Reactions - X 2 C C X X (Anti) M X M M 1/2M C C BH 3 THF H...

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C C H X Base See Footnote #1 C C C C HX See Footnote #2 C C H (Markovnikov's) E2 (Usually Zaitsev) X C C Hg(OAc) 2 NaBH 4 C C H OH (Markovnikov's) C C O 3 Zn dust C O C O C C HX Peroxide C C H X (Anti-Markovnikov's) C C C C OH OH 2KOH C C O 3 /Zn or KMnO 4 C C 2HX C C X H 2 Lindlar's (Syn) X M M 1/2M M C C H X X H (2 E2's) M C C C OH O C OH O X X (Markovnikov's) M C C (Cis) H H C C X Os O 4 Reaction Mechanisms Organic Chemistry X
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C C C C H H 2H 2 Metal Cat. H H X C C H 2 C C H H (Trans) X C O O R or H 2Li Al H 4 C H OH H M C H OH H C OH O Jones (Full Oxidation) C OH OH H oh Ts Cl Base C OTs M C OH HX C Cl (If 1 or 2 Sn2) M C OH HX C X M (If 3 ) C OH NaH *RX C OR M C OH PBr 3 C Br (If 1 or 2 Sn2) M C C Peracid C C (Pericyclic) M Li NH 3 X (Sn2) Sn1 (Sn2) O
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C C H 3 O + C C OH OH (Anti) C* O C* Conc. HI C OH C + I (Sn2- see footnote#3) C C H 2 S OH NaH C C M (~Sn2-must be anti) M C C -OR C C* OH OR Alkanes X 2 Light Alkyl Halides Mg Ether R-Mg-X C OH R C O (No alcohol, NH 2, COOH or SH present) M M M C C Na NH2 R*-X H C C R M M Li / Pentane CuI R*-X R-R' X O O O (Sn2) R-X (Sn2) R-X
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OH C C C O R or H Li Al H 4 C C X C R or H OH C H PCC C O (stops at sec) OH C H acid (Beware rearrangements) C C E1 (Zaitsev's) C C
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Unformatted text preview: X 2 C C X X (Anti) M X M M 1/2M C C BH 3 THF H 2 O 2 OH-C C H OH (Anti-Markovnikov) C C KMnO 4 C OH O C OH O (Free H 3 becomes OH 3 ) X C H NBS C C C Br X C C H 2 Metal Cat. H X (syn) X C X H + Zn C H C C X C C H H X X M 2X 2 Key M- knowledge of mechanism needed X- knowledge of mechanism unneccessary 1/2M- only half of mechanism necessary *- C or R indicated cannot be tertiary Footnotes #1 Hoffman product can be obtained by using O-as a base. #2 In conjugated systems, mutiple products (kinetics & thermodynamic) result. #3 alcohol on more substituted C. X 2 FeX 3 X HNO 3 H 2 SO 4 NO 2 SO 3 H + H 2 SO 4 + H 2 O RX or R-C-X O AlCl 3 R C O R or (Beware rearrangements) + E E (E= electron withdrawing) X M M M M...
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This note was uploaded on 07/03/2011 for the course CHEM 141 taught by Professor Matt during the Spring '11 term at Edmonds Community College.

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Reactions - X 2 C C X X (Anti) M X M M 1/2M C C BH 3 THF H...

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