{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

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

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

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...
View Full Document

{[ snackBarMessage ]}