Organic Chemistry (Loose) -With Access
7th Edition
ISBN: 9780321933805
Author: Bruice
Publisher: PEARSON
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Chapter 14.14, Problem 24P
Interpretation Introduction
Interpretation:
The absorption occurred at larger wavenumber, the carbonyl group bonded to
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Explain why a ketone carbonyl typically absorbs at a lower wavenumber than an aldehyde carbonyl (1715 vs. 1730 cm−1).
Which shows an O¬H stretch at a larger wavenumber: ethanol dissolved in carbon disulfide or an undiluted sample of ethanol?
a) what bond is present in ketones but not alkanes?
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c) is the new band strong or weak compared with a C=C or a C≡C stretch?
Chapter 14 Solutions
Organic Chemistry (Loose) -With Access
Ch. 14.1 - Which of the following fragments produced in a...Ch. 14.2 - What distinguishes the mass spectrum of...Ch. 14.2 - What is the most likely m/z value for the base...Ch. 14.3 - Prob. 5PCh. 14.3 - If a compound has a molecular ion with an...Ch. 14.3 - a. Suggest possible molecular formulas for a...Ch. 14.3 - Identify the hydrocarbon that has a molecular ion...Ch. 14.4 - Predict the relative intensities of the molecular...Ch. 14.5 - Which molecular formula has an exact molecular...Ch. 14.5 - Prob. 11P
Ch. 14.6 - Sketch the mass spectrum expected for...Ch. 14.6 - The mass spectra of 1-methoxybutane,...Ch. 14.6 - Prob. 14PCh. 14.6 - Identify the ketones responsible for the mass...Ch. 14.6 - Prob. 16PCh. 14.6 - Using curved arrows, show the principal fragments...Ch. 14.6 - The reaction of (Z)-2-pentene with water and a...Ch. 14.9 - Prob. 19PCh. 14.9 - Prob. 20PCh. 14.9 - Prob. 21PCh. 14.13 - Prob. 22PCh. 14.14 - Which occur at a larger wavenumber: a. the C O...Ch. 14.14 - Prob. 24PCh. 14.14 - Prob. 25PCh. 14.14 - Rank the following compounds from highest...Ch. 14.14 - Which shows an O H stretch at a larger...Ch. 14.15 - Prob. 28PCh. 14.15 - a. An oxygen-containing compound shows an...Ch. 14.15 - Prob. 30PCh. 14.15 - For each of the following pair of compounds, name...Ch. 14.16 - Which of the following compounds has a vibration...Ch. 14.16 - Prob. 33PCh. 14.17 - A compound with molecular formula C4H6O gives the...Ch. 14.19 - Prob. 35PCh. 14.19 - Prob. 36PCh. 14.20 - Predict the max of the following compound:Ch. 14.20 - Prob. 38PCh. 14.21 - a. At pH = 7 one of the ions shown here is purple...Ch. 14.21 - Prob. 40PCh. 14.22 - Prob. 41PCh. 14.22 - Prob. 42PCh. 14 - In the mass spectrum of the following compounds,...Ch. 14 - Prob. 44PCh. 14 - For each of the following pairs of compounds,...Ch. 14 - Draw structures for a saturated hydrocarbon that...Ch. 14 - a. How could you use IR spectroscopy to determine...Ch. 14 - Assuming that the force constant is approximately...Ch. 14 - In the following boxes, list the types of bonds...Ch. 14 - A mass spectrum shows significant peaks at m/z. =...Ch. 14 - Prob. 51PCh. 14 - Prob. 52PCh. 14 - Prob. 53PCh. 14 - How can you use UV spectroscopy to distinguish...Ch. 14 - Rank the following compounds from highest...Ch. 14 - Rank the following compounds from highest...Ch. 14 - What peaks in their mass spectra can be used to...Ch. 14 - Each of the IR spectra shown below is accompanied...Ch. 14 - Prob. 59PCh. 14 - Prob. 60PCh. 14 - How can IR spectroscopy distinguish between...Ch. 14 - 62. Draw the structure of a carboxylic acid that...Ch. 14 - Prob. 63PCh. 14 - Give approximate wavenumbers for the major...Ch. 14 - Prob. 65PCh. 14 - Prob. 66PCh. 14 - Prob. 67PCh. 14 - The IR spectrum of a compound with molecular...Ch. 14 - Which one of the following live compounds produced...Ch. 14 - Prob. 70PCh. 14 - Phenolphthalein is an acid-base indicator. In...Ch. 14 - Which one of the following five compounds produced...Ch. 14 - The IR and mass spectra for three different...
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- Which of the attached compounds has a C=O that absorbs at the lowest wavenumber?arrow_forwardIdentifying Isomers from Fragmentation Patterns Which mass spectrum (A or B) corresponds to each isomer: 2methylpentane [(CH3)2CHCH2CH2CH3] or 2,2-dimethylbutane [(CH3)3CCH2CH3]?arrow_forwardWhich occurs at a larger wavenumber: a. the C - O stretch of phenol or the C - O stretch of cyclohexanol? b. the C - O stretch of a ketone or the C - O stretch of an amide? c. the C - N stretch of cyclohexylamine or the C - N stretch of aniline?arrow_forward
- The carbonyl absorptions of esters X and Y differ by 25 cm−1. Whichcompound absorbs at higher wavenumber and why?arrow_forwardRank the following compounds by their expected C-O wavenumber stretch. Use a 1 for the highest wavenumber, followed by a 2, and a 3 for the lowest wavenumber.arrow_forwardCarbonyl (C=O) group of acetone stretches at 1724 cm-1 in IR but the same group stretches at much lower (1691 cm-1) wave number for 3-Nitroacetophenone. Why?arrow_forward
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- Select an approximate region where carbonyls stretches typically occur in FTIR spectra (cm-1).arrow_forward9. rank absorption of the indicated bonds in decreasing (highest to lowest) order of wavenumberarrow_forwardConsider isomeric alcohols A and B and mass spectra [1] and [2].(a) Label the molecular ion and base peak in each spectrum. (b) Use the fragmentation patterns to determine which mass spectrum corresponds to isomer A and which corresponds to isomer B.arrow_forward
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