(a) State and illustrate the following :(i) Wolff-Kishner reduction (ii) Aldol condensation(b) An organic compound (A) which has characteristic odour, on treatment with NaOH forms two compounds (B) and (C). Compound (B) has the molecular formula C7H8O which on oxidation with CrO3 gives back compound (A). Compound (C) is the sodium salt of the acid. Compound (C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of (A), (B), (C) and (D). Write chemical equations for all reactions taking place.

(a) State and illustrate the following :(i) Wolff-Kishner reduction (ii) Aldol condensation(b) An organic compound (A) which has characteristic odour, on treatment with NaOH forms two compounds (B) and (C). Compound (B) has the molecular formula C7H8O which on oxidation with CrO3 gives back compound (A). Compound (C) is the sodium salt of the acid. Compound (C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of (A), (B), (C) and (D). Write chemical equations for all reactions taking place.

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

Chapter23: Amines

Section: Chapter Questions

Problem 23.37P

See similar textbooks

Similar questions

3. Obtain acetophenone and acetaldehyde by reaction of glycols with periodic acid. Justify your answer with the reaction mechanism.
Explain the differences in acidity between p-cyanobenzoic acid and m-cyanobenzoic acid. Illustrate your answer appropriately, showing the acid-base reaction that takes place with each of these and explaining in such terms as electronic (inductive or resonance) and/or steric effects.
(a) suggest the suitable mechanism and illustrate the stepwise of the (heptyloxy)cyclopentane mechanism. (b) illustrate, and write the mechanism the formation of iodocyclopentane and 1-iodoheptane.
Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
Draw/outline a reasonable and detailed mechanism for the dehydration of 2-methylcyclohexanol catalyzed by phosphoric acid. Use curved arrows to show the flow of electrons and draw the structures of all intermediates and byproducts formed in the reaction. Predict and rationalize the expected product distribution based on thermodynamic aspects
Compound A was oxidized with periodic acid to give B, which after acid hydrolysis gave C. Bromine oxidation of C gave D. Suggest structural formulas, including stereochemistry, for compounds B, C, and D.
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.
Wolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.
A student was given from the list of the compounds below A, B and D blindly and asked to identify them all. He treated each of them with Brady's reagent (2,4-ditrophenylhydrazine) and isolated a bright yellow compound for one of them, but the other two gave false negatives. The student reasoned that the false negatives may be due to sterics and, on further thinking, it dawned on him that he might be able to rule out one of the false negatives with the haloform test. What compound did he find compatible with the haloform test? That compound did indeed give a false negative in the Brady test. Which of the other two was positive in the Brady test? A = haloform B = Brady A = haloform D = Brady B = haloform A = Brady B = haloform D = Brady D = haloform A = Brady D = haloform B = Brady
A task is assigned to an undergraduate student to test two samples (known as compounds K and L) in the laboratory. She placed these two compounds through various scientific tests. She discovered that these compounds have the same molecular formula, C8H8O. When treated with 2,4-dinitrophenylhydrazine, all of these compounds produce brightly coloured precipitate, and both are reduced to an organic compound with the molecular formula C8H10O. However, compound K can be easily oxidized by chromic acid to formed compound N and vice versa for compound L. Furthermore, when both compounds reach with Fehling's solutions, they produce negative results. However, only compound K forms a silver mirror when it reacts with Tollen's reagent, and compound L does not. Identify the possible formulae for compounds K, L, and N by ignoring their possible isomerism. Indicate the formation of compound N from compound K. Predict the chemical reaction that occurs when compound L reacts with…
Benzenediazonium carboxylate decomposes when heated to yield N2, CO2, and a reactive substance that can't be isolated. When benzenediazonium carboxylate is heated in the presence of furan, the following reaction is observe. Propose a structure for the intermediate in this reaction.
Suggest with explanation on how you would prepare the compound, 4-chloroaniline from aniline