ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 14, Problem 14.29P
Esters of chrysanthemic acid are naturally occurring insecticides. How many lines are present in the
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Esters of chrysanthemic acid are naturally occurring insecticides. How many lines are present in the 13C NMR spectrum of chrysanthemic acid?
QUESTION 42
Propose a structure for an amine with molecular formula C6H7N by interpreting the given 1H and 13C NMR data below. 1H NMR δ 2.35 ppm singlet (3) δ 7.10 ppm doublet (2) δ 8.46 ppm doublet (2)
Determine the hybridization around the N atom in each amine, andexplain why cyclohexanamine is 106 times more basic than aniline.
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 NMR signals does each compound show?
a....Ch. 14 - How many 1H NMR signals does each...Ch. 14 - How many 1H NMR signals does each compound give?...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. 14.8PCh. 14 - For each compound, first label each different type...Ch. 14 - Label each statement as True or False. a. When a...
Ch. 14 - Prob. 14.11PCh. 14 - Problem 14.12 Which compound give a NMR spectrum...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Problem 14.18 Describe the NMR spectrum of each...Ch. 14 - Problem 14.19 Draw a splitting diagram for 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 - Problem 14.22 What protons in alcohol A give rise...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 -
Problem 14.24 Propose a structure for a compound...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 - Problem 14.27 How many lines are observed in the ...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Problem 14.29 Esters of chrysanthemic acid are...Ch. 14 - Prob. 14.30PCh. 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 - Prob. 14.36PCh. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - 14.39 What effect does increasing the operating...Ch. 14 - Prob. 14.40PCh. 14 - 14.41 How could you use chemical shift and...Ch. 14 - Prob. 14.42PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - 14.48 How many NMR signals does each compound...Ch. 14 - 14.49 Rank the highlighted carbon atoms in each...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.52 Answer the following questions about each of...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 - 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. 14.73PCh. 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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- 16-17 Propylamine (bp 48°C), ethylmethylamine (bp 37°C), and trimethylamine (bp 3°C) are constitutional isomers with the molecular formula C3HgN. Account for the fact that trimethylamine has the lowest boiling point of the three and propylamine has the highest.arrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a) C5H10O2 (b) C7H14O2 (c) C6 H12O2 (d) C7H12O4 (e) C4H7ClO2 (f) C4H6O2arrow_forwardHow would you use NMR (either 13C or 1H) to distinguish between the following pairs of isomers?arrow_forward
- The 1H NMR spectrum shown is that of a cyclic ether with the formula C4H8O. Propose a structure.arrow_forwardCompound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardFollowing are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.arrow_forward
- 3) For the following questions draw the structure of the compound based off of the molecular formula and NMR that is given. a) CHa Draw the structure of the compound. 12H 8H CH PPM b) CioH12O2 Draw the structure of the compound. t 3H d, 2H d. 2H L 2H brs, 1H 12 PPM c) CH10O3 (IR stretches: strong signals at 1750 and 1730 cm") Don't worry about stereochemistry of the product. Draw the structure of the compound. d. 3H s, 1H t 3H 9. 2H q. 1H 10 6. PPM 2.arrow_forwardBased on the structures given below, which of the following statements is entirely true? N Quinoline NH Isoquinoline Indole Isoindole All four compounds are non-aromatic, with 12 pi-electrons each and are equal in basicity. All four compounds are aromatic, with 10 pi-electrons each and are equal in basicity. Only quinoline and isoquinoline having 10 pi-electrons each are aromatic while indole and isoindole are antiaromatic having 8 pi-electrons each. All four compounds are aromatic, with 10 pi-electrons each, and with quinoline and isoquinoline being stronger bases than indole and isoindole. The nitrogen atoms of quinoline and isoquinoline are sp2 hybridized while the nitrogen atoms of indole and isoindole are sp³ hybridized Previousarrow_forwardUsing the 1H NMR complete the following table and draw the structure.arrow_forward
- Draw 1H NMR of the following compoundarrow_forward5. How many ¹H NMR signals does each natural product exhibit? Write the number of ¹H NMR signals inside the box. a. CH CH3 N CH3 caffeine (from coffee beans and tea leaves) NMR signals b. CHO OH OCH₂ vanillin (from the vanilla bean) NMR signals LOH thymol (from thyme) NMR signalsarrow_forwardQuestion 24 Multiple response question, 15% Penalty for each incorrect responses. DO NOT GUESS, it may reduce your score. Which of the following compounds will display a singlet, a doublet and a quartet in the ¹H NMR spectruin? CH3OCH₂CH2CH2CH₂OCH3 DERBOOK □ □ CH3OCH2CH2OCH3 □ CH3CH(OCH3)2 HCCOCH₂CH₂CH₂CH₂OCCH CH3O-(Br)C=C(H)-CH3 OHCCOCH₂CH₂CH₂OCCH 538BBBBRAI (ody motoare Ecomarrow_forward
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