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- Identify the frequency of both carbonyl stretches in your IR. Which one corresponds to the benzyl ester? Wavenumber (cm-1) Bond Vibration Shape Intensity Functional Group 3288.63 cm-1 N-H Stretch Sharp Weak Amine/Amide 3078.39 cm-1 C-H Stretch Sharp Weak Aromatic/Alkene 2976.16 cm-1 C-H Stretch Sharp Weak Alkane 1720.50 cm-1 C=O Stretch Sharp Medium Ester 1653.00 cm-1 C=O Stretch Sharp Medium Amide 1556.55 cm-1 C=C Stretch Sharp Medium Aromatic10)Pyrrolium (1) and pyridinium (2) have markedly H different pK, values. Circle the compound with the lower pK₂ value. -N-H 11) The 1H NMR spectrum of phenol is shown below. Of note, the aryl proton signals resolve in this molecule. Assign protons to specific signals in the spectrum 8 7 6 H₂ H₁ 5 ppm H3 H₂ *CHCl3 2 H₁Circle the solvents from the following list that can be used with 1H NMR spectroscopy that do not interfere with the spectrum. carbon tetrachloride chloroform benzene-d6 hexachloroacetone acetonitrile acetone methylene chloride D2O DMF (dimethylformamide)
- 16 Draw the structures of Compound 16a and 16b, clearly indicate your assignments of all proton resonances. Calculate the unsaturation index of each compound Compound 16a- c8h6o2 A=10.2 ppm singlet 2h B=7.69 ppm singlet 4h Compound 16b C8H10 A=7.00 ppm, singlet 4h B= 2.25 ppm singlet 6H (Excess) H2NNH2, KOH, (HOCH2CH2)2O heatAn oxidation reaction was conducted using cyclohexanol and NaOCl to make cyclohexanone. How can we know that the NMR for cyclohexanone is in fact cyclohexanone( the NMR for cyclohexanone is not labeled). Analyze the spectra to prove its identity along with the NMR of the starting material which is the spectra labeled cyclohexanol below.3. For the given molecules 1 H NMR (a) label all the hydrogen atoms, (b) State how many signals are possible (c) Predict chemical shift values (d) and Multiplicity. CH, *CH, 1-pentene 3-methylbutanal p-ethylanisole HO, Br butanoic acid 2-bromobutane diethyl malonate OH Br 1-propanol 1-bromopropane diethyl ethylmalonate
- When methyl 5-oxopentanoate is treated with vinyl Grignard, a compound is produced whose formula is C,H1002. In the IR spectrum of C7H1002, an intense absorption appears at 1740 cm-1 and a weaker absorption appears at 1650 cm-1. Seven signals appear in the 13C NMR spectrum of C,H1002. The DEPT spectrum shows that there is one carbon that is bonded to no hydrogens, two CH carbons, and four CH2 carbons. Draw the structure of C,H1002. 1.AMGB., THF → C7H10O2 `OCH3 2. NH4CI, H2O Methyl 5-oxopentanoate o=/This question relates to the1H-NMR spectrum of an alkane and two alkenes. How many proton environments are there in 2-methylbut-2-ene? How many proton environments are there in 1-bromo-4-chlorobutane? How many proton environments are there in trans-2-pentene What are the multiplicities of each proton environment in 2-methylbut-2-ene? What are the multiplicities of each proton environment in 1-bromo-4-chlorobutane? What are the multiplicities of each proton environment in trans-2-pentene?There are four isomers shown below (compounds A-D). TWO of these isomeric nitrogen- containing compounds were extracted and isolated from tobacco leaves. Their structures were determined using 1H NMR. These two 1H NMR spectra are shown below. Make peak assignments of the NON-AROMATIC signals to determine which TWO isomers are represented. Use the specific labels (a-h) provided with spectra.
- What is the stretching frequency (in cm-¹) of the following carbonyl? 1745 1715 1685 none of the aboveFollowing are the 'H and 13C NMR spectra for each of three isomeric ketones with formula C7H14O. Determine a structure to each pair of spectra and assign each H and C. Carbon spectrum А C,H140 Carbon spectrum В C;H140 CDCI3 200 150 100 50 Proton spectrum CDC13 A C,H140 200 150 100 50 1.96 2.00 2.91 3.0 2.5 2.0 1.5 1.0 0.5 0.0 211.04 -44.79 –17.39 – 13.78 -218.40 - 38.85 –18.55Which of the following compounds will have the fewest 13C NMR signals? CH;CH,CH,CH,CH,OH (pentanol) CH,CH,CH,COCH; (methyl propyl ketone) CH,CH,COCH,CH; (diethyl ketone) O CH;CH,CH,CH,CHO (pentanal)