Determine if the following transformation can be carried out via the formation of the corresponding tosylate followed by an SN2 attack by methoxide. If it cannot be carried out, explain why and propose a synthetic route that allows obtaining the product in high yield. OCH3 OH

Determine if the following transformation can be carried out via the formation of the corresponding tosylate followed by an SN2 attack by methoxide. If it cannot be carried out, explain why and propose a synthetic route that allows obtaining the product in high yield. OCH3 OH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter17: Alcohols And Phenols

Section17.SE: Something Extra

Problem 35MP: When the alcohol below is treated with POCI3 and pyridine, the expected elimination product is...

See similar textbooks

Related questions

Q: dilute HCI

A: The addition of HCl to alkene yield alkyl chloride. The addition process follow Markovnikov rule.…

Q: The C2H3 + NO reaction has been observed to form CH2O and HCN. Propose a mechanism by which these…

A: 1. Initiation: C2H3 + NO -> C2H2 + HONO Homolytic cleavage of the C2H3 radical generates a C2H2…

Q: Using the carbon-containing starting material(s), propose a synthesis the following retrosynthesis…

A: The objective of the question is to propose a synthesis scheme for the production of an alcohol (OH)…

Q: Propose a synthesis to convert the shown reactants into the shown products. For the first synthesis,…

Q: Starting with ammonia as the nitrogen source, the compound shown can be practically synthesized…

A: We have to prepare the given compound from ammonia.To solve this question we should know the basics…

Q: Synthesize the following compound via Claisen condensation and any other necessary reagent.

Q: When the hydroxyether below (A) is heated with a catalytic amount of acid, it rapidly forms a…

Q: Predict the product(s) that forms and explain why it forms. Cl₂CO OCH 1 eq Et₂NH Devise a synthetic…

A: Step 1:∆ The given compound is a β-keto ester, and it reacts with 1 equivalent of diethylamine…

Q: 4. Show how you would perform the following syntheses. Provide the reagents and intermediates…

A: A) In the given synthesis the amide group is removed from the benzene ring.

Q: Show how the following compounds could be prepared from cyclohexanone. Propose mechanisms. CH,CH,CH3…

A: Since you have posted a question with multiple sub-parts, we will solve first three subpartsfor you.…

Q: An elimination step is involved in the synthesis of aromatic amino acids. We can also envision this…

A: Decarboxylation, which is a chemical reaction that removes a carboxylic acid group (-COOH) from a…

Q: 8) Suggest how the following compound may be made by the alkylation of an enol or enolate. EtO₂C…

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

Q: Cyclohexanone + (CH₃)₂NH and continue with catalyze by H+. Predict the product of this reaction

A: Carbonyl compound reacts with the secondary amine to form an iminium ion. The iminium ion is…

Q: Predict the product(s) of the following reaction. Provide a complete mechanism showing the synthesis…

A: Presence of light in a reaction suggest that the reaction is going through rradical mechanism.Cl2…

Q: Using the carbon-containing starting material(s), propose a synthesis the following retrosynthesis…

A: The objective of the question is to propose a synthesis for the given retrosynthesis scheme using…

Q: When 2,2-dimethylcyclohexanol is treated with acid, 1,2-dimethylcyclohexene and iso-…

A: The given reaction is an acid-catalyzed dehydration of 2, 2-dimethylcyclohexanol.Explanation:Step…

Q: Explain in detail which of the following compounds (A or B) when reacted with acetophenone under…

Q: Using the carbon-containing starting material(s), propose a synthesis the following retrosynthesis…

A: "This isn't straightforward because you have to remember what each reagent does. By looking at the…

Q: The following compound undergoes Benzilic Acid Rearrangementto yield ahydroxyacid salt. Proposea…

A: In benzylic acid rearrangement, OH- (nucleophile), attacks the partial positively charged C of…

Q: When a methyl ester is hydrolyzed under acidic conditions in H,180, the 180 isotope ends up in the…

A: To Find: To find the mechanism involved in the given reaction and explain why each ester undergoes…

Q: Show how the following starting materials are converted to the givenproduct by a series of two…

A: The pericyclic reactions are very useful in the synthesis of organic compounds. They occur in the…

Q: 5. The biosynthesis of cholesterol involves epoxidation of squalene followed by sequential…

Q: Starting with triphenylphosphine and any desired alkyl halide, plus any desired aldehyde or ketone,…

A: Given triphenylphosphine Starting material

Q: 5) Show how you would carry out the following synthesis using inorganic or organic reagents…

Q: When 5-bromopentanal is treated with sodium borohydride, a compound is produced whose 13C NMR…

Q: Give the major product of the following reaction. HO 2) NAOH, H,O, 1) ВН/THF но

Q: Draw the structure of the major product for the following two reactions. (PhH = toluene) H L H + +…

A: Aldehyde acts as protecting group of 1,3-diols. Carbonyl compounds on reaction with phosphorus…

Q: NaOEt, A Ph Ph. H20 N. ОН

Q: Treatment of the chloro enonone with sodium ethoxide in methanol gives the corresponding ethoxy…

Q: 2) How would you synthesize the following compounds from cyclohexanone? CH₂Br CH₂C6H5 A Br B D…

A: Given are organic compounds. Given compounds can be synthesized from cyclohexanone. Note: According…

Q: If heated Time4 decomposes giving the elimination products ethane and ethylene (see below) explain…

A: The objective of the question is to understand the decomposition of TiMe4 when heated and to propose…

Q: H;C H3C `OCH; CH3 CH3

A: In the first step we will do basic hydrolysis followed by acidic work up. In the next step we will…

Q: OCH3 LOH

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

Determine if the following transformation can be carried out via the formation of the
corresponding tosylate followed by an SN2 attack by methoxide. If it cannot be carried out,
explain why and propose a synthetic route that allows obtaining the product in high yield.
OH
OCH 3
to doon

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: SN2 Reaction

VIEW

Step 2: Explanation

VIEW

Solution

VIEW

Step by step

Solved in 3 steps with 2 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

When the following compound undergoes solvolysis in ethanol, three products are obtained. Propose a mechanism to account for the formation ofthese products.
Provide a retrosynthesis and a synthesis for each of the following compounds starting from the designated starting materials and any other necessary reagents.
When the alcohol below is treated with POCI3 and pyridine, the expected elimination product is formed. However, when the same alcohol is treated with Î—2SÎŸ4, the elimination product is 1, 2-dimethyl- cyclopentene. Propose a mechanism for each pathway to account for these differences.
When diethyl ether (CH3CH2OCH2CH3) is treated with concentrated HBr, the initial products are CH3CH2Br and CH3CH2OH. Propose a mechanism to account for this reaction.
Meo `H Me,N `H Propose a synthesis for the following transformations.
Solvolysis of the following bicyclic compound in acetic acid gives a mixture of products, two of which are shown. The leaving group is the anion of a sulfonic acid, ArSO,H. A sulfonic acid is a strong acid, and its anion, ARSO, , is a weak base and a good leaving group. Propose a mechanism for this reaction. voso OČCH, CH,COH
When treated with base, the following compound undergoes an intramolecular aldol reaction and dehydration to give a product containing a ring. H Propose a structure for this product. base C4H6O + HO
Draw the structures of the initially formed enol tautomers in the reactions of propyne and dicyclohexylethyne with dicyclohexylborane followed by NaOHNaOH and H2O2H2O2
When the following compound undergoes solvolysis in ethanol, three products are obtained. Propose a mechanism to account for the formation of these products.
Predict the major product(s) of the following reaction sequence. 1) HCECNa Me 2) H₂O Me OH CH ||| OH phoph Me Me Me OH C Me CH OI O II Me O III and IV I and II ||| IV Solution Me ??? CH CH IV C Me Me OH The reaction shows a ring-opening of an epoxide with a strong nucleophile. In the first step, there is a nucleophilic attack (SN2) by the acetylide ion to any of the epoxide's two carbons since they are equally substituted, causing the ring to open. The second step is the protonation of the anionic oxygen by H₂O. The nucleophilic attack happens through a back-side attack to where the epoxide oxygen is bonded. Hence, the alkyne is bonded with a dash bond, and the alcohol's oxygen is bonded with a wedge bond. This corresponds to the formation of Product II.
When a methyl ester is hydrolyzed under acidic conditions in H,180, the 180 isotope ends up in the carboxylic acid. When a tert-butyl ester is hydrolyzed under the same conditions, the labeled oxygen ends up in the alcohol product. (a) Propose mechanisms to account for these observations. (b) Explain why each ester undergoes the respective mechanism. CH3 + Но-СНЗ 18 + H180 H ОН
provide a synthesis for the following molecule. Starting materials are shown in the left hand side. You don't need to show the mechanism, just show the needed reagents and DO NOT skip any step