Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 14.4, Problem 9P
Predict the relative intensities of the molecular ion peak, the M+ 2 peak, and the M + 4 peak for a compound that contains two bromine atoms.
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Consider this step in a radical reaction:
Y
What type of step is this? Check all that apply.
Draw the products of the step on the right-hand side of the drawing area
below. If more than one set of products is possible, draw any set.
Also, draw the mechanism arrows on the left-hand side of the drawing
area to show how this happens.
ionization
propagation
initialization
passivation
none of the above
22.16 The following groups are ortho-para directors.
(a)
-C=CH₂
H
(d)
-Br
(b)
-NH2
(c)
-OCHS
Draw a contributing structure for the resonance-stabilized cation formed during elec-
trophilic aromatic substitution that shows the role of each group in stabilizing the
intermediate by further delocalizing its positive charge.
22.17 Predict the major product or products from treatment of each compound with
Cl₁/FeCl₂-
OH
(b)
NO2
CHO
22.18 How do you account for the fact that phenyl acetate is less reactive toward electro-
philic aromatic substitution than anisole?
Phenyl acetate
Anisole
CH
(d)
Chapter 14 Solutions
Organic Chemistry
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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- Show how to convert ethyl benzene to (a) 2,5-dichlorobenzoic acid and (b) 2,4-dichlorobenzoic acid.arrow_forwardHelp me solve this problem. Thank you in advance.arrow_forward22.7 Predict the monoalkylated products of the following reactions with benzene. (a) AlCl3 Ya (b) AlCl3 (c) H3PO4 (d) 22.8 Think-Pair-Share AICI3 The reaction below is a common electrophilic aromatic substitution. SO3 H₂SO4 SO₂H (a) Draw the reaction mechanism for this reaction using HSO,+ as the electrophile. (b) Sketch the reaction coordinate diagram, where the product is lower in energy than the starting reactant. (c) Which step in the reaction mechanism is highest in energy? Explain. (d) Which of the following reaction conditions could be used in an electrophilic aro- matic substitution with benzene to provide substituted phenyl derivatives? (i) AICI3 HNO3 H₂SO4 K2Cr2O7 (iii) H₂SO4 (iv) H₂PO₁arrow_forward
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- V Consider this step in a radical reaction: Br: ? What type of step is this? Check all that apply. Draw the products of the step on the right-hand side of the drawing area below. If more than one set of products is possible, draw any set. Also, draw the mechanism arrows on the left-hand side of the drawing area to show how this happens. ⚫ionization termination initialization neutralization none of the abc Explanation Check 80 Ο F3 F1 F2 2 F4 01 % do5 $ 94 #3 X 5 C MacBook Air 25 F5 F6 66 ©2025 ˇ F7 29 & 7 8arrow_forwardShow how to convert ethyl benzene to (a) 2,5-dichlorobenzoic acid and (b) 2,4-dichlorobenzoic acid.arrow_forwardno aiarrow_forward
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