organc chem slides

organc chem slides - 131 II Sn1 a RATE OF REACTION = k RX b...

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Unformatted text preview: 131 II) Sn1 a) RATE OF REACTION = k [ RX ] b) If carbon is chiral, racemic product is formed . C X C n + X C n n C + RACEMIC MIXTURE SLOW FAST 133 B) Sn2 versus Sn1 I) NATURE OF ALKYL HALIDE a) Sn2 – primary> secondary > tertiary C X C X C X H H H R R R R' R' R" primary secondary tertiary n n n 134 b) Sn1 – tertiary >secondary > primary C C C R R R R' R' R" H H H primary secondary tertiary Stability of carbocation- Tertiary > secondary > primary > methyl 135 II) NATURE OF NUCLEOPHILE a) The stronger the nucleophile the greater the tendency toward Sn2. EXAMPLE I + H 2 O OH + HI Sn1 I + OH- OH + I- Sn2 136 C) ELIMINATION REACTIONS 137 I) FACTORS AFFECTING ELIMINATIONS a) NATURE OF ALKYL HALIDE TERTIARY > SECONDARY > PRIMARY b) NATURE OF BASE The stronger the base the greater the tendency for elimination c) NATURE OF SOLVENT ETHYL ALCOHOL favors elimination + Cl + _ Cl CH 3 CH 2 ALCOHOL KOH CH 2 CH 2 + H 2 O 138 ALCOHOLS,PHENOLS & ETHERS 1- STRUCTURE H O H R O H Ar O H R' O R Ar O R Ar' O Ar water alcohol phenol ethers dialkyl alkyl aryl diaryl NOTE : These substances can be considered to be derived from water. One might expect that their properties are similar. CHAPTER 7 & 8 139 H O H Ar O water + H + H O H H O H H hydronium ion + H + H O R O H R H O H + H + R O R' O R' O H R + H + R O Ar R H O Ar O + H + Ar' O Ar' Ar H O + H + H O Ar H O Ar H O H 140 A)Alcohols and Phenols – soluble in water due to hydrogen bonding....
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This note was uploaded on 05/15/2008 for the course CHEM 120 taught by Professor Krishnamachari during the Spring '08 term at CUNY Hunter.

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organc chem slides - 131 II Sn1 a RATE OF REACTION = k RX b...

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