidising agents while secondary alcohols yield ketones. The presence of -OH
groups in phenols activates the ring towards electrophilic substitution. Various important
products are obtained from phenol like salicylaldehyde, salicylic acid, picric acid etc.
Read the given passage carefully and give the answer of the following questions: (CBSE
2021 Term-1)
Q1. Which of the following alcohols is resistant to oxidation?
Q2. Which of the following group increases the acidic character of phenol?
a. CH₂O
b. CH3
c. NO₂
d. All of these
Q3. Consider the following reaction:
Answers
1. (a) Tertiary alcohols do not undergo oxidation.
2. (c) -NO₂, - CN, -X (halogens), etc., groups will increase the acidic character of phenol.
3. (d) Kolbe's reaction:
Case Study 3
Alkene hydration is a catalytic process that involves the addition of water across the
double bond of an alkene to produce an alcohol. This is most direct and atom-
economical approach to the synthesis of alcohols. Acid-catalysed alkene hydration is the
most well-known hydration process. This process is used industrially with several
different acidic species as the catalyst, including zeolites, oxides, phosphoric acid and
sulphuric acid. There are several major drawbacks with this catalytic process. The first
drawback is the acidic environment which is very corrosive and can lead to degradation
of reactors or the need to use specially engineered and expensive reactors to resist the
acidic conditions. Another drawback is the acidic environment required for hydration
which is not suitable for alkenes with acid- sensitive functional groups. Thus, this process
is typically only used with simple alkenes such as ethylene, propylene and butene. The
final and biggest drawback is the selectivity of the reaction. Acid catalysed hydration
follows Markovnikov's rule which states that the proton will add to the carbon with the
most hydrogens attached to it. Therefore, starting with propylene, acid-catalysed
hydration will always be selective for internal alcohols (secondary or tertiary). Except for
ethanol, primary alcohol cannot be synthesized by acid- catalysed hydration. Generally,
primary alcohols are the more valuable commodity industrially. Therefore, different
synthetic strategies have to be invented for the synthesis of primary alcohols.
Read the given passage carefully and give the answer of the following questions:
Q1. When propene reacts with water under acidic condition, what is the product formed?
Q2. What is the product formed when propyne in the presence of HgSO, and sulphuric
acid is hydrated?
Q3. Methylpropene when undergoes hydration in presence of acid catalyst, what is the
product obtained? Also give its structure.
OR
But-1-ene (P) on acidic condition hydration will produce 'X' compound, which on
dehydration produce 'Y', acidic condition hydration of 'Y' will produce 'Z'. What happens
when X reacts with Na?
Answers
1. Propan-2-ol
2. Propanone
3. 2-methylpropan-2-ol is obtained and its structure is
OR
X on reaction with Na, does not produce H₂ gas.
Solutions for Questions 4 to 13 are Given Below
Case Study 4
Case Study 5
Case Study 6
Case Study 7
Case Study 8
Case Study 9
Case Study 10
Case Study 11
Case Study 12
Case Study 13
4.
5.
7.
6.
9.
8.
10.
11.
13.
12.
