HW 3Key_F07 - Chemistry 223 HW 3 Name Section 1 The following compounds undergo Mclafferty rearrangement in the mass spectroscopy Predict the

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Chemistry 223 Name ____________________ HW 3 Section____________________ September 26, 2007 1- The following compounds undergo Mclafferty rearrangement in the mass spectroscopy. Predict the masses of the resulting charged fragments. (10 pts) (a) pentanal (b) methylbutyrate Key CH O H + O H H m/z 44 m/z 86 mass 42 a) b) H 2 C O OCH 3 H m/z102 + O OCH 3 H m/z 74 mass 28 2- Propose mechanisms for the following reactions: (18 pts) H 3 C O H PhNHNH 2 , H + H 3 C N H NHPh CH 2 O Ph 3 P=CH 2 a) b) c) N H H + , H 2 O + NH 3 CHO Key 1
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H 3 C O H H 3 C N H NHPh a) H 3 C O H PhNHNH 2 + NNHPh H 3 O + H 2 O H H H 3 C + OH 2 H NNHPh H -H2O H 3 C H NNHPh H + H 3 C H NNHPh H + OH 2 H + H CH 2 O Ph 3 P-CH 2 b) Wittig reaction + - CH 2 - O Ph 3 P+ CH 2 PPh 3 O c) N H + NH 3
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This homework help was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Chahoua during the Fall '07 term at Wake Forest.

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HW 3Key_F07 - Chemistry 223 HW 3 Name Section 1 The following compounds undergo Mclafferty rearrangement in the mass spectroscopy Predict the

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