Q5 (8 pts) Predict the structure of a compound with molecular formula C,H,,O, wh

Question

Q5 (8 pts) Predict the structure of a compound with molecular formula C,H,,O, whose C. 13 NMR gives the following peaks. Provide assignment for the peaks 1. 25 ppm, quartet 2. 30 ppm, quartet 3. 80 ppm, singlet 4. 120 ppm, doublet 5. 160 ppm, doublet 6 200 ppm, singlet 6. What is the appearance of the signal corresponding to the CHa protons in the 'H NMR spectrum of ethyl methyl ether, CH,CH OCHy? a a doublet b. a triplet c. a quartet d. a septet 7. Which of the following combinations of peaks appears in the 'HNMR spectrum of butane? a. a triplet and a doublet b. a triplet and a quartet c. a triplet and a sextet d. two singlets 8. Which C,HoBr compound gives a doublet at approximately 3.3 ppm in the 'H NMR spectrum? Br a. b. 2 C. d. 4 9. How many signals appear in proton-decoupled SC NMR spectrum of 2,5- dimethylhexane? a. 3 b. 4 c. 5 d. 6 10. Which of the protons in the following molecule appear at the highest o-value in the 'H NMR spectrum?

Explanation / Answer

6. Signal corresponding to CH2 in CH3CH2OCH3 is,

c. a quartet

7. Butane 1H NMR shows,

b. a triplet & a quartet

8. C4H9Br shows a doublet at 3.3 ppm for,

c. 3

9. Number of signal in 1H NMR for compound,

b. 4

10. The proton with highest shift value would be,

d. iv

11. No. of signals for 4-bromotoluene in 13C NMR,

c. 5

12. The carbon atom most downfield in 13C NMR is,

c. iii

13. Compound C6H12O2 with given NMR data matches structure,

b. 2

14. Compound C8H10 with given NMR data matches structure,

c. 3

15. Carbon most downfield in the 13C NMR for the compound is,

d. iv

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