ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 19, Problem 19.59P
An unknown compound
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A compound (C7H14O) has a strong peak in its IR spectrum at 1710 cm–1. Its 1H NMR spectrum consists of three singlets in the ratio 9:3:2 at δ 1.0, 2.1, and 2.3, respectively. Identify the compound.
A compound has the molecular formula C6H12O2. Its IR spectrum shows a strong absorption band near 1740 cm-1. Its 1H NMR spectrum consists of two singlets at δ 1.2 and δ 3.6. Which is the most likely structure of the compound?
An unknown compound C (molecular formula C4H8O3) exhibits IR absorptions at 3600–2500 and 1734 cm–1, as well as the following 1H NMR spectrum. What is the structure of C?
Chapter 19 Solutions
ORGANIC CHEMISTRY
Ch. 19 - Prob. 19.1PCh. 19 - Problem 19.2 Give the structure corresponding to...Ch. 19 - Problem 19.3 Draw the structure corresponding to...Ch. 19 - Prob. 19.4PCh. 19 - Prob. 19.5PCh. 19 - Problem 19.6 Rank the following compounds in order...Ch. 19 - Problem 19.7 Explain how you could use IR...Ch. 19 - Prob. 19.8PCh. 19 - Problem 19.9 How many tetrahedral stereogenic...Ch. 19 - Problem 19.10 What alcohol can be oxidized to each...
Ch. 19 - Problem 19.11 Identify A-D in the following...Ch. 19 - Problem 9.12 Draw the cation that results when a...Ch. 19 - Problem 19.13 Draw the products of each acid-base...Ch. 19 - Problem 19.14 Given the values in Appendix A,...Ch. 19 - Problem 19.15 Rank the labeled protons in...Ch. 19 - Problem 19.16 Match each of the following values ...Ch. 19 - Problem 19.17 Rank the compounds in each group in...Ch. 19 - Problem 19.18 Rank the compounds in each group in...Ch. 19 - Prob. 19.19PCh. 19 - Problem 19.20 Which of the following pairs of...Ch. 19 - Problem 19.21 Two other commonly used sulfonic...Ch. 19 - Problem 19.22 Draw both enantiomers of each amino...Ch. 19 - Problem 19.23 Explain why amino acids, unlike most...Ch. 19 - Problem 19.24 Draw the positively charged,...Ch. 19 - Prob. 19.25PCh. 19 - Problem 19.26 Explain why the of the group of...Ch. 19 - Answer each question for A and B depicted in the...Ch. 19 - Prob. 19.28PCh. 19 - 19.29 Give the IUPAC name for each compound.
a....Ch. 19 - 19.30 Draw the structure corresponding to each...Ch. 19 - Prob. 19.31PCh. 19 - 19.32 Rank the following compounds in order of...Ch. 19 - 19.33 Draw the organic products formed in each...Ch. 19 - 19.34 Identify the lettered compounds in each...Ch. 19 - 19.35 Using the table in Appendix A, determine...Ch. 19 - 19.36 Draw the products of each acid-base...Ch. 19 - 19.37 Which compound in each pair has the lower ?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - 19.39 Rank the compounds in each group in order of...Ch. 19 - 19.40 Match the values to the appropriate...Ch. 19 - Prob. 19.41PCh. 19 - 19.42 Which carboxylic acid has the lower ,...Ch. 19 - Prob. 19.43PCh. 19 - 19.44 Explain the following statement. Although...Ch. 19 - Prob. 19.45PCh. 19 - 19.46 Explain why the of compound A is lower than...Ch. 19 - 19.47 Rank the following compounds in order of...Ch. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.52PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.55PCh. 19 - Can octane and octan -1- ol be separated using an...Ch. 19 - 19.57 Identify each compound from its spectral...Ch. 19 - 19.58 Use the NMR and IR spectra given below to...Ch. 19 - 19.59 An unknown compound (molecular formula )...Ch. 19 - 19.60 Propose a structure for (molecular formula...Ch. 19 - 19.61 Match the data to the appropriate...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - 19.65 For each amino acid ,draw its neutral,...Ch. 19 - Calculate the isoelectric point for each amino...Ch. 19 - 19.67 Lysine and tryptophan are two amino acids...Ch. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
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- Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.arrow_forwardAn unknown compound C3H2NCl shows moderately strong IR absorptions around 1650 cm-1 and 2200 cm-1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ 5.9 and δ 7.1. Propose a structure consistent with this data?arrow_forwardClick the "draw structure" button to launch the drawing utility. An unknown compound C (molecular formula C,H3O3) exhibits IR absorptions at 3600–2500 and 1734 cm, as well as the following 'H NMR spectrum. What is the structure of C? 1Η ΝMR of C 2 H 3 H 2H 1H 12 10 8 2 nnmarrow_forward
- Identify the structures of D and E, isomers of molecular formulaC6H12O2, from their IR and 1H NMR data. Signals at 1.35 and 1.60 ppm inthe 1H NMR spectrum of D and 1.90 ppm in the 1H NMR spectrum of Eare multipletsarrow_forwardCompound A of molecular formula C3H6O shows a noteworthy infrared absorption at 1716 cm-1. Its 1H-NMR spectrum shows one singlet – δ 2.2 (6H) ppm. Its 13C-NMR spectrum has two signals – δ 30, 207 ppm. Suggest a structure for this compound.arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2), which has an IR absorption at 1699 cm−1 and the 1H NMR spectrum shown below.arrow_forward
- Three isomeric compounds, A, B, and C, all have molecular formulaC8H11N. The 1H NMR and IR spectral data of A, B, and C are given below.What are their structures?arrow_forwardIdentify the structures of isomers H and I (molecular formula C8H11N).a.Compound H: IR absorptions at 3365, 3284, 3026, 2932, 1603, and 1497 cm−1b.Compound I: IR absorptions at 3367, 3286, 3027, 2962, 1604, and 1492 cm−1arrow_forwardA compound with molecular formula C3H8O produces a broad signal between 3200 and 3600 cm1 in its IR spectrum and produces two signals in its 1°C NMR spectrum. Draw the structure of the compound.arrow_forward
- Compound B has molecular formula C9H12O. It shows five signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.22 ppm, a septet of integral 1 at 2.86 ppm, a singlet of integral 1 at 5.34 ppm, a doublet of integral 2 at 6.70 ppm, and a doublet of integral 2 at 7.03 ppm. The 13C-NMR spectrum of B shows six unique signals (23.9, 34.0, 115.7, 128.7, 148.9, and 157.4). Identify B and explain your reasoning.arrow_forwardUse the 1H NMR and IR data to determine the structure of each compound.arrow_forwardThe '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_forward
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