please help with IR spectroscopy problems #9-11 and 13-15

9. Without providing wavenumbers, qualitatively, which bond requires more energy to stretch and as such will be associated with a peak of higher wavenumber: C=N or CN ? 1DCN (19. List the wavenumber to commit as a boundary point and list the two types of peaks sitting across from this boundary. 11) Identify the threshold for the fingerprint region below which peak identification becomes less trustworthy. 12. The CCH,OH, and NH peaks are coincident at 3300cm1. Assign each band to a particular peak shape. CCH; SharP, OH; broad, NH; broad w/ SDiKeS 13. Use line-angle formula. Draw a five carbon alcohol ROH. Draw a five carbon ether ROR. List one peak by wavenumber present in the alcohol but not present in the ether. 3300cm1 14. Use line-angle formula. Draw a five carbon aldehyde ROCH. Draw a five carbon ketone ROCR. List one peak by wavenumb present in the aldehyde but not present in the ketone. 2750cm1 15 Use line-angle formula. Draw a five carbon carboxylic acid RCOOH. Draw a five carbon alcohol ROH. List one peak by wavenumber present in the carboxylic acid but not present in the alcohol