Organic Chemistry II – Spring 2006 – Exam #2 Name ________________________ /12 1. Please answer the following questions about cyclohexanone, shown to the left. a. How many carbon signals will be present in the carbon NMR? b. How many hydrogen signals will be present in the hydrogen NMR? c. Predict the multiplicity (splitting) of the peak produced by the hydrogens on the carbon atom at the bottom of the figure. (i.e. Singlet? Doublet?...) d. How many signals will be observed in a DEPT spectrum? e. What two differences in their IR spectra will allow you to easily distinguish cyclohexanone from cyclohexanol? 2. Identify the compound whose mass spectrum appears below. Label the species causing peaks at 110, 108, and 29 m/z. /9 3. If the compound shown to the below undergoes fragmentation during MS, what three fragments (in addition to the molecular ion) will be observed? Draw out each fragment, paying attention to charges and unpaired electrons. (You don’t need to calculate the masses for each fragment...