Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 16.SE, Problem 73AP
Use your knowledge of directing effects, along with the following data, to deduce the directions of the dipole moments in aniline and bromobenzene.
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Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Prob. 1PCh. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SŪ4. deuterium...Ch. 16.3 - Prob. 5PCh. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P
Ch. 16.4 - Prob. 11PCh. 16.4 - Acetanilide is less reactive than aniline toward...Ch. 16.4 - Prob. 13PCh. 16.5 - At what position would you expect electrophilic...Ch. 16.5 - Show the major product(s) from reaction of the...Ch. 16.6 - The herbicide oxyfluorfen can be prepared by...Ch. 16.7 - Treatment of p-bromotoluene with NaOH at 300°C...Ch. 16.8 - Prob. 18PCh. 16.8 - Prob. 19PCh. 16.8 - Prob. 20PCh. 16.9 - Prob. 21PCh. 16.10 - Prob. 22PCh. 16.10 - Prob. 23PCh. 16.SE - Prob. 24VCCh. 16.SE - The following molecular model of a...Ch. 16.SE - Prob. 26VCCh. 16.SE - Prob. 27VCCh. 16.SE - Aromatic iodination can be carried out with a...Ch. 16.SE - Prob. 29MPCh. 16.SE - The carbocation electrophile in a Friede1-Crafts...Ch. 16.SE - Prob. 31MPCh. 16.SE - The nitroso group, —N=O, is one of the few...Ch. 16.SE - Triphenylmethane can be prepared by reaction of...Ch. 16.SE - Using resonance structures of the intermediates,...Ch. 16.SE - Benzene and alkyl -substituted benzenes can be...Ch. 16.SE - Prob. 36MPCh. 16.SE - Hexachlorophene, a substance used in the...Ch. 16.SE - Benzenediazonium carboxylate decomposes when...Ch. 16.SE - 4-Chloropyridine undergoes reaction with...Ch. 16.SE - Propose a mechanism to account for the following...Ch. 16.SE - In the Gatterman-Kochreaction, a formyl group...Ch. 16.SE - Treatment of p-tert-butylphenol with a strong acid...Ch. 16.SE - Benzyl bromide is converted into benzaldehyde by...Ch. 16.SE - Prob. 44MPCh. 16.SE - Prob. 45MPCh. 16.SE - Prob. 46APCh. 16.SE - Prob. 47APCh. 16.SE - Prob. 48APCh. 16.SE - Predict the major monoalkylation products you...Ch. 16.SE - Name and draw the major product(s) of...Ch. 16.SE - Prob. 51APCh. 16.SE - Prob. 52APCh. 16.SE - What product(s) would you expect to obtain from...Ch. 16.SE - Prob. 54APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 56APCh. 16.SE - Prob. 57APCh. 16.SE - Prob. 58APCh. 16.SE - Prob. 59APCh. 16.SE - Prob. 60APCh. 16.SE - Prob. 61APCh. 16.SE - Prob. 62APCh. 16.SE - Prob. 63APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 65APCh. 16.SE - Prob. 66APCh. 16.SE - Draw resonance structures of the intermediate...Ch. 16.SE - Prob. 68APCh. 16.SE - p-Bromotoluene reacts with potassium amide to give...Ch. 16.SE - Prob. 70APCh. 16.SE - Prob. 71APCh. 16.SE - Prob. 72APCh. 16.SE - Use your knowledge of directing effects, along...Ch. 16.SE - Identify the reagents represented by the letters...Ch. 16.SE - Phenols (ArOH) are relatively acidic, and the...Ch. 16.SE - Prob. 76APCh. 16.SE - Prob. 77APCh. 16.SE - Melamine, used as a fire retardant and a component...
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- 7. Draw the following ions. (a) cis- [PF.CI.) (b) trans- [PF.CI.J (c) fac- [PF.CIJ ( (d) Predict the P NMR spectra of a and c. From your 8. Draw Molecular orbital diagrams for O, 0, (superoxide) and O (peroxide) diagrams predict which, if any are paramagnetic? 구는 구 Paramagnetir Paramagnetic 구글arrow_forwardFor the 1H NMR spectra of cis-2,2-dimethyl-4,5-diphenyl-1,3-dioxolane, tabulate the data as detailed in the following example. Identify each signal on the NMR spectrum as a, b, c… 1H NMR Spectroscopic data for Dioxolane Derivative Hydrogen δ(ppm) Integration Splitting Identity peak a 1.19 3H (2.9) doublet CH3arrow_forwardHow would you explain why phenol is the o-p driver, while nitro benzene is m-directional? Resonance Describe by showing their structures.arrow_forward
- Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forwardThe 1H- and 13C-NMR data of an ester of molecular formula C6H10O2 are given below. Also shown are the COSY and HETCOR NMR spectra of the ester. Draw the structure of the ester, explaining how you reach your conclusion. 1H-NMR: 7.20-6.90 (1H), 5.85 (1H), 4.16 (2H), 1.88 (3H), 1.31 (3H) ppm 13C-NMR: 166.7, 144.5, 123.0 , 60.2, 18.0, 14.3 ppmarrow_forward5) Using Molecular Orbital Energy diagram, explain why the absorption maximum of methylvinylketone (A) is at 320 nm while the absorption maximum of 2-methylbutadiene (B) is at 224 nm. Aarrow_forward
- Нас 3. (5S,7R) -7-bromo-3,9-diethyl-6,6-dimethylundec-3,8-dien-5-ol H C Н.С Ay statuvos OH CH3 Ay si Br Н CH3 CH3 I b. number of peaks = С.arrow_forwardFor each of the molecules below: (a) Provide the bond line structures (b) Indicate the number of peaks that would be seen in their ¹H-NMR spectra. Number each unique type of hydrogen peaks as shown in the example on the right. (c) Label the diasterotopic and enantiotopic atoms and/or groups. 1. (1R,4S) 4-secbutyl-2,3-diethyl-6,6-dimethylcyclohex-2-enol 2. (2R,6S) 2,6-dibromo-4,4-dimethylcyclohexanol Example: ¹H 2 O 2 1arrow_forwardBased on the 13C NMR data provided with multiplicity, deduce the structures of each of the benzenoid aromatic compounds below, where the molecular formula for compound is C10H14. a. 134(s), 131(d), 19(q)arrow_forward
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