Chapter 5 Homework

Carey, pages 223 - 229:
Problems 5.22 - 5.48

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

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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.