Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 10.13, Problem 19P
Interpretation Introduction
Interpretation:
The reason for
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Why is the C¬O absorption band of 1-hexanol at a smaller wavenumber (1060 cm-1) than the C¬Oabsorption band of pentanoic acid (1220 cm-1)?
Which functional group, except alkane, is presence in the following IR spectrum?
INFRARED SPECTRUM
Relative Transmittance
0.96
0.92
carboxylic acid
ether
alcohol
alkene
3000
2000
Wavenumber (cm-1)
m
1000
Assign the peaks in the spectrum to the functional groups in n-butyl acetate.
Microns (µm)
2.5
3.0
3.5
4.0
5.0
6.0
8
10
15 20
100
a
2787 cm-1
1083 cm-1
2965 cm-
1742 cm
1246 cm-1
4000
3500
3000
2500
2000
1500
1000
500
Wavenumber (cm1)
C=O peak =|
С-Н рeak
C-O peak
Submit
Transmittance (%)
Chapter 10 Solutions
Essential Organic Chemistry, Global Edition
Ch. 10.1 - Prob. 1PCh. 10.2 - What would distinguish the mass spectrum of...Ch. 10.2 - Prob. 3PCh. 10.3 - Prob. 5PCh. 10.3 - Suggest possible molecular formulas for a compound...Ch. 10.3 - Prob. 7PCh. 10.4 - Prob. 8PCh. 10.4 - Prob. 9PCh. 10.5 - Prob. 10PCh. 10.5 - Prob. 11P
Ch. 10.6 - Identify the ketone responsible for the mass...Ch. 10.6 - Prob. 13PCh. 10.8 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10.12 - Which will occur at a larger wavenumber: a. a C :...Ch. 10.13 - Which will occur at a larger wavenumber: a. the C...Ch. 10.13 - Prob. 18PCh. 10.13 - Prob. 19PCh. 10.13 - Which will show an O 8 H stretch at a larger...Ch. 10.14 - Prob. 21PCh. 10.14 - Prob. 22PCh. 10.15 - Prob. 23PCh. 10.15 - Prob. 24PCh. 10.17 - Prob. 25PCh. 10.18 - Prob. 26PCh. 10.18 - Prob. 27PCh. 10.19 - Prob. 28PCh. 10.19 - Prob. 29PCh. 10.22 - How many signals would you expect to see in the 1H...Ch. 10.22 - Prob. 31PCh. 10.22 - Prob. 32PCh. 10.23 - Where would you expect to find the 1H NMR signal...Ch. 10.24 - Prob. 34PCh. 10.25 - Prob. 35PCh. 10.25 - Prob. 36PCh. 10.25 - Prob. 37PCh. 10.26 - Prob. 38PCh. 10.26 - Which of the following compounds is responsible...Ch. 10.27 - Prob. 40PCh. 10.27 - Prob. 41PCh. 10.27 - The 1H NMR spectra of two carboxylic acids with...Ch. 10.28 - Prob. 43PCh. 10.28 - Prob. 44PCh. 10.28 - Prob. 45PCh. 10.28 - Describe the 1H NMR spectrum you would expect for...Ch. 10.28 - Identify the compound with molecular formula...Ch. 10.29 - Prob. 48PCh. 10.29 - Prob. 49PCh. 10.29 - Identify the compound with a molecular formula of...Ch. 10 - In the mass spectrum of the following compounds,...Ch. 10 - For each of the following pairs of compounds,...Ch. 10 - Draw the structure of a saturated hydrocarbon that...Ch. 10 - Prob. 54PCh. 10 - Prob. 55PCh. 10 - How could you use UV spectroscopy to distinguish...Ch. 10 - Prob. 57PCh. 10 - Predict the relative intensities of the molecular...Ch. 10 - Prob. 59PCh. 10 - List the following compounds in order from highest...Ch. 10 - How can 1H NMR be used to prove that the addition...Ch. 10 - There are four esters with molecular formula...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - Each of the IR spectra presented here is...Ch. 10 - Prob. 66PCh. 10 - Five compounds are shown for each of the following...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Phenolphthalein is an acidbase indicator. In...Ch. 10 - Which one of the following five compounds produced...Ch. 10 - Prob. 72PCh. 10 - Prob. 73PCh. 10 - Prob. 74PCh. 10 - How could 1H NMR distinguish between the compounds...Ch. 10 - Prob. 76PCh. 10 - Prob. 77PCh. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - Identify the following compounds. (Relative...Ch. 10 - An alkyl halide reacts with an alkoxide ion to...Ch. 10 - Determine the structure of a compound with...
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- Which one of these four compounds would give a 13C NMR spectrum with only these three peaks, one at 210, one at 40 and one at 20? H3C OB OD 13C NMR delta (8) values C=O of ketones, aldehydes C=O of acids, esters, amides C=C and C=N C-X (where X = halogen, O) base position, alkyl C OC A OA CH3 H3C B CH3 H3C1 220-200 160-180 100-150 40-70 0 - 40 CH3 H₂C D CH3arrow_forward3-Pentanol can be oxidized to 3-pentanone using sodium dichromate. How can the completeness of conversion be gauged using IR spectroscopy? The absence of a strong, broad O-H peak (1700 cm-1) The absence of a strong C=0 peak (3200-3600 cm-1) The absence of a strong broad O-H peak (3200-3600 cm-1) The Presence of a strong C-H peak (2800-3000cm-1) The absence of a wake snarp 0-H peak (3200-3600 cm-1)arrow_forwardWhich C-H bonds are responsible for the following peaks in the 1H NMR of this molecule? B= C=|| CTH1602 B PPM 10arrow_forward
- The carbonyl absorptions of esters X and Y differ by 25 cm−1. Which compound absorbs at higher wavenumber and why?arrow_forwardYou have an unknown with an absorption at 1680 cm-1; it might be an amide, an isolated double bond, a conjugated ketone, aconjugated aldehyde, or a conjugated carboxylic acid. Describe what spectral characteristics you would look for to help youdetermine which of these possible functional groups might be causing the 1680 peak.arrow_forwardFollowing is a 1H-NMR spectrum of 2-butanol. Explain why the CH2 protons appear as a complex multiplet rather than as a simple quintet.arrow_forward
- The two mass spectra below correspond to two isomers of C4H10O: 1-butanol and 2-butanol. Match the spectrum with the appropriate compound. Place the m/z ratio and the structures for the labeled fragments in the table below. 100 Compound 00 2 GO 40 - 1 20 - 10 20 30 40 50 60 70 80 90 100 m/ 7 100 Compound 3 80 60 40 20 0 TH 10 15 20 25 30 35 40 45 50 55 60 65 70 75 m/z Fragment 1 Fragment 2 Fragment 3 Fragment 4 m/z Fragment Relative Intensity Re-ative Intersityarrow_forwardA low-resolution mass spectrum of 2-methyl-2-butanol (MW 88) shows 16 peaks. The molecular ion is absent. Account for the formation of peaks at m/z 73, 70, 59, and 55 and propose a structural formula for each cation.arrow_forwardHow many signals are expected in the decoupled ¹³C NMR spectrum of 3-bromotoluene? Br CH3arrow_forward
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