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Consider cyclohexanol as the reference molecule for acid-catalyzed dehydration. Among the following compounds, how many will undergo acid-catalyzed dehydration at a faster rate than cyclohexanol? (i) 1-Methylcyclohexan-1-ol (ii) Cyclohexa-2,4-dien-1-ol (iii) Cyclohex-2-en-1-ol (iv) 1-Phenylethan-1-ol (v) Cyclohexylmethanol (vi) Phenol

Options

  1. A4
  2. B3
  3. C5
  4. D2

Correct answer

A. 4

Step-by-step solution

The rate of acid-catalyzed dehydration of an alcohol is directly proportional to the stability of the intermediate carbocation formed. Cyclohexanol dehydrates via a secondary carbocation (cyclohexyl cation). Let us evaluate the intermediate carbocations for the given compounds: (i) 1-Methylcyclohexan-1-ol forms a tertiary carbocation, which is more stable than a secondary carbocation. (Faster) (ii) Cyclohexa-2,4-dien-1-ol forms a resonance-stabilized dienyl cation and loses a proton to form the highly stable aromat

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