Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 18, Problem 18.74P
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What is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?
The 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.
An unknown compound has the molecular formula C7H14O, and its 1H NMR and 13C NMR spectra are shown below. Determine the structure of the unknown compound and draw it below. Note that there are no peaks above 3 ppm in the 1H NMR, and the numbers present on the 1H NMR are the integration values for each set of peaks.
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - Prob. 18.6PCh. 18 - Prob. 18.7PCh. 18 - Prob. 18.8PCh. 18 - Problem 18.9 Draw the product of each reaction
a....Ch. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Problem 18.15 Classify each substituent as...Ch. 18 - Prob. 18.16PCh. 18 - Problem 18.17 Label each compound as more or less...Ch. 18 - Problem 18.18 Rank the following compounds in...Ch. 18 - Prob. 18.19PCh. 18 - Problem 18.20 Draw the products of each...Ch. 18 - Prob. 18.21PCh. 18 - Problem 18.22 Draw the products formed when each...Ch. 18 - Problem 18.23 Devise a synthesis of each compound...Ch. 18 - Problem 18.24 Draw the products of each...Ch. 18 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 18 - Problem 18.26 Draw the products of each...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Problem 18.29 How could you use ethylbenzene to...Ch. 18 - Prob. 18.30PCh. 18 - Problem 18.31 What steps are needed to convert...Ch. 18 - Problem 18.32 Synthesize each compound from...Ch. 18 - Problem 18.33 Synthesize each compound from...Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - 18.36 Draw the products formed when phenol is...Ch. 18 - Problem 18.37 Draw the products formed when each...Ch. 18 - 18.38 Draw the products of each reaction.
a. d....Ch. 18 - 18.39 What products are formed when benzene is...Ch. 18 - 18.40 Draw the products of each reaction.
c.
d....Ch. 18 - 18.41 You have learned two ways to make an alkyl...Ch. 18 - 18.42 Draw the structure of A, an intermediate in...Ch. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.46PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - 18.48 Consider the tetracyclic aromatic compound...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Prob. 18.50PCh. 18 - 18.51 Using resonance structures, explain why a...Ch. 18 - Prob. 18.52PCh. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - 18.54 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.55PCh. 18 - 18.56 Draw a stepwise, detailed mechanism for the...Ch. 18 - Prob. 18.57PCh. 18 - 18.58 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - 18.63 Synthesize each compound from benzene and...Ch. 18 - Problem 18.64 Synthesize each compound from...Ch. 18 - Prob. 18.65PCh. 18 - Prob. 18.66PCh. 18 - Prob. 18.67PCh. 18 - Prob. 18.68PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.70PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - 18.72 Reaction of p-cresol with two equivalents of...Ch. 18 - Prob. 18.73PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.76PCh. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79P
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- Propose 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_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_forwardPhenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?arrow_forward
- Compound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C- NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…arrow_forwardBased on its 13C NMR spectrum, how many types of nonequivalent carbons exist in benzonitrile and how many different types of aromatic (benzene) carbons can be seen in 13C NMR of benzonitrile?arrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.arrow_forward
- The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forwardDraw the structure of a compound with the molecular formula C8H₁0 that exhibits five signals in its ¹3C NMR spectrum, four of which appear between 100 and 150 ppm.arrow_forwardCompound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-NMR shows five signals. The mass spectrum of A shows a peak at m/z = 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The 1H-NMR spectrum of C shows…arrow_forward
- Describe how you could use NMR spectroscopy to distinguish between benzoyl chloride and para-chlorobenzaldehyde. O The H NMR spectrum of para-chlorobenzaldehyde should have a signal at approximately 6.5-8 ppm corresponding to the aryle protone. The H NMR spectrum of benzoyl chloride should not have a signal near 6.5-8 ppm. O The H NMR spectrum of para-chlorobenzaldehyde should have a signal at approximately 12 ppm. The 'H NMR spectrum of benzoyl chloride should not have a signal near 12 ppm. O The 'H NMR spectrum of para-chlorobenzaldehyde should have a signal at approximately 10 ppm corresponding to the aldehydic protone. The H NMR spectrum of benzoyl chloride should not have a signal near 10 ppm. O The H NMR spectrum of benzoyl chloride should have a signal at approximately 12 ppm. The 'H NMR spectrum of para- chlorobenzaldehyde should not have a signal near 12 ppm.arrow_forwardCompound A shows a molecular peak of 56 in Mass Spectrum. When compound A is treated with HBr and peroxides, it produces compound B, which shows twin molecular peaks with weights 136 and 138 in 1:1 ratio. The 'H NMR spectra of both compounds shown below. Identify the structures of A and B in the respective boxes. 2H Compound A 'H NMR of Compound A (integration is listed next to peaks) لد HBr peroxides 2H PPM 'H NMR of Compound B (integration is listed next to peaks, expansions in above) М 1H Compound B PPM 6H 6Harrow_forwardEthyl benzoate PhCO₂Et has these peaks in its 13C NMR spectrum: 17.3, 61.1, 100- 150 (four peaks) and 166.8 ppm. Which peak belongs to which carbon atom? Draw the structure of ethyl benzoate and clearly identify each carbon with its corresponding chemical shift.arrow_forward
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