Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 18, Problem 18.83AP
Interpretation Introduction
Interpretation:
The mechanism for the reaction of chlorobenzene, containing an isotopic
Concept introduction:
Nucleophilic
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(a) Discuss the aromaticity of a six membered heterocyclic compound which is weak base in nature.
24.82 When the compound shown here is heated, ethene gas
is evolved and a product with the formula C14H3O2 is
formed. The 'H NMR and 13C NMR spectra of C14H8O2
are shown below. (There are two signals >150 ppm in
the 13C NMR spectrum. Recall that the 13C NMR signal
at 77 ppm is from the CDCI3 solvent.)
(a) Draw the structure of C,14H3O2.
(b) Draw the mechanism that accounts for its formation.
(c) What is the main driving force that favors the products of this reaction?
? C14H3O2
C14H8O2
9.
8
7
6
4
3
2
1
250
200
150
100
50
Chemical shift (ppm)
Chemical shift (ppm)
Give reasons :(a) n-Butyl bromide has higher boiling point than f-butyl bromide.(b) Racemic mixture is optically inactive.(c) The presence of nitro group (-NO2) at o/p positions increases the reactivity of haloarenes towards nucleophilic substitution reactions.
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - Prob. 18.6PCh. 18 - Prob. 18.7PCh. 18 - Prob. 18.8PCh. 18 - Prob. 18.9PCh. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Prob. 18.16PCh. 18 - Prob. 18.17PCh. 18 - Prob. 18.18PCh. 18 - Prob. 18.19PCh. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Prob. 18.25PCh. 18 - Prob. 18.26PCh. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Prob. 18.30PCh. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Prob. 18.36PCh. 18 - Prob. 18.37PCh. 18 - Prob. 18.38PCh. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Prob. 18.41PCh. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46APCh. 18 - Prob. 18.47APCh. 18 - Prob. 18.48APCh. 18 - Prob. 18.49APCh. 18 - Prob. 18.50APCh. 18 - Prob. 18.51APCh. 18 - Prob. 18.52APCh. 18 - Prob. 18.53APCh. 18 - Prob. 18.54APCh. 18 - Prob. 18.55APCh. 18 - Prob. 18.56APCh. 18 - Prob. 18.57APCh. 18 - Prob. 18.58APCh. 18 - Prob. 18.59APCh. 18 - Prob. 18.60APCh. 18 - Prob. 18.61APCh. 18 - Prob. 18.62APCh. 18 - Prob. 18.63APCh. 18 - Prob. 18.64APCh. 18 - Prob. 18.65APCh. 18 - Prob. 18.66APCh. 18 - Prob. 18.67APCh. 18 - Prob. 18.68APCh. 18 - Prob. 18.69APCh. 18 - Prob. 18.70APCh. 18 - Prob. 18.71APCh. 18 - Prob. 18.72APCh. 18 - Prob. 18.73APCh. 18 - Prob. 18.74APCh. 18 - Prob. 18.75APCh. 18 - Prob. 18.76APCh. 18 - Prob. 18.77APCh. 18 - Prob. 18.78APCh. 18 - Prob. 18.79APCh. 18 - Prob. 18.80APCh. 18 - Prob. 18.81APCh. 18 - Prob. 18.82APCh. 18 - Prob. 18.83APCh. 18 - Prob. 18.84APCh. 18 - Prob. 18.85APCh. 18 - Prob. 18.86APCh. 18 - Prob. 18.87APCh. 18 - Prob. 18.88APCh. 18 - Prob. 18.89APCh. 18 - Prob. 18.90APCh. 18 - Prob. 18.91APCh. 18 - Prob. 18.92AP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?arrow_forwardAccount for the following:(i) Aniline does not give Friedel-Crafts reaction.(ii) Ethylamine is soluble in water whereas aniline is not.(iii) pKb of methylamine is less than that of aniline.arrow_forwardGive reasons: (i) Bond length of C = O in carboxylic acids is slightly larger than C = O bond length in carbonyl compounds. (ii) There are two –NH2 groups in semicarbazide. However, only one –NH2 group is involved in the formation of semicarbazones. (iii) Benzoic acid is less soluble in water than acetic acid. (iv) Formic acid is a stronger acid than acetic acid.arrow_forward
- Toluene contains a benzene ring with three double bonds in it but still does not show any sign of undergoing a reaction with bromine solution. why?arrow_forwardGive reasons :(i) Electrophilic substitution in aromatic amines takes place more readily than benzene.(ii) CH3CONH2 is weaker base than CH3CH2NH2.arrow_forward(b) Compound AA has a molecular formula of CsH&O and gives a positive result using Tollen's reagent. The reaction of compound AA with hot acidified potassium permanganate, KMNO4 gives compound BB. The catalytic hydrogenation of compound AA with nickel, Ni produced compound Cc. The reaction of compound BB with ethanamine, CH:CH2NH2 produces compound DD. Sebatian AA mempunyai formula molekul C3He0 dan memberikan keputusan yang positif menggunakan reagen Tollen. Tindak balas sebatian AA dengan larutan panas kalium permanganat, KMNO4 berasid menghasilkan sebatian BB. Penghidrogenan bermangkin bagi sebatian AA dengan nikel, Ni menghasilkan sebatian CC. Tindak balas sebatian BB dengan etanamina, CH3;CH2NH2 menghasilkan sebatian DD. (1) Draw the structural formula of compounds AA, BB, CC and DD. Lukiskan formula struktur bagi sebatian AA, BB, CC dan DD. (i) Name the type of chemical reaction for the formation of compound CC. Namakan jenis tindak balas kimia bagi penghasilan sebatian Cc.arrow_forward
- Explain the following behaviours :(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.arrow_forwardA hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.arrow_forward2. (18pts) (a) Draw bond-line structures and include appropriate wedge and dash notation for the following compounds. (b) Identify each pair that would be optically inactive as a 50/50 mixture. (c) Identify pair of compounds that represent diastereomers. H H A Br Br Br H B Br Br H-Et H Br C Br Br CH3 D H Harrow_forward
- . [10]-Annulene may be represented by the following isomeric structures. (a) Say whether any of these is aromatic or not, and explain your answer. (b) If [10]-annulene were to be disubstituted with methyl groups at positions C1 & C6, which of the two structures would be preferred and why? (c) If C1 & C6 were linked (i) directly to each other or (ii) through a methylene group, would you expect any aromaticity from the resulting compounds. If not, why? And if so to what degree?arrow_forwardAnswer ALL parts of this question. The structure shown below is that of the E-isomer of tripolidine, an antihistamine (the E-isomer is more active than the Z-isomer in this capacity): (a) (b) H3C- oto Explain how the Cahn Ingold Prelog sequence rules can be used to rank groups in order of priority, using the four groups attached to the C=C double bond in tripolidine as illustrations. Based on the order of priority of the four groups determined in part (a) of this question, explain why the isomer of tripolidine shown above is defined as the E-isomer. (c) In general terms, explain why this isomer might have different effects in the human body from its geometric isomer.arrow_forwardGamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236). H₂N. CH3 GABA CO₂H CH3 dddd CH3 H₂N Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi bonds. CH3 CO₂H CH3 solddd CH3 CH3 2 CH₂ CO₂Etarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY