Answered: Which electrophile is most likely to…

Which electrophile is most likely to undergo a 1,2-hydride shift during an electrophilic aromatic substitution reaction with benzene and AICI2?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 7CTQ

See similar textbooks

Related questions

Q: Which of the following molecules gives a disproportionation reaction in a basic medium? A. benzyl…

Q: Which of the structures A through D is an intermediate in the synthesis of N-methyl phthalimide (2)…

A: In the given reaction CH3NH2 (methyl amine ) acts as like nucleophile, which attacks on anyhdride…

Q: Consider the following reaction schemes involving the reaction of an imine with an organolithium…

A: Organolithium reagent used as base, nucleophile, ortho chelation reaction and halogen exchange…

Q: How does the pKe of the conjugate acid of benzylamine (C3H5CH,NH2) compare to the pK,'s of the…

A: The acid dissociation constant, pKa is a measure to understand the acidic behaviour of any molecule.…

Q: Which electrophile is most likely to undergo a 1,2-hydride shift during an electrophilic aromatic…

A: In electrophilic aromatic substitution of benzene in presence of AlCl3. First of all the alkyl…

Q: Why an amino group (NH2) directs electrophilic aromatic substitutionto the ortho and para positions…

A: Amino group i.e -NH2 directs electrophilic aromatic substitution to the ortho and para positions.

Q: Does the coupling partner of a diazonium dye contain an activating or a deactivating group. Explain…

A: We have to discuss about activating or a deactivating group of coupling partner of a diazonium dye.

Q: ? HO 1. SOCI2 2 AICI3

A: Benzene is react first SOCl2 then AlCl3, and final product is asked.

Q: Explain the mechanism of electrophilic aromatic substitution ?

A: Electrophile, E+ is the e- deficient species. Aromatic ring consists of Π e- and therefore acts as a…

Q: As shown below, electrophilic aromatic substitution on N,N-dimethylaniline is faster than on the…

Q: The 1H NMR spectra for two esters with molecular formula C8H8O2 are shown next. Which of the esters…

Q: What is the mol ratio of acetanilide and para nitroacetanilide in para nitroacetanilide synthesis

Q: Choose the best explanation of why the hydroxy group is an o,p-director in electrophilic aromatic…

A: why the hydroxy group is an o,p-director in electrophilic aromatic substitution reactions is given…

Q: For the following synthesis of guaifenesin, identify the nucleophile and electrophile. Name one…

A: Given reaction:

Q: In electrophilic aromatic substitution reactions a Iodine substituent on the aromatic ring is: a)…

Q: Explain the observed stereo-selectivity in the formation of product using Felkin-Anh model. (c) Ph.…

Q: Which of the following is not a super electrophile in Electrophilic Aromatic Substitution (EAS)…

A: Among the given ions, the ion which is not a super electrophile in Electrophilic aromatic…

Q: Consider the following reaction schemes involving the reaction of an imine with an organolithium…

A: Lithium halogen exchange reaction :

Q: Give the major product(s) of the following reactions, if there is a reaction. For electrophilic…

A: Note: OH is o,p directing group. Isopropyl is o,p directing group. No2 is m-directing group.

Q: 8. Why was it imp 9. What removes the hydrogen from the sp³ carbon in the cationic reaction…

Q: Enamines and imines are tautomers that contain N atoms. Draw a stepwise mechanism for the…

A: The first step of the acid-catalyzed conversion of enamine X to imine Y is shown as,

Q: How does anisole as a director and acetic anhydride as an acylating agent affect the…

A: Acylation of anisole selectivity determined by steric effect.

Q: Which electrophile is most likely to undergo a 1,2-hydride shift during an electrophilic aromatic…

Q: Which of the following does not support a nucleophilic attack of a covalent catalysis? a. Hydroxyl…

A: For a nucleophilic attack, the nucleophile should have a electron pair density which it can donate…

Q: The pKa of protonated acetone is about -7.5, and the pKa of protonated hydroxylamine is 6.0. a. In a…

A: a).

Q: In the Friedel-Crafts acylation (acid chloride), which of the following can serve as the active…

A: The question is based on the concept of organic reactions. we have to identify the correct…

Q: A meta- directing group will place the electrophile into a 1,2- or 1,4- relationship with the…

A: Electron withdrawing groups are acts as meta directing groups in electrophilic aromatic substitution…

Q: 22. What feature is common to all meta-directing groups for electrophilic aromatic substitution?

A: This is multipart question. According to Guidelines in multipart question, we can solve only the…

Q: Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in…

A: NOTE

Q: What is/are the major product(s) obtained from the bromination of dimethylaniline? NME2 FeBr3, Br2…

A: N,N-Dimethylamine group is an ortho/para directing group

Q: In the reaction indicated above, aniline (C6H5NH2) is NOT a candidate for nucleophilic aromatic…

A: Aniline is an aromatic compound, having NH2 substituent on Benzene ring.

Q: Which of the following methods does not work to synthesize benzoic acid? CrO3, H2SO4, H,O A)…

A: Benzoic acid is a derivative of benzene containing -COOH functional group. It is usually prepared by…

Q: Groups which deactivate aromatic rings towards nucleophilic substitution reactions are: O A.…

A: For nucleophilic substitution reaction, benzene ring which is electron deficient will react faster…

Q: Explain why cyclopentadiene (pKa = 15) is more acidic than pyrrole (pKa = 17) even though nitrogen…

A: Since you have asked multiple questions, we will solve the first question for you. If you want any…

Q: Describe how an electron withdrawing group on an aromatic ring affects the proton chemical shifts of…

A: The NMR spectrum provides the following details about the structure of the molecules: The number of…

Q: Consider the following reaction schemes involving the reaction of an imine with an organolithium…

A: We have find out the reaction of an imine with an organolithium compound.

Q: Match each item to a choice: Choices: alkene Reductive amination Curtius rearrangement Hoffman…

A: Match the following of amine reactions

Q: The protonated form of aniline has a pk, of about 4.6. At what pH would you expect the species to…

A: Aniline is a six-membered ring (Benzene) attached to an amine functional group. The Amine group is a…

Q: Which of the following dicarbonyl species would also be successful nucleophiles in the…

A: The reactions in which the two molecules combine together and form a single molecule is known as…

Q: (enamine form) (imine form) Porphobilinogen Draw curved arrows to illustrate the movement of…

A: Topic-- Arrow pushing mechanism of the given reaction.

Q: Consider the following reaction schemes involving the reaction of an imine with an organolithium…

A: n-BuLi being a non-bulky organolithium can undergo halogen exchange as well as a nucleophile that…

Q: Br Br. Br

A: Aromatic electrophilic substitution reaction: Benzene and other aromatic compound gives mainly…

Q: Which of the following reaction is mot likely to activate a drug molecule from orally administered…

Q: acid esters Base Initiation Only meta para and meta lonic bonding Nucleophile Acid Chlorides…

A: solution~

Q: Explain the problem o-hydroxy Benzene sulfonic acid is being subjected to Bromination. Clearly…

A: Given statement is :

Q: (m) DMP, CH2CI2 PCC, CH2CI2 Pyridinium chlorochromate in methylene chloride solvent Aco OAc -OAc OH…

Q: Which of the following compounds is the most reactive in the nucleophilic aromatic substitution…

A: In general benzene undergo electrophilic aromatic substitution reactions When electron…

Question

100%

Which electrophile is most likely to undergo a 1,2-hydride shift during an
electrophilic aromatic substitution reaction with benzene and AICI2?

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

Step 2

Step 3

Step 4

Trending now

This is a popular solution!

Step by step

Solved in 4 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Protection of Groups in Organic Synthesis

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

p-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?
Determine which nucleophilic aromatic substitutions are likely, and proposemechanisms for both the addition–elimination type and the benzyne type.
In the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen of the diazonium ion rather than on the nitrogen that has the formal positive charge?
Using the pKa values of the conjugate acids of the leaving groups (the pKa of HBr is -9, and the pKa of H2O is 15.7), explain the difference in reactivity between CH3Br and CH3OH in a nucleophilic substitution reaction.
Can you help find the functional groups and which of these functional groups will be more reactive to nucleophilic addition?
How common electron-donating and electron-withdrawinggroups affect both the rate of reaction of a benzene ring toward electrophiles and the acidity of substituted benzoic acids ?
Which of the following is a correct statement regarding electrophilic aromatic substitution? A. Many suitable electrophiles are unreactive and can be stored for long periods of time prior to use. B. The carbocation intermediate will lose a proton to regain aromaticity, usually from a position other than the site of the electrophilic attack. C. Formation of the carbocation intermediate has a high activation barrier due to loss of aromaticity. D. Reformation of the aromatic ring has a low activation barrier and therefore occurs slowly. E. The carbocation intermediate has several resonance structures and is negatively charged.
As shown below, electrophilic aromatic substitution on N,N-dimethylaniline is faster than on the unsubstituted aniline.In other words, the aromatic ring in N,N-dimethylaniline is more activated than the ring is in aniline itself. If the ring is methylated at the 2 and 6 positions, however, then the N,N-dimethyl-substituted compound reacts more slowly in electrophilic aromatic substitution than the unsubstituted compound. Explain both of these results. Hint: It does not have to do with the number of H atoms on the ring.
Arrange these compounds in increasing order of reactivity in SN2 nucleophilic substitution?
Draw the benzoic acid structure and explain which products will be formed as a result of the reaction with the nitronium ion in the electrophilic aromatic displacement reaction.
Which of the following statements about substituent effect in electrophilic aromatic substitution reactions (E.A.S.) is false? Electron-withdrawing groups (EWGs) passivates the benzene ring for ortho and para substitution Carbonyl group which are bonded directly to the ring are called electron withdrawing groups (EWGs) In nitration of benzaldehyde, major products are ortho and para-nitro benzaldehyde Regioselectivity in multiple subtitution is determined by the substituent which has a higher activation effect F, Cl, Br, and I are orto-para directing groups, but have passivating effect
Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.