Battle of Mechanisms / Properties

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Last updated 12:49 PM on 4/19/26
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11 Terms

1
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Sn1 Conditions / Mechanism

Mechanism: 2 Steps

Conditions:

  • Weak Nucleophile

  • Polar Protic Solvent (H bonds slow the nucleophile)

  • Electrophiles must be capable of stabilizing carbocation (good resonance/hyperconjugation)

<p>Mechanism: 2 Steps</p><p>Conditions: </p><ul><li><p>Weak Nucleophile</p></li><li><p>Polar Protic Solvent (H bonds slow the nucleophile)</p></li><li><p>Electrophiles must be capable of stabilizing carbocation (good resonance/hyperconjugation)</p></li></ul><p></p>
2
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Sn2 Conditions / Mechanism

Mechanism: 1 Step

Conditions:

  • Strong Nucleophile

  • Polar Aprotic Solvent

  • Carbon electrophiles must have least steric hinderance and resonance withdrawing)

<p>Mechanism: 1 Step</p><p>Conditions:</p><ul><li><p>Strong Nucleophile</p></li><li><p>Polar Aprotic Solvent</p></li><li><p>Carbon electrophiles must have <strong>least steric hinderance and resonance withdrawing</strong>)</p></li></ul><p></p>
3
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E1 Conditions / Mechanism

Mechanism: 2 Steps

Conditions:

  • Weak base

  • Heat

  • carbon electrophile needs electron donating (C-H) groups

<p>Mechanism: 2 Steps</p><p>Conditions:</p><ul><li><p>Weak base</p></li><li><p>Heat</p></li><li><p>carbon electrophile needs electron donating (C-H) groups</p></li></ul><p></p>
4
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E2 Conditions / Mechanism

Mechanism: 1 Step

Conditions:

  • heat

  • carbon electrophile must have sigma beta C-H bond anti to sigma alpha C-LG bond)

  • Strong Base

<p>Mechanism: 1 Step</p><p>Conditions:</p><ul><li><p>heat</p></li><li><p>carbon electrophile must have sigma beta C-H bond anti to sigma alpha C-LG bond)</p></li><li><p>Strong Base</p></li></ul><p></p>
5
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Weak Base & Weak Nucleophile

Neutral, highly electronegative atoms

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Weak Base & Strong Nucleophile

  1. Large, Polarizable Atom

  2. Resonance Stabilized negative charge on smallest atom

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Strong Base & Strong Nucleophile

Negative charge on smallest atom without any resonance stabilization

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Strong Base & Weak Nucleophile

Sterically hindered / BONUS if negative charge on smallest atom

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pKa Factors

  1. Electronegativity —> Higher the EN of atom directly bonded to H = Higher acidity

  2. Hybridization —> Higher the S% character = Higher Acidity

  3. Polarizability —> The larger/more distortable the electron cloud of atom directly bonded to H = Higher Acidity

  4. Resonance —> if lone pair of conjugate base can be delocalized through resonance, more acidic

  5. Induction —> the more Electronegative the atom near the H = higher acidity

  6. Hyperconjugation —> more alkyl groups = lower acidity

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Differences in Enantiomer Properties

  1. How they interact with other chiral molecules

  2. How they rotate plane polarized light in different directions

11
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Types of Enantiomer Mixtures

  1. Enantiomerically Pure —> Only one type of enantiomer = light rotated only to one direction

  2. Enantiomer Excess —> Major Enantiomer % - Minor Enantiomer %

  3. Racemic (50/50) —> No light rotation (cancels out)