Alkyl Halides and Substitution

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7 Terms

1
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alkyl halides

C-X

Carbon is sp3 hybridized

X can be F, Cl, Br, I

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nucleophile

  • has electrons that it wants to share

  • needs lone pairs or pi bonds (has electrons to attack with)

  • bases grab/attack Hs

  • nucleophiles attack other electron deficient atoms (often carbon)


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what makes something a good leaving group?

stable once they are kicked out (i.e. weak bases (strong conjugate acids))

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how does nucleophilicity relate to basicity?

  1. for 2 Nu w/ same nucleophilic atom, stronger base = stronger Nu

  2. negatively charged nucleophile is stronger than its conjugate acid

  3. across a row, more basic = more nucleophilic (ex: CH3>NH2>OH>F (CH3 is the best base here so it is the best Nu)

  4. steric hindrance impacts nucleophilicity NOT basicity (non-nucleophilic base “big bulky base (BBB)) this means that bulkier molecules make the nucleophile bad at being a nucleophile since it’s harder for the Nu to grab, bulkiness DOES NOT affect bases

  5. size effects on nucleophilicity—> scale can either go up or down


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what makes something a bad base?

strong bases (so weaker conjugate acids), usually higher pKas

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polar aprotic

no hydrogen bond donors, solvents cannot hydrogen bond

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polar protic

hydrogens on heteroatoms, solvents can hydrogen bond (with themselves)