Question

Please provide molecular structure for the follwoing and their corresponding signals.(listed below are the CNMR chemical shifts)

Typical 'H and 18C NMR Chemical Shifts Type of Proton Structure Chemical Shift, ppm Alkyl groups RxCH 0.9 1.5 Vinyl C=C-H 4.6 - 5.9 Acetylene triple bond,CFC-H 2 - 3 Aromatic Ar-H 6 - 8.5 Benzylic Ar-C-H 2.3 - 3 Allylie CFC-CHS 1.7 - 2.5 Halides H-C-X 2 - 4.5 Oxygen adjacent carbons H-C-OH 3.4 Carbonyl adjacent carbons H-CCFO 1.9 2.7 Aldehyde hydrogen R-CHO 9 - 10 Hydroxyl and amino groups R-C-OH and RNH2 5.5 Carboxylic acid (acidic hydrogen ) RCOOH 10.5 -12 Amides RNHCOR' 5 - 8.5 Nitro H-C-NO2 4.3 - 5.3 Typical 13C NMR Chemical Shifts Carbon environment Chemical shift (ppm) CFO (ketones and aldehydes) 180 - 220 C=0 (acids, esters and amides) 165 - 185 115 - 150 Csp? 65 – 120 Csp 40 - 75 0 and N attached 0 - 20, 20 - 40, 50 - 60, 60 - 88 RCHIBr, C1 and F 0 - 50 Cspº