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- 1 /3 > 248% O 上 2. Determine the structure of a compound with a molecular formula of C,H12O and exhibits the following 'H NMR and 13C NMR spectra. No peaks exchange in D2O. | = 6 | = 3 13 C NMR 1.0 |= 2 the | = 1 2.6 2.4 8.e 7.8 3.e 2.0 wwww 8.0 9.0 6.0 5.0 4.0 1.0 1 H NMR1. Which of the following compound will show two absorption bands at around 2700 cm³¹ and around 2800 cm¹ along with the carbonyl absorption [Select] 4 Click here to preview the image B :0: A A CO :0: lg i l N B C 2. Which of the following compound will show absorption band ~3300 cm¹ [Select] Click here to preview image A B B D C H 3. Which the following compound will show absorption band ~1735 cm1 [Select] Click here to preview image e D NH23 N-C HO 3000 INFRARED SPECTRUM H3C. 2000 Wwvember (11 st Chemistry WebBook (webbook nistghemistry) Which molecular compound below is consistent with the IR data above. C=0 C-C H3C N NH₂ CH3 C-H He plan H3C CH3 CH3 CH3 1000
- QUESTION 3 Predict the IR absorption bands (peaks) observed in the spectrum of 3-methylcyclohexanone. sp3 C-H stretching (-2850-2960 cm 1) sp2 C-H stretching (-3000-3100 cm-1) Alcohol O-H stretch (-3300 cm-1, broad) C-O double bond stretch (-1700 cm-1) Aromatic out of plane bend for monosubstitution (690-710 and 730-770 cm-1). Aromatic out of plane bend for para (1,4) disubstitution (810-840 cm-1). Aromatic out of plane bend for meta (1,3) disubstitution (690-750 and 750-810 cm 1). Aldehyde C-H stretch (2750 and 2850 cm-1). Carboxylic acid (carboxy group) O-H stretch (-2500-3000 cm-1, broad) N-H stretch (2 bands at -3400 cm-1) N-H bend (-1600 cm*1) Aromatic C-C double bond stretches (-1500 and 1600 cm-1). Aromatic overtones (1667-2000 cm-1) O O O OQUESTION 2 Predict the IR absorption bands (peaks) observed in the spectrum of isobutyl alcohol. sp3 C-H stretching (-2850-2960 cm-1) sp2 C-H stretching (-3000-3100 cm 1) Alcohol O-H stretch (-3300 cm1, broad) C-O double bond stretch (-1700 cm-1) Aromatic out of plane bend for monosubstitution (690-710 and 730-770 cm-1). Aromatic out of plane bend for para (1,4) disubstitution (810-840 cm-1). Aromatic out of plane bend for meta (1,3) disubstitution (690-750 and 750-810 cm 1). Aldehyde C-H stretch (2750 and 2850 cm-1). Carboxylic acid (carboxy group) 0-H stretch (-2500-3000 cm-1, broad) N-H stretch (2 bands at -3400 cm-1) N-H bend (-1600 cm-1) Aromatic C-C double bond stretches (-1500 and 1600 cm-1). Aromatic overtones (1667-2000 cm cm1) O O O O O O Oa. b. C. Describe and explain the molecular ion region in the mass spectra of compounds D, E & F, below. CH3CH₂Br D Predict the major IR signals generated in an IR spectrum of compounds G and H, below. CH3CH₂CI BrCH₂CH₂Br E F Ph `N´ Me G Me Me-C=CH H Compound J, C₁2H17NO, shows a strong absorption band at 1650 cm¹ in its IR spectrum. The ¹H NMR spectrum for compound J is shown in Figure 1 (on attached page). Deduce the structure of J. Indicate clearly your reasoning involved in developing the proposed structure and include a justification of your signal assignments and an explanation of the splitting patterns in your answer.
- For the following reaction, what significant changes would be expected by IR absorptions, (ignoring C-H absorption): * a. CH;MgBr HO. b. H;0 A peak around 3300-3500/cm would appear O A peak around 1710/cm would appear No change observed. A peak around 3300-3500/cm would disappearFor each compound below, identify all peaks (both frequency ranges and strengths) that you would expect to find between 1500 and 4000 cm-1 on an IR spectrum. a) b) c) = d) OH Draw the bond-line structure of a compound that would be consistent with each set of IR data and chemical formula below. a. C4H10O; IR (cm-1): 3328 (strong, broad), 2950 (strong, sharp) b. C4H10O; IR (cm-1): 2950 (strong, sharp) c. C6H6; IR (cm-1): 2080 (medium, sharp), 1961 and 1815 (small, sharp) d. C6H6: IR (cm-1): 3297 (strong, sharp), 2922 (strong, sharp), 2123 (medium, sharp)12. An unknown compound C (molecular formula C4H&O3) exhibits IR absorptions at 3600-2500 and 1734 cm -1, as well as the following 1 H NMR spectrum. What is the structure of C? Copyright McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 1H NMR of C 2H 3 H 2 H 1 H 12 10 8. 6. 2. ppm
- 3. Which C7H₁40 isomers give rise to the spectra shown below? (Hint: the IR spectra of both molecules would contain a strong peak at ~1710 cm-¹.) a. C. 8 7 8 7 6 5 5 4 8 (ppm) 4 8 (ppm) Note: From left to right, the peak multiplicities are septet and doublet. 3 3 2 All singlets 2 1 0 01. An aliphatic ketone absorbs at 1,715 cm-1. What is the frequency of this vibration in hertz, which is cycles per second or just per second, reciprocal seconds? 2. What is the energy equivalent of this stretching vibration in kcal/mole? 3. Why does 3,4-diethyl-3-hexene not have a carbon to carbon double bond stretching absorption band? 4. Why does a carbon to oxygen double bond absorption band have a greater intensity than a carbon to carbon double bond absorption band? 5. Using only IR, explain in detail how one could most easily differentiate between oct-1-ene and oct-1-yne if all carbon to carbon bonds are ignored. 6. Using only IR, explain in detail how one could most easily differentiate between butan-1-ol and butanoic acid.For the following reaction, what significant changes would be expected by IR absorptions, (ignoring C-H absorption): * a. NaNH2 b. CH;CHI a peak around 1710/cm would appear a peak around 2150/cm would disappear a peak around 1710/cm would disappear O No change observed.