ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
12th Edition
ISBN: 9781119766919
Author: Solomons
Publisher: WILEY
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Chapter 9, Problem 33P
Ethyl bromide and methoxybenzene (shown below) have the same nominal molecular weights, displaying a significant peak at m/z 108. Regarding their molecular ions, what other features would allow the two compounds to be distinguished on the basis of their mass spectra?
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2,3-Dimethylbutane and 2,2-dimethylbutane have the same molecular ion in the mass spectrum, but only one of these isomers gives a significant fragment at m/z = 57. (a) Which isomer shows an intense peak at m/z = 57? (b) Propose a structure for the ion that gives rise to this peak. (c) The base peak in the mass spectrum of the other isomer occurs at m/z = 43. What ion gives rise to this peak?
The mass spectrum of an alkene, C8H16, exhibits a peak at m/z = 41. Draw two isomers that are consistent with these data.
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Chapter 9 Solutions
ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...
Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
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- Assigning Possible Structures to Fragments in a Mass Spectrum The mass spectrum of 2,3-dimethylpentane [(CH3)2CHCH(CH3)CH2CH3] shows fragments at m/z = 85 and 71. Propose possible structures for the ions that give rise to these peaks.arrow_forwardThe molecular ion peak in a mass spectrum of compound W appears at m/z = 107. Predict the molecular formula of compound W. (Hint: Compound W contains a heteroatom, not only carbon and hydrogen).arrow_forwardWhat distinguishes the mass spectrum of 2,2-dimethylpropane from the mass spectra of pentane and isopentane?arrow_forward
- The mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. One appears at m/z = 111 and the other appears at m/z = 97. Determine the identity and structure of each of these fragmentsarrow_forwardThe mass spectrum of 2,3-dimethylpentane shows peaks at m/z = 57 and 43. Propose possible structures for the ions that give rise to these peaksarrow_forwardThe base peak in the mass spectrum of an alkane, C7H16, appears at m/z =57. Draw a molecule that is consistent with these data.arrow_forward
- A mass spectrum shows significant peaks at m/z = 87, 115, 140, and 143. Which of the following compounds is responsible for that mass spectrum?arrow_forwardPropose a molecular formula for cedrol, an alcohol found in cedar oil. Cedrol has three degrees of unsaturation and a molecular ion in its mass spectrum at m/z = 222.arrow_forwardButanal and methylpropanal give slightly different mass spectra. Both give a molecular ion peak at m/z = 72, but butanal gives four other peaks whereas methylpropanal only gives three. State the species responsible for the four other peaks in the mass spectrum of butanal and write equations to show their formation from the molecular ion.arrow_forward
- 1 (c) 2-Methyl-3-pentanol reacts with PCC to form compound F. (i) Draw the structure of F. (ii) In the mass spectrum, identify the m/z value of the molecular ion peak for compound F. (ii) Fragmentation of radical cation F exhibits two fragment ion peaks at m/z 57 and m/z 71. Propose the structures of these two fragments. (iv) Draw the resonance structure for each of the cation in (iii).arrow_forwardAter analyzing a mass spectrum you conclude that the molecule being analyzed has the molecular formula C4H8; however, there are five possible constitutional isomers with that same molecular formula. the only thing that stands out in the mass spectrum is a strong fragment signal at m/z=41. Determine the possible constitutional isomers for C4H8 and explain which isomer matches the mass spectrum.arrow_forwardPredict the masses and the structures of the most abundant fragments observed in the mass spectra of the following compounds. (a) acetophenone (b) 3-bromo-2-methylpentanearrow_forward
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