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Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers


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20 Questions MCQ Test Chemistry for JEE | Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers

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Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 1

During dehydration of alcohols to alkenes by heating withconc. H2SO4 the initiation step is [2003]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 1

The dehydration of alcohol to form alkene occurs in following three step. Step (1) is initiation step.
Step (1) Formation of protonated alcohol.

Step (2) Formation of carbocation

Step (3)Elimination of a proton to form ethene

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 2

Among the following compounds which can be dehydrated very easily is                 [2004]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 2

3-methyl pentanol-3 will be dehydrated most readily since it produces tertiary carbonium ion as intermediate.

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 3

The best reagent to convert pent-3-en-2-ol into pent-3-in-2-one is     [2005]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 3


Pyridiminum chloro-chromate (PCC) is specific for the conversion.

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 4

p -cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to form, the
compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic acid is
[2005]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 4

 

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 5

HBr reacts with CH2 = CH – OCH3 under anhydrous conditions at room temperature to give         [ 2006]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 5

Methyl vinyl ether under anhydrous condition at room temperature undergoes addition reaction.

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 6

Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH is [ 2006]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 6

Only those alcohols which contain –CHOHCH3 group undergo haloform reaction. Among the given options only (b) contain this group, hence undergo haloform
reaction.

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 7

The structure of the compound that gives a tribromo derivative on treatment with bromine water is [2006]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 7

NOTE : OH group activates the benzene nucleus and

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 8

The electrophile involved in the above reaction is

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 8

NOTE : This is Riemer-Tiemann reaction and the electrophile is dichlorocarbene.

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 9

In the following sequence of reactions, 

the compound D is              [2007

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 9

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 10

Phenol, when it first reacts with concentrated sulphuric acidand then with concentrated nitric acid, gives             [2008]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 10

Phenol on reaction with conc. H2SO4 gives a mixture of o- and p- products (i.e., –SO3H group, occupies o-, p- position). At room temperature o-product is more stable, which on treatment with conc. HNO3 will yield
o-nitrophenol.

At room temperature o- product is more stable

Hence (b) is the correct answer.

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 11

The major product obtained on interaction of phenol withsodium hydroxide and carbon dioxide is       [2009]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 11

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 12

From amongst the following alcohols the one that wouldreact fastest with conc. HCl and anhydrous ZnCl2, is [2010]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 12

Tertiary alcohols react fastest with conc. HCl and anhydrous ZnCl2 (lucas reagent) as its mechanism proceeds through the formation of stable tertiary carbocation.
Mechanism

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 13

The main product of the following reaction is 

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 13

Whenever dehydration can produce two different alkenes, major product is formed according to Saytzeff rule i.e. more substituted alkene (alkene having lesser
number of hydrogen atoms on the two doubly bonded carbon atoms) is the major product.
Such reactions which can produce two or more structural isomers but one of them in greater amounts than the other are called regioselective ; in case a reaction is 100% regioselective, it is termed as regiospecific.
In addition to being regioselective, alcohol
dehydrations are stereoselective (a reaction in which a single starting material can yield two or more stereoisomeric products, but gives one of them in greater amount than any other).

 

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 14

Phenol is heated with a solution of mixture of KBr and KBrO3. The major product obtained in the above reaction is :[2011]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 14

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 15

Arrange the following compounds in order of decreasing acidity :

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 15

Electron withdrawing substituents like –NO2, Cl increase the acidity of phenol while electron releasing substituents like – CH3, – OCH3 decreases acidity. hence the correct order of acidity will be

Further (– I) NO2 > (–I) Cl and (+ I) CH3 > (+I) OCH3

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 16

An unknown alcohol is treated with the “Lucas reagent” todetermine whether the alcohol is primary, secondary ortertiary. Which alcohol reacts fastest and by what mechanism:[JEE M 2013]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 16

Tertiary alchols reacts fastest with lucas reagnet as the rate of reaction is directly proportional to the stability of carbocation formed in the reaction. Since most stable
3° carbocation is formed in the reaction hence it will react fastest further tetriary alcohols appears to react by SN1 mechanism.

 

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 17

Sodium phenoxide when heated with CO2 under pressure at 125ºC yields a product which on acetylation produces C.

The major product C would be                           [JEE M 2014]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 17

 

 

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 18

Thiol group is present in :                     [JEE M 2016]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 18

Among 20 naturally occuring amino acids "Cysteine" has '– SH' or thiol functional group.
⇒ General formula of amino acid 

⇒ Value of R = –CH2–SH in Cysteine.

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 19

The product of the reaction given below is:                 [JEE M 2016]

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 19

N – bromosuccinimide results into bromination at allylic and benzylic positions

Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 20

2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields: [JEE M 2016]
 

(i) 

 

(ii)

 

(iii)

Detailed Solution for Test: 35 Year JEE Previous Year Questions: Alcohols, Phenols & Ethers - Question 20

When tert -alkyl halides are used in Williamson synthesis elimination occurs rather than substitution resulting into formation of alkene. Here alkoxide ion abstract one of the b-hydrogen atom along with acting
as a nucleophile.

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