Advanced Organic Synthesis Design
Advanced Organic Synthesis Design CHE 686
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This 6 page Class Notes was uploaded by Dr. Alana Bauch on Wednesday October 21, 2015. The Class Notes belongs to CHE 686 at Syracuse University taught by Nancy Totah in Fall. Since its upload, it has received 54 views. For similar materials see /class/225658/che-686-syracuse-university in Chemistry at Syracuse University.
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Date Created: 10/21/15
Electrophilic Aromatic Substitution Rxn Type E Reagent Catalyst Halogenation X X2 FeX3 AIX3 2 Cul stoich Nitration NO2 HNO3 H2804 Sulfonation 803H 803 H2804 Alkylation R RX AICI3 R ROII H2804 R CC H2804 o o Acylatlon J i AICI3 Nitration of Monosubstituted Benzene Compounds G G G N02 1 1 ltj N02 N02 3 HNo3 gt H2804 Group RRelattiv ortho meta para Ratio eac IVI y oplm OH very fast 50 0 50 1000 0 NH6CH3 fast 19 2 79 982 CH3 24 63 3 34 973 CCH33 16 12 8 80 928 H benzene 10 standard for relative reactivities CH2C 03 32 16 52 8416 F 003 13 1 86 991 CI 003 35 1 64 991 Br 003 43 1 56 991 I 45 1 54 991 0 4 3OCHZCH3 1o 28 66 6 3466 0 5H slow 19 72 9 2872 0 5CH3 slow 26 72 2 2872 SosH SIOW 21 72 7 2872 0 CquotOH SIOW 22 76 2 2476 CEN SIOW 17 81 2 1981 3043 slow 2 87 11 1387 N02 107 7 91 2 991 CF3 slow 0 100 0 0100 Stereochemical Nomenclature absolute stereochemistry R S denotes absolute stereochemistry for stereogenic atoms CI CI H39 O H O H H E 1S2R 2 chloro1cycohexano refers to optical rotation Does not correlate to absolute configuration refers to those molecules that rotate plane polarized light in a clockwise direction refers to those molecules that rotate plane polarized light in a counterclockwise direction H N H 0 H02C002H N CH3 H H R methylsuccinic acid R2 methypiperidine relative stereochemistry R 3 denotes relative stereochemistry for stereogenic atoms in racemic systems with more than one stereocenter less frequently used 0 H o H or 0 1S2R2 chloro1cycohexano CI IIIIQ cis trans describes relationship between two substituents in cyclic systems and in simple alkenes OH OH CH3 CH3 H CH3 CH3 CH3 lt gt lt H H CH3 H cis trans cis trans E Z describes stereochemistry of alkenes simple and more complex CH3 CH3 H CH3 5 CI OH3 OI OH3 H H CH3 H 5 CH3 H H OOH3 z E E z E syn anti describes relationship between two substituents in an acyclic system longest chain on zig zag CH3 CH3 5 CH3 OH3 OH WOH E 002Me OH OH 5 OH syn anti E 23 anti 34 syn 24 anti erythro threo traditional terminology used to describe relationship between two substituents on an acyclic molecule Originally designed for glycols With other systems gets confusing do not use except for glycols H O O H H O O H H HquotH H HquotR R R R H erythro threo Regioselectivity Rules for Allylic Oxidation with SeO2 1 Oxidation occurs on the more highly substituted side of a tricyclic olefin so long as a nonbridged allylic H is available gt 8802 H 0 HO 2 Oxidation of 1alkylcyclohexenes occurs within the ring not on the side chain HO C Log C 3 Oxidationn Ler occurs at bridgehead positions amp 8902 L540 H 4 After taking into consideration the above rules the preferred order of reactivity is CH2 gt CHa gtCH OH M M gt8802 M M O H decreasing reactivity Reduction of Various Functional Groups with Hydride Reducing Agents Rcoc gt R CHzOH RCHO R CH2OH o HO H RJLR39 R R39 0 R H Av RJ ltOH R R R R 0 JL gt RCHgOH HoR39 R OR39 RCOz39 Na gt RCHzOH slow RENE R CH2NR392 or R CHO I R R CEN gt R CHzNHz or RCHO R N02 R NH2 R CHzX gt R CH3 X H x Br CI I OSOzR RAR RAR R R39 gt R R reduced only under special circumstances R CH20H2R39
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