Which among the following alcohols will undergo acid-catalyzed...

The rate of acid-catalyzed dehydration of an alcohol depends on the stability of the carbocation intermediate formed during the rate-determining step.

Let us analyze the carbocations formed from each given alcohol after the protonation and loss of a water molecule:

(A) 1-phenylpropan-1-ol forms a secondary benzylic carbocation: $\text{Ph}-\text{CH}^{+}-\text{CH}_2\text{CH}_3$.
(B) 2-phenylpropan-2-ol forms a tertiary benzylic carbocation: $\text{Ph}-\text{C}^{+}(\text{CH}_3)_2$.
(C) 1-phenylpropan-2-ol forms a secondary carbocation: $\text{Ph}-\text{CH}_2-\text{CH}^{+}-\text{CH}_3$.
(D) 3-phenylpropan-1-ol forms a primary carbocation: $\text{Ph}-\text{CH}_2-\text{CH}_2-\text{CH}_2^{+}$.

The stability order of these carbocations is: Tertiary benzylic > Secondary benzylic > Secondary > Primary.

Since the tertiary benzylic carbocation formed in option (B) is the most stable due to resonance with the phenyl ring and hyperconjugation from six $\alpha$-hydrogens, 2-phenylpropan-2-ol will undergo acid-catalyzed dehydration most rapidly.

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