Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 14, Problem 14.18P
Draw a splitting diagram for
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The 13C NMR spectrum of ethanoic acid (acetic acid) shows a quartet centred at δ = 21 with a splitting of 130 Hz. When the same spectrum is recorded using proton decoupling, the multiplet collapses to a single line. Another quartet, but with a much smaller spacing, is also seen centred at δ =178; this quartet collapses when decoupling is used. Explain these observations.
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Chapter 14 Solutions
Organic Chemistry
Ch. 14 - Problem 14.1 The NMR spectrum of recorded on a ...Ch. 14 - Prob. 14.2PCh. 14 - How many 1H NMR signals does each compound show?Ch. 14 - How many 1H NMR signals does each...Ch. 14 - Label the protons in each highlighted CH2 group as...Ch. 14 - How many 1H NMR signals would you expect for each...Ch. 14 - Prob. 14.7PCh. 14 - For each compound, first label each different type...Ch. 14 - Prob. 14.9PCh. 14 - Which compound give a 1H NMR spectrum with two...
Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Describe the 1H NMR spectrum of each compound....Ch. 14 - Draw a splitting diagram for Hb in...Ch. 14 - Problem 14.20 Identify A and B, isomers of...Ch. 14 - Problem 14.21 How many signals are present in the ...Ch. 14 - What protons in alcohol A give rise to each signal...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 - Propose a structure for a compound of molecular...Ch. 14 - Problem 14.25 Propose a structure for a compound...Ch. 14 - Problem 14.26. Identify products A and B from the...Ch. 14 - How many lines are observed in the 13C NMR...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Esters of chrysanthemic acid are naturally...Ch. 14 - Prob. 14.29PCh. 14 - Problem 14.31 Identify the carbon atoms that give...Ch. 14 - Problem 14.32 A compound of molecular formula ...Ch. 14 - Problem 14.33 Draw the structure of a compound of...Ch. 14 - 14.34 (a) How many NMR signals does each of the...Ch. 14 - 14.35 (a) How many NMR signals does each compound...Ch. 14 - How many different types of protons are present in...Ch. 14 - How many 1H NMR signals does each compound give?...Ch. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - Acetone exhibits a singlet in its 1H NMR spectrum...Ch. 14 - Prob. 14.40PCh. 14 - Prob. 14.41PCh. 14 - How could you use chemical shift and integration...Ch. 14 - Which compounds give one singlet in the 1H NMR...Ch. 14 - Prob. 14.44PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - Which compounds in Problem 14.43 give one signal...Ch. 14 - Prob. 14.49PCh. 14 - How many 13C NMR signals does each compound...Ch. 14 - Rank the highlighted carbon atoms in each compound...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.53 Propose a structure consistent with each set...Ch. 14 - 14.54 Identify the structures of isomers A and B...Ch. 14 - 14.55 Reaction of with affords compound W,...Ch. 14 - 14.56 Treatment of with , followed by aqueous
...Ch. 14 - 14.57 Compound C has a molecular ion in its mass...Ch. 14 - 14.58 As we will learn in Chapter 20, reaction of ...Ch. 14 - 14.59 Identify the structures of isomers E and F...Ch. 14 - 14.59 Identify the structures of isomers H and I...Ch. 14 - 14.61 Propose a structure consistent with each set...Ch. 14 - 14.62 Reaction of with , followed by treatment...Ch. 14 - Reaction of aldehyde D with amino alcohol E in the...Ch. 14 - 14.64 Propose a structure consistent with each set...Ch. 14 - 14.65 In the presence of a small amount of acid, a...Ch. 14 - 14.66 Treatment of with affords two products (M...Ch. 14 - 14.67 Compound O has molecular formula and shows...Ch. 14 - 14.68 Compound P has molecular formula . Deduce...Ch. 14 - 14.69 Treatment of with strong base followed by ...Ch. 14 - Low molecular weight esters RCO2R often have...Ch. 14 - 14.70 When -bromo--dimethylbutane is treated with...Ch. 14 - 14.71 Propose a structure consistent with each set...Ch. 14 - 14.72 Reaction of unknown A with forms...Ch. 14 - Prob. 14.75PCh. 14 - 14.74 -Annulene shows two signals in its ...Ch. 14 - 14.75 Explain why the spectrum of-methylbutan--ol...Ch. 14 - 14.76 Because has an odd mass number, nuclei...Ch. 14 - 14.77 Cyclohex--enone has two protons on its...
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- Propanone (acetone, (CH3)2CO) has a strong absorption at 189 nm and a weaker absorption at 280 nm. Identify the chromophore and assign the absorptions to π* ← n or π* ← π transitions.arrow_forwardThe 13C NMR spectrum of fluoroethanoic acid shows a multiplet centred at δ = 79. When the same spectrum is recorded using proton decoupling, the multiplet collapses to a doublet with a splitting of 160 Hz. Another multiplet, but with much smaller splittings, is also seen centred at δ =179; this multiplet collapses to a doublet when decoupling is used. Explain these observations.arrow_forward3. Identify C-Cl stretching peaks in CDC13 and CHC13 spectra. Do these peaks have exactly the same frequencies for both compounds? Explain your answer. 4. Is the C==O stretching frequency the same for acetone and deuterated acetone? Explain your answer. 5. Identify C==O overtone in acetone spectrum which corresponds to the transition from ground level, n=0, to the second excited level, n=2.arrow_forward
- 4. Is the C=O stretching frequency the same for acetone and deuterated acetone? Explain your answer. Identify C O overtone in acetone spectrum which corresponds to the transitionn from ground level n= 0, to the second excited levarrow_forwardDoes the exclusion rule apply to H2O?arrow_forward2143 cm. What is the probability of The vibrational absorption band of 12 C160 occurs at v。 = finding CO molecules in the first excited vibrational state at 2000 K?arrow_forward
- The benzene radical anion has g = 2.0025. At whatfield should you search for resonance in a spectrometeroperating at (a) 9.302 GHz, (b) 33.67 GHz?arrow_forwardThe benzene radical anion has g = 2.0025. At what field should you search for resonance in a spectrometer operating at (i) 9.313 GHz, (ii) 33.80 GHz?arrow_forwardexplain why C–O stretching occurs at 1100 cm-1 and C=O stretching occurs at 1750 cm-1arrow_forward
- Determine the Ka for CH 3NH 3* at 25 °C. The Kb for CH 3NH 2 is 4.4 x 10 -4.arrow_forwardWhat is the relationship between wavenumber and wavelength and how wavenumber is related to energy? Why stretching frequencies decrease from C−Cl to C−Br to C−I?arrow_forwardWhy is 133C-133C spin-spin splitting not observed in ordinary organic compounds?arrow_forward
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