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Alcohols, Phenols and Ethers

JEE Main 2024 (Online) 27th January Evening ShiftMCQMedium📈 Topic in 10% papers+4−1
Ques. 1JEE Main 2024, 27 January (Evening Shift)

The final product A, formed in the following reaction sequence is: [figure]

  1. [figure]
  2. [figure]
  3. Ph-CH2-CH2-CH2-OH
  4. Ph-CH2-CH2-CH3

Answer

(3) Ph-CH2-CH2-CH2-OH

Solution

Ph-CH=CH2 [(ii) H2O2, OH](i) BH3 Ph-CH2-CH2-OH

Hydroboration–oxidation adds H2O anti-Markovnikov, so –OH goes to the terminal C.

Ph-CH2-CH2-OH HBr Ph-CH2-CH2-Br

Here HBr protonates –OH; as H2O leaves, the neighbouring phenyl ring helps push it out (NGP) and a bridged phenonium ion forms. Since both ring-bonded carbons of this ion are CH2, Br attacks either one and gives the same unbranched bromide, so the skeleton does not change.

Ph-CH2-CH2-Br Mg, ether Ph-CH2-CH2-MgBr

[(ii) H3O+](i) HCHO Ph-CH2-CH2-CH2-OH

Because RMgX adds to HCHO, we get a 1° alcohol that has one more carbon.

(1) and (2) are branched at the benzylic C, which would need Markovnikov addition, so they are wrong; (4) has no –OH, so it is wrong.

Answer: (3)

Keep practising — Alcohols, Phenols and Ethers

Ques. 2JEE Main 2026, 6 April (Morning Shift)

Consider the following sequence of reactions [figure] The major product P is:

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
Ques. 3JEE Main 2026, 6 April (Morning Shift)

4.7 g of phenol is heated with Zn to give product X. If this reaction goes to 60% completion then the number of moles of compound X formed will be 10-2. (Nearest Integer) (Given molar mass in g mol-1 : H:1, C:12, O:16)

Ques. 4JEE Main 2026, 6 April (Evening Shift)

Consider the following reaction. [figure] In the light of the above statements, choose the correct answer from the options given below :

  1. Both Statement I and Statement II are true
  2. Both Statement I and Statement II are false
  3. Statement I is true but Statement II is false
  4. Statement I is false but Statement II is true
Ques. 5JEE Main 2026, 5 April (Morning Shift)

Consider compounds A, B and C with following structural formulae A = CH3-CH2-CH2-CH2-CH2-OH B = CH2=CH-CH2-CH2-CH3 C = HO-CH2-CH2-CH(OH)-CH3 For the conversion of B from A , reagent (D) required is and structural formula of product (E) obtained when C undergoes same reaction using excess reagent (D) is .

  1. D: Conc. H2SO4; E: CH2=CH-CH(OH)CH3
  2. D: PCC; E: HO-CH2-CH2-CH=CH2
  3. D: PCC; E: CH2=CH-CH=CH2
  4. D: Conc. H2SO4 or H3PO4; E: CH2=CH-CH=CH2
Ques. 6JEE Main 2026, 5 April (Morning Shift)

One mole of phenol is treated with dilute HNO3 at 298 K to give a mixture of products. The mixture is separated by steam distillation. The steam volatile compound (X) is separated. The increase in percentage of oxygen in (X) with respect to phenol is 10-1% (Given molar mass in g mol-1 H : 1, C : 12, N : 14, O : 16)

Ques. 7JEE Main 2026, 4 April (Morning Shift)

Amongst the following, the total number of compounds soluble in aqueous NaOH at room temperature is: [figure]

  1. 5
  2. 4
  3. 6
  4. 3
Ques. 8JEE Main 2026, 28 January (Morning Shift)

Consider the following reaction sequence : [figure] Compound (y) develops characteristic colour with neutral FeCl3 solution. Identify the INCORRECT statement from the following for the above sequence.

  1. Compound y will dissolve in NaHCO3 and evolve a gas.
  2. Compound x is more acidic than compound y.
  3. Both compounds x and y will dissolve in NaOH.
  4. Both compounds x and y will burn with sooty flame.
Ques. 9JEE Main 2026, 24 January (Morning Shift)

Consider the following two reactions A and B. [figure] Numerical value of [molar mass of x + molar mass of y] is

  1. 46
  2. 160
  3. 88
  4. 4
Ques. 10JEE Main 2026, 24 January (Morning Shift)

A hydroxy compound (X) with molar mass 122 g mol-1 is acetylated with acetic anhydride, using a large excess of the reagent ensuring complete acetylation of all hydroxyl groups. The product obtained has a molar mass of 290 g mol-1. The number of hydroxyl groups present in compound (X) is:

  1. 2
  2. 4
  3. 3
  4. 5
Ques. 11JEE Main 2026, 24 January (Evening Shift)

From the following, how many compounds contain at least one secondary alcohol? [figure] Choose the correct answer from the options given below :

  1. Three
  2. Two
  3. Four
  4. Five

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