HINTS for PROBLEM #9

• Find the molecular weight from molecular ion in the mass spectrum
• What functional groups are present from the IR ?
• What do the peaks at 7-8 ppm in the H-nmr and at 120-180 ppm in the 13C-nmr reveal ?
• Look at the integration in the H-nmr
• Use the above to get the molecular formula (make sure it matches the MW)
• Count the number of types of C in the 13 C-nmr. What does this tell you ?

(particularly those between 120-180ppm)
• What hydrocarbon pieces the H-nmr indicate ?
• Using the chemical shifts how are these pieces connected together ?
• Symmetry ?