You have just entered the chemistry stockroom to look for several isomeric bromopentanes. There are three bottles

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You have just entered the chemistry stockroom to look for several isomeric bromopentanes. There are three bottles on the shelf marked C5H11Br, but their labels have fallen off. The NMR machine is broken, so you devise the following experiment in an attempt to determine which isomer is in which bottle: You first treat a sample of the contents in each bottle with NaOH in aqueous ethanol, and then you determine the IR spectrum of each product or product mixture. Here are the results:

NaOH 1 (i) CŞH„Br isomer in bottle A IR bands at 1660, 2850-3020, and 3350 cm NaOH (ii) C3HBr isomer in bottle B IR bands at 1670 and 2850-3020 cm NaOH (iii) C;H„Br isomer in bottle C IR bands at 2850- 2960 and 3350 cm- 11


(a) What do the data tell you about each product or product mixture?

(b) Suggest possible structures for the contents of each bottle.

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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