Answer Happy

Three bottles, each containing a ketone of molecular formula Chuo, have lost their labels and need to be identified by you for an upcoming safety inspection. You run the 'H NMR spectrum (in COCI: containing TMS) of each substance and obtain the spectra shown below. The integral value for each set of signals is indicated beside them. STRUCTURE BH 2H STRUCTURE BH BH ІН эн 1H 8 STRUCTURE 3H БН ill 2H 1H 3 S
CHEMICAL SHIFT & pom CHEMICAL SHIFT id, ppe Approximate carbon-13 chemical shifts TYPE OF CARBON ATOM 1. Alkyl. RCH 2 Alkyl. RCHER 3. Alkyl. RCHR 0.8-1.0 1.2.1.4 1.4.1.7 1.6.19 0-40 10-50 15-50 Approximate proton chemical shifts TYPE OF PROTON 1 Alkyl RCH 2 Alkyl. RCHER 3' Alk) R,CH Allylle. RCC-CH R Benzylie, ACH Alkyl chloride. RCH.CH Alkyl bromide, RCHBE Akytaide. RCHI Ether. ROCHER Alcohol. HOCHER Ketone RCCH Alkyl halide or amine. -C- 10-65 --+-x(x-ci, 3.or) ---- Alcohol or ether, CO 50-90 22-23 3.6-38 3.4.3.6 3.1-33 3.3.3.9 3.3.40 21-26 Alkyne. - 60-90 Alkene, 100-170 Aldehyde RCH 9.5-10.5 Aryl 100-170 Nitriles - CN 120-130 Vinylie, R.C-CH Vinile RCCH 46-3.0 3.2-57 O Amides -C-N- 150-180 Aromatic Art Acetylerie RCCH Alcohol hydrox. ROH Carboxylic. RCOH 6.0-9,5 2.5-3.1 0.5-6.04 10-13 --- Carboxylic acids, esters-c- 160-185 Aldehydes. Ketones -- 182-215 Phenolic. AIOH 45-77- Amino, RNH 10-30 "The chemical shots of these protons vary in different solvents and with temperature and concentration