Need help drawing a detailed mechanisms with all 6 resonance structures. And a detailed explanation. I've done the six structures but I'm not sure if its correct. And I'm not sure how to explain the enhanced acidity of phenol. Please help. b. Draw all possible resonance structures for the phenoxide ion derived fromp- nitrophenol(e.g., first treat p-nitrophenol with OH-) and explain why p- nitrophenol is much moreacidic than phenol. to explain the enhanced acidity of the phenol. (There is also a 6 one,can you find it?)

The resonating structure of p-nitro phenoxide ion is shown below

Draw all possible resonance structures for the phenoxide ion derived from p- nitrophenol (e.g., first treat p-nitrophenol with OH-) and explain why p- nitrophenol is much more acidic than phenol. to explain the enhanced acidity of the phenol. (There is also a 6 one, can you find it?)

Draw all possible resonance structures for the phenoxide ion derived from p- nitrophenol (e.g., first treat p-nitrophenol with OH-) and explain why p- nitrophenol is much more acidic than phenol. to explain the enhanced acidity of the phenol. (There is also a 6 one, can you find it?)

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 20E

See similar textbooks

Related questions

Q: How will the acid (4-meythyl hexanoic acid) be deprotonated if the pH of the solution is adjusted so…

A: Deprotonation is removal of proton (H+) from acid. At half equivalence point, pH = pKa. The half…

Q: Identify the conjugate acid of the compound shown in the box below. Provide a curved arrow mechanism…

Q: What is the correct way to arrange the numbered protons in increasing order of acidity and why

A: Answer is 2> 5> 1>3>4

Q: Arrange each group of compounds in order of increasing basicity.(a) CH3COO-, ClCH2COO-, and PhO- (b)…

Q: One of the heptanedione isomers below has a pka of approximately 9 rather than 20. Which isomer?…

Q: a. Which indicated hydrogen on the molecule below is more acidic? Draw the conjugate base of each…

Q: ank the following acid derivative classes in order of increasing reactivity with the same…

A: 8) the increasing order of reactivity with the same nucleophile is:

Q: Which carboxylic compound of each pair would you expect to be stronger acid? Indicate (a) or (b) on…

A: In case 1) Me3N+ is an electron withdrawing group. It with draws electron from O-H bond through…

Q: 2. Each of the circled hydrogens in the compound shown below could potentially be removed by…

A: Here we have to predict which of the following bases will deprotonate the following indicated acidic…

Q: Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine…

A: Note: Since we only answer up to 3 sub-parts, we’ll answer the first 3. Please resubmit the question…

Q: 2. Compare the pka of pyrrole and imidazole. Which heterocycle is more basic? Applying the Hückel…

A: A. Greater is the pKa lower will be the Ka and hence, lower will be the acidity. Hence, higher will…

Q: Which of (a)-(d) shows the increasing order of basicity of compounds 1-4?

Q: 2. p-Nitrophenol is not intensely yellow until it is deprotonated under the basic conditions of the…

A: p-nitrophenol undergoes deprotonation in basic condition to form p-nitrophenolate ion.

Q: Which acid is stronger, 4-phenylphenol or3-phenylphenol? Why?

A: 3-phenyl phenol is more acidic than 4-phenyl phenol. Due to inductive effect of phenyl ring on…

Q: Q8:- Arrange the compounds of each set in order of basicity:? Explain your choice ? Aniline…

A: Hey, since there are multiple questions posted, we will answer first question. If you want any…

Q: This is the reaction I was referring to, I have no idea of what reagents can lead me to the…

A: In this reaction, the reagents are H2O and KMnO4.

Q: Which of the following carbonyl compounds has the most acidic hydrogen? Show why it has the most…

A: The acidic hydrogen means the hydrogen atom which will easily release from the compound and form…

Q: - Rank the following substances in order of increasing acidity: (a) Phenol, p-methylphenol,…

A: Acid is substance which release hydrogen ions and base is substance which release hydroxyl ions.

Q: (a) How will you convert the following :(i) Propanone to Propan-2-ol (ii) Ethanal to…

A: Oxidation It is the process of gaining of oxygen Different oxidizing agents are; alkaline KMnO4, Br2…

Q: 4. Write out the steps necessary-to convert the compound on the left into the compound on the right…

A: The questions has been answered.

Q: `NH HNO3 `NH H2SO4 NO2 Acetanilide para-Nitroacetanilide

A: We have to draw two alternative isomers of nitroacetanilide and suggest two reasons why, during this…

Q: 2. Show the step(8) necessary to transform the compound on the left into the acid on the right.…

A: (2) Transformation of p-nitrobenzoic acid from p-nitrotoluene - When p-nitrotoluene is treated…

Q: 8. Rank the following compounds in order of increasing base strength (weakest base first-to the…

A: Higher the availability of electrons, higher will be the basicity. Electron donating groups increase…

Q: The major reason that phenol is a more acidic than cyclohexanol is It is a better proton donor The…

Q: Draw the product of attached reductive amination reaction.

A: The product of the above reductive amination reaction is drawn below,

Q: earn the term “oxime” and then look up a reaction called the “Beckmann rearrangement.” Why is this…

Q: Identify the most and the least basic compound in each of the following sets. Leave the remaining…

Q: The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons…

Q: Draw all resonance structures of the conjugate bases formed by removal of the labeled protons (Ha,…

A: On removing the hydrogen Ha from acetanilide, the conjugate base formed does not exhibits the…

Q: h resonance structures of the anion formed by the reaction of the most acidic C-H bond of the…

A: Acidity of hydrogen strength depends on the conjugate base formed when treated with base.The…

Q: Draw the major product of this reaction. Ignore inorganic byproducts and the carboxylic acid side…

A: LiAlH4 is a strong reducing agent . It reduces almost all compounds like Ketone , aldehyde or…

Q: Rank the derivatives of phenol in order of increasing acidity (Please explain)

A: The compounds given are,

Q: Show how any ONE the following would be made through use of a Grignard in as few steps as possible,…

A: We can design the synthetic pathway for the desired product by properly placing the partial charges…

Q: Which of the following is more nucleophilic and why? CH30 (CH3)3CO 1 2 Compound 2, because its…

A: Strong nucleophile means an atom or a group carry lone pair of electrons. It effectively go to…

Q: 1. The nitroso group is a deactivating group but ortho/para directing. Explain its deactivating…

A: The resonance shows the polarity developed in a molecule. It is the interaction between lone pair of…

Q: Place the following compounds in order of their basicity with #1 being the most basic and #4 being…

A: Bases are those substances which have tendency to gives lone pair of electrons and accept a proton…

Q: Q1:- Arrange the following compounds of each set in order of decreasing acidity ? Explain your…

A: Since you have posted multiple questions, we will solve only first question for you. To get the…

Q: 2. Explain why phenols, including the B-naphthol, which is used in the current experiment, would be…

A: Why phenols are acidic it is to be explained. Acid is the one which can donate a proton and form…

Q: Give a reaction showing that benzoic acid behaves as an acid.

A: Benzoic acid (C6H5COOH) behaves as an acid.

Q: In the following pairs of compounds, which is the most acidic? Benzoic acid and 4-nitrobenzoic acid…

Q: Identify the most and the least basic compound in each of the following sets. Leave the remaining…

A: The basicity of the compound depends on several factors available. For example the electronegative…

Q: Suppose you have just synthesized heptanoic acid from heptan-1-ol. The product iscontaminated by…

A: SOLUTION: Step 1: Let sodium dichromate, sulfuric acid, 1-heptanol and heptanol be impurities. The…

Q: 3. Indicate the most acidic hydrogens and draw the important resonance contributors of the anion…

A: Since there are multiple question, we will answer only first question, that is, no. 3. If you…

Q: H2PO4- is amphoteric. Which of the following will be the product in the acid-base reaction where…

Q: Answer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D…

A: Only those acid -base reactions are feasible which forms weaker acid and base on product side as…

Q: 5-Methylene- 1,3-cyclopentadiene "Fulvene" 6-Dimethylamino- fulvene 6,6-Dimethyl- fulvene…

A: 4th molecule is most acidic molecule because when bond break then negative charge comes in ring so…

Q: Rank each set of compounds in order of increasing basicity.aniline, p-methylaniline, p-nitroaniline

A: Among the given set of compounds, p-nitroaniline has the lowest basicity because it contains phenyl…

Question

Need help drawing a detailed mechanisms with all 6 resonance structures. And a detailed explanation. I've done the six structures but I'm not sure if its correct. And I'm not sure how to explain the enhanced acidity of phenol. Please help.

b. Draw all possible resonance structures for the phenoxide ion derived fromp- nitrophenol
(e.g., first treat p-nitrophenol with OH-) and explain why p- nitrophenol is much more
acidic than phenol. to explain the enhanced acidity of the phenol. (There is also a 6 one,
can you find it?)

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

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 2 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

The pKa of our product is ~ 2-3 units lower than the pKa of phenol. Draw all possible resonance structures of the conjugate base of the product, and use these to explain why our product is so much more acidic than phenol.
How does the negative inductive effect (−I) of chlorine in the ortho position of the phenol, reduce the negative charge, located on the oxygen of the phenolate anion? Is this why the Oxygen in the phenolate ion will act as a worse nucleophile if the Chlorine is in the ortho position vs the para position?
Any help with this would be great! Explanations definitely welcome, thank you in advance:) What is the product of the reactions?
Why is the bromination (EAS) of phenyl ester slower than phenol?
Based on Steric Effect and Electron Delocalization Explain: 1. Phenol is not easily attacked by a positive reagent as aniline 2. Solubility of acetylinic compound in may bases Please do answer all question for an upvote!! Thank you!
Classify following solvent as protic or aprotic NH3
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.
Any help with these would be great! Thanks in advance:) What is the major product of the reactions?
In an Electrophilic Aromatic Reaction explain: 1. why the –NHCOCH3 group in acetanilide is only moderately activating while the -NH2 group in aniline is strongly activating? 2.Also explain why in a Electrophilic Aromatic Reaction why potassium bromate is used in this reaction instead of Br2 directly?
Using resonance structures, explain why a nitroso group (– NO) is an ortho, para director that deactivates a benzene ring toward electrophilic attack.
Why is the reaction of the type shown below usually done? a.To make an aldehyde or ketone less water soluble b.To make the molecule more reactive c.To protect a ketone or aldehyde carbonyl d.To increase the oxygen content e.To make the alpha hydrogens more acidic
can someone pls help me find the product of this