Identifying the products of chemical reactions

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Question 2
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The reaction scheme below outlines a two-step organic synthesis starting from pent-1-ene:

Reaction scheme starting from pent-1-ene

Which statement correctly identifies Organic Product Y and provides the correct chemical justification for its formation as the major product?

Product Y\text{Product Y}Product Y is (E)(E)(E)-pent-2-ene. In Step 1, electrophilic addition proceeds via the more stable secondary carbocation to form 2-bromopentane. In Step 2, elimination of 2-bromopentane yields (E)(E)(E)-pent-2-ene as the major product because it is the more stable stereoisomer, minimizing steric repulsion between the bulky methyl and ethyl groups on opposite sides of the double bond.

Product Y\text{Product Y}Product Y is (Z)(Z)(Z)-pent-2-ene. In Step 1, electrophilic addition proceeds via the secondary carbocation to form 2-bromopentane. In Step 2, elimination yields (Z)(Z)(Z)-pent-2-ene as the major product because the cis-like configuration allows the alkyl groups on the same side of the double bond to maximize stabilizing intramolecular London dispersion forces.

Product Y\text{Product Y}Product Y is pent-1-ene. In Step 1, electrophilic addition proceeds via a primary carbocation to form 1-bromopentane. In Step 2, elimination of 1-bromopentane selectively occurs to regenerate pent-1-ene because terminal alkenes are thermodynamically more stable due to reduced hyperconjugation.

Product Y\text{Product Y}Product Y is (E)(E)(E)-pent-2-ene. In Step 1, electrophilic addition proceeds via a radical mechanism to yield 1-bromopentane as the major product. In Step 2, this undergoes nucleophilic substitution to form pentan-1-ol, which then dehydrates to yield (E)(E)(E)-pent-2-ene.

Identifying the products of chemical reactions Questions

  1. GCSE
  2. /Chemistry
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