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:

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

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

Transcribed Image Text:

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