Solutions_Manual_for_Organic_Chemistry_6th_Ed 319

Solutions_Manual_for_Organic_Chemistry_6th_Ed 319 - o A G...

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Unformatted text preview: o A G (X " 0H "' G The student turned in the wrong product ! Three pieces of information are consistent with the desired product: molecular formula C4HIOO; O-H stretch in the IR at 3 300 cm-I (although it should be strong, not weak); and mass spectrum fragment at rnJz 59 (loss of CH3). The NM R o f the product should have a 9H singlet at 8 1 .0 and a IH singlet between 8 2 and 8 5. Instead, the NMR shows CH3CH2 bonded to oxygen. The student isolated diethyl ether, the typical solvent used in Grignard reactions. 1 4-40 0 Na � (X " " '0 0 Na - D + CH3Br C � (X 0CH] '' '" H 0 Predicted product 59 CH3 CH] H Isolated product 1 4-4 1 (a) U OH O-H at 3 300 cm-I - CH3 C 4HIOO Na - OH /"-.../ OH \ }OH PBr3 U O- Na+ � (b) NaOH� � Br \ }- } C4HIOO O-H at 3 300 cm-I due to water contamination O _U� O- Na+ � OH TsCI � �OTs pyridine � \ }- o � 3 12 ...
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