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Chapter 6: Q80P (page 235)

Propose a mechanism for each of the following reactions:

Short Answer

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鈥+ (an electrophile) binds to the most hydrogen-bonded sp2 carbon of the alkene (a nucleophile).

鈥� A protonated alcohol is formed when H2O (a nucleophile) reacts with the carbocation (an electrophile).

鈥� Because the pH of the solution is higher than the protonated alcohol's pKa, the protonated alcohol loses a proton.

Step by step solution

01

Mechanism for the acid-catalysed addition of water to an alkene-

鈥+ (an electrophile) binds to the most hydrogen-bonded sp2 carbon of the alkene (a nucleophile).

鈥� A protonated alcohol is formed when H2O (a nucleophile) reacts with the carbocation (an electrophile).

鈥� Because the pH of the solution is higher than the protonated alcohol's pKa, the protonated alcohol loses a proton.

02

Mechanism for the addition of H-Cl to an alkene via an acid catalysed reaction

  • H+ (the electrophile) adds to the most hydrogen-bonded sp2 carbon.
  • The nucleophile, CH3OH, reacts with the carbocation to generate a protonated ether.
  • Because the pH of the solution exceeds the protonated ether's pKa (pKa -3.6), the protonated ether loses a proton.

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