Answered: (3) Propose a mechanism for the…

(3) Propose a mechanism for the exothermic formation of TCDD from 1,2,4,5- Tetrachlorobenzene and Sodium Hydroxide. NaOH OH high temp. D Da

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

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.42P: When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established...

See similar textbooks

Related questions

Q: b) c) H 1. LDA 2. 3. A NaBH4 i

A: (a) this is an Haloform reaction.(b) this is an reduction reaction.(c) first protonation reaction…

Q: A buffer solution that is 0.401 Min HF and 0.401 M in KF has a pH of 3.14. The addition of 0.01 mol…

A: A buffer is a solution which resists any change in pH on adding a small amount of acid or base.It is…

Q: 5. Using reactions from Chapter 7, provide the reagents needed to convert the starting material into…

A: Given is organic reaction. in which alcohol is converted into an ester.We can prepare it by various…

Q: b) c) N d) CI "N CI OH POCI KCN,DMSO H₂N NH₂

A: Nucleophilic substitution reactions are chemical reactions where an atom or a group of atoms (the…

Q: Check the box under each compound that exists as a pair of mirror-image twins. If none of them do,…

A: Given are organic compounds.Compounds that contain chiral center can exist as a pair of mirror image…

Q: j A CH₂CH₂CH3 -CH₂ PhCO₂H 1. 03 2. (CH₂)₂S 1.03 2. (CH₂)₂S

A: Perbenzoic acid oxidises alkene to epoxide.Alkene reaction with ozone followed by treatment with…

Q: Draw a structural formula for the molecular (not ionic) compound t with two equivalents of ammonia.…

Q: 1. Cetrizine is a nonsedating antihistamine. The first step in a synthesis of cetirizine involves…

A: Carbonyl compounds on treatment with Grignard reagent followed by hydrolysis form alcohols.

Q: О 0 Selected Answer: OMe 1. НО 2. EtMgBr 3. H3O+ ? OH он о OMe

A: The question is based on the concept of organic synthesis.We need to synthesize the product using…

Q: Which of these compounds are electro-rich and which of them are electro-poor?

A: Given:Electron-rich species are chemical species that have an excess of electrons as compared to the…

Q: Identify the relationship between the following structures. THOM OH O enantiomers O identical O…

A: Answer:Stereoisomers, that are non-superimposable mirror images of each other are called as…

Q: ered Identify the sequence of reactions that completes the synthesis below. Answer OH 1) conc.…

A: The given reaction requires reagent to prepare the given compound.The given compound synthesis…

Q: Using the reagents listed in the table below, show how to convert 1-pentyne to the following…

A: We have to choose the reagents form the options.

Q: 10. What product would you expect from addition of deuterium chloride to…

A: The addition of DCl to alkene takes place according to Markovnikov rule.It states that the negative…

Q: 3. Lewis structures of two chemical species are shown below. For each, give (i) the formal charge on…

Q: Correct each molecule in the drawing area below so that it has the structure it would have if it…

A: Given questions related to writing the structure of the molecules in HCl solution.

Q: In a NaOH and HCl titration lab: Suppose you add 40 ml of water instead of the 45 mL. How will this…

A: 1]Molarity=Molarity (M) is a measure of the concentration of a solute in a solution. It is defined…

Q: 2-methylcyclohexanol Montmorillonite KSF Clay Disposal Montmorillonite KSF Clay can be recycled and…

A: The question is based on the concept of experimental chemistry. We need to calculate percentage…

Q: 3. Write the empirical formula for the following compounds a. Glucose b. 9H-adenine c. Nitrous oxide…

A: Empirical formula:- The formula giving the proportions of the elements present in a compound but not…

Q: Given the following reaction: IO3−(aq) + I−(aq) + H+(aq) ⇋ I2(s) + H2O(l) Identify the oxidizing…

A: Answer:Oxidizing agent is the specie that oxidizes others and itself gets reduced during a redox…

Q: Li C

A: The given compound is an organometallic compound as it has a lithium metal attached to an aliphatic…

Q: For the reaction I₂ + Br₂(g) 2 IBr(g), Kc = 280 at 150 °C. Suppose that 0.500 mol IBr in a 2.00-L…

A: Since initially we have only moles of IBr i.e productHence it will react in a backward direction to…

Q: Draw the mechanism showing how this enol tautomerizes to form an aldehyde. OH CH3-CH=CH H3O 0=2 O…

A: Tautomerisation reaction is given.We have to draw the mechanism of the reaction.

Q: d The following initial rate data are for the reaction of ammonium ion with nitrite ion in aqueous…

Q: (b) OEt Ph Me

A: An organic compound can be converted to another by reacting the given compound with other organic…

Q: Consider the reaction below (published in J. Am. Chem. Soc. ] The circled component is the:…

A: Nucleophiles are species that carry negative charge or neutral species containing lone…

Q: ? + ? + + : NH3

A: An acid is a species which donates Proton while a base accepts proton.An acid after donating protons…

Q: One term in a balanced chemical equation contained the coefficient 2 in front of the formula…

A: The number of atoms of each element as a reactant is equal to the number of atoms of that element as…

Q: When CH3CH2Ch2COOH is treated with Na2CO3, one of the products is NaHCO3. Draw the other product.

A: A chemical equation is a process where reactants are converted into different products. In a…

Q: Fill in the missing starting material, reagent or product. You may assume that all reagents are…

A: Multi-step synthesis

Q: ----Calculate the hydronium ion concentration of blood if pH is 7.275.

A: NOTE: “Since you have posted multiple questions, we will provide the solutiononly to the first…

Q: Shown below is a plot of the solubility of benzoic acid in water as a function of temperature.…

A: The amount of solute present in a one-liter solution is known as solubility. The solubility of a…

Q: What reagent is needed to carry out the following transformation? COOH HO CN OSO4, NMO O a) 03,…

Q: Propose an efficient synthesis for the following transformation: The transformation above can be…

A: Given is organic reaction. This is reaction of benzene. We can prepare given compound by…

Q: H.C H.C H Н OH 7CH₂ H H Н -CH3 OH H H C H H H.C H CH₂ H H.C H Н

A: [Since you have posted a question with multiple sub parts, we will provide the solution only to the…

Q: (14.6)Which of the following aqueous solution has the highest boiling point? O 1.00 M NaCl O 1.00 M…

A: Boiling point depends on the number of solute particles in the solution. Higher the solute…

Q: You need to dilute 20.0 mL of a Training 1.40M solution of LiCN to make a 0.0235M solution of LiCN.…

Q: Identify the products of the following addition reaction. A) В) Н.С C) D) нс Sc Н. С 1) BH₂-THF 2)…

A: The given reaction is an example of Hydroboration Oxidation Reaction which is a two step reaction,…

Q: i | # tsbi B чни 0 I

A: Substituents are named such that the sum of position of substituents is minimum.Substituents are…

Q: How much heat is needed to completely vaporize (from a liquid to a gas) 85 grams of ice, initially…

A: In the given question we have to calculate the heat of the reaction when temperature increases and…

Q: Draw the major and minor products of the E2 elimination shown below. Ignore any inorganic…

A: Given is E2 reaction.E2 stands for bimolecular elimination reaction.It is single step reaction.It is…

Q: Write an expression for the enthalpy of combustion of methanol ?cH (CH3OH,I) in terms of the…

A: Standard heat of formation of a compound is the change in enthalpy during the formation of 1 mole of…

Q: 4. Number these in order of ease of hydrolysis. 1 = easiest to hydrolyze, 4 = hardest to hydrolyze.…

A: Given are carboxylic acid derivatives.

Q: Draw the organic product(s) of the following reaction. CH₂ H₂C-CH-CEC-H Vt/85 0 You do not have to…

A: The given reaction is an example of elimination reaction deprotonation of terminal alkyne. Strong…

Q: Which of the choices is a substitution reaction? 1 III Ï-i·l-X OH I || ||| O IV L-i ·X-l Br SH CI IV

A: Substitution reaction is the one in which a group of atoms/atom is substituted by another group of…

Q: A carboxylic acid reacts with water to form a carboxylate ion and H₂O+. Complete the reaction.…

A: an acid is a species which donates Proton while a base accepts proton.An acid after donating protons…

Q: What is the energy in kj/mol of UV radiation with a wavelength of 400 nm

A: Wavelength of UV radiation = 400 nm To determine: Energy of radiation 1 nm = 10-9 m

Q: The following nucleophilic substitution reaction has been reported in the chemical literature. Using…

A: The given reaction is a simple nucleophilic substitution reaction. In this reaction, the Iodide…

Q: a) Propose mechanism for the following reaction: -OH Hesoun H+ H₂0 CH₂OH -CH он

A: The given reactions are shown below.We have to provide the mechanism for those reactions.

Q: A reaction profile (not to scale!) for the reaction 03+02 02 is shown below: E (kJ) 03 + O Submit…

A: Given chemical reaction:O3 + O ----> 2O2 Here, enthalpy of reactant is much higher in…

Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

(3) Propose a mechanism for the exothermic formation of TCDD from 1,2,4,5-
Tetrachlorobenzene and Sodium Hydroxide.
goa
NaOH
OH
high temp.
CI
CI

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: Reaction

VIEW

Step 2: Mechanism

VIEW

Solution

VIEW

Step by step

Solved in 3 steps with 5 images

SEE SOLUTION Check out a sample Q&A here

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

6. Provide the product for the following selective reaction: NO₂ HO * = Ch₂ AICI,
When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.
From the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH,CH,CO,H Use the minimum number of steps; from one to five are required. List reagents by letter in the order that they are used; example: fa. Reagents Available a. BH3, THF; followed by H₂O₂, OH b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C₂H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br j. Ph3P+--CH₂ k. pyridine, heat I. PhBr
4. Suggest a plausible arrow-pushing mechanism for the following reaction. NH N Me NH OH OH conc. HCI H₂O 110 °C, 3 h NT ΤΗ Me OH OH 76%
Propose a mechanism for the conjugate addition of a nucleophile ( Nuc:" ) to acrylonitrile ( CH,=CHCN ). Use resonance forms to show how the cyano group activates the double bond for conjugate addition.
Which set of reagents would be appropriate to synthesize bromobenzene from benzene? 1. HNO3 in H2SO4; 2. H2Cr04 and heat 1. H2CrO4 and heat; 2. H2 Pd/C Br2 and FeBr3 1. CH3CH2CHCI and AICI3; 2. H204 and heat 4B12 and Fe Heat and Br2 Br2, HCI
From the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH₂ Use the minimum number of steps; from one to five are required. List reagents by letter in the order that they are used; example: fa. Reagents Available a. BH3, THF; followed by H₂O2, OH g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C2H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 j. Ph3P+-CH₂ k. pyridine, heat I. PhBr
10-Bromo-a-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from y-bisabolene by the following route: "Br* Bromonium Cyclic carbocation -H*) Base ion Bromo peroxidase Br y-Bisabolene 10-Bromo-a- chamigrene
Qa 18. Bromination of 5a-cholestan-3-one occurs at C-2 or C-4 to give 2 regioisomers. Two unsaturated ketones with lambdamax = 230 nm and lambdamax = 241 nm are yielded during dehydrobromination. Use Woodward-Fieser rules to distinguish between the two.
Choose the best reagent(s) for carrying out the conversion of the reaction below: CH3CH=CHCH2COOH ----> CH3COH + HOCCH2COOH A) NABH4, ethanol B KMNO4, H30* Оз, Zn/Hz0 D) (1) ВНз, (2) Hзо*
Propose a mechanism for the conjugate addition of a nucleophile (Nuc:-) to acrylonitrile(H2C“CHCN) and to nitroethylene. Use resonance forms to show how the cyano andnitro groups activate the double bond toward conjugate addition.
Q2) a) Write a mechanism for the following reaction. 1.NH₂OH CI N N +ZnCl₂ 2. CINCI MeCN, Reflux 2 hr NH