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Chapter 6: Q80P (page 235)

Propose a mechanism for each of the following reactions:

Short Answer

Expert verified

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

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

• 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-

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

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

• 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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Most popular questions from this chapter

When fumarate reacts with D2O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti-addition of D2O?

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mixture?

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