ps4 - NMe 2 NMe 2 3. Provide two syntheses of the following...

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Massachusetts Institute of Technology 5.13: Organic Chemistry II Fall 2003, S. Tabacco Problem Set 4 Due: Thursday, 10/30/03 at 4 PM 1. Several factors (sterics, electronics, orbital interactions, etc.) can affect the inversion barrier of an amine. For each of the following pairs, provide an explanation for the relative magnitude of the given inversion barriers. a) Me i Pr N vs/ N Me Me i Pr Me G = 7.9 kcal/mol G = 0.2 kcal/mol b) N vs/ N Me Me G =20.5 kcal/mol G = 7.0 kcal/mol c) Me Cl N vs/ N Me Me Cl Cl G = 7.9 kcal/mol G = 22.9 kcal/mol d) H H N vs/ N H H H G = 6.5 kcal/mol G = 4.2 kcal/mol 2. Provide a mechanism for each of the following transformations. Your mechanisms must account for the observed selectivity. OTs O CH 3 CH 3 CO 2 Na O NMe 2 CH 3 CO 2 H NMe 2 O CH 3 OTs CH 3 CO 2 Na enantiomer O CH 3 CO 2 H
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Unformatted text preview: NMe 2 NMe 2 3. Provide two syntheses of the following primary amine from (R)-2-pentanol. Both methods must avoid over-alkylation. NH 2 H 3 C CH 3 4. Predict the products of the following reactions. Assume the appropriate work-up is included. H 3 C a) d) O 1. H 2 O 2 NMe 2 NMe 2 H 2. Na(AcO) 3 BH CH 3 O b) O 1. H 2 NOH, H + e) Cl 2 , OH, H 2 O NH 2 H 3 C H 2. Zn, HCl c) O N O f) 1. HCN, KCN CH 3 H 2 NNH 2 2.LiAlH 4 O 5. Provide syntheses for each of the following molecules from the given starting material. Show all synthetic intermediates. Your syntheses must avoid over-alkylation. a) H 2 N OH from CH 3 CH 3 H 3 C H 3 C b) CH 3 O N H from H 3 C H c) H 3 C CH 3 H 3 C CH 3 O NH 2 from H 3 C Cl H 3 C CH 3 NH 2 N d) H 3 C CH 3 from CH 3 e) NMe 2 CH 3 from CH 3 H 3 C...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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ps4 - NMe 2 NMe 2 3. Provide two syntheses of the following...

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