Problem_set_7 - Problem set 7 Chem 127/227 Fall quarter...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Problem set 7; Chem. 127/227, Fall quarter 2007 1. (a) Formulate a mechanism illustrating the E 2 elimination sequence that places the π - bond between C2 and C3, starting from the substrate shown below. Pay particular attention to stereochemistry. Br 2 3 1 (b) Does the structure of the product correspond to an E- or to a Z-alkene? Provide a name that is consistent with IUPAC rules of nomenclature. (Note that your mechanism must be formulated so that it accounts for the stereochemical outcome.) (c) Formulate a rate expression for the process. 2. Now look at the β -hydroxy aldehyde shown below, the product of an aldol condensation. H OH O (a) Use an aldol condensation to illustrate how the substance could be synthesized. (b) β -Hydroxy aldehydes, ketones, ester, nitriles (etc.) often undergo β -elimination, leading to the formation of an α , β -unsaturated adduct. Using hydroxide ion as the base, illustrate the elimination process, and provide the structure of the product(s) derived from the
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 10/15/2010 for the course CHEM chem 127 taught by Professor Littlerd during the Fall '09 term at UCSB.

Ask a homework question - tutors are online