The main product of the following reaction is $\ce{C6H5CH2CH(OH)CH(CH3)2} \xrightarrow{\text{conc. } \ce{H2SO4}}$ ?

JEE Main · 2010 · 11 Apr 2010 · Offline · Alcohols Phenols and Ethers

The main product of the following reaction is

C X_{6} H X_{5} CH X_{2} CH (OH) CH (CH X_{3}) X_{2} conc. H X_{2} SO X_{4}

(A)(see structure)
✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)

Answer: (A)

Solution

Concentrated sulphuric acid dehydrates the alcohol by an acid-catalysed carbocation route: the hydroxyl is protonated and leaves as water, and loss of a

β

-hydrogen forms the alkene. Elimination follows Zaitsev's rule towards the more stable alkene, and here that double bond is the one conjugated with the benzene ring, which also favours the trans geometry. The major product is the conjugated alkene

C_{6} H_{5} CH = CHCH (C H_{3})_{2}

in its trans form.

JEE Main · 2010 · 11 Apr 2010 · Offline · Single correct option

Practise more: all JEE Main PYQs on Alcohols Phenols and Ethers →

More JEE Main questions on Alcohols Phenols and Ethers

Given below are two statements :

Statement I: Phenol on treatment with $CHCl_{3} /$ aq. KOH under refluxing condition, followed by acidification produces $p$ -hydroxy benzladehyde as the major product and $o$ -hydroxy benzaldehyde as the minor product.

Statement II …
JEE Main 2026View solution →
3,3-Dimethyl-2-butanol cannot be prepared by:
A.
B.
C.
D.
E.
Choose the correct answer from the options given below:
JEE Main 2026View solution →
A mixed ether ( P ), when heated with excess of hot concentrated hydrogen iodide produces two different alkyl iodides which when treated with aq. NaOH give compounds (Q) and (R). Both (Q) and (R) give yellow precipitate with NaOI. Identify the mixed ether (P):
JEE Main 2026View solution →
Consider the following two reactions A and B .
(A) (see structure)
(B) (see structure)

Numerical value of [molar mass of $x +$ molar mass of y ] is ______。
JEE Main 2026View solution →
From the following, how many compounds contain at least one secondary alcohol?
JEE Main 2026View solution →
Consider the following reaction sequence

vapour density 47]
Compound (y) develops characteristic colour with neutral $FeCl_{3}$ solution.
Identify the INCORRECT statement from the following for the above sequence.
JEE Main 2026View solution →