Chemistry Reactions and Mechanisms

Recitation Attendance Issues

• Some students reported problems with recitation attendance not reflecting their IDs being scanned accurately.
• Teacher is actively working on resolving this issue.
• Students are encouraged to reach out if they have not already emailed regarding the attendance discrepancy.

Exam Logistics

• Last 15-20 minutes of class will be dedicated to answering questions about the upcoming exam.
• Students queried about specific topics like hydrochloration, indicating they were uncertain about certain content areas.

Substitution and Elimination Reactions Overview

• Focus shifted to discussing substitution and elimination reactions, specifically:

  • Substitution Reactions:
  • Two main types: SN1 and SN2.
  • In substitution, a nucleophile replaces a leaving group in either:
    • A single step (for S_N2) where nucleophile and leaving group interact simultaneously.
    • A two-step process (for S_N1) where a carbocation is formed first before nucleophile attachment.

• Comparing SN1 vs. SN2 reactions:

  • For S_N2 reactions:
  • Nucleophile and electrophile are both involved in the rate-determining step.
  • Efficient with good nucleophiles and polar aprotic solvents.
  • For S_N1 reactions:
  • Only the electrophile is involved in the rate-determining step, as it forms a stable carbocation before nucleophile attack.
  • The nature of the leaving group and stability of carbocation is crucial (tertiary > secondary > primary).

Key Factors in Reactions

• Various factors affect the reaction type:

  • Nature of Electrophile:

  • S_N2 prefers small electrophiles.

  • S_N1 favors bulkier electrophiles for carbocation stability.

  • Nature of Nucleophile:

  • Good nucleophiles favor S_N2 processes.

  • Ineffective during S_N1 since carbocation stability prevails.

  • Leaving Group Quality:

  • A better leaving group enhances both SN1 and SN2 reactions.

  • Solvent Effect:

  • Polar protic solvents promote S_N1.

  • Polar aprotic solvents favor S_N2 reactions.

Elimination Reactions (E1 and E2)

• Overview of elimination reactions:

  • E1 Reactions:

  • Include two steps:

    • Formation of a carbocation (same as in S_N1).
    • Base removes a proton, forming a double bond.

  • E2 Reactions:

  • A simultaneous mechanism where base removes a proton while the leaving group departs.

  • Needs coplanarity and anti-coplanar configuration for effective elimination.

Key Rules and Observations

• Zaitsev's Rule: In elimination reactions, the most substituted alkene will be the primary product.
• In some scenarios with sterically hindered bases, anti-Zaitsev products can form instead by selectively removing less substituted hydrogens.
• Various bases utilized can significantly impact whether E1 or E2 mechanisms are observed, especially concerning base sterics and strength.

Mechanisms and Stereochemistry

• Stereochemical outcomes vary depending on whether the process is SN2 or SN1, with:
  • S_N2 reactions causing inversion of configuration.
  • S_N1 reactions scrambling the configuration.

Examination Points

• Students are reminded that not all reactions and mechanisms need to be memorized, particularly for well-defined processes, but recognizing key functional group transformations and mechanisms is essential.