Provided below is the IR and 'H NMR for a compound having the molecular formula of C,H,O, Using this information, determine the degrees of unsaturation for this structure and solve and draw the structure responsible for these spectral data. To validate your answer, you need to assign the type of bond (ie, stretch) responsible for each peak highlighted by a box in the IR. You must also assign each 'H NMR peak (a)-(e) to the correct set of protons in your proposed structure. The integration for each peak has been provided for you. You must label the multiplicity observed for each peak. Is your structure consistent with all of this data? If not, chances are you do not have the correct structure, or the peaks have been assigned incorrectly. In your peer review, offer feedback concerning the accuracy of the submitted structures and spectral assignments. If you believe the answers are incorrect, then you need to provided explanation. In the end, you should all be getting the same correct structure. Please draw the final structure in the box provided underneath the NMR. TH NMR - for clarity, expansions have been provided for peaks that are not a singlets. Proposed Structure: Remember to assign it to the NMR per instructions. IR FREQUENCY TABLE (in wavenumber) Frequency Range (om ) Intensity Group A. Alky! C-H (stretching) Isopropy. -CH(CH), tert-Butyl, -C(CH) ( -5) and 2853-2002 1380-1385 1365-1370 1385-1395 - 1366 (m) and B. Alkenyl C-H(stretching) C- (stretching) R-CH-CH, m) (v) 3010-3095 1620-1600 085-1000 905-920 80-900 (6) (out of plane >C-H bondinga) and BCHCH cafe Esses se s8 s (8) 675-730 960-975 (6) (s) -3300 2100-2260 (8) () cle-RCH-CHR trans-RCH-CHR C. Alkyny! C H (stretching) C-C (stretching) D. Aromatic Ar-H(stretching) Aromatic substitution type (C-Hout-of-plane bendings) Monosubstituted o-Disubstituted m-Disubstituted -3030 and (very s) (very s) (s) 690-710 730-770 735-770 680-725 750-810 800-860 and (very s) (very s) 3590-3650 3200-3550 2500-3000 (sharp ) (broad, s) (broad, p-Disubstituted E. Alcohol, Phenols, and Carboxylic Acids O H (stretching) Alcohols, phenols (dilute solutions) Alcohols, phenols (hydrogen bonded) Carboxylic acids (hydrogen bonded) F. Aldehydes, Ketones, Esters, and Carboxylic Acids C-O (stretching) Aldehydes Ketones Esters Carboxylic acids Amides G. Amines N- H H. Nitriles CON 1630-1780 1690-1740 1680-1750 1735-1750 1710-1780 1630-1690 (s) (s) (s) (s) (s) (5) 3300-3500 (m) 2220-2260 (m) weak edium w - variatie p rowity Abbreviations strong m NMR CHEMICAL SHIFT TABLE (in ppm) CHARACTERISTIC PROTON CHEMICAL SHIFTS Type of Preton Structure Chemical Shin, ppm Cycopropane CHE Primary R-CH Secondary R-CH: Tertiary R; C-11 Vinylic C=C-H Acetylanic triple bond.CC-H Aromate Ar-H Benzyle Arc- Allylic CHCCH Fluorides H-C-F Chlorides H-C-a Bromides H-C-Br Iodides H-C- Alcohol H-C-OH Ethors H-C-OR 33-4 Esters RCOO-C- 3.7-4.1 Esters H-C-COOR 2-22 Acids H-C-COOH 2-26 Carbonyl Compounds H-C-C-0 2-27 Aldehydie R-CH-)C=0 9-10 Hydroxylic R-C-OH 1-55 Phenolie Ar-OH 4-12 Enolic C-C-OH 15-17 Carboxylic ROOOH 10.5-12 Amino RNH, 1-5