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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

Consider the following reaction sequence: If x and y represent the total number of products (including stereoisomers) formed in the respective steps, what are the values of x and y ?

Options

  1. A3 and 5
  2. B2 and 4
  3. C2 and 3
  4. D3 and 6

Correct answer

D. 3 and 6

Step-by-step solution

Dehydration of 2-pentanol with concentrated H₂SO₄ and heat proceeds via an E1 mechanism to form alkenes. The intermediate is a secondary carbocation at C-2: CH₃- + C H-CH₂-CH₂-CH₃ . Elimination of a proton from C-1 yields 1-pentene (no stereoisomers). Elimination of a proton from C-3 yields 2-pentene, which exhibits geometrical isomerism and exists as cis-2-pentene and trans-2-pentene. Thus, the total number of alkene products is x = 1 + 2 = 3 . Bromination of these alkenes with Br₂/CCl₄ proceeds via anti-addition:

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