1. A student obtains an IR spectrum with an intense, broad absorption at about 3350 cm-'. The student claims that the sample is an alcohol, but the professor says that the absorption is there because the sample is contaminated by water. What peak(s) could be looked for to show that the sample is indeed an alcohol? Which functional groups would make it difficult to use this strategy?
2. The labels on two bottles were not properly secured and they came off. One bottle contains cyclohexanone and the other contains cyclohexanol. List three ways (besides the example below) that you could you tell which liquid is in which bottle, and describe how your results would distinguish between the two liquids. Not all these ways need to employ spectroscopy. Do not simply name tests or techniques. Instead, describe what you would observe. For example, "Cyclohexanone would give a positive DNP test and a negative chromic acid test, but cyclohexanol would give a negative DNP test and a positive chromic acid test?' (You may wish to look up the properties and structures of these compounds in a catalog or handbook before answering this question.)