614 - Practice Problem 6‐14 – Answer In each part below...

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Unformatted text preview: Practice Problem 6‐14 – Answer In each part below, one contributing resonance structure is given. Draw the number of additional resonance structures requested. Used curved arrows to show how electrons move in the conversion of one resonance structure to the next. (a) (b) Practice Problem 6‐15 – Answer Which of the molecules and ions shown below are aromatic according to the Hückel criteria. Which, if planar, would be antiaromatic? Practice Problem 6‐16 – Answer Give IUPAC names for the following compounds: (a) (b) (c) (d) (e) (f) Practice Problem 6‐17 – Answer Draw structures corresponding to the following names: (a) 3‐Methyl‐1,2‐benzenediamine (b) 3‐Methyl‐2‐phenylhexane (c) m‐Bromophenol (d) p‐Iodonitrobenzene (e) 1,3,5‐Benzenetriol (f) o‐Aminobenzoic acid (g) 2,4,6‐Trinitrophenol (picric acid) (h) m‐Nitrobenzaldehyde The spectra/spectral data for Problems 6‐18 through 6‐24 are not reproduced in this answer key! Please see me in office hours if you have questions about how to work these spectroscopy problems! Practice Problem 6‐18 (1st one) – Answer Compound C has molecular formula C10H12O and the 1H NMR and IR spectra given below. Propose a structure for this compound. Practice Problem 6‐18 (2nd one) – Answer Compound D has molecular formula C9H12O and the 1H NMR and IR spectra given below. Propose a structure for this compound. Practice Problem 6‐19 – Answer Compound E is a neutral compound having molecular formula C8H10O2 and the 1H NMR and IR spectra given below. Propose a structure for this compound. Practice Problem 6‐20 – Answer Compound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol, and a silver mirror when treated with Tollens’ reagent. The 1H NMR spectrum of this compound is given below. Propose a structure. Practice Problem 6‐21 – Answer An unknown compound having molecular formula C10H12O2 is insoluble in water, 10% NaOH, and 10% HCl. Given this information and the following 1H and 13C NMR data, propose a structure. Practice Problem 6‐22 – Answer Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline conditions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and the 1H NMR spectrum below, propose a structure. Practice Problem 6‐23 – Answer An unknown compound having molecular formula C10H10O has the following 1H and 13C NMR data. Propose a structure. Practice Problem 6‐24 – Answer Propose a structure for Compound J (C11H14O3) consistent with the 1H NMR and IR spectra given below. ...
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