Organic Chemistry I

Chem 334 - Fall 2011

Homework 5

Professor Carl C. Wamser

Carey, end-of-chapter problems
ARIS problems


1. Write IUPAC names for each of the following, including designation of stereochemistry where needed.


2. There are four isomeric alkenes of formula C4H8 . There are four isomeric alcohols of formula C4H10O . There are four isomeric alkyl bromides of formula C4H9Br .

For each of the four alcohols, predict the alkene product(s), including the expected major product, from an acid-catalyzed dehydration (E1) reaction.

For each of the four alkyl bromides, predict the alkene product(s), including the expected major product, from a base-promoted dehydrohalogenation (E2) reaction.

For each of the four alkenes, select the best synthetic route to make that alkene, starting from any of the available alcohols or alkyl halides.