Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12C.10, Problem 25P
Propose a structure for a compound of molecular formula
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Propose a structure for a compound of molecular formula C7H14O2 with an IR absorption at 1740 cm−1 and the following 1H NMR data:
Absorption ppm Relative area
singlet 1.2 9 triplet 1.3 3 quartet 4.1 2
Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.
An aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made:
A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution.
B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below.
C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K.
D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields.
On the basis of these observations draw the structures of…
Chapter 12C Solutions
Organic Chemistry (6th Edition)
Ch. 12C.1 - Problem 14.1 The NMR spectrum of recorded on a ...Ch. 12C.1 - Prob. 2PCh. 12C.2 - How many 1H NMR signals does each...Ch. 12C.2 - How many 1H NMR signals does each compound give?...Ch. 12C.2 - Label the protons in each highlighted CH2 group as...Ch. 12C.2 - How many 1H NMR signals would you expect for each...Ch. 12C.3 - Prob. 9PCh. 12C.3 - For each compound, first label each different type...Ch. 12C.3 - Label each statement as True or False. a. When a...Ch. 12C.4 - Prob. 12P
Ch. 12C.5 - Problem 14.12 Which compound give a NMR spectrum...Ch. 12C.5 - Prob. 14PCh. 12C.6 - Prob. 15PCh. 12C.6 - For each compound give the number of 1H NMR...Ch. 12C.6 - Prob. 17PCh. 12C.7 - Prob. 18PCh. 12C.7 - Problem 14.18 Describe the NMR spectrum of each...Ch. 12C.8 - Problem 14.19 Draw a splitting diagram for in ,...Ch. 12C.8 - Problem 14.20 Identify A and B, isomers of...Ch. 12C.9 - Problem 14.21 How many signals are present in the ...Ch. 12C.9 - Problem 14.22 What protons in alcohol A give rise...Ch. 12C.9 - How many peaks are observed in the NMR signal for...Ch. 12C.10 -
Problem 14.24 Propose a structure for a compound...Ch. 12C - 14.34 (a) How many NMR signals does each of the...Ch. 12C - 14.35 (a) How many NMR signals does each compound...Ch. 12C - Prob. 38PCh. 12C - 14.37 How many NMR signals does each natural...Ch. 12C - Prob. 40PCh. 12C - 14.39 What effect does increasing the operating...Ch. 12C - Prob. 43PCh. 12C - Prob. 44PCh. 12C - Prob. 45PCh. 12C - Prob. 47PCh. 12C - Prob. 48PCh. 12C - 14.48 How many NMR signals does each compound...Ch. 12C - 14.49 Rank the highlighted carbon atoms in each...Ch. 12C - 14.50 Identify the carbon atoms that give rise to...Ch. 12C - 14.62 Reaction of with , followed by treatment...Ch. 12C - Reaction of aldehyde D with amino alcohol E in the...Ch. 12C - 14.64 Propose a structure consistent with each set...
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- What is the structure of the compound with the formula C5H12O, if it has a strong broad IR signal centered near 3330 cm-2, and the 1H-NMR spectrum is: 0.91 ppm (3H triplet) 1.19 ppm (6H singlet) 1.50 ppm (2H quartet) 2.24 ppm (1H singlet)arrow_forward1. There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppmarrow_forwardThere are several isomeric alcohols and ethers of molecular formula C5H12O. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.92 (t, 7.8 Hz, 3 H), 1.20 (s, 6H), 1.49 (q, 7.8 Hz, 2H), 1.85 (s, 1H) ppm Isomer B: δ = 1.19 (s, 9 H), 3.21 (s, 3H) ppmarrow_forward
- An organic compound B with formula C6H14O has the following: IR Spectroscopy 2974 cm-1, 1080 cm-1 Mass Spectrometry 102 (M+), 87, 73 1H NMR Spectroscopy Eight signals at δ 1.10 (d, 3H), 1.13 (dd, 3H), 1.14 (dd, 3H), 1.59 (ddq, 1H), 1.60 (ddq, 1H), 3.19 (ddq, 1H), 3.51 (dq, 1H), 3.50 (dq, 1H). Compound B is obtained by the reaction of compound A with NaH followed by CH3CH2Br. The stereochemistry of A is "S" Using this information, deduce a plausible structure for Compound A with correct stereochemistry.arrow_forwardIdentify this compound with molecular formula C9H10O IR peak at 1742 cm-^1,H nmr data (ppm) at 2.15(singlet,3H),3.70(singlet.2H) and 7.20(broad singlet,5H)arrow_forwardThere are several isomeric alkanes of molecular formula C6H14. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (t, 9H), 1.22 (q, 2H) ppmarrow_forward
- Deduce a possible structure for the compound with the IR absorptions below. C5H8O: 2950, 1750 cm-1 C4H8O: 2950, 2820, 2715, 1715 cm-1arrow_forwardThe 1H-NMR spectrum of compound R, C6H14O, consists of two signals: d 1.1 (doublet) and d 3.6 (septet) in the ratio 6:1. Propose a structural formula for compound R consistent with this informationarrow_forwardPropose a structure consistent with each set of data.a.) C9H10O2: IR absorption at 1718 cm−1 b.) C9H12: IR absorption at 2850–3150 cm−1arrow_forward
- Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.arrow_forwardPropose a structure for the compounds that display IR spectra with the following peaks : A) C2H3O2CL: 3200-2500 BROAD ,1720,1410cm-1 B) C8H8O: 3030, 2820, 2760, 1715, 1605, 1495, 1410, 750, 695cm-1arrow_forwardAddition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forward
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