Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 13.14, Problem 23P
Interpretation Introduction
Interpretation:
The absorption occurred at larger wavenumber, the carbonyl group bonded to
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Which of the following is not true regarding infrared spectroscopy?
wavenumbers units are inverse centimeters (cm-¹)
a stronger bond will have a higher wavenumber stretch
conjugated carbonyls have a lower wavenumber stretch
A larger bond dipole will lead to a lower intensity IR absorption
Identify the frequency of both carbonyl stretches in your IR. Which one corresponds to the benzyl ester?
Wavenumber (cm-1)
Bond
Vibration
Shape
Intensity
Functional Group
3288.63 cm-1
N-H
Stretch
Sharp
Weak
Amine/Amide
3078.39 cm-1
C-H
Stretch
Sharp
Weak
Aromatic/Alkene
2976.16 cm-1
C-H
Stretch
Sharp
Weak
Alkane
1720.50 cm-1
C=O
Stretch
Sharp
Medium
Ester
1653.00 cm-1
C=O
Stretch
Sharp
Medium
Amide
1556.55 cm-1
C=C
Stretch
Sharp
Medium
Aromatic
Which shows an O¬H stretch at a larger wavenumber: ethanol dissolved in carbon disulfide or an undiluted sample of ethanol?
Chapter 13 Solutions
Organic Chemistry (8th Edition)
Ch. 13.1 - Which of the following fragments produced in a...Ch. 13.2 - What distinguishes the mass spectrum of...Ch. 13.2 - What is the most likely m/z value for the base...Ch. 13.3 - Prob. 5PCh. 13.3 - a. Suggest possible molecular formulas for a...Ch. 13.3 - If a compound has a molecular ion with an...Ch. 13.3 - Identify the hydrocarbon that has a molecular ion...Ch. 13.4 - Predict the relative intensities of the molecular...Ch. 13.5 - Which molecular formula has an exact molecular...Ch. 13.5 - Prob. 11P
Ch. 13.6 - Sketch the mass spectrum expected for...Ch. 13.6 - The mass spectra of 1-methoxybutane,...Ch. 13.6 - Primary alcohols have a strong peak at m/z = 31....Ch. 13.6 - Identify the ketones responsible for the mass...Ch. 13.6 - Prob. 16PCh. 13.6 - Using curved arrows, show the principal fragments...Ch. 13.6 - The reaction of (Z)-2-pentene with water and a...Ch. 13.9 - a. Which is higher in energy: electromagnetic...Ch. 13.9 - Prob. 20PCh. 13.13 - Prob. 21PCh. 13.14 - Which occur at a larger wavenumber: a. the C O...Ch. 13.14 - Prob. 23PCh. 13.14 - Prob. 24PCh. 13.14 - Rank the following compounds from highest...Ch. 13.14 - Which shows an O H stretch at a larger...Ch. 13.16 - Prob. 27PCh. 13.16 - a. An oxygen-containing compound shows an...Ch. 13.16 - Prob. 29PCh. 13.16 - For each of the following pair of compounds, name...Ch. 13.17 - Which of the following compounds has a vibration...Ch. 13.17 - Prob. 32PCh. 13.18 - A compound with molecular formula C4H6O gives the...Ch. 13.20 - Prob. 34PCh. 13.20 - Prob. 35PCh. 13.21 - Predict the max of the following compound:Ch. 13.21 - Prob. 37PCh. 13.23 - a. At pH = 7 one of the ions shown here is purple...Ch. 13.23 - Prob. 39PCh. 13.23 - Prob. 40PCh. 13 - In the mass spectrum of the following compounds,...Ch. 13 - Prob. 42PCh. 13 - Draw structures for a saturated hydrocarbon that...Ch. 13 - Rank the following compounds in order of...Ch. 13 - For each of the following pairs of compounds,...Ch. 13 - a. How could you use IR spectroscopy to determine...Ch. 13 - Assuming that the force constant is approximately...Ch. 13 - Norlutin and Enovid are ketones that suppress so...Ch. 13 - In the following boxes, list the types of bonds...Ch. 13 - A mass spectrum shows significant peaks at m/z. =...Ch. 13 - Prob. 51PCh. 13 - Prob. 52PCh. 13 - Prob. 53PCh. 13 - The IR spectrum of a compound with molecular...Ch. 13 - Rank the following compounds from highest...Ch. 13 - Rank the following compounds from highest...Ch. 13 - What peaks in their mass spectra can be used to...Ch. 13 - Prob. 58PCh. 13 - Which one of the following five compounds produced...Ch. 13 - Prob. 60PCh. 13 - Each of the IR spectra shown below is accompanied...Ch. 13 - Prob. 62PCh. 13 - Prob. 63PCh. 13 - How can IR spectroscopy distinguish between...Ch. 13 - Prob. 65PCh. 13 - Prob. 66PCh. 13 - Give approximate wavenumbers for the major...Ch. 13 - Prob. 68PCh. 13 - Which one of the following live compounds produced...Ch. 13 - Phenolphthalein is an acid-base indicator. In...Ch. 13 - Prob. 71PCh. 13 - How can you use UV spectroscopy to distinguish...Ch. 13 - Prob. 73PCh. 13 - The IR and mass spectra for three different...
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- In an IR spectrum, the C-0 stretch for an alcohol (ROH) or an ether (ROR) appears near 1050 cm¯1, but for a carboxylic acid (RCO,H) or an ester (RCO,R), the C-0 stretch appears near 1250 cm-1. Explain why. -1050 cm-1 -1050 cm-1 -1250 cm-1 -1250 cm-1 R R R Rarrow_forwardPlease don't provide handwriting solutionarrow_forwardWhich of the following has an IR carbonyl stretch at a higher wavenumber? 1 1 O 2 f2 f3 f4 fs f6 fe 7 & 5 Q W R T 图 # Marrow_forward
- 2. Both the compounds shown below contain a carbonyl group but there is slight variation in the wavenumber of the peak as shown below. h f 1720 cm-1 1680 cm-1 Explain the possible reason of this variation.arrow_forwardWhen the 1HNMR spectrum of an alcohol is run in dimethylsulfoxide (DMSO) solvent rather than in chloroform, exchange of the Ο-H proton is slow and spin-spin splitting is seen between the Ο-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols? (a) 2-Methyl-2-propanol (b) Cyclohexanol (c) Ethanol (d) 2-Propanol (e) Cholesterol (f) 1-Methylcyclohexanolarrow_forwardSignal b in the spectrum for 2-ethoxyethyl acetate ( comes from the Hs connected to: O C4 C1 C3 O C2 O C5 PPM G11C2 CA C5arrow_forward
- 3arrow_forwardIs this HNMR spectrum for 3-methoxybenzoic acid, 4 methoxybenzoic acid or 4 methylbenzoic acid? Please explain why and explain peaks, shifts, etc.arrow_forwardChoose the best explanation for why -OH and -NH peaks are often broad singlets in a ¹H NMR spectrum. A) The greater electronegativity difference in the N-H or O-H bond compared to a C-H bond makes the peak broader. B) The greater mass involved in the N-H or O-H bond compared to a C-H bond makes the peak broader. C) The hydrogen nuclei on the carbon next to the -OH or -NH are too far away to impact the multiplicity. D) Protons in OH or NH groups are acidic enough to rapidly exchange between different molecules, so the coupling to vicinal hydrogens is not clearly observed.arrow_forward
- Consider isomeric alcohols A and B and mass spectra [1] and [2]. (a) Label the molecular ion and base peak in each spectrum. (b) Use thefragmentation patterns to determine which mass spectrum correspondsto isomer A and which corresponds to isomer B.arrow_forwardWhat are the peaks and chemical shifts in this H NMR? What is the major product and minor product in the H NMR (between 1-methylcyclohexene and 3-methylcyclohexene)? What was the percentage od the major and minor products in the product picture (which is the H NMR)? This is like the ratio between 1-methylcyclohexene and 3-methylcyclohexene.arrow_forwardWhere can you find the IR absorption band of the O-H stretching vibration of carboxylic acids? A 1740-1720 cm-1 В 1439-1399 cm-1 C) 2260-2240 cm-1 D) 3300-2500 cm-1arrow_forward
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