Reactive Intermediates

Reactive Intermediates - o Stability-...

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Reactive Intermediates Carbocations o Carbon with three bonds and no lone pairs o Trigonal planar geometry o sp 2 -hybridized o empty p-orbital o stability - 3°>2°>1°> methyl o electron-deficient o only intermediate which can undergo rearrangement 1° carbocation with 3° position next door hydride shift H H + + We’ll see a lot of this later in the course. It’s a good idea to think “carbocations can rearrange” every time you see a carbocation intermediate for the rest of your life! Radicals o Carbon with three bonds and one unpaired electron o Trigonal planar geometry o sp 2 -hybridized o one electron in the p-orbital o stability - 3°>2°>1°> methyl o electron-deficient Carbanions
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o Carbon with three bonds and a lone pair o sp 3 -hybridized o Tetrahedral geometry
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Unformatted text preview: o Stability- methyl>1°>2°>3° o Strong bases/nucleophiles Carbenes o Carbon with two bonds and one lone pair o Neutral o Rare o sp 2-hybridized o empty p-orbital o can be electrophile or nucleophile Radicals, carbocations, and carbanions are stabilized by resonance o One away from a double bond is called “allylic” + Being directly on the double bond is particularly unstable and this position is called “vinyl” + o One away from an aromatic ring is called “benzylic” + Being directly on the aromatic ring is particularly unstable and this position is called “aryl” +...
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This note was uploaded on 03/06/2012 for the course CHEM 102 taught by Professor Henshaw during the Spring '08 term at VCU.

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Reactive Intermediates - o Stability-...

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