Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 13.21, Problem 30P
Interpretation Introduction
Interpretation:
The chemical equations that not only relate the mechanism but also outline the structure of the intermediate that forms in the rate determining step of the addition-elimination reaction of hexafluoro benzene and sodium methoxide are to be determined.
Concept introduction:
Nucleophilic
The aromatic ring is itself act as a nucleophile, hence the ring undergoes this substitution only in the presence of a strong electron withdrawing so that it stabilized the negative charge on the ring.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Isoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 mol of hydrogen bromide to isoprene to give 1,3-dibromo-3-methylbutane.Write a series of equations describing the mechanism of this reaction.
Bromine reacts with alkenes in methanol according to the equation
when this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield). Which of the following is the structure more reasonable for this compound? Explain your reasoning through a corresponding mechanism.
3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene.
For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product.
(a) the same quantities of reagents are dissolved in half the volume of methanol
(b) 3-bromo-2-methylpropene is used in place of 3-chloro-2-methylpropene
(c) sodium methanethiolate (CH3SNa) is used in place of of sodium methoxide
Chapter 13 Solutions
Organic Chemistry - Standalone book
Ch. 13.2 - Based on Hammonds postulate which holds that the...Ch. 13.3 - Prob. 2PCh. 13.3 - Using : O =N+= O : as the electrophile, write a...Ch. 13.4 - Prob. 4PCh. 13.5 - Prob. 5PCh. 13.6 - Prob. 6PCh. 13.6 - Write a reasonable mechanism for the formation of...Ch. 13.6 - tert-Butylbenzene can be prepared by alkylation of...Ch. 13.6 - Prob. 9PCh. 13.7 - The reaction shown gives a single product in 88...
Ch. 13.7 - Prob. 11PCh. 13.8 - Using benzene and any necessary organic or...Ch. 13.10 - Prob. 13PCh. 13.11 - Prob. 14PCh. 13.12 - Prob. 15PCh. 13.12 - Prob. 16PCh. 13.13 - Prob. 17PCh. 13.13 - Prob. 18PCh. 13.14 - Reaction of chlorobenzene with p-chlorobenzyl...Ch. 13.15 - Prob. 20PCh. 13.15 - Prob. 21PCh. 13.15 - Prob. 22PCh. 13.16 - Prob. 23PCh. 13.16 - Prob. 24PCh. 13.17 - Prob. 25PCh. 13.18 - Prob. 26PCh. 13.19 - Write the structure of the expected product from...Ch. 13.20 - Prob. 28PCh. 13.20 - Prob. 29PCh. 13.21 - Prob. 30PCh. 13.21 - Offer an explanation for the observation that...Ch. 13.21 - Prob. 32PCh. 13 - Write the structure of the organic product in each...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Treatment of the alcohol shown with sulphuric acid...Ch. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Arrange the following five compounds in order of...Ch. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Give reagents suitable for carrying out each of...Ch. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Which is the best synthesis of the compound shown?Ch. 13 - What combination of acyl chloride or acid...Ch. 13 - A standard synthetic sequence for building a...Ch. 13 - Prob. 54PCh. 13 - Prob. 55PCh. 13 - Prob. 56PCh. 13 - Prob. 57PCh. 13 - Prob. 58PCh. 13 - Prob. 59PCh. 13 - Prob. 60DSPCh. 13 - Prob. 61DSPCh. 13 - Prob. 62DSPCh. 13 - Prob. 63DSP
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
- Write equations for the preparation of n-pentane from:arrow_forwardOzonolysis process was carried out towards an unknown organic compound, X, to produce propanal, C3H6O and compound Y. Propanal was then further oxidized into compound Z, C3H6O2 by using potassium permanganate, KMnO4 under acidic condition and heating. As an alternative, compound Y can be produced from the reaction of benzene with ethanoyl chloride, CH3COCl with the presence of aluminium trichloride, AlCl3. (i) Draw the structural formula of compounds X, Y, and Z (ii) Show the formation of electrophile that will be reacted with benzene for the formation of compound Y. (iii) What is the name of reaction to convert benzene into compound Y?arrow_forward3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropenearrow_forward
- Write chemical equations expressing each of the following: (a) Preparation of o-nitrophenyl acetate by sulfuric acid catalysis of the reaction between a phenol and an acid anhydride. (b) Esterification of 2-naphthol with acetic anhydride in aqueous sodium hydroxide (c) Reaction of phenol with benzoyl chloridearrow_forwardThe following reaction has been reported in the chemical literature and gives a single organic product in high yield. Write the structure of the product for the reaction of 2−phenylpropene treated with diborane in tetrahydrofuran followed by oxidation with basic hydrogen peroxide.arrow_forwardPentafluorophenol is readily prepared by heating hexafluorobenzene with potassium hydroxide in tert-butyl alcohol:What is the most reasonable mechanism for this reaction? Comment on the comparative ease with which this conversion occurs.arrow_forward
- Carototoxin is a natural pesticide produced by carrots, with formula C₁H2O. It undergoes hydrogenation with Pd to: give product A, C,H,O, and with Lindlar's catalyst to give product B, C,H2O. Ozonolysis followed by zinc leads to a mixture of methanal, octanal, 1,2-ethanedioic acid, 3-oxopropanoic acid, and 2-hydroxy-3-oxopropanoic acid. Draw possible structures for carototoxin, A, and B. Product B structure H2, Lindlar's Structure of carototoxin H2, Pd/C Product A structurearrow_forwardThe ethylation of benzene is an electrophilic substitution reaction. Identify the electrophile in the reaction. Write the equation including reagents and conditions for the ethylation of benzene to produce ethylbenzene. Hence outline the mechanism for the reaction.arrow_forwardThe formation of the following cyclic compound has been observed in the hydration of the following alkene, write a mechanism that explains the product.arrow_forward
- (a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.arrow_forward(b) Ozonolysis process was carried out towards an unknown organic compound, X, to produce propanal, C3H6O and compound Y. Propanal was then further oxidized into compound z, C3H6O2 by using potassium permanganate, KMNO4 under acidic condition and heating. As an alternative, compound Y can be produced from the reaction of benzene with ethanoyl chloride, CH3COCI with the presence of aluminium trichloride, AICI3. Proses ozonolisis telah dijalankan terhadap sebatian organik yang tidak dikenali, X untuk menghasilkan propanal, C3H6O dan sebatian Y. Propanal kemudiannya dioksidakan menjadi sebatian Z menggunakan KMNO4 dalam keadaan berasid dan panas. Sebagai alternatif, sebatian Y boleh dihasilkan daripada tindak balas antara benzena dengan etanoil klorida, CH3COCI dengan kehadiran aluminium triklorida, AICI3. (1) Draw the structural formula of compounds X, Y, and z. Lukiskan formula struktur bagi sebatian X, Y, dan Z. (ii) Show the formation of electrophile that will be reacted with benzene…arrow_forwardWhich of the following statements about 3-iodo-2-methylprop-1-ene is/are true? (i) It has an E isomer and a Z isomer. (ii) It can be converted to an alkyl lithium compound in one step by reacting with lithium metal. (iii) It would react with the following reagent to give 2-methylhept-1-ene as the product: CuLiarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning