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
- A3 and 5
- B2 and 4
- C2 and 3
- 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: