pls solve this problem with in 1 hour. Explain it also (b) The reaction (R)-2-chloro-3-methylbutane with KOH shown below, resulted in a mixture ofthree alcohols: W and its enantiomer X and compound Y.H3CCH3H3CонКонEthanol+ Enantiomer X + YHH3CH3CCH3W(R)-2-chloro-3-methylbutane(i) Deduce the structures of compounds X and Y and assign the stereochemistry for compoundsW and X.(i) Use reaction mechanisms to account for the formation of the MAJOR product.

Answered: Image /qna-images/answer/f879a6dd-5cd6-4871-bfe0-051161aa45a5.jpg

(b) The reaction (R)-2-chloro-3-methylbutane with KOH shown below, resulted in a mixture of three alcohols: W and its enantiomer X and compound Y. H3C CH3 H3C он H7 H3C кон Ethanol + Enantiomer X + Y CI H3C CH3 (R)-2-chloro-3-methylbutane (1) Deduce the structures of compounds X and Y and assign the stereochemistry for compounds W and X. (i) Use reaction mechanisms to account for the formation of the MAJOR product.

(b) The reaction (R)-2-chloro-3-methylbutane with KOH shown below, resulted in a mixture of three alcohols: W and its enantiomer X and compound Y. H3C CH3 H3C он H7 H3C кон Ethanol + Enantiomer X + Y CI H3C CH3 (R)-2-chloro-3-methylbutane (1) Deduce the structures of compounds X and Y and assign the stereochemistry for compounds W and X. (i) Use reaction mechanisms to account for the formation of the MAJOR product.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 36MP: Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds...

See similar textbooks

Similar questions

Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?
Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?
A hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.
A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. c. Suggest a reagent to convert A to the single stereoisomer X.
A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired conguration.a. Label this stereogenic center as R or S.b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.c. Suggest a reagent to convert A to the single stereoisomer X.
The reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent. Identify compounds A, B, C, and D and give their names. By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur? By what mechanism does the reaction of A with strong base to form B occur? Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.
γ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?
Aspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.
Give the structure of the compound that satisfies the criterion given in each instance: a) A compound of formula C5H11Br that cannotyield analkene upon treatment withtBuOK. b). A four carbon alkene that yields a meso diol upon treatment with m-CPBA/H2O. c). A six carbon secondaryalcohol (C6H14O) that yields only a single alkene upon acid catalyzeddehydration
Compound A has molecular formula C4H10, and gives two monochlorides, B and C, on photochemical chlorination. Treatment of either of these monochlorides with potassium tert-butoxide gives the same alkene (C4H8) as the product, but B leads to just one isomer of the alkene, D, where C gives D and another isomer of the alkene, E. Treatment of monochlorides B and C with aqueous ethanol gives products F and G, respectively, both of which are of molecular formula C4H10O. What are the names of compounds A-G?
An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions, and show your reasoning.
Most alkyl bromide are water-insoluble liquids. But when the following alkyl bromide Awas first isolated, its high melting point of 203oC (solid at room temperature) and its water solubility led its discoverers to comment that it behaves more like a salt (hint: like NaCl). Explain the salt-like behavior of compound A in under thirty words.