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- 5. Consider the molecular formula of C,H,O a) Draw three constitutional isomers with this formula. b) Predict the chemical shift for each proton in each of the compounds you drew in part a). c) NMR and IR spectra were measured for a compound with the formula C,H,O, and the following was observed: 'H NMR & 5.21 (s); IR (diagnostic region) 1770 cm-!, 3068 cm-1 and 3096 cm-'. Which of the structures you drew in part a) would be most consistent with this data, briefly explain your reasoning?(c) How can the following compounds be distinguished. by 'H-NMR? Provide chemical shift, splitting patterns and peak area ratio for each: G'2 CH3 CH3 (ü) H3COCH;C=CCH2OCH3 (üi) H3C–C-CH2 CH2-C-CH34. Propose a structure for a compound, C4H7C1O2, that has the following IR and 'H NMR spectra : 100 80 60 - 40 - 20 - 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm- TMS 10 O ppm Chemical shift (6)
- Give the structure that corresponds to the following molecular formula and ¹H NMR spectrum:: C₂H₁604: 8 1.93 (t, J = 6 Hz); 8 3.35 (s); 8 4.49 (t, J = 6 Hz); relative integral 1:6:1. 16 Draw the structure. Select Draw Rings More C H OSet #1: CHCHCHCH, CHOCHSCHICHI CHCHCHCHCH a b C Shown are 4 isomeric structures with the formula C5H100. Which isomer shows 3 peaks in its ¹³C-NMR spectrum, none of which is very far downfield? Set #2: CH3CH₂CH₂CCH3 CH3CH₂CH₂CH₂CH CH₂=CHCH₂CH₂CH₂OH b C a Shown are 4 isomeric structures with the formula C5H100. Which isomer shows 3 peaks in both its ¹H and 13C NMR spectra? -OHProvide a structure for the compound with the formula C,H, NO using the given information. IR: 3360, 3280 cm (doublet); 1611 cm¯"; no carbonyl absorption; 'H NMR spectrum: chemical shift, Hz 1200 2400 2100 1800 1500 900 600 300 3H J = 6.9 Hz J= 6.9 Hz J = 8.7 Hz J = 8.7 Hz 4H 2H 2H 2H 8. 6. 4 chemical shift, ppm (8) 3 APR étv Aa MacBook Air
- 2. The following 'HNMR spectrum is for a compound with formula C4H3O2, which shows a strong peak at ~1700 cm-' and a broad peak between 3000~3400 cm-l in IR. Propose the structure of the compound in the box below. 1 H (exchanges with D2O) 3 H 2 H 1 H 1 H 10 8 7 3 21 (a) In the following reactions, (1) LIAIH, A (2) H2O mCPBA B (i) Draw the structure of compounds A and B. (ii) For each reaction, explain the type of reaction involved. (iii) Explain the successful transformation of compound A using mass spectra.13. A compound with the molecular formula C.lH0 gives a 'H NMR spectrun consisting only of a quartet centered at 6 3.5 and a triplet at & 1.1. The most likely structure for the compound is: A) CH, CH,COH B) CH, сн,оснон C) CH,CH;CH,CH,OH D) CHSCII,OCH;CIHl, E) CH,CHCH,OH CH
- Provide a structure that is consistent with the data: molecular formula C6H10. 1H NMR: 2.0 ppm (1H, septet), 1.8 ppm (3H, singlet), 0.9 ppm (6H, doublet) A) B) C) D) E) "i CH3CH2C=CH -CC-CH₂ O A OB OC OD OE CH₂Identify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound.a. CH3CH2CH2CH2OH; 13C NMR: 14, 19, 35, and 62 ppmb. (CH3)2CHCHO; 13C NMR: 16, 41, and 205 ppmc. CH2 = CHCH(OH)CH3; 13C NMR: 23, 69, 113, and 143 ppmUsing the 'H NMR chemical shift table, predict the proton chemical shifts range of the following molecule. (c) (c) H (a) (b) (b) (a) H;C-CH,-O 0–CH2-CH3 (a) CH, bonded to C? (b) CH, bonded to O? (c) H bonded to C=C?