4) The classic synthesis of hydroquinone consists of two steps:a) oxidation of aniline with manganese dioxide in aqueous acid (HCI) to afford p-benzoquinoneandb) reduction of the thus-produced quinone with iron powder in water (acid solution) to givehydroquinone.Formulate the respective (balanced) half reactions for the oxidation of aniline with MnO2 and thereduction of the pertinent quinone with Fe powder, respectively. On either side of the half reactions,indicate the oxidation state(s) of the element(s) that is (are) oxidized or reduced, respectively. Assumethat the oxidation produces inorganic chlorides as byproducts whereas the reduction affords iron(II)oxide as waste and give a qualitative assessment of the atom-efficiency of this way of producinghydroquinone.Hints: Manganese ends up in the +2 oxidation state and the amino group is converted into anammonium cation.

For the oxidation of aniline with manganese dioxide (MnO2) in aqueous acid (HCl) to afford…

Answered: 4) The classic synthesis of…

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.60P

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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, 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?
The synthesis of triphenylphosphine was carried out. Firstly the synthesis of the reagent, phenyl magnesium bromide followed by the addition of phosphorous tribromide which was further quenched, extracted and purified to give triphenylphosphine as a product. Write a reaction mechanism for this reaction. Discuss the reaction and what occurs.
(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…
Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)
(a) Illustrate the following name reactions :(i) Hell-Volhard-Zelinsky reaction (ii) Wolff-Kishner reduction reaction(b) How are the following conversions carried out:(i) Ethylcyanide to ethanoic acid (ii) Butan-l-ol to butanoic acid(iii) Methylbenzene to benzoic acidWrite chemical equations for the involved reactions.
Cadaverine (1,5-diaminopentane) and putrescine (1,4-diaminobutane) are two compounds that are formed by bacterialaction and are responsible for the odor of rotting flesh. Drawtheir structures. Suggest a series of reactions to synthesize pu-trescine from 1,2-dibromoethane and any inorganic reagents
(a) Give chemical tests to distinguish between :(i) Propanol and propanone (ii) Benzaldehyde and acetophenone(b) Arrange the following compounds in an increasing order of their property as indicated :(i) Acetaldehyde, Acetone, Methyl tert-butyl ketone (reactivity towards HCN)(ii) Benzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(iii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH, (CH3)2CHCOOH (acid strength)
(a) Write the structures of main products when benzene diazonium chloride reacts with the following reagents :(i) H3PO2 + H2O (ii) CuCN/KCN (iii) H2O(b) Arrange the following in the increasing order of their basic character in an aqueous solution :C2H5NH2, (C2H5)2NH, (C3H5)3N(c) Give a simple chemical test to distinguish between the following pair of compounds :C6H5—NH2 and C6H5—NH—CH3
Outline the steps invloved in the synthesis of 3-chloro-4-fluroacetophenone from 4-aminoacetophenone. provide the bond line structure for the major organic product obtained in each step of the proposed synthesis.
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. 1g of phenylamine yielded 1.2g of compound A. Calculate the percentage yield of the reaction.
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Write the equation for the reaction between compound A and phenol Give the name and suggest the colour of the precipitate B. Why is it necessary to recrystallize B several times?
The following is an experimental account of the preparation of compound B from Phenylamine. 2cm3 of phenylamine are dissolved in 10cm3 of 0.5M hydrochloric acid in a test tube and cooled in an ice bath. 5cm3 of 0.2M sodium nitrate solution cooled to about 5o are added to the solution above and shaken. A salt A, C6H5N2Cl is formed, collected and dried. 1g of salt A is dissolved in 10cm3 of water, cooled and added drop by drop to a cold solution of 0.3g phenol in 5cm3 of 0.1M sodium hydroxide solution. B is precipitated, filtered, dried and the melting point determined. B is further crystallized twice and the melting point taken each time and found to be constant. Give the structure of the product formed when an acidified solution of compound A is reacted with (i)Naphthalen-2-ol (2-naphthol) (ii) Sodium cyanide

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