2Dstructuredrawing Chem314 Beauchamp
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1 2Dstructuredrawing hem314 Beauchamp (neutral) (cation) (anion) (free radical) use zig-zag drawing for sp 3 chains 1 o carbocation 1 o carbanion 1 o free radical (cation) (anion) (free radical) 2 o carbocation 2 o carbanion 2 o free radical 3 2 (neutral) alcohol (cation) 3 2 (anion) use zig-zag drawing for sp 3 chains protonated alcohol alkoxide 3 2 (neutral) (cation) (anion) (free radical) ether use zig-zag drawing for sp 3 chains protonated ether carbanion free radical
2 2Dstructuredrawing hem314 Beauchamp o amine use zig-zag drawing for sp 3 chains dialkylammonium ion 2 o amide anion (free radical) monosubstituted alkene 1 o allylic carbocation 1 o allylic carbanion 1 o allylic free radical imine
3 2Dstructuredrawing hem314 Beauchamp aldehyde enolate anion protonated carbonyl ketone enolate anion protonated carbonyl
4 2Dstructuredrawing hem314 Beauchamp () (dianion) carboxylic acid carboxylate anion protonated carboxylic acid carboxylate dianion (free radical) alkyne propargyl carbocation propargyl carbanion propargyl free radical
5 2Dstructuredrawing hem314 Beauchamp nitrile protonated nitrile nitrile enolate () ester protonated ester ester enolate
6 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) (free radical) 2 more times (in the ring) 2 more times (in the ring) 2 more times (in the ring)
7 2Dstructuredrawing hem314 Beauchamp 3 2 F 3 F 3 F F use zig-zag drawing for sp 3 chains fluoroalkane F F F F 3 F 3 F F
8 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 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
9 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 () ()' ()' l 2 l 2 ( 2 )' 2 ( 3 ) ( 3 ) 2 ( 2 3 )' ( 2 3 )' 3 2 ( 3 ) ( 3 ) 3 () () ( 3 ) 3 2 ( 2 )'
10 2Dstructuredrawing hem314 Beauchamp ' ' l l ' 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
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Chem 231 Summer 2015 Assigned Homework Problems Last updated: Friday, July 24, 2015 Problems Assigned from Essential Organic Chemistry, 2 nd Edition, Paula Yurkanis Bruice, Prentice Hall, New York, NY,
General Infrared Absorption Ranges of Various Functional Groups
General Infrared Absorption Ranges of Various Functional Groups Frequency Range Bond Type of Compound cm -1 Intensity C Alkanes 2850-2970 Strong 1340-1470 Strong C Alkenes 3010-3095 Medium 675-995 Strong