Pls help ASAP In the case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles while one on C1 is unreactivetowards nucleophiles. Rationalize this difference in behavior.N14 UNREAD MESSAGES6Examination of the resonance structures that can be drawn in the SNAr intermediate in the first case reveals that thefive -membered ring has cyclopentadienylcharacter. This is a stabilizing feature. In the latter case,anionSeven Membered ring electrons in that ring, which is not aelectron-delocalization in the seven -membered ring results instabilizing feature.

Nucleophilic substitution reactions of azulene at C1 and C6.Azulene is aromatic compound and its an…

Answered: In the case of halogen-substituted…

In the case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles while one on C1 is unreactive towards nucleophiles. Rationalize this difference in behavior. 0

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.48P: The Williamson ether synthesis involves treatment of a haloalkane with a metal alkoxide. Following...

See similar textbooks

Related questions

Q: 3. predict the products and draw mechanism for each of the following reactions: a) b) c) d) Excess…

A: As HI is a strong acid thus the oxygen atom present in the ether moiety takes up an acidic proton…

Q: Type in a proper name for the structure below. type your answer....

A: IUPAC nomenclature of ketone:• Identify the longest continuous carbon ring• Identify the substituent…

Q: Given the information A+ B C AG = 2D D calculate AG at 298 K for the reaction A+B 2C x10 AH = 792.8…

Q: PBr3 DMF Select to Draw NaH Select to Draw THF 1.9-BBN, THF 2.H2O2, NaOH Select to Draw 1

A: Multisteps synthesis reactions.

Q: 6.0 mol of ammonia gas is injected into a 3.0 L container. At equilibrium, 1.5 mol of hydrogen gas…

A: Moles of ammonia = 6.0 molMoles of H2 at equilibrium = 1.5 molVolume of container = 3.0 L

Q: Time Elapsed Gas Buret (min) 20°C: ONDHANDS 0 5 10 15 20 25 30 35 40 00 30°C: 0 5 Vol O₂ (in mL;…

A: Half-life of the reaction at 200C is to be determined.

Q: what is the mmol of vanillin acetate used? Used: 0.50 g molecular weight: 194.18 g/mol

Q: 4000 structure that best fits this data. 5 3000 4 2000 1500 Wavenumbers (cm^¹) 2H + 3 2 1000 3H 3H…

A: Site of unsaturation:

Q: # M ✓ 8 8 O Apple Google Disney ESPN Yahoo! Biomedical Careers Program B 2 ☆ 2 2 2 6 25 Submit…

A: 1. Answer :-----From lowest to highest entropy are :---MgO(s) < MgCO3 (s) < CaCO3 (s) <…

Q: Use the standard reaction enthalpies given below to determine AH°rxn for the following reaction:…

Q: aqueous Answer Species List Oxidizing agents Reducing agents Spontaneous? Reduction half- reaction…

A: GivenAn aqueous silver nitrate and solid copper metal

Q: 9) Identify the most stable carbocation. A) B) C) D) n O CHCH₂ 40 CH₂CH₂ CH₂CH₂ CH₂CH₂Ⓒ CH₂CH₂

A: Carbocations are the species having positive charge on C atom. The given carbocations are the…

Q: Rank the elements or compounds in the table below in decreasing order of their boiling points. That…

A: The boiling point is directly proportional to the intermolecular forces present in a particular…

Q: 6. 13.116 Strontium-90, a radioactive isotope, is a major on product of an atomic bomb explosion. It…

Q: The Ke for the equilibrium shown below is 50. Some methane and hydrogen sulfide are added to the…

A: The equilibrium constant of a chemical reaction is defined as the ratio of the product of the active…

Q: Study the following phase diagram of Substance X. pressure (atm) 28 14. 0. 0 solid 100 liquid 200…

A: Phase diagram of a sample X is given.

Q: Match the following properties with the correct type of solid. melts below 100°C to give a…

A: Solid metals conduct electricity and heat, while ionic solids do not. Many solids are opaque but…

Q: A 40.0 g sample of glass, which has a specific heat capacity of 0.670 Jg=¹°C¯¹, is dropped into an…

Q: Consider the reaction 2NO(g) + O₂(g) →→→2NO₂(g) Using the standard thermodynamic data in the tables…

A: Since you have asked multiple questions, I will answer first question for you. Please upload second…

Q: An electron volt, eV, is, in many cases, a more convenient unit of energy to use to describe atomic…

A: 1 m = 109 nm 1 nm = 10-9 m

Q: Show by suitable net ionic equations that each of the following species can act as a Brønsted-Lowry…

A: According to, the Bronsted-Lowry concept, Acid is a chemical substance that can give a…

Q: using the lewis structures and vsepr theory explain why the bond angeles are different between…

Q: chiral centers and r and s for each, please

A: After giving priority if the lowest priority group is present below the planeThen rotation is…

Q: Which of the following describes the biological energy to do work like muscle contractions? Group…

A: Gibbs's free energy change of the system is equal to the net useful work done by the system at…

Q: Stan Taizing A chemistry student needs to standardize a fresh solution of sodium hydroxide. She…

Q: A 19.0-m by 7.0-m by 3.0-m basement had a high radon content. On the day the basement was sealed off…

A: To calculate the number of 222 Rn isotopes (atoms) at the beginning and end of 28 days, we need to…

Q: Calculate the cell potential for the galvanic cell in which the given reaction occurs at 25 °C,…

A: Answer :----- Given :---- [Cd2+ ] = 0.00100 M[Au3+ ] = 0.784 MThe overall balanced reaction are…

Q: The equilibrium constant for the reaction Sr(s) + Mg2+ (aq) = Sr²+ (aq) + Mg(s) is 2.69 x 1012 at…

Q: onsider the diagrams of two weak acids given below. O Ka of Acid B > Ka of Acid A O Both have…

Q: efinitions of Acids and Bases Drag the appropriate items to their respective bins. ▸ View Available…

A: (a). Given equation is : H2PO3- (aq) + H2O (l) --->H3PO3 (aq) + OH- (aq) Now, In this equation,…

Q: For each reaction, predict what mechanism will account for the major product(s) formed and write…

A: SN1 reaction involves the formation of a carbocation first, followed by the attack of nucleophile…

Q: Calculate the concentration of Br (MW = 79.904 g/mol), in milligrams per milliliter (mg/mL), in an…

Q: Write a complete electron configuration for Calcium (Ca)

A: The electron configuration of an atom represents how electrons are distributed among its energy…

Q: what is the IUPAC name of the following

A: The IUPAC name of the compound is given by using the rules of IUPAC nomenclature.Select the longest…

Q: A chemist combined chloroform (CHCl3)(CHCl3) and acetone (C3H6O)(C3⁢H6O) to create a solution where…

Q: The pKa values of alpha-amino group, carboxylic acid group and the sidechain group of arginine are…

A: pH of the system = 13Amino acid considered = ArgininepKa of alpha-amino = 9.04pKa of carboxylic…

Q: Complete the following table by calculating the missing entries. In each case indicate whether the…

A: The formula used :

Q: Give the full electron configurations of: As

A: Electrons are filled in a different atomic orbital in an atom. According to the Aufbau rule, the…

Q: In which one of the following solutions will acetic acid have the greatest percent ionization? Ka =…

A: Common ion effect:The decrease in the dissociation of weak acid/base due to the presence of a common…

Q: Predict the producted of the following reactions. If No reaction occurs, write NR. CH3 CH₂ COO TO…

A: In this reaction, given ester when reacts with Lithium Aluminium hydride, then acidic workup, gives…

Q: 17.5 L N₂ at 25 °C and 125 kPa and 44.3 L O₂ at 25 °C and 125 kPa were transferred to a tank with a…

Q: 8. C4H8(g) 2C₂H₂(g) Determine the order of the reaction and the rate con- stant based on the…

A: Order can be determined by plotting time versus pressure graph, time versus ln[P] graph and also…

Q: 1a. Describe the secondary quantum number if l =2 i) letter designation of this sublevel ii) m₂…

A: Quantum numbers are the numbers that describe the position and energy of an electron in an atom.…

Q: Draw the products of the two step reaction sequence shown below. Use dash and/or wedge bonds to…

A: In the first step of this reaction, grignard reagent attacks at the carbonyl carbon and forms 2°…

Q: 1. Balance each equation. Use the oxidation number method for a), c), and e). Use the half reaction…

A: In the oxidation number method, we can determine the oxidation numbers of all atoms. Then…

Q: 1916w ni Y bas X to viiliduloa sru sušquon A 1.4745 g sample of Y was burned in a combustion…

A: Answer :-----

Q: C D -CH₂ & Brz T CH3CO₂ H O Brz/PBr3 CH3 CH₂ CH ₂ COH 3) H₂0/H+

A: Carbonyl compounds containing alpha hydrogen atoms on treatment with bromine in the presence of…

Q: Which of the following products is always a gas during a double displacement reaction? Hydrochloric…

A: Hydrochloric acid: It is formed in aqueous phase during the chemical reactionSodium chloride: It is…

Q: The spectator ion in the equation A1(NO₂), (aq) + Zn(s) → Al(s)+Zn(NO₂)₂ (aq) is aluminum ions zinc…

A: We have to find the spectator ion in the given reaction.

Q: A galvanic (voltaic) cell consists of an inert platinum electrode in a solution containing 1.0 M…

A: A galvanic (voltaic) cell consists of an inert platinum electrode in a solution containing 1.0 M…

Question

Pls help ASAP

In the case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles while one on C1 is unreactive
towards nucleophiles. Rationalize this difference in behavior.
N
14 UNREAD MESSAGES
6
Examination of the resonance structures that can be drawn in the SNAr intermediate in the first case reveals that the
five -membered ring has cyclopentadienyl
character. This is a stabilizing feature. In the latter case,
anion
Seven Membered ring electrons in that ring, which is not a
electron-delocalization in the seven -membered ring results in
stabilizing feature.

Expert Solution

This question has been solved!

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

SEE SOLUTION Check out a sample Q&A here

Step 1: Introduction

VIEW

Step 2: Explanation

VIEW

Solution

VIEW

Step by step

Solved in 3 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

How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?
Although dehydrohalogenation occurs with anti periplanar geometry,some eliminations have syn periplanar geometry. Examine the startingmaterial and product of attached elimination, and state whether the elimination occurs with syn or anti periplanar geometry.
Hydrocarbon 10 and ester 12 react upon heating to give a cycloaddition product D. (i) Suggest a structure for product D and provide a curved arrow mechanism that accounts for its formation. (ii) Draw the molecular orbitals corresponding to the HOMO of 10 and the LUMO of 12 and show that these are of suitable symmetry for a concerted cycloaddition to take place. (iii) Use frontier molecular orbital theory to account for the observation that the formation of D is faster in the presence of AlCl3. please answer all thank you
Explain the difference of reactivities for solvolysis of cis and trans - 4 -t - butyl cyclohexyl tosylate with the help of energy profile diagram. Draw an energy profile diagram Please
Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(CzHs)3). 3SnCl4 + 4Al(C2H5)3 → 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d= 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
what structure show the transition state for the rate determining step in the sn1 reaction with this picture?
Friedel–Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.
Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides.One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4AI(C2H5)3 →3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d = 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3): d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257 L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
Provide a reasonable synthetic strategy for the synthesis of a racemic mixture of (1R,2R) and (1S,2S)-2-bromo-1-methylcyclopentanol from methylcyclopentane
(a) Give a mechanism for this reaction, showing how the two products arise as aconsequence of the resonance-stabilized intermediate.(b) The bromination of cyclohexene using NBS gives only one major product, as shown onthe previous page. Explain why there is no second product from an allylic shift.
For each of the following statements, indicate if they apply to SN1 reactions, SN2 reactions, or both. (a) involve a nucleophile in the rate determining step _______________________ (b) enhanced by use of strong nucleophiles _______________________ (c) carbocation intermediate _________________________ (d) inversion of configuration ___________________________