2Dstructuredrawing hem314 Beauchamp 3 2 3 3 2 2 3 2 2 3 2 2 (neutral) (cation) (anion) (free radical) use zig-zag drawing for sp 3 chains 1 o carbocation 1 o carbanion 1 o free radical 3 3 3 3 3 3 (cation) (anion) (free radical) 2 o carbocation 2 o carbanion 2 o free radical 3 2 (neutral) alcohol 3 2 2 (cation) 3 2 (anion) use zig-zag drawing for sp 3 chains protonated alcohol alkoxide 3 2 (neutral) 3 2 2 3 2 3 2 (cation) (anion) (free radical) ether use zig-zag drawing for sp 3 chains protonated ether carbanion free radical
2Dstructuredrawing hem314 Beauchamp 3 3 3 2 3 3 3 2 o amine use zig-zag drawing for sp 3 chains dialkylammonium ion 2 o amide anion 2 3 2 2 2 2 2 2 (free radical) monosubstituted alkene 1 o allylic carbocation 1 o allylic carbanion 1 o allylic free radical 3 3 2 2 imine
2Dstructuredrawing hem314 Beauchamp 3 3 2 aldehyde enolate anion protonated carbonyl 3 3 3 3 3 2 ketone enolate anion protonated carbonyl
2Dstructuredrawing hem314 Beauchamp 3 2 3 () 2 3 2-2 2 2 (dianion) carboxylic acid carboxylate anion protonated carboxylic acid carboxylate dianion 3 2 2 2 (free radical) alkyne propargyl carbocation propargyl carbanion propargyl free radical
2Dstructuredrawing hem314 Beauchamp 3 3 2 nitrile protonated nitrile nitrile enolate 3 2 3 3 () 3 2 2 3 ester protonated ester ester enolate
2Dstructuredrawing hem314 Beauchamp 3 l 3 l 2 l l acid chloride l l l l poor due to inefficient overlap of 3p chlorine orbital with 2p carbon orbital l acid chloride enolate (unstable to elimination, forms ketene) 6 5 3 6 5 2 6 5 2 6 5 2 (free radical) 2 more times (in the ring) 2 more times (in the ring) 2 more times (in the ring)
2Dstructuredrawing hem314 Beauchamp 3 2 F 3 F 3 F F use zig-zag drawing for sp 3 chains fluoroalkane F F F 6 5 3 6 5 2 6 5 2 6 5 2 6 5 2 6 5 3 6 5 6 5 6 5 2 6 5 3 2 F 3 F 3 F F 3 2 3 2 2 2 3 3 2 3 2 3 2 2 2 2 2 2 2 2 2 3
2Dstructuredrawing hem314 Beauchamp 2D and 3D structures with carbon and heteroatoms acid and base reactions neutral and formal charge sigma skeleton sigma + pi bonds Y X Y X F sigma skeleton sigma + pi bonds Y X Y X sigma skeleton no pi bonds Y X F l In acid (-A) - Do not make +2. 1. react with lone pair electrons, "A" keeps electrons (as conjugate base) 2. react with pi bond electrons In base (B: ) - Quench "+" if possible. 1. remove proton (+), leave electrons behind 2. attack carbon, push electrons away to heteroatom A A B B B
2Dstructuredrawing hem314 Beauchamp antidisestablishmenttarianism - opposition to disestablishmentof a church or religoius body an - ti - dis - es - tab - lish - ment - ta - ri - an - ism Break a complicated problem down into simpler parts. 3 2 ( 3 ) 2 2 2 2 2 2 ( 2 ) 2 () 2 () 2 2 6 4 2 2 ()' 2 3 2 ()' l 2 l 2 ( 2 )' 2 ( 3 ) 3 3 3 ( 3 ) 2 ( 2 3 )' 2 2 2 3 ( 2 3 )' 3 2 ( 3 ) 2 2 2 3 ( 3 ) 3 () 2 3 3 6 4 () ( 3 ) 3 2 ( 2 )' 6 5 6 4 3 2 2 3 3
2Dstructuredrawing hem314 Beauchamp ' ' l l ' 3 ' 3 ' 3 3 3 ' ketone alkene nitroso nitrite aromatic alcohol azide diazonium aldehyde alkyne nitro nitro alkyne alkyne nitrile ester ketone aromatic alkene alcohol carboxylic acid alkene alkene nitrile alkyne nitrile thio ether / sulfide amide sulfonamide sulfonamide amide ether ether amine t-butyl ester methyl sulfonate amine thio ether sulfide thiol acid chloride sulfonyl chloride thiol alcohol carboxylic acid sulfonic acid alcohol aldehyde aldehyde aromatic ketone