Ch_322b_16.12

Ch_322b_16.12 - Chapter 16.12 lecture note

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Products of the Grignard Synthesis: A Review The type of alcohol formed in a Grignard reaction depends on the carbonyl compound used: C H H O = (i) RMgX (ii) H 3 O + formaldehyde C R' H O C R' R'' O aldehydes (i) RMgX (ii) H 3 O + (i) RMgX (ii) H 3 O + ketones R- CH 2 OH primary R- CHOH R' secondary R- COH R' R'' tertiary
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Some Examples CH 3 CH 2 CH 2 MgBr (i) C 6 H 5 CH O = (ii) H 3 O + C 6 H 5 MgBr (1) O (ii) H 3 O + C 6 H 5 CH CH 2 CH 2 CH 3 OH 1-phenyl-1-butanol HO C 6 H 5 1-phenyl-1-cyclohexanol
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Planning a Grignard Synthesis Retrosynthetic Analysis of 2-methyl-2-hexanol Isolate the carbon center with the alcohol and evaluate C-C cleavages: CH 3 CH 2 CH 2 CH 2 C CH 3 OH CH 3 CH 3 CH 2 CH 2 CH 2 MgBr butylmagnesium bromide CH 3 CCH 3 O = acetone CH 3 CH 2 CH 2 CH 2 C CH 3 OH CH 3 CH 3 CH 2 CH 2 CH 2 CCH 3 O 2-hexanone CH 3 MgBr methylmagnesium bromide
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Retrosynthetic Analysis of 1-Phenylethanol C CH 3 H OH MgBr CH 3 CH O = phenylmagnesium bromide acetaldehyde Br bromobenzene CH 3 CH 2 OH ethanol benzene starting materials
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Synthetic Scheme CH 3 CH 2 OH Br 2 Fe Br Mg ether MgBr C 5 H 5 NH.CrO 3 .Cl + - CH 2 Cl 2 CH 3 CH O = C CH 3 H O-MgBr H 3 O + C CH 3 H OH
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

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Ch_322b_16.12 - Chapter 16.12 lecture note

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