(A) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 (B) Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. (C) Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂0 CI).

(A) The literature reports that when alcohol 1 (see structure below) is treated with thionyl chloride in diethyl ether, the single product is (35,5S)-3- chloro-5-methylcyclohexene (2) (no enantiomer of diastereomer of 2 is formed). Explain by writing a detailed mechanism. Look at the solution to LC-39 (B) Using a mechanism, predict what single stereoisomer of 2 should form when pyridine is substituted for the diethyl ether. (C) Finally, predict mechanistically what additional stereoisomers of 3- chloro-5-methylcyclohexene should form when 1 is treated with Lucas reagent (ZnCl₂/H₂0 CI).

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

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.59P

See similar textbooks

Similar questions

An unknown hydrocarbon G, whose formula is C16H26 contains two triple bonds. Ozonolysis followed by reduction with (CH3)2S gave CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. Suggest a reasonable structure for compound G.
On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produced a mixture of two alkenes B and C, each of which had the molecular formula C7H14. Catalytic hydrogenation of major isomer B or minor isomer C gave only 3-ethylpentane. Suggest structures and mechanisms for compounds A, B, and C consistent with these observations.
Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solutionresults. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears.Suggest a structure for the bright yellow species, and explain this unusual behavior.1
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.
Compound A is an alcohol that undergoes oxidation to produce compound B.Compound B is a ketone that gives positive triiodomethane reaction. Compound B isthen reacted with phenyl magnesium bromide, C6H5MgBr in the presence of aqueousacid to form compound C. Compound C has the molecular formula of C9H12O. Deducethe structure for compound A, B and C. PLEASE PROVIDE CLEAR DRAWINGS AND EXPLANATIONS
Describe a synthetic plan with suitable justification of the sequence of reactions you would understate to complete synthesis of compound 1 from compounds 2,3,4. Suggest suitable reagents
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
3. Obtain acetophenone and acetaldehyde by reaction of glycols with periodic acid. Justify your answer with the reaction mechanism.
Consider the monosubstituted benzene reagent X. Nitration of X yields product Y. Product Y is analysed by 1H and 13C NMR spectroscopy (see Figures 1 to 4). Determine the structure of X and Y on the basis of the spectral data provided.
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.
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
Compound A(C10H12O)gives off oxygen on treatment with sodium metal and also decolorizes Br2 in CCl4 to give organic compound B. Compound A on treatment with I2 in NaOH gives iodoform and salt C which after acidification gives a white solid D(C7H6O2). Using knowledge of organic chemistry identify structures A,B,C and D